Peridinin Is an Exceptionally Potent and Membrane-Embedded Inhibitor of Bilayer Lipid Peroxidation
Antilipoperoxidant protein dysfunction is associated with many human diseases, suggesting that bilayer lipid peroxidation may contribute broadly to pathogenesis. Small molecule inhibitors of this membrane-localized chemistry could in theory enable better understanding and/or treatment of such diseas...
Saved in:
| Published in | Journal of the American Chemical Society Vol. 140; no. 45; pp. 15227 - 15240 |
|---|---|
| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
14.11.2018
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
Cover
Loading…
| Abstract | Antilipoperoxidant protein dysfunction is associated with many human diseases, suggesting that bilayer lipid peroxidation may contribute broadly to pathogenesis. Small molecule inhibitors of this membrane-localized chemistry could in theory enable better understanding and/or treatment of such diseases, but currently available compounds have important limitations. Many biological questions thus remain unanswered, and clinical trials have largely been disappointing. Enabled by efficient, building block-based syntheses of three atypical carotenoid natural products produced by microorganisms that thrive in environments of extreme oxidative stress, we found that peridinin is a potent inhibitor of nonenzymatic bilayer lipid peroxidation in liposomes and in primary human endothelial cells. We also found that peridinin blocks monocyte-endothelial cell adhesion, a key step in atherogenesis. A series of frontier solid-state NMR experiments with a site-specifically 13C-labeled isotopolog synthesized using the same MIDA boronate building block-based total synthesis approach revealed that peridinin is completely embedded within and physically spans the hydrophobic core of POPC membranes, maximizing its effective molarity at the site of the targeted lipid peroxidation reactions. Alternatively, the widely used carotenoid astaxanthin is significantly less potent and was found to primarily localize extramembranously. Peridinin thus represents a promising and biophysically well-characterized starting point for the development of small molecule antilipoperoxidants that serve as more effective biological probes and/or therapeutics. |
|---|---|
| AbstractList | Antilipoperoxidant protein dysfunction is associated with many human diseases, suggesting that bilayer lipid peroxidation may contribute broadly to pathogenesis. Small molecule inhibitors of this membrane-localized chemistry could in theory enable better understanding and/or treatment of such diseases, but currently available compounds have important limitations. Many biological questions thus remain unanswered, and clinical trials have largely been disappointing. Enabled by efficient, building block-based syntheses of three atypical carotenoid natural products produced by microorganisms that thrive in environments of extreme oxidative stress, we found that peridinin is a potent inhibitor of nonenzymatic bilayer lipid peroxidation in liposomes and in primary human endothelial cells. We also found that peridinin blocks monocyte-endothelial cell adhesion, a key step in atherogenesis. A series of frontier solid-state NMR experiments with a site-specifically
C-labeled isotopolog synthesized using the same MIDA boronate building block-based total synthesis approach revealed that peridinin is completely embedded within and physically spans the hydrophobic core of POPC membranes, maximizing its effective molarity at the site of the targeted lipid peroxidation reactions. Alternatively, the widely used carotenoid astaxanthin is significantly less potent and was found to primarily localize extramembranously. Peridinin thus represents a promising and biophysically well-characterized starting point for the development of small molecule antilipoperoxidants that serve as more effective biological probes and/or therapeutics. Antilipoperoxidant protein dysfunction is associated with many human diseases, suggesting that bilayer lipid peroxidation may contribute broadly to pathogenesis. Small molecule inhibitors of this membrane-localized chemistry could in theory enable better understanding and/or treatment of such diseases, but currently available compounds have important limitations. Many biological questions thus remain unanswered, and clinical trials have largely been disappointing. Enabled by efficient, building block-based syntheses of three atypical carotenoid natural products produced by microorganisms that thrive in environments of extreme oxidative stress, we found that peridinin is a potent inhibitor of nonenzymatic bilayer lipid peroxidation in liposomes and in primary human endothelial cells. We also found that peridinin blocks monocyte-endothelial cell adhesion, a key step in atherogenesis. A series of frontier solid-state NMR experiments with a site-specifically 13 C-labeled isotopolog synthesized using the same MIDA boronate building block-based total synthesis approach revealed that peridinin is completely embedded within and physically spans the hydrophobic core of POPC membranes, maximizing its effective molarity at the site of the targeted lipid peroxidation reactions. Alternatively, the widely used carotenoid astaxanthin is significantly less potent and was found to primarily localize extramembranously. Peridinin thus represents a promising and biophysically well-characterized starting point for the development of small molecule antilipoperoxidants that serve as more effective biological probes and/or therapeutics. Antilipoperoxidant protein dysfunction is associated with many human diseases, suggesting that bilayer lipid peroxidation may contribute broadly to pathogenesis. Small molecule inhibitors of this membrane-localized chemistry could in theory enable better understanding and/or treatment of such diseases, but currently available compounds have important limitations. Many biological questions thus remain unanswered, and clinical trials have largely been disappointing. Enabled by efficient, building block-based syntheses of three atypical carotenoid natural products produced by microorganisms that thrive in environments of extreme oxidative stress, we found that peridinin is a potent inhibitor of nonenzymatic bilayer lipid peroxidation in liposomes and in primary human endothelial cells. We also found that peridinin blocks monocyte-endothelial cell adhesion, a key step in atherogenesis. A series of frontier solid-state NMR experiments with a site-specifically C-13-labeled isotopolog synthesized using the same MIDA boronate building block-based total synthesis approach revealed that peridinin is completely embedded within and physically spans the hydrophobic core of POPC membranes, maximizing its effective molarity at the site of the targeted lipid peroxidation reactions. Alternatively, the widely used carotenoid astaxanthin is significantly less potent and was found to primarily localize extramembranously. Peridinin thus represents a promising and biophysically well-characterized starting point for the development of small molecule antilipoperoxidants that serve as more effective biological probes and/or therapeutics. Antilipoperoxidant protein dysfunction is associated with many human diseases, suggesting that bilayer lipid peroxidation may contribute broadly to pathogenesis. Small molecule inhibitors of this membrane-localized chemistry could in theory enable better understanding and/or treatment of such diseases, but currently available compounds have important limitations. Many biological questions thus remain unanswered, and clinical trials have largely been disappointing. Enabled by efficient, building block-based syntheses of three atypical carotenoid natural products produced by microorganisms that thrive in environments of extreme oxidative stress, we found that peridinin is a potent inhibitor of nonenzymatic bilayer lipid peroxidation in liposomes and in primary human endothelial cells. We also found that peridinin blocks monocyte-endothelial cell adhesion, a key step in atherogenesis. A series of frontier solid-state NMR experiments with a site-specifically 13C-labeled isotopolog synthesized using the same MIDA boronate building block-based total synthesis approach revealed that peridinin is completely embedded within and physically spans the hydrophobic core of POPC membranes, maximizing its effective molarity at the site of the targeted lipid peroxidation reactions. Alternatively, the widely used carotenoid astaxanthin is significantly less potent and was found to primarily localize extramembranously. Peridinin thus represents a promising and biophysically well-characterized starting point for the development of small molecule antilipoperoxidants that serve as more effective biological probes and/or therapeutics. Antilipoperoxidant