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Pharmacophore-based small molecule CXCR4 ligands
SAR studies of low molecular weight CXCR4 ligands are reported. Low molecular weight CXCR4 ligands were developed based on the peptide T140, which has previously been identified as a potent CXCR4 antagonist. Some compounds with naphthyl, fluorobenzyl and pyridyl moieties as pharmacophore groups in t...
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| Published in: | Bioorganic & medicinal chemistry letters 2012-06, Vol.22 (12), p.4169-4172 |
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| Main Authors: | , , , , , , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c542t-c82e7bb3399d3aff65447ab2b9f7f224096074a7a4abfd4ad0e7e8a4086ac64f3 |
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| cites | cdi_FETCH-LOGICAL-c542t-c82e7bb3399d3aff65447ab2b9f7f224096074a7a4abfd4ad0e7e8a4086ac64f3 |
| container_end_page | 4172 |
| container_issue | 12 |
| container_start_page | 4169 |
| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 22 |
| creator | Narumi, Tetsuo Tanaka, Tomohiro Hashimoto, Chie Nomura, Wataru Aikawa, Haruo Sohma, Akira Itotani, Kyoko Kawamata, Miyako Murakami, Tsutomu Yamamoto, Naoki Tamamura, Hirokazu |
| description | SAR studies of low molecular weight CXCR4 ligands are reported.
Low molecular weight CXCR4 ligands were developed based on the peptide T140, which has previously been identified as a potent CXCR4 antagonist. Some compounds with naphthyl, fluorobenzyl and pyridyl moieties as pharmacophore groups in the molecule showed significant CXCR4-binding activity and anti-HIV activity. Structure–activity relationships were studied and characteristics of each of these three moieties necessary for CXCR4 binding were defined. In this way, CXCR4 ligands with two types of recognition modes for CXCR4 have been found. |
| doi_str_mv | 10.1016/j.bmcl.2012.04.032 |
| format | article |
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Low molecular weight CXCR4 ligands were developed based on the peptide T140, which has previously been identified as a potent CXCR4 antagonist. Some compounds with naphthyl, fluorobenzyl and pyridyl moieties as pharmacophore groups in the molecule showed significant CXCR4-binding activity and anti-HIV activity. Structure–activity relationships were studied and characteristics of each of these three moieties necessary for CXCR4 binding were defined. In this way, CXCR4 ligands with two types of recognition modes for CXCR4 have been found.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2012.04.032</identifier><identifier>PMID: 22579418</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>AIDS ; antagonists ; Anti-HIV Agents - chemical synthesis ; Anti-HIV Agents - pharmacology ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; antiretroviral agents ; Antiviral activity ; Antiviral agents ; Biological and medical sciences ; Cell Line ; Chemokine receptor ; HIV entry inhibitors ; HIV-1 - drug effects ; HIV-1 - physiology ; Human immunodeficiency virus ; Humans ; Ligands ; Low molecular weight CXCR4 ligands ; Medical sciences ; molecular weight ; Oligopeptides - chemical synthesis ; Oligopeptides - chemistry ; Oligopeptides - pharmacology ; pharmacology ; Pharmacology. Drug treatments ; Receptors, CXCR4 - antagonists & inhibitors ; Receptors, CXCR4 - chemistry ; Small Molecule Libraries ; Structure-Activity Relationship ; structure-activity relationships ; T-Lymphocytes - drug effects ; T-Lymphocytes - virology ; Virus Replication - drug effects</subject><ispartof>Bioorganic & medicinal chemistry letters, 2012-06, Vol.22 (12), p.4169-4172</ispartof><rights>2012 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2012 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c542t-c82e7bb3399d3aff65447ab2b9f7f224096074a7a4abfd4ad0e7e8a4086ac64f3</citedby><cites>FETCH-LOGICAL-c542t-c82e7bb3399d3aff65447ab2b9f7f224096074a7a4abfd4ad0e7e8a4086ac64f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=26103361$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22579418$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Narumi, Tetsuo</creatorcontrib><creatorcontrib>Tanaka, Tomohiro</creatorcontrib><creatorcontrib>Hashimoto, Chie</creatorcontrib><creatorcontrib>Nomura, Wataru</creatorcontrib><creatorcontrib>Aikawa, Haruo</creatorcontrib><creatorcontrib>Sohma, Akira</creatorcontrib><creatorcontrib>Itotani, Kyoko</creatorcontrib><creatorcontrib>Kawamata, Miyako</creatorcontrib><creatorcontrib>Murakami, Tsutomu</creatorcontrib><creatorcontrib>Yamamoto, Naoki</creatorcontrib><creatorcontrib>Tamamura, Hirokazu</creatorcontrib><title>Pharmacophore-based small molecule CXCR4 ligands</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>SAR studies of low molecular weight CXCR4 ligands are reported.
