Structural study of electrolysis-induced degradation of the growth hormone releasing peptide His-D-Trp-Ala-Trp-D-Phe-Lys-NH2

Growth hormone releasing peptide (GHRP, sequence His-D-Trp-Ala-Trp-D-Phe-Lys-NH2) is a synthetic hexapeptide under consideration for transdermal iontophoretic drug delivery. Cyclic voltammetry, controlled-potential electrolysis, HPLC/UV analysis, LC/MS/MS analysis, and EPR spin-trapping studies indi...

Full description

Saved in:
Bibliographic Details
Published inAnalytical chemistry (Washington) Vol. 67; no. 22; pp. 4053 - 4056
Main Authors Cheng, Hung-Yuan, Davis, Louisa L, Huddleston, Michael J, Carr, Stephen A
Format Journal Article
LanguageEnglish
Published Washington, DC American Chemical Society 15.11.1995
Subjects
Online AccessGet full text

Cover

Loading…
Abstract Growth hormone releasing peptide (GHRP, sequence His-D-Trp-Ala-Trp-D-Phe-Lys-NH2) is a synthetic hexapeptide under consideration for transdermal iontophoretic drug delivery. Cyclic voltammetry, controlled-potential electrolysis, HPLC/UV analysis, LC/MS/MS analysis, and EPR spin-trapping studies indicate that the electrolysis-induced oxidative degradation of GHRP is likely to be mediated by electrogenerated oxygen radicals from the electrolysis of water. Within 2 h and up to 2.5 V versus an Ag/AgCl reference electrode, the peptide backbone remains largely intact. The chemical modifications are selectively on imidazole (histidine) and indole (tryptophan). Strategies for alleviating the electrolysis-induced degradation of GHRP are proposed.
AbstractList Cyclic voltammetry, controlled-potential electrolysis and high-performance liquid chromatography/ultraviolet analysis indicate that the electrolysis-induced oxidative degradation of growth hormone releasing peptide is likely to be mediated by electrogenerated oxygen radicals from the electrolysis of water.
Growth hormone releasing peptide (GHRP, sequence His-D-Trp-Ala-Trp-D-Phe-Lys-NH2) is a synthetic hexapeptide under consideration for transdermal iontophoretic drug delivery. Cyclic voltammetry, controlled-potential electrolysis, HPLC/UV analysis, LC/MS/MS analysis, and EPR spin-trapping studies indicate that the electrolysis-induced oxidative degradation of GHRP is likely to be mediated by electrogenerated oxygen radicals from the electrolysis of water. Within 2 h and up to 2.5 V versus an Ag/AgCl reference electrode, the peptide backbone remains largely intact. The chemical modifications are selectively on imidazole (histidine) and indole (tryptophan). Strategies for alleviating the electrolysis-induced degradation of GHRP are proposed.
Author Huddleston, Michael J
Carr, Stephen A
Cheng, Hung-Yuan
Davis, Louisa L
Author_xml – sequence: 1
  givenname: Hung-Yuan
  surname: Cheng
  fullname: Cheng, Hung-Yuan
– sequence: 2
  givenname: Louisa L
  surname: Davis
  fullname: Davis, Louisa L
– sequence: 3
  givenname: Michael J
  surname: Huddleston
  fullname: Huddleston, Michael J
– sequence: 4
  givenname: Stephen A
  surname: Carr
  fullname: Carr, Stephen A
BackLink http://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=2916164$$DView record in Pascal Francis
https://www.ncbi.nlm.nih.gov/pubmed/8633765$$D View this record in MEDLINE/PubMed
