Membrane-Targeting Neolignan-Antimicrobial Peptide Mimic Conjugates to Combat Methicillin-Resistant Staphylococcus aureus (MRSA) Infections
Infections caused by methicillin-resistant Staphylococcus aureus (MRSA) continue to endanger public health. Here, we report the synthesis of neolignan isomagnolone (I) and its isomer II, and the preparation of a series of novel neolignan-antimicrobial peptide (AMP) mimic conjugates. Notably, conjuga...
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| Published in | Journal of medicinal chemistry Vol. 65; no. 24; pp. 16879 - 16892 |
|---|---|
| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
22.12.2022
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0022-2623 1520-4804 1520-4804 |
| DOI | 10.1021/acs.jmedchem.2c01674 |
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| Abstract | Infections caused by methicillin-resistant Staphylococcus aureus (MRSA) continue to endanger public health. Here, we report the synthesis of neolignan isomagnolone (I) and its isomer II, and the preparation of a series of novel neolignan-antimicrobial peptide (AMP) mimic conjugates. Notably, conjugates III5 and III15 exhibit potent anti-MRSA activity in vitro and in vivo, comparable to that of vancomycin, a current effective treatment for MRSA. Moreover, III5 and III15 display not only fast-killing kinetics and low resistance frequency but also low toxicity as well as effects on bacterial biofilms. Mechanism studies reveal that III5 and III15 exhibit rapid bactericidal effects through binding to the phosphatidylglycerol (PG) and cardiolipin (CL) of the bacterial membrane, thereby disrupting the cell membranes and allowing increased reactive oxygen species (ROS) as well as protein and DNA leakage. The results indicate that these neolignan-AMP mimic conjugates could be promising antimicrobial candidates for combating MRSA infections. |
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| AbstractList | Infections caused by methicillin-resistant Staphylococcus aureus (MRSA) continue to endanger public health. Here, we report the synthesis of neolignan isomagnolone (I) and its isomer II, and the preparation of a series of novel neolignan-antimicrobial peptide (AMP) mimic conjugates. Notably, conjugates III5 and III15 exhibit potent anti-MRSA activity in vitro and in vivo, comparable to that of vancomycin, a current effective treatment for MRSA. Moreover, III5 and III15 display not only fast-killing kinetics and low resistance frequency but also low toxicity as well as effects on bacterial biofilms. Mechanism studies reveal that III5 and III15 exhibit rapid bactericidal effects through binding to the phosphatidylglycerol (PG) and cardiolipin (CL) of the bacterial membrane, thereby disrupting the cell membranes and allowing increased reactive oxygen species (ROS) as well as protein and DNA leakage. The results indicate that these neolignan-AMP mimic conjugates could be promising antimicrobial candidates for combating MRSA infections. Infections caused by methicillin-resistant Staphylococcus aureus (MRSA) continue to endanger public health. Here, we report the synthesis of neolignan isomagnolone (I) and its isomer II, and the preparation of a series of novel neolignan-antimicrobial peptide (AMP) mimic conjugates. Notably, conjugates III5 and III15 exhibit potent anti-MRSA activity in vitro and in vivo, comparable to that of vancomycin, a current effective treatment for MRSA. Moreover, III5 and III15 display not only fast-killing kinetics and low resistance frequency but also low toxicity as well as effects on bacterial biofilms. Mechanism studies reveal that III5 and III15 exhibit rapid bactericidal effects through binding to the phosphatidylglycerol (PG) and cardiolipin (CL) of the bacterial membrane, thereby disrupting the cell membranes and allowing increased reactive oxygen species (ROS) as well as protein and DNA leakage. The results indicate that these neolignan-AMP mimic conjugates could be promising antimicrobial candidates for combating MRSA infections.Infections caused by methicillin-resistant Staphylococcus aureus (MRSA) continue to endanger public health. Here, we report the synthesis of neolignan isomagnolone (I) and its isomer II, and the preparation of a series of novel neolignan-antimicrobial peptide (AMP) mimic conjugates. Notably, conjugates III5 and III15 exhibit potent anti-MRSA activity in vitro and in vivo, comparable to that of vancomycin, a current effective treatment for MRSA. Moreover, III5 and III15 display not only fast-killing kinetics and low resistance frequency