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Structure-activity relationship of linear peptide Bu-His-DPhe-Arg-Trp-Gly-NH(2) at the human melanocortin-1 and -4 receptors: arginine substitution

A series of pentapeptides, based on Bu-His(6)-DPhe(7)-Arg(8)-Trp(9)-Gly(10)-NH(2) and modified at the Arg(8) position, was prepared and pharmacologically characterized. Peptides containing either cyanoguanidine or acylguanidine, two substantially less basic arginine surrogates, were found to retain...

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Published in:	Bioorganic & medicinal chemistry letters 2002-09, Vol.12 (17), p.2407-2410
Main Authors:	Cheung, Adrian Wai-Hing, Danho, Waleed, Swistok, Joseph, Qi, Lida, Kurylko, Grazyna, Franco, Lucia, Yagaloff, Keith, Chen, Li
Format:	Article
Language:	English
Subjects:	Amino Acid Substitution Arginine Binding Sites Guanidines Humans Oligopeptides - chemical synthesis Oligopeptides - pharmacology Protein Binding Receptor, Melanocortin, Type 4 Receptors, Corticotropin - agonists Receptors, Melanocortin Structure-Activity Relationship
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container_title	Bioorganic & medicinal chemistry letters
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creator	Cheung, Adrian Wai-Hing Danho, Waleed Swistok, Joseph Qi, Lida Kurylko, Grazyna Franco, Lucia Yagaloff, Keith Chen, Li
description	A series of pentapeptides, based on Bu-His(6)-DPhe(7)-Arg(8)-Trp(9)-Gly(10)-NH(2) and modified at the Arg(8) position, was prepared and pharmacologically characterized. Peptides containing either cyanoguanidine or acylguanidine, two substantially less basic arginine surrogates, were found to retain the agonist activity of the parent peptide at both hMC1R and hMC4R. This study unequivocally shows that the positive charge of Arg(8) is not essential for efficient interactions of our pentapeptide with both hMC1R and hMC4R.
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Peptides containing either cyanoguanidine or acylguanidine, two substantially less basic arginine surrogates, were found to retain the agonist activity of the parent peptide at both hMC1R and hMC4R. This study unequivocally shows that the positive charge of Arg(8) is not essential for efficient interactions of our pentapeptide with both hMC1R and hMC4R.</description><subject>Amino Acid Substitution</subject><subject>Arginine</subject><subject>Binding Sites</subject><subject>Guanidines</subject><subject>Humans</subject><subject>Oligopeptides - chemical synthesis</subject><subject>Oligopeptides - pharmacology</subject><subject>Protein Binding</subject><subject>Receptor, Melanocortin, Type 4</subject><subject>Receptors, Corticotropin - agonists</subject><subject>Receptors, Melanocortin</subject><subject>Structure-Activity Relationship</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><recordid>eNo10MtKxDAYBeAgijOOvoJkJboI5NY0dTeOOiMMKtiFu5I26TTSm7kI8xy-sBXH1b85fOfnHIE54YIjxnFyDOY4ExjJjL_PwJn3HxgTjjk_BTNCiSCE8zn4fgsuViE6g1QV7JcNe-hMq4Idet_YEQ41bG1vlIOjGYPVBt5FtLEe3b82Bi3dDuVuROt2j5431_QGqgBDY2ATO9XDbpL6oRpcsD0iUPUaIj751UQNzt9C5Xa2n3joY-mDDfG39xyc1Kr15uJwFyB_fMhXG7R9WT-tlls0JpyjuqylzpSUvBRS1yorBUtLYWqaYiYwF7JKSaIpFZKRjBjNFK0zJrSmAieYsgW4-mNHN3xG40PRWV-ZdnrZDNEXKZnm4zKbgpeHYCw7o4vR2U65ffG_IvsB4p5v4w</recordid><startdate>20020902</startdate><enddate>20020902</enddate><creator>Cheung, Adrian Wai-Hing</creator><creator>Danho, Waleed</creator><creator>Swistok, Joseph</creator><creator>Qi, Lida</creator><creator>Kurylko, Grazyna</creator><creator>Franco, Lucia</creator><creator>Yagaloff, Keith</creator><creator>Chen, Li</creator><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20020902</creationdate><title>Structure-activity relationship of linear peptide Bu-His-DPhe-Arg-Trp-Gly-NH(2) at the human melanocortin-1 and -4 receptors: arginine substitution</title><author>Cheung, Adrian Wai-Hing ; Danho, Waleed ; Swistok, Joseph ; Qi, Lida ; Kurylko, Grazyna ; Franco, Lucia ; Yagaloff, Keith ; Chen, Li</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p544-fbf8d9a884b68dfa9b637b6ef270360468c715d22683191ed3a2f936dd2605023</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>Amino Acid Substitution</topic><topic>Arginine</topic><topic>Binding Sites</topic><topic>Guanidines</topic><topic>Humans</topic><topic>Oligopeptides - chemical synthesis</topic><topic>Oligopeptides - pharmacology</topic><topic>Protein Binding</topic><topic>Receptor, Melanocortin, Type 4</topic><topic>Receptors, Corticotropin - agonists</topic><topic>Receptors, Melanocortin</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Cheung, Adrian Wai-Hing</creatorcontrib><creatorcontrib>Danho, Waleed</creatorcontrib><creatorcontrib>Swistok, Joseph</creatorcontrib><creatorcontrib>Qi, Lida</creatorcontrib><creatorcontrib>Kurylko, Grazyna</creatorcontrib><creatorcontrib>Franco, Lucia</creatorcontrib><creatorcontrib>Yagaloff, Keith</creatorcontrib><creatorcontrib>Chen, Li</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Cheung, Adrian Wai-Hing</au><au>Danho, Waleed</au><au>Swistok, Joseph</au><au>Qi, Lida</au><au>Kurylko, Grazyna</au><au>Franco, Lucia</au><au>Yagaloff, Keith</au><au>Chen, Li</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Structure-activity relationship of linear peptide Bu-His-DPhe-Arg-Trp-Gly-NH(2) at the human melanocortin-1 and -4 receptors: arginine substitution</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2002-09-02</date><risdate>2002</risdate><volume>12</volume><issue>17</issue><spage>2407</spage><epage>2410</epage><pages>2407-2410</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><notes>ObjectType-Article-1</notes><notes>SourceType-Scholarly Journals-1</notes><notes>ObjectType-Feature-2</notes><notes>content type line 23</notes><abstract>A series of pentapeptides, based on Bu-His(6)-DPhe(7)-Arg(8)-Trp(9)-Gly(10)-NH(2) and modified at the Arg(8) position, was prepared and pharmacologically characterized. 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subjects	Amino Acid Substitution Arginine Binding Sites Guanidines Humans Oligopeptides - chemical synthesis Oligopeptides - pharmacology Protein Binding Receptor, Melanocortin, Type 4 Receptors, Corticotropin - agonists Receptors, Melanocortin Structure-Activity Relationship
title	Structure-activity relationship of linear peptide Bu-His-DPhe-Arg-Trp-Gly-NH(2) at the human melanocortin-1 and -4 receptors: arginine substitution
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