BookMark eNpt0d-LEzEQB_AgJ2fv9MlnYRHRB4nmx26yfTyunhWKnlzVxzCXzLZ7bjdrkkUL_vGmtlQRn-bh-5lhhjkjJ73vkZDHnL3iTPDXYBnjvAbGyntkwivBqKprcUImjDFJhWbsATmL8W7HGFen5LRWUmpVTcjPmxRGm8YAXRHT6LaFbwrs0Kbgu21sI217N1p0hcNVAAep9f3OpDUWq-C_p3Wx9mGTNypC7oPY9qtiwCG1Dot57p_RZRjoRQe_64xer5EutpG-n4uH5H4DXcRHh3pOPl29WV7O6eLD23eXFwsKJWeJauesdLWrtQArxdSqUgIocdugchJlU1o7tU5JJaqaCy25s1ixSgG32iHIc_J8P3cI_tuIMZlNGy12HfTox2i0riuuBMvw6T_wzo-hz7sZwTNStSwzerlHNvgYAzZmCO0GwtZwZnYPMX89JOsnh5Hj7Qbd0R4-kPNnhxyiha4J0Ns2HpmYcsXVbgzdszYm_HGMIXw1SktdmeX1jfn4Rcw-SybNVfYv9h5s_HPE_xb8BYnSr8s
CODEN ANCHAM
CitedBy_id crossref_primary_10_1016_S0378_4347_01_00030_5
crossref_primary_10_3109_10717549609029464
ContentType Journal Article
Copyright 1996 INIST-CNRS
Copyright American Chemical Society Nov 15, 1995
Copyright_xml – notice: 1996 INIST-CNRS
– notice: Copyright American Chemical Society Nov 15, 1995
DBID BSCLL
IQODW
CGR
CUY
CVF
ECM
EIF
NPM
AAYXX
CITATION
7QF
7QO
7QQ
7SC
7SE
7SP
7SR
7TA
7TB
7TM
7U5
7U7
7U9
8BQ
8FD
C1K
F28
FR3
H8D
H8G
H94
JG9
JQ2
KR7
L7M
L~C
L~D
P64
7X8
DOI 10.1021/ac00118a004
DatabaseName Istex
Pascal-Francis
Medline
MEDLINE
MEDLINE (Ovid)
MEDLINE
MEDLINE
PubMed
CrossRef
Aluminium Industry Abstracts
Biotechnology Research Abstracts
Ceramic Abstracts
Computer and Information Systems Abstracts
Corrosion Abstracts
Electronics & Communications Abstracts
Engineered Materials Abstracts
Materials Business File
Mechanical & Transportation Engineering Abstracts
Nucleic Acids Abstracts
Solid State and Superconductivity Abstracts
Toxicology Abstracts
Virology and AIDS Abstracts
METADEX
Technology Research Database
Environmental Sciences and Pollution Management
ANTE: Abstracts in New Technology & Engineering
Engineering Research Database
Aerospace Database
Copper Technical Reference Library
AIDS and Cancer Research Abstracts
Materials Research Database
ProQuest Computer Science Collection
Civil Engineering Abstracts
Advanced Technologies Database with Aerospace
Computer and Information Systems Abstracts – Academic
Computer and Information Systems Abstracts Professional
Biotechnology and BioEngineering Abstracts
MEDLINE - Academic
DatabaseTitle MEDLINE
Medline Complete
MEDLINE with Full Text
PubMed
MEDLINE (Ovid)
CrossRef
Materials Research Database
Technology Research Database
Computer and Information Systems Abstracts – Academic
Mechanical & Transportation Engineering Abstracts
Nucleic Acids Abstracts
ProQuest Computer Science Collection
Computer and Information Systems Abstracts
Materials Business File
Environmental Sciences and Pollution Management
Aerospace Database
Copper Technical Reference Library
Engineered Materials Abstracts
Biotechnology Research Abstracts
AIDS and Cancer Research Abstracts
Advanced Technologies Database with Aerospace
ANTE: Abstracts in New Technology & Engineering
Civil Engineering Abstracts
Aluminium Industry Abstracts
Virology and AIDS Abstracts
Toxicology Abstracts
Electronics & Communications Abstracts
Ceramic Abstracts
METADEX
Biotechnology and BioEngineering Abstracts
Computer and Information Systems Abstracts Professional
Solid State and Superconductivity Abstracts
Engineering Research Database
Corrosion Abstracts
MEDLINE - Academic
DatabaseTitleList Materials Research Database
MEDLINE - Academic
MEDLINE
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: EIF
  name: MEDLINE