but also low toxicity as well as effects on bacterial biofilms. Mechanism studies reveal that III5 and III15 exhibit rapid bactericidal effects through binding to the phosphatidylglycerol (PG) and cardiolipin (CL) of the bacterial membrane, thereby disrupting the cell membranes and allowing increased reactive oxygen species (ROS) as well as protein and DNA leakage. The results indicate that these neolignan-AMP mimic conjugates could be promising antimicrobial candidates for combating MRSA infections. Infections caused by methicillin-resistant (MRSA) continue to endanger public health. Here, we report the synthesis of neolignan isomagnolone ( ) and its isomer , and the preparation of a series of novel neolignan-antimicrobial peptide (AMP) mimic conjugates. Notably, conjugates and exhibit potent anti-MRSA activity and , comparable to that of vancomycin, a current effective treatment for MRSA. Moreover, and display not only fast-killing kinetics and low resistance frequency but also low toxicity as well as effects on bacterial biofilms. Mechanism studies reveal that and exhibit rapid bactericidal effects through binding to the phosphatidylglycerol (PG) and cardiolipin (CL) of the bacterial membrane, thereby disrupting the cell membranes and allowing increased reactive oxygen species (ROS) as well as protein and DNA leakage. The results indicate that these neolignan-AMP mimic conjugates could be promising antimicrobial candidates for combating MRSA infections. |
| Author | Yang, Ruige Li, Shihong Yao, Hong Hou, Enhua Cheng, Wanqing Liu, Jifeng Yan, Xiaoting Zhang, Tingting Guo, Yong |
| AuthorAffiliation | College of Veterinary Medicine School of Pharmaceutical Sciences |
| AuthorAffiliation_xml | – name: School of Pharmaceutical Sciences – name: College of Veterinary Medicine |
| Author_xml | – sequence: 1 givenname: Ruige orcidid: 0000-0003-2923-1155 surname: Yang fullname: Yang, Ruige organization: School of Pharmaceutical Sciences – sequence: 2 givenname: Enhua surname: Hou fullname: Hou, Enhua organization: School of Pharmaceutical Sciences – sequence: 3 givenname: Wanqing surname: Cheng fullname: Cheng, Wanqing organization: School of Pharmaceutical Sciences – sequence: 4 givenname: Xiaoting surname: Yan fullname: Yan, Xiaoting organization: School of Pharmaceutical Sciences – sequence: 5 givenname: Tingting surname: Zhang fullname: Zhang, Tingting organization: School of Pharmaceutical Sciences – sequence: 6 givenname: Shihong surname: Li fullname: Li, Shihong organization: College of Veterinary Medicine – sequence: 7 givenname: Hong surname: Yao fullname: Yao, Hong email: yaoh0913@henau.edu.cn organization: College of Veterinary Medicine – sequence: 8 givenname: Jifeng orcidid: 0000-0001-6475-0247 surname: Liu fullname: Liu, Jifeng email: Liujf2009y@126.com organization: School of Pharmaceutical Sciences – sequence: 9 givenname: Yong orcidid: 0000-0003-2227-8276 surname: Guo fullname: Guo, Yong email: guoyong_122@zzu.edu.cn organization: School of Pharmaceutical Sciences |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/36512751$$D View this record in MEDLINE/PubMed |
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| Snippet | Infections caused by methicillin-resistant Staphylococcus aureus (MRSA) continue to endanger public health. Here, we report the synthesis of neolignan... Infections caused by methicillin-resistant (MRSA) continue to endanger public health. Here, we report the synthesis of neolignan isomagnolone ( ) and its... |
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| SubjectTerms | Animals Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - pharmacology Anti-Bacterial Agents - therapeutic use Antimicrobial Peptides - chemical synthesis Antimicrobial Peptides - pharmacology Antimicrobial Peptides - therapeutic use Biofilms - drug effects Chemistry, Medicinal Life Sciences & Biomedicine Lignans - chemical synthesis Lignans - pharmacology Lignans - therapeutic use Methicillin-Resistant Staphylococcus aureus - drug effects Mice Microbial Sensitivity Tests Pharmacology & Pharmacy Science & Technology Staphylococcal Infections - drug therapy Vancomycin - pharmacology |
| Title | Membrane-Targeting Neolignan-Antimicrobial Peptide Mimic Conjugates to Combat Methicillin-Resistant Staphylococcus aureus (MRSA) Infections |
| URI | http://dx.doi.org/10.1021/acs.jmedchem.2c01674 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000897537500001 https://www.ncbi.nlm.nih.gov/pubmed/36512751 https://www.proquest.com/docview/2754503760 |
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