Synthesis and in vitro evaluation of targeted tetracycline derivatives: Effects on inhibition of matrix metalloproteinases
Among other non-antibiotic properties, tetracyclines inhibit matrix metalloproteinases and are currently under study for the treatment of osteoarthritis. Quaternary ammonium conjugates of tetracyclines were synthesized by direct alkylation of the amine function at the 4-position with methyl iodide....
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2007-03, Vol.15 (6), p.2368-2374 |
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| container_title | Bioorganic & medicinal chemistry |
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| creator | Vidal, Aurélien Sabatini, Massimo Rolland-Valognes, Gaëlle Renard, Pierre Madelmont, Jean-Claude Mounetou, Emmanuelle |
| description | Among other non-antibiotic properties, tetracyclines inhibit matrix metalloproteinases and are currently under study for the treatment of osteoarthritis. Quaternary ammonium conjugates of tetracyclines were synthesized by direct alkylation of the amine function at the 4-position with methyl iodide. When tested in vitro, they inhibited cytokine-induced MMP expression to a lesser extent than parent tetracyclines. This was compensated by an improved inhibition of MMP catalytic activity. Since inhibition of collagen degradation was maintained these derivatives could be potent drug candidates for cartilage-targeted chondroprotective treatment. |
| doi_str_mv | 10.1016/j.bmc.2007.01.026 |
| format | Article |
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Quaternary ammonium conjugates of tetracyclines were synthesized by direct alkylation of the amine function at the 4-position with methyl iodide. When tested in vitro, they inhibited cytokine-induced MMP expression to a lesser extent than parent tetracyclines. This was compensated by an improved inhibition of MMP catalytic activity. Since inhibition of collagen degradation was maintained these derivatives could be potent drug candidates for cartilage-targeted chondroprotective treatment.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2007.01.026</identifier><identifier>PMID: 17267227</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Animals ; Biological and medical sciences ; Bones, joints and connective tissue. Antiinflammatory agents ; Cartilage, Articular - drug effects ; Cartilage, Articular - enzymology ; Chondrosarcoma - drug therapy ; Chondrosarcoma - enzymology ; Chondrosarcoma - pathology ; Collagen - drug effects ; Collagen - metabolism ; Humans ; In Vitro Techniques ; Matrix Metalloproteinase Inhibitors ; Matrix Metalloproteinases - metabolism ; Medical sciences ; Metalloproteinases ; Osteoarthritis ; Pharmacology. Drug treatments ; Protease Inhibitors - chemical synthesis ; Protease Inhibitors - chemistry ; Protease Inhibitors - pharmacology ; Proteoglycans - drug effects ; Proteoglycans - metabolism ; Quaternary ammonium ; Rabbits ; Tetracyclines ; Tetracyclines - chemical synthesis ; Tetracyclines - chemistry ; Tetracyclines - pharmacology</subject><ispartof>Bioorganic & medicinal chemistry, 2007-03, Vol.15 (6), p.2368-2374</ispartof><rights>2007 Elsevier Ltd</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c381t-b779a2c298897ae860201d7ebe5921d3657eb0e2bec0e792993c9bbffe5fbc7f3</citedby><cites>FETCH-LOGICAL-c381t-b779a2c298897ae860201d7ebe5921d3657eb0e2bec0e792993c9bbffe5fbc7f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0968089607000351$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18539996$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17267227$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Vidal, Aurélien</creatorcontrib><creatorcontrib>Sabatini, Massimo</creatorcontrib><creatorcontrib>Rolland-Valognes, Gaëlle</creatorcontrib><creatorcontrib>Renard, Pierre</creatorcontrib><creatorcontrib>Madelmont, Jean-Claude</creatorcontrib><creatorcontrib>Mounetou, Emmanuelle</creatorcontrib><title>Synthesis and in vitro evaluation of targeted tetracycline derivatives: Effects on inhibition of matrix metalloproteinases</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>Among other non-antibiotic properties, tetracyclines inhibit matrix metalloproteinases and are currently under study for the treatment of osteoarthritis. Quaternary ammonium conjugates of tetracyclines were synthesized by direct alkylation of the amine function at the 4-position with methyl iodide. When tested in vitro, they inhibited cytokine-induced MMP expression to a lesser extent than parent tetracyclines. This was compensated by an improved inhibition of MMP catalytic activity. Since inhibition of collagen degradation was maintained these derivatives could be potent drug candidates for cartilage-targeted chondroprotective treatment.