  url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/medline/basic-search
  sourceTypes: Index Database
DeliveryMethod fulltext_linktorsrc
Discipline Engineering
Chemistry
EISSN 1520-6882
EndPage 4056
ExternalDocumentID 8659738
10_1021_ac00118a004
8633765
2916164
ark_67375_TPS_QW2DV303_F
d267304399
Genre Journal Article
GroupedDBID -
.K2
02
08R
186
1AW
1WB
23M
2KS
3EH
3O-
53G
53T
55A
5GY
5RE
5VS
6XO
85S
AABXI
AAUTI
ABDEX
ABFLS
ABMVS
ABOCM
ABPPZ
ABPTK
ABUFD
ACGFS
ACGOD
ACIWK
ACJ
ACKIV
ACNCT
ACPRK
ACPVT
ACS
AENEX
AETEA
AFFDN
AFFNX
AFMIJ
AFRAH
AGXLV
AIDAL
ALMA_UNASSIGNED_HOLDINGS
ANTXH
AQSVZ
BAANH
CS3
D0L
DZ
EBS
F20
F5P
G8K
GJ
HR
JG
JG~
K2
K78
MVM
NHB
OHM
OHT
OMK
P2P
PQEST
PQQKQ
RNS
ROL
RXW
TAE
TAF
TN5
UBX
UHB
UKR
UNC
UQL
VOH
VQA
W1F
WH7
X
X6Y
XFK
YXE
YZZ
ZCG
ZE2
ZGI
---
-DZ
-~X
.DC
.GJ
.HR
6J9
6TJ
ABHFT
ABHMW
ABJNI
ACBEA
ACGFO
ACKOT
ACQAM
AHGAQ
BSCLL
GGK
KZ1
UBC
VF5
VG9
XOL
XSW
YYP
ZCA
~02
4.4
7~N
ABFRP
ABQRX
ABUCX
ADHLV
AEESW
AFDAS
AFEFF
BKOMP
ED~
EJD
GNL
IH9
IHE
IQODW
LG6
LMP
UI2
YQI
YQJ
AAHBH
CGR
CUY
CVF
ECM
EIF
NPM
AAYXX
CITATION
7QF
7QO
7QQ
7SC
7SE
7SP
7SR
7TA
7TB
7TM
7U5
7U7
7U9
8BQ
8FD
C1K
F28
FR3
H8D
H8G
H94
JG9
JQ2
KR7
L7M
L~C
L~D
P64
7X8
CUPRZ
ID FETCH-LOGICAL-a410t-7ddc3d8d872ac329c643aa62bfe6d3e3f4cc9cd63625812731dce5056a1c7dea3
IEDL.DBID ACS
ISSN 0003-2700
IngestDate Fri Oct 25 09:19:04 EDT 2024
Thu Oct 10 19:47:37 EDT 2024
Thu Sep 26 16:21:02 EDT 2024
Sat Sep 28 08:40:28 EDT 2024
Sun Oct 29 17:08:33 EDT 2023
Wed Jan 17 04:58:30 EST 2024
Thu Aug 27 13:42:39 EDT 2020
IsPeerReviewed true
IsScholarly true
Issue 22
Keywords Chemical analysis
Peptide hormone
EPR spectrometry
HPLC chromatography
Percutaneous route
Electrodes
Cyclic voltammetry
Iontophoresis
Platinum
Oxidation
Hormone releasing factor
Electrochemical reaction
Organic compounds
Sodium Chlorides
Delivery system
Coupled method
Transition metal
Acetate
Experimental study
Buffer solution
Hexapeptide
Hypothalamic hormone
Synthetic product
Degradation product
Mass spectrometry
Language English
License CC BY 4.0
LinkModel DirectLink
MergedId FETCHMERGED-LOGICAL-a410t-7ddc3d8d872ac329c643aa62bfe6d3e3f4cc9cd63625812731dce5056a1c7dea3
Notes istex:F6145A19B17A28137CFBC77F5A466CDFCD6AE558
ark:/67375/TPS-QW2DV303-F
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
PMID 8633765
PQID 217856834
PQPubID 45400
PageCount 4
ParticipantIDs proquest_miscellaneous_77851620
proquest_journals_217856834
crossref_primary_10_1021_ac00118a004
pubmed_primary_8633765
pascalfrancis_primary_2916164
istex_primary_ark_67375_TPS_QW2DV303_F
acs_journals_10_1021_ac00118a004
ProviderPackageCode JG~
55A
AABXI
ACJ
AGXLV
W1F
ANTXH
ACS
.K2
ABMVS
1WB
BAANH
AQSVZ
PublicationCentury 1900
PublicationDate 1995-11-15
PublicationDateYYYYMMDD 1995-11-15
PublicationDate_xml – month: 11
  year: 1995
  text: 1995-11-15
  day: 15
PublicationDecade 1990
PublicationPlace Washington, DC
PublicationPlace_xml – name: Washington, DC
– name: United States
– name: Washington
PublicationTitle Analytical chemistry (Washington)
PublicationTitleAlternate Anal. Chem
PublicationYear 1995
Publisher American Chemical Society
Publisher_xml – name: American Chemical Society
SSID ssj0011016
Score 1.531254
Snippet Growth hormone releasing peptide (GHRP, sequence His-D-Trp-Ala-Trp-D-Phe-Lys-NH2) is a synthetic hexapeptide under consideration for transdermal iontophoretic...