protein dysfunction is associated with many human diseases, suggesting that bilayer lipid peroxidation may contribute broadly to pathogenesis. Small molecule inhibitors of this membrane-localized chemistry could in theory enable better understanding and/or treatment of such diseases, but currently available compounds have important limitations. Many biological questions thus remain unanswered, and clinical trials have largely been disappointing. Enabled by efficient, building block-based syntheses of three atypical carotenoid natural products produced by microorganisms that thrive in environments of extreme oxidative stress, we found that peridinin is a potent inhibitor of nonenzymatic bilayer lipid peroxidation in liposomes and in primary human endothelial cells. We also found that peridinin blocks monocyte-endothelial cell adhesion, a key step in atherogenesis. A series of frontier solid-state NMR experiments with a site-specifically ¹³C-labeled isotopolog synthesized using the same MIDA boronate building block-based total synthesis approach revealed that peridinin is completely embedded within and physically spans the hydrophobic core of POPC membranes, maximizing its effective molarity at the site of the targeted lipid peroxidation reactions. Alternatively, the widely used carotenoid astaxanthin is significantly less potent and was found to primarily localize extramembranously. Peridinin thus represents a promising and biophysically well-characterized starting point for the development of small molecule antilipoperoxidants that serve as more effective biological probes and/or therapeutics. Antilipoperoxidant protein dysfunction is associated with many human diseases, suggesting that bilayer lipid peroxidation may contribute broadly to pathogenesis. Small molecule inhibitors of this membrane-localized chemistry could in theory enable better understanding and/or treatment of such diseases, but currently available compounds have important limitations. Many biological questions thus remain unanswered, and clinical trials have largely been disappointing. Enabled by efficient, building block-based syntheses of three atypical carotenoid natural products produced by microorganisms that thrive in environments of extreme oxidative stress, we found that peridinin is a potent inhibitor of nonenzymatic bilayer lipid peroxidation in liposomes and in primary human endothelial cells. We also found that peridinin blocks monocyte-endothelial cell adhesion, a key step in atherogenesis. A series of frontier solid-state NMR experiments with a site-specifically 13C-labeled isotopolog synthesized using the same MIDA boronate building block-based total synthesis approach revealed that peridinin is completely embedded within and physically spans the hydrophobic core of POPC membranes, maximizing its effective molarity at the site of the targeted lipid peroxidation reactions. Alternatively, the widely used carotenoid astaxanthin is significantly less potent and was found to primarily localize extramembranously. Peridinin thus represents a promising and biophysically well-characterized starting point for the development of small molecule antilipoperoxidants that serve as more effective biological probes and/or therapeutics.Antilipoperoxidant protein dysfunction is associated with many human diseases, suggesting that bilayer lipid peroxidation may contribute broadly to pathogenesis. Small molecule inhibitors of this membrane-localized chemistry could in theory enable better understanding and/or treatment of such diseases, but currently available compounds have important limitations. Many biological questions thus remain unanswered, and clinical trials have largely been disappointing. Enabled by efficient, building block-based syntheses of three atypical carotenoid natural products produced by microorganisms that thrive in environments of extreme oxidative stress, we found that peridinin is a potent inhibitor of nonenzymatic bilayer lipid peroxidation in liposomes and in primary human endothelial cells. We also found that peridinin blocks monocyte-endothelial cell adhesion, a key step in atherogenesis. A series of frontier solid-state NMR experiments with a site-specifically 13C-labeled isotopolog synthesized using the same MIDA boronate building block-based total synthesis approach revealed that peridinin is completely embedded within and physically spans the hydrophobic core of POPC membranes, maximizing its effective molarity at the site of the targeted lipid peroxidation reactions. Alternatively, the widely used carotenoid astaxanthin is significantly less potent and was found to primarily localize extramembranously. Peridinin thus represents a promising and biophysically well-characterized starting point for the development of small molecule antilipoperoxidants that serve as more effective biological probes and/or therapeutics. |
| Author | Hill, Adam G Woerly, Eric M Rienstra, Chad M Greenwood, Alexander I Haley, Hannah M. S Burke, Martin D |
| AuthorAffiliation | Department of Chemistry University of Illinois at Urbana−Champaign Department of Biochemistry Carle Illinois College of Medicine Center for Biophysics and Computational Biology |
| AuthorAffiliation_xml | – name: Department of Chemistry – name: Center for Biophysics and Computational Biology – name: Carle Illinois College of Medicine – name: University of Illinois at Urbana−Champaign – name: Department of Biochemistry |
| Author_xml | – sequence: 1 givenname: Hannah M. S surname: Haley fullname: Haley, Hannah M. S – sequence: 2 givenname: Adam G surname: Hill fullname: Hill, Adam G – sequence: 3 givenname: Alexander I surname: Greenwood fullname: Greenwood, Alexander I – sequence: 4 givenname: Eric M surname: Woerly fullname: Woerly, Eric M – sequence: 5 givenname: Chad M orcidid: 0000-0002-9912-5596 surname: Rienstra fullname: Rienstra, Chad M email: rienstra@illinois.edu – sequence: 6 givenname: Martin D orcidid: 0000-0001-7963-7140 surname: Burke fullname: Burke, Martin D email: mdburke@illinois.edu organization: Carle Illinois College of Medicine |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/30388000$$D View this record in MEDLINE/PubMed |
| BookMark | eNqNkstv1DAQxi1URLeFG2fkIxJN8SNO7AsSrLaw0iJ6gLPl-EG9ytqLnUD3v8dh0woQCE5-zO_7PJ6ZM3ASYrAAPMXoEiOCX26Vzpe8Q42g9AFYYEZQxTBpTsACIUSqljf0FJzlvC3HmnD8CJxSRDkvxwXorm3yxgcf4DpDFeDqVtv94GNQfX-A13GwYSj3Br63uy6pYKvVrrPGWAPX4cZ3fogJRgff-F4dbIIbv_cGFtd4642ajB6Dh0712T6Z13Pw6Wr1cfmu2nx4u16-3lSKMTZUokaIC6Y57rCjtaOClE9x19hWU2fazrSuNlQIgbVqDK85a4QrGodITRtLz8Gro-9-7HbW6JJ4Ur3cJ79T6SCj8vLXSPA38nP8KpuaEd6SYvB8Nkjxy2jzIHc-a9v35ddxzJIQ2jJGBGb_RjERjHLKJ_TZz2nd53PXgwK8OALfbBdd1t4Gbe-xqWkMY4SassO80Pz_6aUffrRgGccwFCk5SnWKOSfrpJ7jpRy-lxjJaaLkNFFynqgiuvhNdPfWX_C5MNPlNo6pzFH-M_odEmzYPg |
| CitedBy_id | crossref_primary_10_3390_jmse9121387 crossref_primary_10_1021_acs_jnatprod_2c00475 crossref_primary_10_1021_acscatal_0c00869 crossref_primary_10_1021_acs_orglett_0c02449 crossref_primary_10_1021_acs_orglett_1c03022 crossref_primary_10_1021_acs_orglett_9b01397 crossref_primary_10_1055_a_1751_1225 crossref_primary_10_1021_acs_orglett_2c01174 crossref_primary_10_1021_jacs_3c10132 crossref_primary_10_1021_acs_joc_0c02474 crossref_primary_10_3390_inorganics12040101 crossref_primary_10_1021_acs_chemrev_0c00986 crossref_primary_10_1007_s10811_024_03189_y crossref_primary_10_1021_acs_jpclett_1c01965 crossref_primary_10_1039_C8CC09044K crossref_primary_10_1002_chem_202000624 crossref_primary_10_1021_acs_joc_9b01768 crossref_primary_10_1016_j_algal_2024_103719 crossref_primary_10_1021_acs_orglett_3c00410 |
