Loading…
Structure-activity relationship study of CXCR4 antagonists bearing the cyclic pentapeptide scaffold: identification of the new pharmacophore
A highly potent CXCR4 antagonist 2 [cyclo (-D-Tyr1-Arg2-Arg3-Nal4-Gly5-)] has previously been identified by screening cyclic pentapeptide libraries that were designed based on pharmacophore residues of a 14-residue peptidic CXCR4 antagonist 1. In the present study, D-Tyr and Arg in peptide 2 were re...
Saved in:
Published in: | Organic & biomolecular chemistry 2008-01, Vol.6 (23), p.4374 |
---|---|
Main Authors: | , , , , , , , , , , , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
cited_by | cdi_FETCH-LOGICAL-c391t-de271e4aa9474d7293f9cd554a32c80eaf1e51e8a29702e1f3170fc87d0ff0cc3 |
---|---|
cites | cdi_FETCH-LOGICAL-c391t-de271e4aa9474d7293f9cd554a32c80eaf1e51e8a29702e1f3170fc87d0ff0cc3 |
container_end_page | |
container_issue | 23 |
container_start_page | 4374 |
container_title | Organic & biomolecular chemistry |
container_volume | 6 |
creator | Tanaka, Tomohiro Tsutsumi, Hiroshi Nomura, Wataru Tanabe, Yasuaki Ohashi, Nami Esaka, Ai Ochiai, Chihiro Sato, Jun Itotani, Kyoko Murakami, Tsutomu Ohba, Kenji Yamamoto, Naoki Fujii, Nobutaka Tamamura, Hirokazu |
description | A highly potent CXCR4 antagonist 2 [cyclo (-D-Tyr1-Arg2-Arg3-Nal4-Gly5-)] has previously been identified by screening cyclic pentapeptide libraries that were designed based on pharmacophore residues of a 14-residue peptidic CXCR4 antagonist 1. In the present study, D-Tyr and Arg in peptide 2 were replaced by a bicyclic aromatic amino acid and a cationic amino acid, respectively, and their binding activity for CXCR4 was evaluated for identification of the novel pharmacophore. |
doi_str_mv | 10.1039/b812029c |
format | article |
fullrecord | <record><control><sourceid>pubmed_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1039_b812029c</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>19005596</sourcerecordid><originalsourceid>FETCH-LOGICAL-c391t-de271e4aa9474d7293f9cd554a32c80eaf1e51e8a29702e1f3170fc87d0ff0cc3</originalsourceid><addsrcrecordid>eNpFkMtKAzEUhoMotlbBJ5As3YzmMtNM3EnxBgXBC7gb0uSkE5nOhCSjzDv40La26uqcw_-db_EjdErJBSVcXi5KygiTeg-NaS5ERgou9_92RkboKMZ3QqgU0_wQjagkpCjkdIy-nlPodeoDZEon9-HSgAM0KrmujbXzOKbeDLizePY2e8qxapNadq2LKeIFqODaJU41YD3oxmnsYZ178MkZwFEra7vGXOH11SZnnf7xbmybnxY-sa9VWCnd-boLcIwOrGoinOzmBL3e3rzM7rP5493D7HqeaS5pygwwQSFXSuYiN4JJbqU2RZErznRJQFkKBYVSMSkIA2o5FcTqUhhiLdGaT9D51qtDF2MAW_ngVioMFSXVptDqt9A1erZFfb9YgfkHdw3yb4eodGg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Structure-activity relationship study of CXCR4 antagonists bearing the cyclic pentapeptide scaffold: identification of the new pharmacophore</title><source>Royal Society of Chemistry Journals</source><creator>Tanaka, Tomohiro ; Tsutsumi, Hiroshi ; Nomura, Wataru ; Tanabe, Yasuaki ; Ohashi, Nami ; Esaka, Ai ; Ochiai, Chihiro ; Sato, Jun ; Itotani, Kyoko ; Murakami, Tsutomu ; Ohba, Kenji ; Yamamoto, Naoki ; Fujii, Nobutaka ; Tamamura, Hirokazu</creator><creatorcontrib>Tanaka, Tomohiro ; Tsutsumi, Hiroshi ; Nomura, Wataru ; Tanabe, Yasuaki ; Ohashi, Nami ; Esaka, Ai ; Ochiai, Chihiro ; Sato, Jun ; Itotani, Kyoko ; Murakami, Tsutomu ; Ohba, Kenji ; Yamamoto, Naoki ; Fujii, Nobutaka ; Tamamura, Hirokazu</creatorcontrib><description>A highly potent CXCR4 antagonist 2 [cyclo (-D-Tyr1-Arg2-Arg3-Nal4-Gly5-)] has previously been identified by screening cyclic pentapeptide libraries that were designed based on pharmacophore residues of a 14-residue peptidic CXCR4 antagonist 1. In the present study, D-Tyr and Arg in peptide 2 were replaced by a bicyclic aromatic amino acid and a cationic amino acid, respectively, and their binding activity for CXCR4 was evaluated for identification of the novel pharmacophore.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/b812029c</identifier><identifier>PMID: 19005596</identifier><language>eng</language><publisher>England</publisher><subject>Animals ; Cattle ; Cell Line ; Drug Discovery ; HIV-1 - drug effects ; Humans ; Oligopeptides - chemical synthesis ; Oligopeptides - chemistry ; Oligopeptides - pharmacology ; Oligopeptides - toxicity ; Peptides, Cyclic - chemical synthesis ; Peptides, Cyclic - chemistry ; Peptides, Cyclic - pharmacology ; Peptides, Cyclic - toxicity ; Receptors, CXCR4 - antagonists & inhibitors ; Structure-Activity Relationship ; Tyrosine - chemistry</subject><ispartof>Organic & biomolecular chemistry, 2008-01, Vol.6 (23), p.4374</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c391t-de271e4aa9474d7293f9cd554a32c80eaf1e51e8a29702e1f3170fc87d0ff0cc3</citedby><cites>FETCH-LOGICAL-c391t-de271e4aa9474d7293f9cd554a32c80eaf1e51e8a29702e1f3170fc87d0ff0cc3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,27905,27906</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19005596$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tanaka, Tomohiro</creatorcontrib><creatorcontrib>Tsutsumi, Hiroshi</creatorcontrib><creatorcontrib>Nomura, Wataru</creatorcontrib><creatorcontrib>Tanabe, Yasuaki</creatorcontrib><creatorcontrib>Ohashi, Nami</creatorcontrib><creatorcontrib>Esaka, Ai</creatorcontrib><creatorcontrib>Ochiai, Chihiro</creatorcontrib><creatorcontrib>Sato, Jun</creatorcontrib><creatorcontrib>Itotani, Kyoko</creatorcontrib><creatorcontrib>Murakami, Tsutomu</creatorcontrib><creatorcontrib>Ohba, Kenji</creatorcontrib><creatorcontrib>Yamamoto, Naoki</creatorcontrib><creatorcontrib>Fujii, Nobutaka</creatorcontrib><creatorcontrib>Tamamura, Hirokazu</creatorcontrib><title>Structure-activity relationship study of CXCR4 antagonists bearing the cyclic pentapeptide scaffold: identification of the new pharmacophore</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>A highly potent CXCR4 antagonist 2 [cyclo (-D-Tyr1-Arg2-Arg3-Nal4-Gly5-)] has previously been identified by screening cyclic pentapeptide libraries that were designed based on pharmacophore residues of a 14-residue peptidic CXCR4 antagonist 1. In the present study, D-Tyr and Arg in peptide 2 were replaced by a bicyclic aromatic amino acid and a cationic amino acid, respectively, and their binding activity for CXCR4 was evaluated for identification of the novel pharmacophore.