</description><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Bones, joints and connective tissue. Antiinflammatory agents</subject><subject>Cartilage, Articular - drug effects</subject><subject>Cartilage, Articular - enzymology</subject><subject>Chondrosarcoma - drug therapy</subject><subject>Chondrosarcoma - enzymology</subject><subject>Chondrosarcoma - pathology</subject><subject>Collagen - drug effects</subject><subject>Collagen - metabolism</subject><subject>Humans</subject><subject>In Vitro Techniques</subject><subject>Matrix Metalloproteinase Inhibitors</subject><subject>Matrix Metalloproteinases - metabolism</subject><subject>Medical sciences</subject><subject>Metalloproteinases</subject><subject>Osteoarthritis</subject><subject>Pharmacology. Drug treatments</subject><subject>Protease Inhibitors - chemical synthesis</subject><subject>Protease Inhibitors - chemistry</subject><subject>Protease Inhibitors - pharmacology</subject><subject>Proteoglycans - drug effects</subject><subject>Proteoglycans - metabolism</subject><subject>Quaternary ammonium</subject><subject>Rabbits</subject><subject>Tetracyclines</subject><subject>Tetracyclines - chemical synthesis</subject><subject>Tetracyclines - chemistry</subject><subject>Tetracyclines - pharmacology</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE1v1DAQhi0EotvCD-gF-QK3BNvZ2DGcUNUPpEocaM-W7UzaWSVOsb0Ry6_Hq92qt55mDs_7zugh5JyzmjMuv25qN_laMKZqxmsm5Buy4mu5rppG87dkxbTsKtZpeUJOU9owxsRa8_fkhCshlRBqRf793oX8CAkTtaGnGOiCOc4UFjtubcY50Hmg2cYHyNDTDDlav_MjBqA9RFwKs0D6Ri-HAXxOtAQwPKLD5-xkc8S_dIJsx3F-inMGDDZB-kDeDXZM8PE4z8j91eXdxU11--v658WP28o3Hc-VU0pb4YXuOq0sdJIJxnsFDloteN_ItuwMhAPPQGmhdeO1c-WddnBeDc0Z-XLoLbf_bCFlM2HyMI42wLxNRurishW6gPwA-jinFGEwTxEnG3eGM7MXbjamCDd74YZxU4SXzKdj-dZN0L8kjoYL8PkI2OTtOEQbPKYXrmsbrfW-6PuBg6JiQYgmeYTgocdYxJp-xlfe-A-5J6Fl</recordid><startdate>20070315</startdate><enddate>20070315</enddate><creator>Vidal, Aurélien</creator><creator>Sabatini, Massimo</creator><creator>Rolland-Valognes, Gaëlle</creator><creator>Renard, Pierre</creator><creator>Madelmont, Jean-Claude</creator><creator>Mounetou, Emmanuelle</creator><general>Elsevier Ltd</general><general>Elsevier Science</general><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></search><sort><creationdate>20070315</creationdate><title>Synthesis and in vitro evaluation of targeted tetracycline derivatives: Effects on inhibition of matrix metalloproteinases</title><author>Vidal, Aurélien ; Sabatini, Massimo ; Rolland-Valognes, Gaëlle ; Renard, Pierre ; Madelmont, Jean-Claude ; Mounetou, Emmanuelle</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c381t-b779a2c298897ae860201d7ebe5921d3657eb0e2bec0e792993c9bbffe5fbc7f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>Bones, joints and connective tissue. Antiinflammatory agents</topic><topic>Cartilage, Articular - drug effects</topic><topic>Cartilage, Articular - enzymology</topic><topic>Chondrosarcoma - drug therapy</topic><topic>Chondrosarcoma - enzymology</topic><topic>Chondrosarcoma - pathology</topic><topic>Collagen - drug effects</topic><topic>Collagen - metabolism</topic><topic>Humans</topic><topic>In Vitro Techniques</topic><topic>Matrix Metalloproteinase Inhibitors</topic><topic>Matrix Metalloproteinases - metabolism</topic><topic>Medical sciences</topic><topic>Metalloproteinases</topic><topic>Osteoarthritis</topic><topic>Pharmacology. 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Quaternary ammonium conjugates of tetracyclines were synthesized by direct alkylation of the amine function at the 4-position with methyl iodide. When tested in vitro, they inhibited cytokine-induced MMP expression to a lesser extent than parent tetracyclines. This was compensated by an improved inhibition of MMP catalytic activity. Since inhibition of collagen degradation was maintained these derivatives could be potent drug candidates for cartilage-targeted chondroprotective treatment.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>17267227</pmid><doi>10.1016/j.bmc.2007.01.026</doi><tpages>7</tpages></addata></record> |
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| subjects | Animals Biological and medical sciences Bones, joints and connective tissue. Antiinflammatory agents Cartilage, Articular - drug effects Cartilage, Articular - enzymology Chondrosarcoma - drug therapy Chondrosarcoma - enzymology Chondrosarcoma - pathology Collagen - drug effects Collagen - metabolism Humans In Vitro Techniques Matrix Metalloproteinase Inhibitors Matrix Metalloproteinases - metabolism Medical sciences Metalloproteinases Osteoarthritis Pharmacology. Drug treatments Protease Inhibitors - chemical synthesis Protease Inhibitors - chemistry Protease Inhibitors - pharmacology Proteoglycans - drug effects Proteoglycans - metabolism Quaternary ammonium Rabbits Tetracyclines Tetracyclines - chemical synthesis Tetracyclines - chemistry Tetracyclines - pharmacology |
| title | Synthesis and in vitro evaluation of targeted tetracycline derivatives: Effects on inhibition of matrix metalloproteinases |
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