| Cites_doi | 10.1111/j.1529-8817.1993.tb00143.x 10.1055/s-0036-1588906 10.1042/bj3220425 10.1126/science.aah3862 10.1021/ja0716204 10.1016/0891-5849(95)00038-Y 10.1063/1.478702 10.1021/la1026202 10.1016/S0005-2736(96)00152-6 10.1016/j.procbio.2012.04.011 10.1021/acs.accounts.5b00128 10.1021/ja072349t 10.1126/science.aaa5414 10.1007/s00249-007-0146-2 10.1016/j.phytochem.2017.04.012 10.1002/adsc.201700733 10.1074/jbc.M608589200 10.1074/jbc.M707348200 10.1016/j.molstruc.2005.02.038 10.1016/j.freeradbiomed.2007.09.009 10.1016/S0005-2736(99)00194-7 10.1016/0076-6879(90)86135-I 10.1194/jlr.M500555-JLR200 10.1161/01.ATV.0000186181.19909.a6 10.1002/hlca.19860690104 10.1016/j.atherosclerosis.2004.06.007 10.1021/bi00619a024 10.1021/ol0478281 10.1021/ja901416p 10.3945/ajcn.115.115477 10.1021/acs.joc.6b01166 10.1021/ja034416z 10.1073/pnas.1117280109 10.1016/j.bbadis.2004.11.015 10.1007/s12035-015-9092-7 10.1016/j.freeradbiomed.2016.09.017 10.1016/j.abb.2004.03.007 10.1021/np800310b 10.1096/fasebj.9.15.8529834 10.1016/S0040-4039(00)01618-X 10.1016/S0009-2614(01)00791-6 10.1038/nchembio.2105 10.1016/j.hlc.2016.07.005 10.1161/CIRCRESAHA.111.256859 10.1016/0031-9422(80)85056-4 10.1002/anie.201203093 10.1063/1.475661 10.1016/0076-6879(92)13124-G 10.1006/bbrc.2001.5765 10.1021/acs.jpcb.7b04814 10.1021/jacs.6b03283 10.1016/S0040-4039(98)02274-6 10.1016/j.tet.2016.02.040 10.1016/0005-2736(78)90379-6 10.1007/s00216-015-9102-7 10.1124/jpet.105.087114 10.3389/fpls.2016.00531 10.1016/S0891-5849(98)00315-3 10.1021/ol403441c 10.1021/jacs.5b05765 10.1016/j.abb.2010.07.007 10.1021/ja017001r 10.1021/acs.orglett.5b03030 10.1021/acs.jmedchem.6b00544 10.1002/anie.201710482 10.1038/s41570-018-0115 10.1002/anie.201102688 10.1126/science.272.5269.1788 10.1074/jbc.M303857200 10.1590/1678-4685-gmb-2017-0034 10.1038/nchembio.2238 10.1002/14651858.CD007176.pub2 10.1016/j.bbagen.2011.04.016 10.1006/bbrc.2000.2142 10.1021/ol4008475 10.1016/j.atherosclerosis.2012.02.002 10.1002/anie.201504297 10.1016/0040-4020(72)80040-1 10.5114/aoms.2015.50960 10.1016/j.tetlet.2010.12.078 10.1016/S0140-6736(94)90566-5 10.1161/STROKEAHA.116.015609 10.1126/science.6710156 10.1016/S0009-3084(01)00136-0 10.1038/nchembio.1496 10.1093/carcin/15.1.15 10.1021/jacs.7b07444 10.1246/cl.2011.1434 10.1002/jssc.201600315 10.1016/j.rmed.2008.11.009 10.1248/cpb.c12-00382 10.1021/ja102721p 10.1016/S0968-0004(02)00003-8 10.1016/0005-2736(90)90133-9 10.1038/nrd1330 10.1016/j.tetlet.2005.03.099 10.1016/j.phytochem.2007.06.025 10.1021/jp500267y 10.1016/j.bbagen.2012.11.020 10.1016/j.jmr.2010.08.012 10.1016/S0005-2736(01)00326-1 10.1111/j.1527-3466.2005.tb00166.x 10.1016/0003-9861(92)90675-M 10.1103/PhysRev.99.559 10.1002/anie.200300628 10.1016/j.bbabio.2013.07.005 10.1016/j.bbamem.2006.09.010 10.1002/ptr.2867 10.1021/acs.orglett.5b00042 10.1021/ja00212a010 10.1038/s41598-017-10183-7 10.1038/nchem.1947 10.1016/j.freeradbiomed.2016.10.493 10.1111/resp.12097 10.1038/NCHEM.1947 10.1590/1678-4685-GMB-2017-0034 10.1016/j.phytochem.2017.04.912 10.1038/NCHEMBIO.2105 10.1038/NCHEMBIO.2238 |
| ContentType | Journal Article |
| DBID | AAYXX CITATION 17B 1KM BLEPL DTL EGQ HBEAY CGR CUY CVF ECM EIF NPM 7X8 7S9 L.6 5PM |
| DOI | 10.1021/jacs.8b06933 |
| DatabaseName | CrossRef Web of Knowledge Index Chemicus Web of Science Core Collection Science Citation Index Expanded Web of Science Primary (SCIE, SSCI & AHCI) Web of Science - Science Citation Index Expanded - 2018 Medline MEDLINE MEDLINE (Ovid) MEDLINE MEDLINE PubMed MEDLINE - Academic AGRICOLA AGRICOLA - Academic PubMed Central (Full Participant titles) |
| DatabaseTitle | CrossRef Web of Science MEDLINE Medline Complete MEDLINE with Full Text PubMed MEDLINE (Ovid) MEDLINE - Academic AGRICOLA AGRICOLA - Academic |
| DatabaseTitleList | MEDLINE Web of Science AGRICOLA MEDLINE - Academic |
| Database_xml | – sequence: 1 dbid: NPM name: PubMed url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed sourceTypes: Index Database – sequence: 2 dbid: 1KM name: Index Chemicus url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.IC sourceTypes: Enrichment Source Index Database |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Chemistry |
| EISSN | 1520-5126 |
| EndPage | 15240 |
| ExternalDocumentID | PMC6452872 30388000 000451100600018 10_1021_jacs_8b06933 c747945498 |
| Genre | Research Support, Non-U.S. Gov't Journal Article Research Support, N.I.H., Extramural |
| GrantInformation_xml | – fundername: National Institutes of Health; United States Department of Health & Human Services; National Institutes of Health (NIH) - USA grantid: GM118185; GM112845; GM123455 – fundername: American Asthma Foundation grantid: 14-0070 – fundername: NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES; United States Department of Health & Human Services; National Institutes of Health (NIH) - USA; NIH National Institute of General Medical Sciences (NIGMS) grantid: R01GM123455 – fundername: NIGMS NIH HHS grantid: R35 GM118185 – fundername: NIGMS NIH HHS grantid: R01 GM123455 – fundername: NIGMS NIH HHS grantid: R01 GM112845 |
| GroupedDBID | - .K2 02 53G 55A 5GY 5RE 5VS 7~N 85S AABXI ABFLS ABMVS ABPPZ ABPTK ABUCX ABUFD ACGFS ACJ ACNCT ACS AEESW AENEX AETEA AFEFF ALMA_UNASSIGNED_HOLDINGS AQSVZ BAANH BKOMP CS3 DU5 DZ EBS ED ED~ EJD ET F5P GNL IH9 JG JG~ K2 LG6 P2P ROL RXW TAE TN5 UHB UI2 UKR UPT VF5 VG9 VQA W1F WH7 X XFK YZZ ZHY --- -DZ -ET -~X .DC 4.4 AAHBH AAYXX ABBLG ABJNI ABLBI ABQRX ACBEA ACGFO ADHLV AGXLV AHDLI AHGAQ CITATION CUPRZ GGK IH2 XSW YQT ZCA ~02 17B 1KM AAYWT BLEPL DTL GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED GROUPED_WOS_WEB_OF_SCIENCE CGR CUY CVF ECM EIF NPM 7X8 7S9 L.6 5PM |
| ID | FETCH-LOGICAL-a555t-9400895c81b1f34f392b068f6e7c3fd7bd7f4d39991ca6d848569f008f02436e3 |
| IEDL.DBID | ACS |
| ISICitedReferencesCount | 22 |
| ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000451100600018 |
| ISSN | 0002-7863 1520-5126 |
| IngestDate | Thu Aug 21 18:21:45 EDT 2025 Mon Jul 21 11:45:05 EDT 2025 Fri Jul 11 15:55:34 EDT 2025 Thu Apr 03 06:56:29 EDT 2025 Wed Aug 06 04:57:42 EDT 2025 Fri Aug 29 16:14:01 EDT 2025 Thu Apr 24 23:05:37 EDT 2025 Tue Jul 01 03:21:37 EDT 2025 Thu Aug 27 13:42:20 EDT 2020 |
| IsDoiOpenAccess | false |
| IsOpenAccess | true |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 45 |
| Keywords | BETA-CAROTENE OXIDATIVE STRESS ROTATING SOLIDS LIQUID-CHROMATOGRAPHY BUILDING-BLOCKS NUCLEAR-MAGNETIC-RESONANCE PHOSPHOLIPID-BILAYER MONOCYTE ADHESION ALGA CHLAMYDOMONAS-NIVALIS IMMERSION DEPTH |
| Language | English |
| LinkModel | DirectLink |
| LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
| MergedId | FETCHMERGED-LOGICAL-a555t-9400895c81b1f34f392b068f6e7c3fd7bd7f4d39991ca6d848569f008f02436e3 |
| Notes | NIH RePORTER ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 H.M.S.H. and A.G.H. contributed equally to this work. |
| ORCID | 0000-0002-9912-5596 0000-0001-7963-7140 |
| OpenAccessLink | https://www.ncbi.nlm.nih.gov/pmc/articles/6452872 |
| PMID | 30388000 |
| PQID | 2129538385 |
| PQPubID | 23479 |
| PageCount | 14 |
| ParticipantIDs | pubmedcentral_primary_oai_pubmedcentral_nih_gov_6452872 crossref_primary_10_1021_jacs_8b06933 proquest_miscellaneous_2237552915 proquest_miscellaneous_2129538385 webofscience_primary_000451100600018 webofscience_primary_000451100600018CitationCount crossref_citationtrail_10_1021_jacs_8b06933 pubmed_primary_30388000 acs_journals_10_1021_jacs_8b06933 |
| ProviderPackageCode | JG~ 55A AABXI GNL VF5 7~N ACJ VG9 W1F ACS AEESW AFEFF .K2 ABMVS ABUCX IH9 BAANH AQSVZ ED~ UI2 CITATION AAYXX |
| PublicationCentury | 2000 |
| PublicationDate | 2018-11-14 |
| PublicationDateYYYYMMDD | 2018-11-14 |
| PublicationDate_xml | – month: 11 year: 2018 text: 2018-11-14 day: 14 |
| PublicationDecade | 2010 |
| PublicationPlace | WASHINGTON |
| PublicationPlace_xml | – name: WASHINGTON – name: United States |
| PublicationTitle | Journal of the American Chemical Society |
| PublicationTitleAbbrev | J AM CHEM SOC |
| PublicationTitleAlternate | J. Am. Chem. Soc |
| PublicationYear | 2018 |
| Publisher | American Chemical Society Amer Chemical Soc |
| Publisher_xml | – name: American Chemical Society – name: Amer Chemical Soc |
| References | ref45/cit45 ref99/cit99 ref3/cit3 ref81/cit81 ref16/cit16 ref52/cit52 ref114/cit114 ref115/cit115 ref116/cit116 ref110/cit110 ref111/cit111 ref2/cit2 ref112/cit112 ref77/cit77 ref113/cit113 ref71/cit71 ref20/cit20 ref48/cit48 ref74/cit74 ref10/cit10 ref35/cit35 ref89/cit89 ref19/cit19 ref93/cit93 ref42/cit42 ref96/cit96 ref107/cit107 ref109/cit109 ref13/cit13 ref105/cit105 ref61/cit61 ref67/cit67 ref38/cit38 ref90/cit90 ref64/cit64 ref54/cit54 ref6/cit6 ref18/cit18 ref65/cit65 ref97/cit97 ref101/cit101 ref11/cit11 ref102/cit102 ref29/cit29 ref76/cit76 ref86/cit86 ref32/cit32 ref39/cit39 ref5/cit5 ref43/cit43 ref80/cit80 ref28/cit28 ref91/cit91 ref55/cit55 ref12/cit12 ref66/cit66 ref22/cit22 ref33/cit33 ref87/cit87 ref106/cit106 ref44/cit44 ref70/cit70 ref98/cit98 ref9/cit9 ref27/cit27 ref63/cit63 ref56/cit56 ref92/cit92 ref8/cit8 ref31/cit31 ref59/cit59 ref85/cit85 ref34/cit34 ref37/cit37 ref60/cit60 ref88/cit88 ref17/cit17 ref82/cit82 ref53/cit53 ref21/cit21 ref46/cit46 ref49/cit49 Tanaka T. (ref23/cit23) 1995; 55 ref75/cit75 ref24/cit24 ref50/cit50 ref78/cit78 ref36/cit36 ref83/cit83 ref79/cit79 ref100/cit100 ref25/cit25 ref103/cit103 ref72/cit72 ref14/cit14 ref57/cit57 ref51/cit51 ref40/cit40 ref68/cit68 ref94/cit94 ref26/cit26 ref73/cit73 ref69/cit69 ref15/cit15 ref62/cit62 ref41/cit41 ref58/cit58 ref95/cit95 ref108/cit108 ref104/cit104 ref4/cit4 ref30/cit30 ref47/cit47 ref84/cit84 ref1/cit1 ref7/cit7 Re, R (WOS:000080705000021) 1999; 26 Yu, H (WOS:000228768300032) 2005; 46 Lauver, DA (WOS:000230550300024) 2005; 314 Voynow, JA (WOS:000296946000011) 2011; 1810 Cioffi, AG (WOS:000359962000018) 2015; 137 Kagan, VE (WOS:000393267200017) 2017; 13 Samitas, K (WOS:000265462600013) 2009; 103 Bin Go, E (WOS:000377725700023) 2016; 72 Hoffmann-Roder, A (WOS:000220120000003) 2004; 43 Trost, BM (WOS:000077712400009) 1999; 40 Cox, PA (WOS:000380730000034) 2016; 138 PEDERSEN, TR (WOS:A1994PR78600007) 1994; 344 Grillo, AS (WOS:000400975200049) 2017; 