Low molecular weight CXCR4 ligands were developed based on the peptide T140, which has previously been identified as a potent CXCR4 antagonist. Some compounds with naphthyl, fluorobenzyl and pyridyl moieties as pharmacophore groups in the molecule showed significant CXCR4-binding activity and anti-HIV activity. Structure–activity relationships were studied and characteristics of each of these three moieties necessary for CXCR4 binding were defined. In this way, CXCR4 ligands with two types of recognition modes for CXCR4 have been found.</description><subject>AIDS</subject><subject>antagonists</subject><subject>Anti-HIV Agents - chemical synthesis</subject><subject>Anti-HIV Agents - pharmacology</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>antiretroviral agents</subject><subject>Antiviral activity</subject><subject>Antiviral agents</subject><subject>Biological and medical sciences</subject><subject>Cell Line</subject><subject>Chemokine receptor</subject><subject>HIV entry inhibitors</subject><subject>HIV-1 - drug effects</subject><subject>HIV-1 - physiology</subject><subject>Human immunodeficiency virus</subject><subject>Humans</subject><subject>Ligands</subject><subject>Low molecular weight CXCR4 ligands</subject><subject>Medical sciences</subject><subject>molecular weight</subject><subject>Oligopeptides - chemical synthesis</subject><subject>Oligopeptides - chemistry</subject><subject>Oligopeptides - pharmacology</subject><subject>pharmacology</subject><subject>Pharmacology. Drug treatments</subject><subject>Receptors, CXCR4 - antagonists & inhibitors</subject><subject>Receptors, CXCR4 - chemistry</subject><subject>Small Molecule Libraries</subject><subject>Structure-Activity Relationship</subject><subject>structure-activity relationships</subject><subject>T-Lymphocytes - drug effects</subject><subject>T-Lymphocytes - virology</subject><subject>Virus Replication - drug effects</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNqN0U1v1DAQBmALUdFt4Q9wgL0g9ZLgj4ntSFzQii-pUhFQqTdr4ozbrJzNYu8i8e_rsAvcqp58eeb16B3GXgpeCy7023XdjT7WkgtZc6i5kk_YQoCGSgFvnrIFbzWvbAs3p-ws5zXnAjjAM3YqZWNaEHbB-Nc7TCP6aXs3Jao6zNQv84gxLscpkt9HWq5uVt9gGYdb3PT5OTsJGDO9OL7n7Prjhx-rz9Xl1acvq_eXlW9A7ipvJZmuU6pte4Uh6AbAYCe7NpggJcyrGUCDgF3oAXtOhiwCtxq9hqDO2cUhd5umn3vKOzcO2VOMuKFpn53gCqy0wjaPo8JoLR9BhTFNyZypPFCfppwTBbdNw4jpd0Gz027t5v7d3L_j4PifoVfH_H03Uv9v5G_hBbw5AsweY0i48UP-73RZVmlR3OuDCzg5vE3FXH8vPzXliIobq4t4dxBUrvBroOSyH2jjqR8S-Z3rp-GhTe8BIs6p6g</recordid><startdate>20120615</startdate><enddate>20120615</enddate><creator>Narumi, Tetsuo</creator><creator>Tanaka, Tomohiro</creator><creator>Hashimoto, Chie</creator><creator>Nomura, Wataru</creator><creator>Aikawa, Haruo</creator><creator>Sohma, Akira</creator><creator>Itotani, Kyoko</creator><creator>Kawamata, Miyako</creator><creator>Murakami, Tsutomu</creator><creator>Yamamoto, Naoki</creator><creator>Tamamura, Hirokazu</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>FBQ</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20120615</creationdate><title>Pharmacophore-based small molecule CXCR4 ligands</title><author>Narumi, Tetsuo ; Tanaka, Tomohiro ; Hashimoto, Chie ; Nomura, Wataru ; Aikawa, Haruo ; Sohma, Akira ; Itotani, Kyoko ; Kawamata, Miyako ; Murakami, Tsutomu ; Yamamoto, Naoki ; Tamamura, Hirokazu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c542t-c82e7bb3399d3aff65447ab2b9f7f224096074a7a4abfd4ad0e7e8a4086ac64f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>AIDS</topic><topic>antagonists</topic><topic>Anti-HIV Agents - chemical synthesis</topic><topic>Anti-HIV Agents - pharmacology</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>antiretroviral agents</topic><topic>Antiviral activity</topic><topic>Antiviral agents</topic><topic>Biological and medical sciences</topic><topic>Cell Line</topic><topic>Chemokine receptor</topic><topic>HIV entry inhibitors</topic><topic>HIV-1 - drug