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Novel cilengitide-based cyclic RGD peptides as αvβ 3 integrin inhibitors
In this letter, we report a series of five new RGD-containing cyclic peptides as potent inhibitors to αvβ integrin protein. We have incorporated various unnatural lipophilic amino acids into the cyclic RGD framework of cilengitide, which is selective for αvβ integrin. All the newly synthesized cycli...
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Published in: | Bioorganic & medicinal chemistry letters 2020-04, Vol.30 (8), p.127039 |
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creator | Meena, Chhuttan L Singh, Dharmendra Weinmüller, Michael Reichart, Florian Dangi, Abha Marelli, Udaya Kiran Zahler, Stefan Sanjayan, Gangadhar J |
description | In this letter, we report a series of five new RGD-containing cyclic peptides as potent inhibitors to αvβ
integrin protein. We have incorporated various unnatural lipophilic amino acids into the cyclic RGD framework of cilengitide, which is selective for αvβ
integrin. All the newly synthesized cyclic peptides were evaluated in vitrosolid phase binding assay and investigated for their bindingbehaviourtowards integrin subtypes. All the cyclic peptides were synthesized in excellent yield following solution-phase coupling strategy. The cyclic RGD peptides 1a-e exhibited IC
of 9.9, 5.5, 72, 11 and 3.3 nM, respectively, towardsαvβ
integrin protein. This finding offers further opportunities for the introduction unusual amino acids into the cyclic peptide framework of cilengitide. |
format | article |
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integrin protein. We have incorporated various unnatural lipophilic amino acids into the cyclic RGD framework of cilengitide, which is selective for αvβ
integrin. All the newly synthesized cyclic peptides were evaluated in vitrosolid phase binding assay and investigated for their bindingbehaviourtowards integrin subtypes. All the cyclic peptides were synthesized in excellent yield following solution-phase coupling strategy. The cyclic RGD peptides 1a-e exhibited IC
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integrin protein. We have incorporated various unnatural lipophilic amino acids into the cyclic RGD framework of cilengitide, which is selective for αvβ
integrin. All the newly synthesized cyclic peptides were evaluated in vitrosolid phase binding assay and investigated for their bindingbehaviourtowards integrin subtypes. All the cyclic peptides were synthesized in excellent yield following solution-phase coupling strategy. The cyclic RGD peptides 1a-e exhibited IC
of 9.9, 5.5, 72, 11 and 3.3 nM, respectively, towardsαvβ
integrin protein. This finding offers further opportunities for the introduction unusual amino acids into the cyclic peptide framework of cilengitide.</description><subject>Dose-Response Relationship, Drug</subject><subject>Humans</subject><subject>Integrin alphaVbeta3 - antagonists & inhibitors</subject><subject>Integrin alphaVbeta3 - metabolism</subject><subject>Molecular Structure</subject><subject>Peptides, Cyclic - chemical synthesis</subject><subject>Peptides, Cyclic - chemistry</subject><subject>Peptides, Cyclic - pharmacology</subject><subject>Structure-Activity Relationship</subject><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNpjYuA0NDEz0TU2MTDlYOAqLs4yMDA0MTAxYWfgMDYysDQxMLDkZPDyyy9LzVFIzsxJzUvPLMlMSdVNSixOTVFIrkzOyUxWCHJ3UShILQBJFCskFiuc21h2bpOCsUJmXklqelFmHpCRkZmUWZJfVMzDwJqWmFOcyguluRnk3FxDnD10C0qTclNT4guKMnMTiyrjYZYbE1QAAIScOv0</recordid><startdate>20200415</startdate><enddate>20200415</enddate><creator>Meena, Chhuttan L</creator><creator>Singh, Dharmendra</creator><creator>Weinmüller, Michael</creator><creator>Reichart, Florian</creator><creator>Dangi, Abha</creator><creator>Marelli, Udaya Kiran</creator><creator>Zahler, Stefan</creator><creator>Sanjayan, Gangadhar J</creator><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope></search><sort><creationdate>20200415</creationdate><title>Novel cilengitide-based cyclic RGD peptides as αvβ 3 integrin inhibitors</title><author>Meena, Chhuttan L ; Singh, Dharmendra ; Weinmüller, Michael ; Reichart, Florian ; Dangi, Abha ; Marelli, Udaya Kiran ; Zahler, Stefan ; Sanjayan, Gangadhar J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-pubmed_primary_320940093</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Dose-Response Relationship, Drug</topic><topic>Humans</topic><topic>Integrin alphaVbeta3 - antagonists & inhibitors</topic><topic>Integrin alphaVbeta3 - metabolism</topic><topic>Molecular Structure</topic><topic>Peptides, Cyclic - chemical synthesis</topic><topic>Peptides, Cyclic - chemistry</topic><topic>Peptides, Cyclic - pharmacology</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Meena, Chhuttan L</creatorcontrib><creatorcontrib>Singh, Dharmendra</creatorcontrib><creatorcontrib>Weinmüller, Michael</creatorcontrib><creatorcontrib>Reichart, Florian</creatorcontrib><creatorcontrib>Dangi, Abha</creatorcontrib><creatorcontrib>Marelli, Udaya Kiran</creatorcontrib><creatorcontrib>Zahler, Stefan</creatorcontrib><creatorcontrib>Sanjayan, Gangadhar J</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Meena, Chhuttan L</au><au>Singh, Dharmendra</au><au>Weinmüller, Michael</au><au>Reichart, Florian</au><au>Dangi, Abha</au><au>Marelli, Udaya Kiran</au><au>Zahler, Stefan</au><au>Sanjayan, Gangadhar J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Novel cilengitide-based cyclic RGD peptides as αvβ 3 integrin inhibitors</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2020-04-15</date><risdate>2020</risdate><volume>30</volume><issue>8</issue><spage>127039</spage><pages>127039-</pages><eissn>1464-3405</eissn><abstract>In this letter, we report a series of five new RGD-containing cyclic peptides as potent inhibitors to αvβ
integrin protein. We have incorporated various unnatural lipophilic amino acids into the cyclic RGD framework of cilengitide, which is selective for αvβ
integrin. All the newly synthesized cyclic peptides were evaluated in vitrosolid phase binding assay and investigated for their bindingbehaviourtowards integrin subtypes. All the cyclic peptides were synthesized in excellent yield following solution-phase coupling strategy. The cyclic RGD peptides 1a-e exhibited IC
of 9.9, 5.5, 72, 11 and 3.3 nM, respectively, towardsαvβ
integrin protein. This finding offers further opportunities for the introduction unusual amino acids into the cyclic peptide framework of cilengitide.</abstract><cop>England</cop><pmid>32094009</pmid></addata></record> |
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subjects | Dose-Response Relationship, Drug Humans Integrin alphaVbeta3 - antagonists & inhibitors Integrin alphaVbeta3 - metabolism Molecular Structure Peptides, Cyclic - chemical synthesis Peptides, Cyclic - chemistry Peptides, Cyclic - pharmacology Structure-Activity Relationship |
title | Novel cilengitide-based cyclic RGD peptides as αvβ 3 integrin inhibitors |
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