356 Vaz, B (WOS:000226950100006) 2005; 7 Reilly, KB (WOS:000189265900110) 2004; 279 HAUGAN, JA (WOS:A1992KL57600020) 1992; 213 Woerly, EM (WOS:000336897800009) 2014; 6 Gabrielska, J (WOS:A1996VX69200006) 1996; 1285 SOLOMON, I (WOS:A1955WB70300041) 1955; 99 Plochberger, B (WOS:000283837800093) 2010; 26 Nishioka, Y (WOS:000395410700006) 2017; 28 Castelli, R (WOS:000318588900051) 2013; 15 SWIFT, IE (WOS:A1982PX09200012) 1982; 21 Cornil, J (WOS:000349942600047) 2015; 17 Hohwy, M (WOS:000074379300004) 1998; 108 Shan, YB (WOS:000389044300011) 2016; 39 Lockwood, SF (WOS:000233105700001) 2005; 23 YAMAMOTO, HY (WOS:A1978EQ53700012) 1978; 507 Ursoniu, S (WOS:000353936900001) 2015; 11 Nadaud, PS (WOS:000247240500013) 2007; 129 Ryu, SK (WOS:000302960600015) 2012; 222 El-Agamey, A (WOS:000223663400007) 2004; 430 Jones, CM (WOS:000183359300031) 2003; 125 Cox, PA (WOS:000411659000042) 2017; 139 BIDIGARE, RR (WOS:A1993LU69500005) 1993; 29 Hofmann, E (WOS:A1996UT11000043) 1996; 272 GRUSZECKI, WI (WOS:A1990DC21500013) 1990; 1023 TANAKA, T (WOS:A1994MR10300004) 1994; 15 Fujita, K (WOS:000306314300041) 2012; 51 Goto, S (WOS:000169415700011) 2001; 1512 DRAPER, HH (WOS:A1990MC42000043) 1990; 186 Song, YD (WOS:000397255800011) 2017; 26 Nishigaki, I (WOS:000273691400011) 2010; 24 Patel, RP (WOS:A1997WM10700010) 1997; 322 Murray, IVJ (WOS:000245421700005) 2007; 282 Woerly, EM (WOS:000277999700033) 2010; 132 Knapp, DM (WOS:000266484700035) 2009; 131 Coombes, JS (WOS:000367869500033) 2016; 103 Morita, M (WOS:000368016700026) 2016; 408 (000451100600018.1) 2000 Grudzinski, W (WOS:000408535300003) 2017; 7 Liang, SQ (WOS:000320784500008) 2013; 18 Schnitzer, E (WOS:000245826200023) 2007; 36 BLOOM, M (WOS:A1978GB77300024) 1978; 17 Rengel, D (WOS:000084889300020) 2000; 1463 Li, JQ (WOS:000359892700015) 2015; 48 Guo, Z (WOS:000252829500012) 2008; 44 Galli, F (WOS:000392361200002) 2017; 102 Pinto, E (WOS:000085427400046) 2000; 268 Delaunay, T (WOS:000299364600041) 2011; 40 Muir, CW (WOS:000366878300024) 2015; 17 Kopsel, C (WOS:000231403400016) 2005; 750 TANAKA, T (WOS:A1995RV09900023) 1995; 55 Brigelius-Flohe, R (WOS:000317797600011) 2013; 1830 Davoren, JE (WOS:000379989800025) 2016; 59 Shah, MMR (WOS:000374931000001) 2016; 7 Anderson, TM (WOS:000334672700015) 2014; 10 Huber, J (WOS:000237936000019) 2006; 47 Lee, S (WOS:000308527000017) 2012; 111 PALOZZA, P (WOS:A1992JH36600015) 1992; 297 Chu, SD (WOS:000283631400011) 2010; 207 Weber, A (WOS:000330098400062) 2014; 16 BURTON, GW (WOS:A1984SP77000007) 1984; 224 Wood, ZA (WOS:000180486600007) 2003; 28 EASTMOND, R (WOS:A1972N495800013) 1972; 28 PARASASSI, T (WOS:A1995RN64800014) 1995; 19 Fujii, S (WOS:000294175700025) 2011; 50 Zhu, YH (WOS:000283673300013) 2010; 504 Awasthi, YC (WOS:000406049900020) 2017; 111 Wang, M (WOS:000370187100045) 2016; 53 Trobe, M (WOS:000429536600011) 2018; 57 Bolick, DT (WOS:000232930900013) 2005; 25 Huster, D (WOS:000173628900036) 2002; 124 Barros, MP (WOS:000171813400034) 2001; 288 Mohamed, YMA (WOS:000287778300002) 2011; 52 Takegoshi, K (WOS:000170860900026) 2001; 344 Gruszecki, WI (WOS:000230060600004) 2005; 1740 Maltsev, S (WOS:000335113600012) 2014; 118 Rezanka, T (WOS:000253267300023) 2008; 69 FORBES, J (WOS:A1988M188300010) 1988; 110 Gillis, EP (WOS:000246686700027) 2007; 129 Lu, N (WOS:000309333600021) 2012; 47 Grubisa, I (WOS:000430181600005) 2018; 41 Graham, JE (WOS:000259574900030) 2008; 71 Ishigaki, M (WOS:000409394900004) 2017; 121 Igarashi, Y (WOS:000307040600023) 2012; 60 Hohwy, M (WOS:000079739600039) 1999; 110 MILON, A (WOS:A1986AZF3200003) 1986; 69 Yamada, K (WOS:000380640100007) 2016; 12 Shibata, A (WOS:000172436300002) 2001; 113 Brun, E (WOS:000383639500011) 2016; 81 Britton, G (WOS:A1995TM76100008) 1995; 9 David-Quillot, F (WOS:000165960100012) 2000; 41 Zille, M (WOS:000398207000046) 2017; 48 Rezanka, T (WOS:000401889000011) 2017; 139 Barnham, KJ (WOS:000189362700011) 2004; 3 Lehmann, JW (WOS:000425906900005) 2018; 2 McNulty, HP (WOS:000243733600019) 2007; 1768 Seath, CP (WOS:000360215100041) 2015; 54 Lee, CY (WOS:000416935100017) 2017; 359 Bjelakovic, G (WOS:000301505600064) 2012 Li, JQ (WOS:000350824300030) 2015; 347 Gray, KC (WOS:000300489200022) 2012; 109 Wang, XS (WOS:000225234800008) 2004; 177 Di Valentin, M (WOS:000328724800008) 2014; 1837 Greenberg, ME (WOS:000252501000065) 2008; 283 |
| References_xml | – ident: ref38/cit38 doi: 10.1111/j.1529-8817.1993.tb00143.x – ident: ref61/cit61 doi: 10.1055/s-0036-1588906 – ident: ref73/cit73 doi: 10.1042/bj3220425 – ident: ref30/cit30 doi: 10.1126/science.aah3862 – ident: ref43/cit43 doi: 10.1021/ja0716204 – volume: 55 start-page: 4059 issue: 18 year: 1995 ident: ref23/cit23 publication-title: Cancer Res. – ident: ref81/cit81 doi: 10.1016/0891-5849(95)00038-Y – ident: ref102/cit102 doi: 10.1063/1.478702 – ident: ref80/cit80 doi: 10.1021/la1026202 – ident: ref79/cit79 doi: 10.1016/S0005-2736(96)00152-6 – ident: ref41/cit41 doi: 10.1016/j.procbio.2012.04.011 – ident: ref45/cit45 doi: 10.1021/acs.accounts.5b00128 – ident: ref93/cit93 doi: 10.1021/ja072349t – ident: ref44/cit44 doi: 10.1126/science.aaa5414 – ident: ref71/cit71 doi: 10.1007/s00249-007-0146-2 – ident: ref39/cit39 doi: 10.1016/j.phytochem.2017.04.012 – ident: ref48/cit48 doi: 10.1002/adsc.201700733 – ident: ref115/cit115 doi: 10.1074/jbc.M608589200 – ident: ref10/cit10 doi: 10.1074/jbc.M707348200 – ident: ref107/cit107 doi: 10.1016/j.molstruc.2005.02.038 – ident: ref8/cit8 doi: 10.1016/j.freeradbiomed.2007.09.009 – ident: ref26/cit26 doi: 10.1016/S0005-2736(99)00194-7 – ident: ref97/cit97 – ident: ref74/cit74 doi: 10.1016/0076-6879(90)86135-I – ident: ref75/cit75 doi: 10.1194/jlr.M500555-JLR200 – ident: ref78/cit78 doi: 10.1161/01.ATV.0000186181.19909.a6 – ident: ref89/cit89 doi: 10.1002/hlca.19860690104 – ident: ref9/cit9 doi: 10.1016/j.atherosclerosis.2004.06.007 – ident: ref82/cit82 doi: 10.1021/bi00619a024 – ident: ref98/cit98 doi: 10.1021/ol0478281 – ident: ref65/cit65 doi: 10.1021/ja901416p – ident: ref28/cit28 doi: 10.3945/ajcn.115.115477 – ident: ref59/cit59 doi: 10.1021/acs.joc.6b01166 – ident: ref84/cit84 doi: 10.1021/ja034416z – ident: ref64/cit64 doi: 10.1073/pnas.1117280109 – ident: ref88/cit88 doi: 10.1016/j.bbadis.2004.11.015 – ident: ref7/cit7 doi: 10.1007/s12035-015-9092-7 – ident: ref16/cit16 doi: 10.1016/j.freeradbiomed.2016.09.017 – ident: ref19/cit19 doi: 10.1016/j.abb.2004.03.007 – ident: ref35/cit35 doi: 10.1021/np800310b – ident: ref87/cit87 doi: 10.1096/fasebj.9.15.8529834 – ident: ref100/cit100 doi: 10.1016/S0040-4039(00)01618-X – ident: ref103/cit103 doi: 10.1016/S0009-2614(01)00791-6 – ident: ref76/cit76 doi: 10.1038/nchembio.2105 – ident: ref4/cit4 doi: 10.1016/j.hlc.2016.07.005 – ident: ref11/cit11 doi: 10.1161/CIRCRESAHA.111.256859 – ident: ref108/cit108 doi: 10.1016/0031-9422(80)85056-4 – ident: ref46/cit46 doi: 10.1002/anie.201203093 – ident: ref101/cit101 doi: 10.1063/1.475661 – ident: ref42/cit42 doi: 10.1016/0076-6879(92)13124-G – ident: ref72/cit72 doi: 10.1006/bbrc.2001.5765 – ident: ref105/cit105 doi: 10.1021/acs.jpcb.7b04814 – ident: ref67/cit67 doi: 10.1021/jacs.6b03283 – ident: ref70/cit70 doi: 10.1016/S0040-4039(98)02274-6 – ident: ref58/cit58 doi: 10.1016/j.tet.2016.02.040 – ident: ref106/cit106 doi: 10.1016/0005-2736(78)90379-6 – ident: ref110/cit110 doi: 10.1007/s00216-015-9102-7 – ident: ref22/cit22 doi: 10.1124/jpet.105.087114 – ident: ref25/cit25 doi: 10.3389/fpls.2016.00531 – ident: ref85/cit85 doi: 10.1016/S0891-5849(98)00315-3 – ident: ref52/cit52 doi: 10.1021/ol403441c – ident: ref31/cit31 doi: 10.1021/jacs.5b05765 – ident: ref36/cit36 doi: 10.1016/j.abb.2010.07.007 – ident: ref104/cit104 doi: 10.1021/ja017001r – ident: ref53/cit53 doi: 10.1021/acs.orglett.5b03030 – ident: ref49/cit49 doi: 10.1021/acs.jmedchem.6b00544 – ident: ref56/cit56 doi: 10.1002/anie.201710482 – ident: ref57/cit57 doi: 10.1038/s41570-018-0115 – ident: ref63/cit63 doi: 10.1002/anie.201102688 – ident: ref32/cit32 doi: 10.1126/science.272.5269.1788 – ident: ref77/cit77 doi: 10.1074/jbc.M303857200 – ident: ref5/cit5 doi: 10.1590/1678-4685-gmb-2017-0034 – ident: ref15/cit15 doi: 10.1038/nchembio.2238 – ident: ref12/cit12 doi: 10.1002/14651858.CD007176.pub2 – ident: ref112/cit112 doi: 10.1016/j.bbagen.2011.04.016 – ident: ref34/cit34 doi: 10.1006/bbrc.2000.2142 – ident: ref69/cit69 doi: 10.1021/ol4008475 – ident: ref21/cit21 doi: 10.1016/j.atherosclerosis.2012.02.002 – ident: ref55/cit55 doi: 10.1002/anie.201504297 – ident: ref99/cit99 doi: 10.1016/0040-4020(72)80040-1 – ident: ref29/cit29 doi: 10.5114/aoms.2015.50960 – ident: ref50/cit50 doi: 10.1016/j.tetlet.2010.12.078 – ident: ref116/cit116 doi: 10.1016/S0140-6736(94)90566-5 – ident: ref113/cit113 doi: 10.1161/STROKEAHA.116.015609 – ident: ref14/cit14 doi: 10.1126/science.6710156 – ident: ref90/cit90 doi: 10.1016/S0009-3084(01)00136-0 – ident: ref96/cit96 doi: 10.1038/nchembio.1496 – ident: ref24/cit24 doi: 10.1093/carcin/15.1.15 – ident: ref66/cit66 doi: 10.1021/jacs.7b07444 – ident: ref51/cit51 doi: 10.1246/cl.2011.1434 – ident: ref40/cit40 doi: 10.1002/jssc.201600315 – ident: ref111/cit111 doi: 10.1016/j.rmed.2008.11.009 – ident: ref54/cit54 doi: 10.1248/cpb.c12-00382 – ident: ref62/cit62 doi: 10.1021/ja102721p – ident: ref3/cit3 doi: 10.1016/S0968-0004(02)00003-8 – ident: ref91/cit91 doi: 10.1016/0005-2736(90)90133-9 – ident: ref114/cit114 doi: 10.1038/nrd1330 – ident: ref68/cit68 doi: 10.1016/j.tetlet.2005.03.099 – ident: ref37/cit37 doi: 10.1016/j.phytochem.2007.06.025 – ident: ref94/cit94 doi: 10.1021/jp500267y – ident: ref2/cit2 doi: 10.1016/j.bbagen.2012.11.020 – ident: ref95/cit95 doi: 10.1016/j.jmr.2010.08.012 – ident: ref17/cit17 doi: 10.1016/S0005-2736(01)00326-1 – ident: ref20/cit20 doi: 10.1111/j.1527-3466.2005.tb00166.x – ident: ref18/cit18 doi: 10.1016/0003-9861(92)90675-M – ident: ref92/cit92 doi: 10.1103/PhysRev.99.559 – ident: ref109/cit109 doi: 10.1002/anie.200300628 – ident: ref33/cit33 doi: 10.1016/j.bbabio.2013.07.005 – ident: ref13/cit13 doi: 10.1016/j.bbamem.2006.09.010 – ident: ref27/cit27 doi: 10.1002/ptr.2867 – ident: ref60/cit60 doi: 10.1021/acs.orglett.5b00042 – ident: ref83/cit83 doi: 10.1021/ja00212a010 – ident: ref86/cit86 doi: 10.1038/s41598-017-10183-7 – ident: ref47/cit47 doi: 10.1038/nchem.1947 – ident: ref1/cit1 doi: 10.1016/j.freeradbiomed.2016.10.493 – ident: ref6/cit6 doi: 10.1111/resp.12097 – volume: 3 start-page: 205 year: 2004 ident: WOS:000189362700011 article-title: Neurodegenerative diseases and oxidative stress publication-title: NATURE REVIEWS DRUG DISCOVERY doi: 10.1038/nrd1330 – volume: 26 start-page: 17322 year: 2010 ident: WOS:000283837800093 article-title: Cholesterol SlOWS down the Lateral Mobility of an Oxidized Phospholipid in a Supported Lipid Bilayer publication-title: LANGMUIR doi: 10.1021/la1026202 – volume: 322 start-page: 425 year: 1997 ident: WOS:A1997WM10700010 article-title: Reduction of Cu(II) by lipid hydroperoxides: Implications for the copper-dependent oxidation of low-density lipoprotein publication-title: BIOCHEMICAL JOURNAL – volume: 113 start-page: 11 year: 2001 ident: WOS:000172436300002 article-title: Molecular characteristics of astaxanthin and beta-carotene in the phospholipid monolayer and their distributions in the phospholipid bilayer publication-title: CHEMISTRY AND PHYSICS OF LIPIDS – volume: 51 start-page: 7271 year: 2012 ident: WOS:000306314300041 article-title: Concise Total Synthesis of (-)-Myxalamide A publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201203093 – volume: 314 start-page: 686 year: 2005 ident: WOS:000230550300024 article-title: Disodium disuccinate astaxanthin (Cardax) attenuates complement activation and reduces myocardial injury following ischemia/reperfusion publication-title: JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS doi: 10.1124/jpet.105.087114 – volume: 102 start-page: 16 year: 2017 ident: WOS:000392361200002 article-title: Vitamin E: Emerging aspects and new directions publication-title: FREE RADICAL BIOLOGY AND MEDICINE doi: 10.1016/j.freeradbiomed.2016.09.017 – volume: 268 start-page: 496 year: 2000 ident: WOS:000085427400046 article-title: Peridinin as the major biological carotenoid quencher of singlet oxygen in marine algae Gonyaulax polyedra publication-title: BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS – volume: 132 start-page: 6941 year: 2010 ident: WOS:000277999700033 article-title: Stereoretentive Suzuki-Miyaura Coupling of Haloallenes Enables Fully Stereocontrolled Access to (-)-Peridinin publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja102721p – volume: 279 start-page: 9440 year: 2004 ident: WOS:000189265900110 article-title: 12/15-lipoxygenase activity mediates inflammatory monocyte/endothelial interactions and atherosclerosis in vivo publication-title: JOURNAL OF BIOLOGICAL CHEMISTRY doi: 10.1074/jbc.M303857200 – volume: 125 start-page: 6946 year: 2003 ident: WOS:000183359300031 article-title: EPR spin-trapping evidence for the direct, one-electron reduction of tert-butylhydroperoxide to the tert-butoxyl radical by copper(II): Paradigm for a previously overlooked reaction in the initiation of lipid peroxidation publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja034416z – volume: 359 start-page: 3831 year: 2017 ident: WOS:000416935100017 article-title: Preparation of Building Blocks for Iterative Suzuki-Miyaura Reactions via Direct Bromination of Aryl Boronic Acids: One-Pot Total Syntheses of Dictyoterphenyls A and B publication-title: ADVANCED SYNTHESIS & CATALYSIS doi: 10.1002/adsc.201700733 – volume: 1023 start-page: 405 year: 1990 ident: WOS:A1990DC21500013 article-title: ORIENTATION OF XANTHOPHYLLS IN PHOSPHATIDYLCHOLINE MULTIBILAYERS publication-title: BIOCHIMICA ET BIOPHYSICA ACTA – volume: 6 start-page: 484 year: 2014 ident: WOS:000336897800009 article-title: Synthesis of most polyene natural product motifs using just 12 building blocks and one coupling reaction publication-title: NATURE CHEMISTRY doi: 10.1038/NCHEM.1947 – volume: 111 start-page: 778 year: 2012 ident: WOS:000308527000017 article-title: Role of Phospholipid Oxidation Products in Atherosclerosis publication-title: CIRCULATION RESEARCH doi: 10.1161/CIRCRESAHA.111.256859 – volume: 60 start-page: 1088 year: 2012 ident: WOS:000307040600023 article-title: Total Synthesis of Hydroxy-alpha- and Hydroxy-beta-sanshool Using Suzuki-Miyaura Coupling publication-title: CHEMICAL & PHARMACEUTICAL BULLETIN – volume: 55 start-page: 4059 year: 1995 ident: WOS:A1995RV09900023 article-title: CHEMOPREVENTION OF RAT ORAL CARCINOGENESIS BY NATURALLY-OCCURRING XANTHOPHYLLS, ASTAXANTHIN AND CANTHAXARATHIN publication-title: CANCER RESEARCH – volume: 1830 start-page: 3289 year: 2013 ident: WOS:000317797600011 article-title: Glutathione peroxidases publication-title: BIOCHIMICA ET BIOPHYSICA ACTA-GENERAL SUBJECTS doi: 10.1016/j.bbagen.2012.11.020 – volume: 139 start-page: 13156 year: 2017 ident: WOS:000411659000042 article-title: Base-Catalyzed Aryl-B(OH)(2) Protodeboronation Revisited: From Concerted Proton Transfer to Liberation of a Transient Aryl Anion publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.7b07444 – volume: 18 start-page: 774 year: 2013 ident: WOS:000320784500008 article-title: Significant association between asthma risk and the GSTM1 and GSTT1 deletion polymorphisms: An updated meta-analysis of case-control studies publication-title: RESPIROLOGY doi: 10.1111/resp.12097 – volume: 19 start-page: 511 year: 1995 ident: WOS:A1995RN64800014 article-title: CHOLESTEROL PROTECTS THE PHOSPHOLIPID-BILAYER FROM OXIDATIVE DAMAGE publication-title: FREE RADICAL BIOLOGY AND MEDICINE – volume: 186 start-page: 421 year: 1990 ident: WOS:A1990MC42000043 article-title: MALONDIALDEHYDE DETERMINATION AS INDEX OF LIPID-PEROXIDATION publication-title: METHODS IN ENZYMOLOGY – volume: 26 start-page: 362 year: 2017 ident: WOS:000397255800011 article-title: Glutathione S-Transferase T1 (GSTT1) Null Polymorphism, Smoking, and Their Interaction in Coronary Heart Disease: A Comprehensive Meta-Analysis publication-title: HEART LUNG AND CIRCULATION doi: 10.1016/j.hlc.2016.07.005 – volume: 207 start-page: 89 year: 2010 ident: WOS:000283631400011 article-title: Solid-state NMR paramagnetic relaxation enhancement immersion depth studies in phospholipid bilayers publication-title: JOURNAL OF MAGNETIC RESONANCE doi: 10.1016/j.jmr.2010.08.012 – volume: 2 start-page: ARTN 0115 year: 2018 ident: WOS:000425906900005 article-title: Towards the generalized iterative synthesis of small molecules publication-title: NATURE REVIEWS CHEMISTRY doi: 10.1038/s41570-018-0115 – volume: 99 start-page: 559 year: 1955 ident: WOS:A1955WB70300041 article-title: RELAXATION PROCESSES IN A SYSTEM OF 2 SPINS publication-title: PHYSICAL REVIEW – volume: 138 start-page: 9145 year: 2016 ident: WOS:000380730000034 article-title: Protodeboronation of Heteroaromatic, Vinyl, and Cyclopropyl Boronic Acids: pH-Rate Profiles, Autocatalysis, and Disproportionation publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.6b03283 – volume: 72 start-page: 3790 year: 2016 ident: WOS:000377725700023 article-title: Concise, diastereoconvergent synthesis of endiandric-type tetracycles by iterative cross coupling publication-title: TETRAHEDRON doi: 10.1016/j.tet.2016.02.040 – volume: 344 start-page: 631 year: 2001 ident: WOS:000170860900026 article-title: C-13-H-1 dipolar-assisted rotational resonance in magic-angle spinning NMR publication-title: CHEMICAL PHYSICS LETTERS – volume: 17 start-page: 6030 year: 2015 ident: WOS:000366878300024 article-title: One-Pot Homologation of Boronic Acids: A Platform for Diversity-Oriented Synthesis publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.5b03030 – volume: 103 start-page: 283 year: 2016 ident: WOS:000367869500033 