</description><subject>Animals</subject><subject>Cattle</subject><subject>Cell Line</subject><subject>Drug Discovery</subject><subject>HIV-1 - drug effects</subject><subject>Humans</subject><subject>Oligopeptides - chemical synthesis</subject><subject>Oligopeptides - chemistry</subject><subject>Oligopeptides - pharmacology</subject><subject>Oligopeptides - toxicity</subject><subject>Peptides, Cyclic - chemical synthesis</subject><subject>Peptides, Cyclic - chemistry</subject><subject>Peptides, Cyclic - pharmacology</subject><subject>Peptides, Cyclic - toxicity</subject><subject>Receptors, CXCR4 - antagonists & inhibitors</subject><subject>Structure-Activity Relationship</subject><subject>Tyrosine - chemistry</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><recordid>eNpFkMtKAzEUhoMotlbBJ5As3YzmMtNM3EnxBgXBC7gb0uSkE5nOhCSjzDv40La26uqcw_-db_EjdErJBSVcXi5KygiTeg-NaS5ERgou9_92RkboKMZ3QqgU0_wQjagkpCjkdIy-nlPodeoDZEon9-HSgAM0KrmujbXzOKbeDLizePY2e8qxapNadq2LKeIFqODaJU41YD3oxmnsYZ178MkZwFEra7vGXOH11SZnnf7xbmybnxY-sa9VWCnd-boLcIwOrGoinOzmBL3e3rzM7rP5493D7HqeaS5pygwwQSFXSuYiN4JJbqU2RZErznRJQFkKBYVSMSkIA2o5FcTqUhhiLdGaT9D51qtDF2MAW_ngVioMFSXVptDqt9A1erZFfb9YgfkHdw3yb4eodGg</recordid><startdate>20080101</startdate><enddate>20080101</enddate><creator>Tanaka, Tomohiro</creator><creator>Tsutsumi, Hiroshi</creator><creator>Nomura, Wataru</creator><creator>Tanabe, Yasuaki</creator><creator>Ohashi, Nami</creator><creator>Esaka, Ai</creator><creator>Ochiai, Chihiro</creator><creator>Sato, Jun</creator><creator>Itotani, Kyoko</creator><creator>Murakami, Tsutomu</creator><creator>Ohba, Kenji</creator><creator>Yamamoto, Naoki</creator><creator>Fujii, Nobutaka</creator><creator>Tamamura, Hirokazu</creator><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20080101</creationdate><title>Structure-activity relationship study of CXCR4 antagonists bearing the cyclic pentapeptide scaffold: identification of the new pharmacophore</title><author>Tanaka, Tomohiro ; Tsutsumi, Hiroshi ; Nomura, Wataru ; Tanabe, Yasuaki ; Ohashi, Nami ; Esaka, Ai ; Ochiai, Chihiro ; Sato, Jun ; Itotani, Kyoko ; Murakami, Tsutomu ; Ohba, Kenji ; Yamamoto, Naoki ; Fujii, Nobutaka ; Tamamura, Hirokazu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c391t-de271e4aa9474d7293f9cd554a32c80eaf1e51e8a29702e1f3170fc87d0ff0cc3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Animals</topic><topic>Cattle</topic><topic>Cell Line</topic><topic>Drug Discovery</topic><topic>HIV-1 - drug effects</topic><topic>Humans</topic><topic>Oligopeptides - chemical synthesis</topic><topic>Oligopeptides - chemistry</topic><topic>Oligopeptides - pharmacology</topic><topic>Oligopeptides - toxicity</topic><topic>Peptides, Cyclic - chemical synthesis</topic><topic>Peptides, Cyclic - chemistry</topic><topic>Peptides, Cyclic - pharmacology</topic><topic>Peptides, Cyclic - toxicity</topic><topic>Receptors, CXCR4 - antagonists & inhibitors</topic><topic>Structure-Activity Relationship</topic><topic>Tyrosine - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tanaka, Tomohiro</creatorcontrib><creatorcontrib>Tsutsumi, Hiroshi</creatorcontrib><creatorcontrib>Nomura, Wataru</creatorcontrib><creatorcontrib>Tanabe, Yasuaki</creatorcontrib><creatorcontrib>Ohashi, Nami</creatorcontrib><creatorcontrib>Esaka, Ai</creatorcontrib><creatorcontrib>Ochiai, Chihiro</creatorcontrib><creatorcontrib>Sato, Jun</creatorcontrib><creatorcontrib>Itotani, Kyoko</creatorcontrib><creatorcontrib>Murakami, Tsutomu</creatorcontrib><creatorcontrib>Ohba, Kenji</creatorcontrib><creatorcontrib>Yamamoto, Naoki</creatorcontrib><creatorcontrib>Fujii, Nobutaka</creatorcontrib><creatorcontrib>Tamamura, Hirokazu</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tanaka, Tomohiro</au><au>Tsutsumi, Hiroshi</au><au>Nomura, Wataru</au><au>Tanabe, Yasuaki</au><au>Ohashi, Nami</au><au>Esaka, Ai</au><au>Ochiai, Chihiro</au><au>Sato, Jun</au><au>Itotani, Kyoko</au><au>Murakami, Tsutomu</au><au>Ohba, Kenji</au><au>Yamamoto, Naoki</au><au>Fujii, Nobutaka</au><au>Tamamura, Hirokazu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Structure-activity relationship study of CXCR4 antagonists bearing the cyclic pentapeptide scaffold: identification of the new pharmacophore</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2008-01-01</date><risdate>2008</risdate><volume>6</volume><issue>23</issue><spage>4374</spage><pages>4374-</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>A highly potent CXCR4 antagonist 2 [cyclo (-D-Tyr1-Arg2-Arg3-Nal4-Gly5-)] has previously been identified by screening cyclic pentapeptide libraries that were designed based on pharmacophore residues of a 14-residue peptidic CXCR4 antagonist 1. In the present study, D-Tyr and Arg in peptide 2 were replaced by a bicyclic aromatic amino acid and a cationic amino acid, respectively, and their binding activity for CXCR4 was evaluated for identification of the novel pharmacophore.</abstract><cop>England</cop><pmid>19005596</pmid><doi>10.1039/b812029c</doi></addata></record> |
fulltext | fulltext |
identifier | ISSN: 1477-0520 |
ispartof | Organic & biomolecular chemistry, 2008-01, Vol.6 (23), p.4374 |
issn | 1477-0520 1477-0539 |
language | eng |
recordid | cdi_crossref_primary_10_1039_b812029c |
source | Royal Society of Chemistry Journals |
subjects | Animals Cattle Cell Line Drug Discovery HIV-1 - drug effects Humans Oligopeptides - chemical synthesis Oligopeptides - chemistry Oligopeptides - pharmacology Oligopeptides - toxicity Peptides, Cyclic - chemical synthesis Peptides, Cyclic - chemistry Peptides, Cyclic - pharmacology Peptides, Cyclic - toxicity Receptors, CXCR4 - antagonists & inhibitors Structure-Activity Relationship Tyrosine - chemistry |
title | Structure-activity relationship study of CXCR4 antagonists bearing the cyclic pentapeptide scaffold: identification of the new pharmacophore |
url | http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-19T18%3A04%3A08IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-pubmed_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Structure-activity%20relationship%20study%20of%20CXCR4%20antagonists%20bearing%20the%20cyclic%20pentapeptide%20scaffold:%20identification%20of%20the%20new%20pharmacophore&rft.jtitle=Organic%20&%20biomolecular%20chemistry&rft.au=Tanaka,%20Tomohiro&rft.date=2008-01-01&rft.volume=6&rft.issue=23&rft.spage=4374&rft.pages=4374-&rft.issn=1477-0520&rft.eissn=1477-0539&rft_id=info:doi/10.1039/b812029c&rft_dat=%3Cpubmed_cross%3E19005596%3C/pubmed_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c391t-de271e4aa9474d7293f9cd554a32c80eaf1e51e8a29702e1f3170fc87d0ff0cc3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_id=info:pmid/19005596&rfr_iscdi=true |