Cyclic voltammetry, controlled-potential electrolysis and high-performance liquid chromatography/ultraviolet analysis indicate that the electrolysis-induced...
SourceID proquest
crossref
pubmed
pascalfrancis
istex
acs
SourceType Aggregation Database
Index Database
Publisher
StartPage 4053
SubjectTerms Amino Acid Sequence
Biochemistry
Biological and medical sciences
Chemistry
Electrochemistry
Electrolysis
Electron Spin Resonance Spectroscopy
Exact sciences and technology
General and physical chemistry
General pharmacology
Growth Hormone-Releasing Hormone - chemistry
Hormones
Kinetics and mechanism of reactions
Mass Spectrometry
Medical sciences
Molecular Sequence Data
Peptides
Pharmaceutical technology. Pharmaceutical industry
Pharmacology
Pharmacology. Drug treatments
Title Structural study of electrolysis-induced degradation of the growth hormone releasing peptide His-D-Trp-Ala-Trp-D-Phe-Lys-NH2
URI http://dx.doi.org/10.1021/ac00118a004
https://api.istex.fr/ark:/67375/TPS-QW2DV303-F/fulltext.pdf
https://www.ncbi.nlm.nih.gov/pubmed/8633765
https://www.proquest.com/docview/217856834
https://search.proquest.com/docview/77851620
Volume 67
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwhV1LbxMxELZQewAOPAoV6QN8qLi5xI-1d49R0ihCqCpKCr2t_GykoiTqphKt-uMZex998DrtwfbK9ox3vtkZf4PQgTYuK4wUJEhpCOBbBkcq5wT8MK1Mn4aG7fNYTk7F57Ps7C6J5nEEn9FP2iaeMp1YPzcZWMToYw2G0y5YEB3QtjBejKM21_AeDY7mx1YPzM9m3MmfMR1SV7AjoS5l8XesmWzO-CUatzd36lSTi8OrtTm0N78TOf57Oa_QiwZ14kGtJq_RE7_YQk-HbbG3LfT8Hi_hG3Q7TayykZEDJ_5ZvAy4KZiTKEwIePKgEw67yDVRl2WKfQBN4nNw7NdzPAcwvFx4HIuy6PhDAq9iAo3zeALjR2R2uSKDHzo9R-Rk7smX64ocT9hbdDo-mg0npCnTQLSg_TVRzlnucpcrpi1nhQWQo7VkJnjpuOdBWFtYJ8FUZgAnFKfO-gi8NLXKec230cYCJvQOYVkAPPNBWeGNoE5ozYMyVCthiqBEv4cwyLBsjllVpgg6o-W9Te2hg1bA5aom7Phzt49J-F0ffXkRc9xUVs5OpuXX72z0Dax7Oe6h_Qfa0Q1gAKzB1-yh3VZb7uYFfl6eyZxD64euFSQagzF64ZdXVamgB5UMlrRdq1j34lxy-OpnO_9f6y56lm7Yx6zEbA9tgG74fcBIa_M-nZBftpcH4A
link.rule.ids 315,786,790,2782,27107,27955,27956,57091,57141
linkProvider American Chemical Society