article-title: Astaxanthin has no effect on arterial stiffness, oxidative stress, or inflammation in renal transplant recipients: a randomized controlled trial (the XANTHIN trial) publication-title: AMERICAN JOURNAL OF CLINICAL NUTRITION doi: 10.3945/ajcn.115.115477 – volume: 9 start-page: 1551 year: 1995 ident: WOS:A1995TM76100008 article-title: Structure and properties of carotenoids in relation to function publication-title: FASEB JOURNAL – volume: 69 start-page: 479 year: 2008 ident: WOS:000253267300023 article-title: Identification of astaxanthin diglucoside diesters from snow alga Chlamydomonas nivalis by liquid chromatography-atmospheric pressure chemical ionization mass spectrometry publication-title: PHYTOCHEMISTRY doi: 10.1016/j.phytochem.2007.06.025 – volume: 57 start-page: 4192 year: 2018 ident: WOS:000429536600011 article-title: The Molecular Industrial Revolution: Automated Synthesis of Small Molecules publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201710482 – volume: 25 start-page: 2301 year: 2005 ident: WOS:000232930900013 article-title: 12/15-lipoxygenase regulates intercellular adhesion molecule-1 expression and monocyte adhesion to endothelium through activation of RhoA and nuclear factor-kappa B publication-title: ARTERIOSCLEROSIS THROMBOSIS AND VASCULAR BIOLOGY doi: 10.1161/01.ATV.0000186181.19909.a6 – volume: 430 start-page: 37 year: 2004 ident: WOS:000223663400007 article-title: Carotenoid radical chemistry and antioxidant/pro-oxidant properties publication-title: ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS doi: 10.1016/j.abb.2004.03.007 – volume: 41 start-page: 35 year: 2018 ident: WOS:000430181600005 article-title: Combined GSTM1 and GSTT1 null genotypes are strong risk factors for atherogenesis in a Serbian population publication-title: GENETICS AND MOLECULAR BIOLOGY doi: 10.1590/1678-4685-GMB-2017-0034 – volume: 28 start-page: 32 year: 2003 ident: WOS:000180486600007 article-title: Structure, mechanism and regulation of peroxiredoxins publication-title: TRENDS IN BIOCHEMICAL SCIENCES – volume: 504 start-page: 86 year: 2010 ident: WOS:000283673300013 article-title: Roles of xanthophyll carotenoids in protection against photoinhibition and oxidative stress in the cyanobacterium Synechococcus sp strain PCC 7002 publication-title: ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS doi: 10.1016/j.abb.2010.07.007 – volume: 71 start-page: 1647 year: 2008 ident: WOS:000259574900030 article-title: Synechoxanthin, an aromatic C-40 xanthophyll that is a major carotenoid in the cyanobacterium Synechococcus sp PCC 7002 publication-title: JOURNAL OF NATURAL PRODUCTS doi: 10.1021/np800310b – volume: 81 start-page: 8206 year: 2016 ident: WOS:000383639500011 article-title: Synthesis of the Acyclic Carbon Skeleton of Filipin III publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/acs.joc.6b01166 – volume: 11 start-page: 253 year: 2015 ident: WOS:000353936900001 article-title: Lipid profile and glucose changes after supplementation with astaxanthin: a systematic review and meta-analysis of randomized controlled trials publication-title: ARCHIVES OF MEDICAL SCIENCE doi: 10.5114/aoms.2015.50960 – volume: 48 start-page: 1033 year: 2017 ident: WOS:000398207000046 article-title: Neuronal Death After Hemorrhagic Stroke In Vitro and In Vivo Shares Features of Ferroptosis and Necroptosis publication-title: STROKE doi: 10.1161/STROKEAHA.116.015609 – volume: 47 start-page: 1054 year: 2006 ident: WOS:000237936000019 article-title: Specific monocyte adhesion to endothelial cells induced by oxidized phospholipids involves activation of cPLA(2) and lipoxygenase publication-title: JOURNAL OF LIPID RESEARCH doi: 10.1194/jlr.M500555-JLR200 – volume: 110 start-page: 1059 year: 1988 ident: WOS:A1988M188300010 article-title: HIGH-FIELD, HIGH-RESOLUTION PROTON MAGIC-ANGLE SAMPLE-SPINNING NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPIC STUDIES OF GEL AND LIQUID-CRYSTALLINE LIPID BILAYERS AND THE EFFECTS OF CHOLESTEROL publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – start-page: ARTN CD007176 year: 2012 ident: WOS:000301505600064 article-title: Antioxidant supplements for prevention of mortality in healthy participants and patients with various diseases publication-title: COCHRANE DATABASE OF SYSTEMATIC REVIEWS doi: 10.1002/14651858.CD007176.pub2 – volume: 139 start-page: 88 year: 2017 ident: WOS:000401889000011 article-title: Lipidomic profile in three species of dinoflagellates (Amphidinium carterae, Cystodinium sp., and Peridinium aciculiferum) containing very long chain polyunsaturated fatty acids publication-title: PHYTOCHEMISTRY doi: 10.1016/j.phytochem.2017.04.912 – year: 2000 ident: 000451100600018.1 publication-title: Astaxanthin over-producing strains of Phaffia rhodozyma method for their cultivation and their use in animal feeds. U. S. Patent – volume: 15 start-page: 15 year: 1994 ident: WOS:A1994MR10300004 article-title: CHEMOPREVENTION OF MOUSE URINARY-BLADDER CARCINOGENESIS BY THE NATURALLY-OCCURRING CAROTENOID ASTAXANTHIN publication-title: CARCINOGENESIS – volume: 108 start-page: 2686 year: 1998 ident: WOS:000074379300004 article-title: Broadband dipolar recoupling in the nuclear magnetic resonance of rotating solids: A compensated C7 pulse sequence publication-title: JOURNAL OF CHEMICAL PHYSICS – volume: 1463 start-page: 179 year: 2000 ident: WOS:000084889300020 article-title: Exogenously incorporated ketocarotenoids in large unilamellar vesicles. Protective activity against peroxidation publication-title: BIOCHIMICA ET BIOPHYSICA ACTA-BIOMEMBRANES – volume: 52 start-page: 1057 year: 2011 ident: WOS:000287778300002 article-title: Synthesis of methyl (5Z,8Z,10E,12E,14Z)-eicosapentaenoate publication-title: TETRAHEDRON LETTERS doi: 10.1016/j.tetlet.2010.12.078 – volume: 12 start-page: 608 year: 2016 ident: WOS:000380640100007 article-title: Fluorescence probes to detect lipid-derived radicals publication-title: Nature Chemical Biology doi: 10.1038/NCHEMBIO.2105 – volume: 36 start-page: 499 year: 2007 ident: WOS:000245826200023 article-title: Peroxidation of liposomal lipids publication-title: EUROPEAN BIOPHYSICS JOURNAL WITH BIOPHYSICS LETTERS doi: 10.1007/s00249-007-0146-2 – volume: 16 start-page: 568 year: 2014 ident: WOS:000330098400062 article-title: Total Synthesis of the Antibiotic Elansolid B1 publication-title: ORGANIC LETTERS doi: 10.1021/ol403441c – volume: 15 start-page: 2270 year: 2013 ident: WOS:000318588900051 article-title: 2,2-Dimethyl-4-(4-methoxy-phenoxy) butanoate and 2,2-Dimethyl-4-azido Butanoate: Two New Pivaloate-ester-like Protecting Groups publication-title: ORGANIC LETTERS doi: 10.1021/ol4008475 – volume: 59 start-page: 6313 year: 2016 ident: WOS:000379989800025 article-title: Discovery of the Potent and Selective M1 PAM-Agonist N-[(3R,4S)-3-Hydroxytetrahydro-2H-pyran-4-yl]-5-methyl-4-[4-(1,3-thiazol-4-yl)benzyl]pyridine-2-carboxamide (PF-06767832): Evaluation of Efficacy and Cholinergic Side Effects publication-title: JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1021/acs.jmedchem.6b00544 – volume: 29 start-page: 427 year: 1993 ident: WOS:A1993LU69500005 article-title: EVIDENCE FOR A PHOTOPROTECTIVE FUNCTION FOR SECONDARY CAROTENOIDS OF SNOW ALGAE publication-title: JOURNAL OF PHYCOLOGY – volume: 408 start-page: 265 year: 2016 ident: WOS:000368016700026 article-title: Rapid assessment of singlet oxygen-induced plasma lipid oxidation and its inhibition by antioxidants with diphenyl-1-pyrenylphosphine (DPPP) publication-title: ANALYTICAL AND BIOANALYTICAL CHEMISTRY doi: 10.1007/s00216-015-9102-7 – volume: 507 start-page: 119 year: 1978 ident: WOS:A1978EQ53700012 article-title: CAROTENOID ORGANIZATION IN MEMBRANES - THERMAL TRANSITION AND SPECTRAL PROPERTIES OF CAROTENOID-CONTAINING LIPOSOMES publication-title: BIOCHIMICA ET BIOPHYSICA ACTA – volume: 41 start-page: 9981 year: 2000 ident: WOS:000165960100012 article-title: Cross-coupling reaction: stereoselective synthesis of (E)-aryl or heteroarylvinylgermanes publication-title: TETRAHEDRON LETTERS – volume: 17 start-page: 5750 year: 1978 ident: WOS:A1978GB77300024 article-title: FATTY ACYL CHAIN ORDER IN LECITHIN MODEL MEMBRANES DETERMINED FROM PROTON MAGNETIC-RESONANCE publication-title: BIOCHEMISTRY – volume: 13 start-page: 81 year: 2017 ident: WOS:000393267200017 article-title: Oxidized arachidonic and adrenic PEs navigate cells to ferroptosis publication-title: NATURE CHEMICAL BIOLOGY doi: 10.1038/NCHEMBIO.2238 – volume: 356 start-page: 608 year: 2017 ident: WOS:000400975200049 article-title: Restored iron transport by a small molecule promotes absorption and hemoglobinization in animals publication-title: SCIENCE doi: 10.1126/science.aah3862 – volume: 1285 start-page: 167 year: 1996 ident: WOS:A1996VX69200006 article-title: Zeaxanthin (dihydroxy-beta-carotene but not beta-carotene rigidifies