effects</topic><topic>HIV-1 - physiology</topic><topic>Human immunodeficiency virus</topic><topic>Humans</topic><topic>Ligands</topic><topic>Low molecular weight CXCR4 ligands</topic><topic>Medical sciences</topic><topic>molecular weight</topic><topic>Oligopeptides - chemical synthesis</topic><topic>Oligopeptides - chemistry</topic><topic>Oligopeptides - pharmacology</topic><topic>pharmacology</topic><topic>Pharmacology. Drug treatments</topic><topic>Receptors, CXCR4 - antagonists & inhibitors</topic><topic>Receptors, CXCR4 - chemistry</topic><topic>Small Molecule Libraries</topic><topic>Structure-Activity Relationship</topic><topic>structure-activity relationships</topic><topic>T-Lymphocytes - drug effects</topic><topic>T-Lymphocytes - virology</topic><topic>Virus Replication - drug effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Narumi, Tetsuo</creatorcontrib><creatorcontrib>Tanaka, Tomohiro</creatorcontrib><creatorcontrib>Hashimoto, Chie</creatorcontrib><creatorcontrib>Nomura, Wataru</creatorcontrib><creatorcontrib>Aikawa, Haruo</creatorcontrib><creatorcontrib>Sohma, Akira</creatorcontrib><creatorcontrib>Itotani, Kyoko</creatorcontrib><creatorcontrib>Kawamata, Miyako</creatorcontrib><creatorcontrib>Murakami, Tsutomu</creatorcontrib><creatorcontrib>Yamamoto, Naoki</creatorcontrib><creatorcontrib>Tamamura, Hirokazu</creatorcontrib><collection>AGRIS</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Narumi, Tetsuo</au><au>Tanaka, Tomohiro</au><au>Hashimoto, Chie</au><au>Nomura, Wataru</au><au>Aikawa, Haruo</au><au>Sohma, Akira</au><au>Itotani, Kyoko</au><au>Kawamata, Miyako</au><au>Murakami, Tsutomu</au><au>Yamamoto, Naoki</au><au>Tamamura, Hirokazu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Pharmacophore-based small molecule CXCR4 ligands</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2012-06-15</date><risdate>2012</risdate><volume>22</volume><issue>12</issue><spage>4169</spage><epage>4172</epage><pages>4169-4172</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>SAR studies of low molecular weight CXCR4 ligands are reported.
Low molecular weight CXCR4 ligands were developed based on the peptide T140, which has previously been identified as a potent CXCR4 antagonist. Some compounds with naphthyl, fluorobenzyl and pyridyl moieties as pharmacophore groups in the molecule showed significant CXCR4-binding activity and anti-HIV activity. Structure–activity relationships were studied and characteristics of each of these three moieties necessary for CXCR4 binding were defined. In this way, CXCR4 ligands with two types of recognition modes for CXCR4 have been found.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>22579418</pmid><doi>10.1016/j.bmcl.2012.04.032</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2012-06, Vol.22 (12), p.4169-4172 |
| issn | 0960-894X 1464-3405 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1034828185 |
| source | ScienceDirect Freedom Collection |
| subjects | AIDS antagonists Anti-HIV Agents - chemical synthesis Anti-HIV Agents - pharmacology Antibiotics. Antiinfectious agents. Antiparasitic agents antiretroviral agents Antiviral activity Antiviral agents Biological and medical sciences Cell Line Chemokine receptor HIV entry inhibitors HIV-1 - drug effects HIV-1 - physiology Human immunodeficiency virus Humans Ligands Low molecular weight CXCR4 ligands Medical sciences molecular weight Oligopeptides - chemical synthesis Oligopeptides - chemistry Oligopeptides - pharmacology pharmacology Pharmacology. Drug treatments Receptors, CXCR4 - antagonists & inhibitors Receptors, CXCR4 - chemistry Small Molecule Libraries Structure-Activity Relationship structure-activity relationships T-Lymphocytes - drug effects T-Lymphocytes - virology Virus Replication - drug effects |
| title | Pharmacophore-based small molecule CXCR4 ligands |
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