linkToHtml http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV1LbxMxEB5V7aFw4FGoGkqpDxUnXOL1rr17rBKiBdKoKCn0tvJriVSURN1UAsSPZ-x99CEQnPbgh-zxWPPNzvgbgCOlbZJpEdNSCE0R30Z4pVJO0Q9TUvdZ2bB9TkR-Hn-4SC424E37FgYXUeFMVQji37ALsLfKBLoyFcg_txKJds4DocG0ixl4P7Stj-fDqc1rvHuDvRUy1R0rtOUF-t1nRaoKBVPWFS3-DjmD6Rk9htNu0SHj5PL4eq2Pzc97fI7_u6sn8KjBoOSkVpqnsOEWO7A9aEu_7cDDWyyFz-DXNHDMen4OEthoybIkTfmcQGhC0a9HDbHEeuaJukiT74PYknxFN389J3OExsuFI75Ei_K_J8jKp9NYR3IcP6SzqxU9-abCd0jP5o6Of1R0kkfP4Xz0bjbIaVO0gaqY9ddUWmu4TW0qI2V4lBmEPEqJSJdOWO54GRuTGSvQcCYILiRn1jgPwxQz0jrFd2FzgQvaAyIyBGuulCZ2OmY2VoqXUjMlY52VMu73gKBMi-bSVUWIp0esuCXUHhy151ysavqOP3d7HXSg66OuLn3Gm0yK2dm0-PQlGn5GW1-MenBwR0m6ARHCbPQ8e7DfKs3NutDrSxORcmw97FrxRH1oRi3c8roqJPZgIsIt7daa1k2cCo42IHnx770ewnY-Ox0X4_eTj_vwILy99_mKyUvYRD1xB4ie1vpVuDS_AdypEEs
linkToPdf http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwlV1LbxMxELaqVgJ64FGoGkqpDxU3l3jttXePUUIUoIpSJYXeVn4SqSiJuqnUIn48Y--jD1EhTnvwQ37MaL7ZGX-D0JHSNs214MQLoQng2wRUKmME_DAldZf6mu1zLEZn_Mt5er6Bus1bGFhECTOVMYgftHplfc0wQD8qEynLVCQA3Uol5UEVe_1pGzcIvmhTIy-EVOsXeQ8GB0tkynuWaCsc6nXIjFQlHI6vqlo8Djuj-Rm-QKftwmPWycXx1Vofm18POB3_Z2cv0fMai-JeJTyv0IZb7KCn_aYE3A7avsNW-Br9nkau2cDTgSMrLV56XJfRicQmBPx7kBSLbWCgqIo1hT6AMfEPcPfXczwHiLxcOBxKtajwmwKvQlqNdXgE4wdkdrkivZ8qfgdkMnfk5KYk41HyBp0NP836I1IXbyCK0-6aSGsNs5nNZKIMS3ID0EcpkWjvhGWOeW5MbqwAA5oCyJCMWuMCHFPUSOsU20WbC1jQHsIiB9DmvDTcaU4tV4p5qamSXOde8m4HYTjXola-sohx9YQWdw61g46auy5WFY3H37t9iHLQ9lGXFyHzTabFbDItTr8ng29g84thBx3cE5R2QAJwGzzQDtpvBOd2XeD9ZanIGLQetq1woyFEoxZueVUWEnpQkcCWditpayfOBANbkL79914P0ZPJYFicfB5_3UfP4hP8kLaYvkObICbuAEDUWr-PevMHoPcSxQ
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=Structural+study+of+electrolysis-induced+degradation+of+the+growth+hormone+releasing+peptide+His-D-Trp-Ala-Trp-D-Phe-Lys-NH2&rft.jtitle=Analytical+chemistry+%28Washington%29&rft.au=HUNG-YUAN+CHENG&rft.au=DAVIS%2C+L.+L&rft.au=HUDDLESTON%2C+M.+J&rft.au=CARR%2C+S.+A&rft.date=1995-11-15&rft.pub=American+Chemical+Society&rft.issn=0003-2700&rft.eissn=1520-6882&rft.volume=67&rft.issue=22&rft.spage=4053&rft.epage=4056&rft_id=info:doi/10.1021%2Fac00118a004&rft.externalDBID=n%2Fa&rft.externalDocID=2916164
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0003-2700&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0003-2700&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0003-2700&client=summon