lipid membranes: A H-1-NMR study of carotenoid-egg phosphatidylcholine liposomes publication-title: BIOCHIMICA ET BIOPHYSICA ACTA-BIOMEMBRANES – volume: 124 start-page: 874 year: 2002 ident: WOS:000173628900036 article-title: Membrane protein topology probed by H-1 spin diffusion from lipids using solid-state NMR spectroscopy publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja017001r – volume: 177 start-page: 61 year: 2004 ident: WOS:000225234800008 article-title: Peroxiredoxin 6 deficiency and atherosclerosis susceptibility in mice: significance of genetic background for assessing atherosclerosis publication-title: ATHEROSCLEROSIS doi: 10.1016/j.atherosclerosis.2004.06.007 – volume: 69 start-page: 12 year: 1986 ident: WOS:A1986AZF3200003 article-title: ORGANIZATION OF CAROTENOID-PHOSPHOLIPID BILAYER SYSTEMS - INCORPORATION OF ZEAXANTHIN, ASTAXANTHIN, AND THEIR C-50 HOMOLOGS INTO DIMYRISTOYLPHOSPHATIDYLCHOLINE VESICLES publication-title: HELVETICA CHIMICA ACTA – volume: 40 start-page: 219 year: 1999 ident: WOS:000077712400009 article-title: Pd catalyzed kinetic resolution of conduritol B. Asymmetric synthesis of (+)-cyclophellitol publication-title: TETRAHEDRON LETTERS – volume: 111 start-page: 235 year: 2017 ident: WOS:000406049900020 article-title: Regulatory roles of glutathione-S-transferases and 4-hydroxynonenal in stress-mediated signaling and toxicity publication-title: FREE RADICAL BIOLOGY AND MEDICINE doi: 10.1016/j.freeradbiomed.2016.10.493 – volume: 54 start-page: 9976 year: 2015 ident: WOS:000360215100041 article-title: Tandem Chemoselective Suzuki-Miyaura Cross-Coupling Enabled by Nucleophile Speciation Control publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201504297 – volume: 17 start-page: 948 year: 2015 ident: WOS:000349942600047 article-title: Heck Coupling Using a Vinyliodo-MIDA Boronate: An Efficient and Modular Access to Polyene Frameworks publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.5b00042 – volume: 1740 start-page: 108 year: 2005 ident: WOS:000230060600004 article-title: Carotenoids as modulators of lipid membrane physical properties publication-title: BIOCHIMICA ET BIOPHYSICA ACTA-MOLECULAR BASIS OF DISEASE doi: 10.1016/j.bbadis.2004.11.015 – volume: 53 start-page: 1355 year: 2016 ident: WOS:000370187100045 article-title: GSTM1 Null Genotype and GSTP1 Ile105Val Polymorphism Are Associated with Alzheimer's Disease: a Meta-Analysis publication-title: MOLECULAR NEUROBIOLOGY doi: 10.1007/s12035-015-9092-7 – volume: 50 start-page: 7862 year: 2011 ident: WOS:000294175700025 article-title: Total Synthesis of Synechoxanthin through Iterative Cross-Coupling publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201102688 – volume: 40 start-page: 1434 year: 2011 ident: WOS:000299364600041 article-title: Sequential Suzuki-Miyaura Cross-coupling Reactions of 4-Halopyrazolyl MIDA 3-Boronates: A Modular Synthetic Entry to 3,4-Bis(hetero)aromatic Pyrazoles publication-title: CHEMISTRY LETTERS doi: 10.1246/cl.2011.1434 – volume: 129 start-page: 6716 year: 2007 ident: WOS:000246686700027 article-title: A simple and modular strategy for small molecule synthesis: Iterative Suzuki-Miyaura coupling of B-protected haloboronic acid building blocks publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja0716204 – volume: 43 start-page: 1196 year: 2004 ident: WOS:000220120000003 article-title: Synthesis and properties of allenic natural products and pharmaceuticals publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200300628 – volume: 118 start-page: 4370 year: 2014 ident: WOS:000335113600012 article-title: Solid-State NMR P-31 Paramagnetic Relaxation Enhancement Membrane Protein Immersion Depth Measurements publication-title: JOURNAL OF PHYSICAL CHEMISTRY B doi: 10.1021/jp500267y – volume: 129 start-page: 7502 year: 2007 ident: WOS:000247240500013 article-title: Long-range structural restraints in spin-labeled proteins probed by solid-state nuclear magnetic resonance spectroscopy publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja072349t – volume: 21 start-page: 2859 year: 1982 ident: WOS:A1982PX09200012 article-title: FORMATION OF NEOXANTHIN, DIADINOXANTHIN AND PERIDININ FROM [C-14]-LABELED ZEAXANTHIN BY A CELL-FREE SYSTEM FROM AMPHIDINIUM-CARTERAE publication-title: PHYTOCHEMISTRY – volume: 103 start-page: 750 year: 2009 ident: WOS:000265462600013 article-title: Exhaled cysteinyl-leukotrienes and 8-isoprostane in patients with asthma and their relation to clinical severity publication-title: RESPIRATORY MEDICINE doi: 10.1016/j.rmed.2008.11.009 – volume: 23 start-page: 199 year: 2005 ident: WOS:000233105700001 article-title: Disodium disuccinate astaxanthin (Cardax (TM)): Antioxidant and antinflammatory cardioprotection publication-title: CARDIOVASCULAR DRUG REVIEWS – volume: 24 start-page: 54 year: 2010 ident: WOS:000273691400011 article-title: Cytoprotective Role of Astaxanthin against Glycated Protein/Iron Chelate-induced Toxicity in Human Umbilical Vein Endothelial Cells publication-title: PHYTOTHERAPY RESEARCH doi: 10.1002/ptr.2867 – volume: 288 start-page: 225 year: 2001 ident: WOS:000171813400034 article-title: Astaxanthin and peridinin inhibit oxidative damage in Fe2+-loaded liposomes: Scavenging oxyradicals or changing membrane permeability? publication-title: BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS – volume: 1768 start-page: 167 year: 2007 ident: WOS:000243733600019 article-title: Differential effects of carotenoids on lipid peroxidation due to membrane interactions: X-ray diffraction analysis publication-title: BIOCHIMICA ET BIOPHYSICA ACTA-BIOMEMBRANES doi: 10.1016/j.bbamem.2006.09.010 – volume: 48 start-page: 2297 year: 2015 ident: WOS:000359892700015 article-title: From Synthesis to Function via Iterative Assembly of N-Methyliminodiacetic Acid Boronate Building Blocks publication-title: ACCOUNTS OF CHEMICAL RESEARCH doi: 10.1021/acs.accounts.5b00128 – volume: 110 start-page: 7983 year: 1999 ident: WOS:000079739600039 article-title: Fivefold symmetric homonuclear dipolar recoupling in rotating solids: Application to double quantum spectroscopy publication-title: JOURNAL OF CHEMICAL PHYSICS – volume: 26 start-page: 1231 year: 1999 ident: WOS:000080705000021 article-title: Antioxidant activity applying an improved ABTS radical cation decolorization assay publication-title: FREE RADICAL BIOLOGY AND MEDICINE – volume: 39 start-page: 3745 year: 2016 ident: WOS:000389044300011 article-title: Lipid profiling of cyanobacteria Synechococcus sp PCC 7002 using two-dimensional liquid chromatography with quadrupole time-of-flight mass spectrometry publication-title: JOURNAL OF SEPARATION SCIENCE doi: 10.1002/jssc.201600315 – volume: 109 start-page: 2234 year: 2012 ident: WOS:000300489200022 article-title: Amphotericin primarily kills yeast by simply binding ergosterol publication-title: PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA doi: 10.1073/pnas.1117280109 – volume: 10 start-page: 400 year: 2014 ident: WOS:000334672700015 article-title: Amphotericin forms an extramembranous and fungicidal sterol sponge publication-title: NATURE CHEMICAL BIOLOGY doi: 10.1038/nchembio.1496 – volume: 46 start-page: 3417 year: 2005 ident: WOS:000228768300032 article-title: 4-Acetoxy-2,2-dimethylbutanoate: a useful carbohydrate protecting group for the selective formation of beta-(1 -> 3)-D-glucans publication-title: TETRAHEDRON LETTERS doi: 10.1016/j.tetlet.2005.03.099 – volume: 121 start-page: 8046 year: 2017 ident: WOS:000409394900004 article-title: Unveiling the Aggregation of Lycopene in Vitro and in Vivo: UV-Vis, Resonance Raman, and Raman Imaging Studies publication-title: JOURNAL OF PHYSICAL CHEMISTRY B doi: 10.1021/acs.jpcb.7b04814 – volume: 28 start-page: 327 year: 2017 ident: WOS:000395410700006 article-title: Stereocontrolled Synthesis of Paracentrone publication-title: SYNLETT doi: 10.1055/s-0036-1588906 – volume: 1512 start-page: 251 year: 2001 ident: WOS:000169415700011 article-title: Efficient radical trapping at the surface and inside the phospholipid membrane is responsible for highly potent antiperoxidative activity of the carotenoid astaxanthin publication-title: BIOCHIMICA ET BIOPHYSICA ACTA-BIOMEMBRANES – volume: 283 start-page: 2385 year: 2008 ident: WOS:000252501000065 article-title: The lipid whisker model of the structure of oxidized cell membranes publication-title: JOURNAL OF BIOLOGICAL CHEMISTRY doi: 10.1074/jbc.M707348200 – volume: 272 start-page: 1788 year: 1996 ident: WOS:A1996UT11000043 article-title: Structural basis of light harvesting by carotenoids: Peridinin-chlorophyll-protein from Amphidinium carterae publication-title: SCIENCE – volume: 347 start-page: 1221 year: 2015 ident: WOS:000350824300030 article-title: Synthesis of many different types of organic small molecules using one automated process publication-title: SCIENCE doi: 10.1126/science.aaa5414 – volume: 297 start-page: 291 year: 1992 ident: WOS:A1992JH36600015 article-title: ASTAXANTHIN AND CANTHAXANTHIN ARE POTENT ANTIOXIDANTS IN A MEMBRANE MODEL publication-title: ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS – volume: 137 start-page: 10096 year: 2015 ident: WOS:000359962000018 article-title: Restored Physiology in Protein-Deficient Yeast by a Small Molecule Channel publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.5b05765 – volume: 344 start-page: 1383 year: 1994 ident: WOS:A1994PR78600007 article-title: RANDOMIZED TRIAL OF CHOLESTEROL-LOWERING IN 4444 PATIENTS WITH CORONARY-HEART-DISEASE - THE SCANDINAVIAN SIMVASTATIN SURVIVAL STUDY (4S) publication-title: LANCET – volume: 131 start-page: 6961 year: 2009 ident: WOS:000266484700035 article-title: A General Solution for Unstable Boronic Acids: Slow-Release Cross-Coupling from Air-Stable MIDA Boronates publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja901416p – volume: 224 start-page: 569 year: 1984 ident: WOS:A1984SP77000007 article-title: BETA-CAROTENE - AN UNUSUAL TYPE OF LIPID ANTIOXIDANT publication-title: SCIENCE – volume: 1810 start-page: 1091 year: 2011 ident: WOS:000296946000011 article-title: Isoprostanes and asthma publication-title: BIOCHIMICA ET BIOPHYSICA ACTA-GENERAL SUBJECTS doi: 10.1016/j.bbagen.2011.04.016 – volume: 222 start-page: 99 year: 2012 ident: WOS:000302960600015 article-title: Effect of an oral astaxanthin prodrug (CDX-085) on lipoprotein levels and progression of atherosclerosis in LDLR-/- and ApoE(-/-) mice publication-title: ATHEROSCLEROSIS doi: 10.1016/j.atherosclerosis.2012.02.002 – volume: 7 start-page: ARTN 9619 year: 2017 ident: WOS:000408535300003 article-title: Localization and Orientation of Xanthophylls in a Lipid Bilayer publication-title: SCIENTIFIC REPORTS doi: 10.1038/s41598-017-10183-7 – volume: 750 start-page: 109 year: 2005 ident: WOS:000231403400016 article-title: Structure investigations on assembled astaxanthin molecules publication-title: JOURNAL OF MOLECULAR STRUCTURE doi: 10.1016/j.molstruc.2005.02.038 – volume: 282 start-page: 9335 year: 2007 ident: WOS:000245421700005 article-title: Membrane-mediated amyloidogenesis and the promotion of oxidative lipid damage by amyloid beta proteins publication-title: JOURNAL OF BIOLOGICAL CHEMISTRY doi: 10.1074/jbc.M608589200 – volume: 7 start-page: 545 year: 2005 ident: WOS:000226950100006 article-title: The Stille reaction in the synthesis of carotenoid butenolides: Synthesis of 6 '-epi-peridinin publication-title: ORGANIC LETTERS doi: 10.1021/ol0478281 – volume: 44 start-page: 343 year: 2008 ident: WOS:000252829500012 article-title: Suppression of atherogenesis by overexpression of glutathione peroxidase-4 in apolipoprotein E-deficient mice publication-title: FREE RADICAL BIOLOGY AND MEDICINE doi: 10.1016/j.freeradbiomed.2007.09.009 – volume: 213 start-page: 231 year: 1992 ident: WOS:A1992KL57600020 article-title: ISOLATION OF FUCOXANTHIN AND PERIDININ publication-title: METHODS IN ENZYMOLOGY – volume: 47 start-page: 1163 year: 2012 ident: WOS:000309333600021 article-title: Regulation of lipid metabolism in the snow alga Chlamydomonas nivalis in response to NaCl stress: An integrated analysis by cytomic and lipidomic approaches publication-title: PROCESS BIOCHEMISTRY doi: 10.1016/j.procbio.2012.04.011 – volume: 28 start-page: 4591 year: 1972 ident: WOS:A1972N495800013 article-title: SILYLATION AS A PROTECTIVE METHOD IN CADIOT-CHODKIEWICZ COUPLINGS - SYNTHESIS OF ARYL-BUTADIYNES AND ARYL-HEXATRIYNES publication-title: TETRAHEDRON – volume: 7 start-page: ARTN 531 year: 2016 ident: WOS:000374931000001 article-title: Astaxanthin-Producing Green Microalga Haematococcus pluvialis: From Single Cellto High Value Commercia Products publication-title: FRONTIERS IN PLANT SCIENCE doi: 10.3389/fpls.2016.00531 – volume: 1837 start-page: 85 year: 2014 ident: WOS:000328724800008 article-title: Evidence for water-mediated triplet-triplet energy transfer in the photoprotective site of the peridinin-chlorophyll a-protein publication-title: BIOCHIMICA ET BIOPHYSICA ACTA-BIOENERGETICS doi: 10.1016/j.bbabio.2013.07.005 |
| SSID | ssj0004281 |
| Score | 2.3944013 |
| Snippet | Antilipoperoxidant protein dysfunction is associated with many human diseases, suggesting that bilayer lipid peroxidation may contribute broadly to... |
| Source | Web of Science |
| SourceID | pubmedcentral proquest pubmed webofscience crossref acs |
| SourceType | Open Access Repository Aggregation Database Index Database Enrichment Source Publisher |
| StartPage | 15227 |
| SubjectTerms | astaxanthin atherogenesis carbon Carotenoids - chemistry Carotenoids - pharmacology cell adhesion Chemistry Chemistry, Multidisciplinary clinical trials endothelial cells human diseases Human Umbilical Vein Endothelial Cells - drug effects Human Umbilical Vein Endothelial Cells - metabolism Humans hydrophobicity isotope labeling Lipid Bilayers - antagonists & inhibitors Lipid Bilayers - metabolism lipid peroxidation Lipid Peroxidation - drug effects microorganisms Molecular Structure nuclear magnetic resonance spectroscopy oxidative stress pathogenesis Physical Sciences Science & Technology stable isotopes therapeutics |
| Title | Peridinin Is an Exceptionally Potent and Membrane-Embedded Inhibitor of Bilayer Lipid Peroxidation |
| URI | http://dx.doi.org/10.1021/jacs.8b06933 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000451100600018 https://www.ncbi.nlm.nih.gov/pubmed/30388000 https://www.proquest.com/docview/2129538385 https://www.proquest.com/docview/2237552915 https://pubmed.ncbi.nlm.nih.gov/PMC6452872 |
| Volume | 140 |
| WOS | 000451100600018 |
| WOSCitedRecordID | wos000451100600018 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV1Zb9QwELagPMAL9xEuuVJ5Qlmtr9j7WFZbWqSiSlCpb5HjQ111m6AmKxV-PTM5tuyWQl-dsZNMxp5v4vE3hOx45gEUCJkGJG6V1sXUchbTyJWPMVrhHP4aOPya7R_LLyfq5CpBdnMHnyM_kKtHphhnEHrfJfd4ZjQGWbvTb1fnH7lhA8zVJhN9gvtmb3RArl53QNdQ5d-TIzccUut89h6Rz8MRni7n5Gy0bIqR-3Wd0fE_7_WYPOzxJ93tDOYJuRPKp-T-dCj79owUR2CTHstG0IOa2pLOLvvMF7tY_KRHFYDsBto9PQznEGqXIZ2dFwHWL08PytN5AUvEBa0i_TRfWMDzFKtjewqjVpfzroDTc3K8N_s-3U_7QgypVUo1KRZPNxPlAOKyKGQETAXPbWIWtBPR68LrKL1ArOls5o00KptE6BOR7zAL4gXZKqsyvCKUKatV4GOpA0aGEsS5g1ENwCJrnUjINugl7ydSnbd75BxiFGzttZWQj8MXzF3PZI4FNRY3SH9YSf_oGDxukNsejCEHleO-CaiwWtY5ePcJ-AVh1D9kuNBK8QkDmZedAa3uJlrGnfE4IXrNtFYCSPG9fqWcn7ZU37jtbDRPyM6fRrjq2NEDMSTVweqKCWG3EZv2OkPWg-b1LRT-hjwAnGjwCCaTb8lWc7EM7wCLNcX7diL-BtBWLkc |
| linkProvider | American Chemical Society |
| linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwzV1LT9tAEB5ReqCXvh_uc5HgVBnFu157c-iBpkFJIQipIHFz1_sQUYNdYUeF_pf-lf62zvpFk5aKC1Kvm_HEmZ3d-SY7-w3Ahg40ggIW-sYRt4ZSWV_SwPqWcm2tlUwp99fAZD8aHYUfj_nxCvxo78LgSxSoqagO8S_ZBRxNEA6KtBdhBt7UUO6ai2-YoRXvxh9wOjcp3RkeDkZ-00TAl5zz0neNv0WfK4RngWWhRTyASoSNTKyY1XGqYxtq5nCSkpEWoeBR3-Iz1nH1RYah3ltwG3EPdbnd9uDT5bVLKoIWXcciYk1d_fLburinisW49weY_XtN5lIcrGLezj342VmrKnX5sjUv0y31fYlI8r81532426Btsl0vjwewYrKHsDZom9w9gvQAV6B2TTLIuCAyI8Pzps5HzmYX5CDHlKLEcU0m5jTFuG784WlqcLfWZJydTFPcEM9Ibsn76Uxi9kJcL3BNUGt-Pq3bVT2Goxv5iU9gNcsz8wxIwGXMDe2FsXF5cIjiVKFWgSBQSsU8WMd5SJpto0iqigCKGZkbbWbHg7et4ySq4W137UNmV0hvdtJfa76SK-TWWx9M0OTulAhNmM-LBLFMH6MgE_wfMpTFnNN-gDJPa7_tvo1V_EK9ngfxgkd3Ao7QfPGTbHpSEZu7Q3YRUw82fvf97sGaDClwFEKul6QHwXXEBo3NHMdD-fwaBn8Da6PDyV6yN97ffQF3ECELd_k0CF_Cank2N68QhZbp62ovIPD5plfLL2Mejrs |
| linkToPdf | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwzV1Lb9NAEB6VIgEX3oXw3ErtCbmKd7325sChpIkaSqtIUKk3s96HGpE6Ve2Iln_DX-GXMeM4hgSKeqnE1R5PnNnZnW-8s98AbNjQIigQUeCIuDXSxgeahz7wXFrvvRbG0KeB_YN49zB6fySPVuD7_CwMvkSBmopqE59m9an1NcMAUQXhDZW1Y8zC6zrKPXfxFbO04u1gB4d0k_N-71N3N6gbCQRaSlkG1PxbdaRBiBZ6EXnEBKhE-dglRnibZDbxkRWElYyOrYqUjDsen_HE1xc7gXpvwE3aIaT8brv78dfRS67COcJOVCzq2vrlt6XYZ4rF2PcHoP17XeZSLKziXv8e_GgsVpW7fNmaltmW-bZEJvlfm_Q-3K1RN9ueTZMHsOLyh3C7O2929wiyIc5ES80y2KBgOme987reR4_HF2w4wdSixOuW7buTDOO7C3onmcNV27JBfjzKcGE8YxPP3o3GGrMYRj3BLUOtk_PRrG3VYzi8lr-4Bqv5JHdPgYVSJ9LxdpQ4yocjFOcGtSoEg1ob0YJ1HIe0Xj6KtKoM4JiZ0dV6dFrwZu48qan526mNyPgS6c1G-nTGW3KJ3PrcD1M0Oe0WoQkn0yJFTNPBaCiU_IcMF4mUvBOizJOZ7za_JiqeoXa7BcmCVzcCRGy-eCcfHVcE57TZrhLego3f_b95cEaKFBKVEPWUbEF4FbFubTPieiifXcHgr-HWcKeffhgc7D2HOwiUFZ1BDaMXsFqeTd1LBKNl9qpaDhh8vu7J8hN0SZE- |
| openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Peridinin+Is+an+Exceptionally+Potent+and+Membrane-Embedded+Inhibitor+of+Bilayer+Lipid+Peroxidation&rft.jtitle=Journal+of+the+American+Chemical+Society&rft.au=Haley%2C+Hannah+M+S&rft.au=Hill%2C+Adam+G&rft.au=Greenwood%2C+Alexander+I&rft.au=Woerly%2C+Eric+M&rft.date=2018-11-14&rft.issn=1520-5126&rft.eissn=1520-5126&rft.volume=140&rft.issue=45&rft.spage=15227&rft_id=info:doi/10.1021%2Fjacs.8b06933&rft.externalDBID=NO_FULL_TEXT |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0002-7863&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0002-7863&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0002-7863&client=summon |