Inhibition of collagenase by aranciamycin and aranciamycin derivatives
Aranciamycin (1), an anthracycline antibiotic, was found to be an inhibitor of Clostridium histolyticum collagenase, with an IC50 = 3.7 x 10(-7) M. Elastase and trypsin were not inhibited at concentrations less-than-or-equal-to 10(-5) M. A number of aranciamycin derivatives 2-13 were prepared and te...
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| Veröffentlicht in: | Journal of medicinal chemistry 1992-07, Vol.35 (15), p.2768-2771 |
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| container_issue | 15 |
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| container_title | Journal of medicinal chemistry |
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| creator | Bols, Mikael Binderup, Lise Hansen, Jytte Rasmussen, Poul |
| description | Aranciamycin (1), an anthracycline antibiotic, was found to be an inhibitor of Clostridium histolyticum collagenase, with an IC50 = 3.7 x 10(-7) M. Elastase and trypsin were not inhibited at concentrations less-than-or-equal-to 10(-5) M. A number of aranciamycin derivatives 2-13 were prepared and tested for collagenase inhibition. While loss of activity was found for derivatives modified in the sugar ring or rings B and D of the aglycone, increased potency was found when the tertiary alcohol at C-9 was esterified. All compounds 1-13 were found to inhibit DNA synthesis of Yoshida sarcoma tumor cells. |
| doi_str_mv | 10.1021/jm00093a008 |
| format | Article |
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Elastase and trypsin were not inhibited at concentrations less-than-or-equal-to 10(-5) M. A number of aranciamycin derivatives 2-13 were prepared and tested for collagenase inhibition. While loss of activity was found for derivatives modified in the sugar ring or rings B and D of the aglycone, increased potency was found when the tertiary alcohol at C-9 was esterified. All compounds 1-13 were found to inhibit DNA synthesis of Yoshida sarcoma tumor cells.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm00093a008</identifier><identifier>PMID: 1322986</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>WASHINGTON: American Chemical Society</publisher><subject>Alicyclic compounds ; Alicyclic compounds, terpenoids, prostaglandins, steroids ; Animals ; Anthracyclines ; Antibiotics, Antineoplastic - chemistry ; Antibiotics, Antineoplastic - pharmacology ; Chemistry ; Chemistry, Medicinal ; Exact sciences and technology ; Life Sciences & Biomedicine ; Magnetic Resonance Spectroscopy ; Microbial Collagenase - antagonists & inhibitors ; Organic chemistry ; Pancreatic Elastase - antagonists & inhibitors ; Pharmacology & Pharmacy ; Preparations and properties ; Rats ; Sarcoma, Experimental ; Science & Technology ; Streptomyces - chemistry ; Trypsin Inhibitors - pharmacology ; Tumor Cells, Cultured</subject><ispartof>Journal of medicinal chemistry, 1992-07, Vol.35 (15), p.2768-2771</ispartof><rights>1992 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>true</woscitedreferencessubscribed><woscitedreferencescount>30</woscitedreferencescount><woscitedreferencesoriginalsourcerecordid>wosA1992JF49600008</woscitedreferencesoriginalsourcerecordid><citedby>FETCH-LOGICAL-a383t-d48f9951fba7d4c02ae1e6631bbdf31ed3de098fadfcec2ab398686d9c8ffdab3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jm00093a008$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm00093a008$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>315,782,786,2769,27085,27201,27933,27934,56747,56797</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=5436034$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/1322986$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Bols, Mikael</creatorcontrib><creatorcontrib>Binderup, Lise</creatorcontrib><creatorcontrib>Hansen, Jytte</creatorcontrib><creatorcontrib>Rasmussen, Poul</creatorcontrib><title>Inhibition of collagenase by aranciamycin and aranciamycin derivatives</title><title>Journal of medicinal chemistry</title><addtitle>J MED CHEM</addtitle><addtitle>J. Med. Chem</addtitle><description>Aranciamycin (1), an anthracycline antibiotic, was found to be an inhibitor of Clostridium histolyticum collagenase, with an IC50 = 3.7 x 10(-7) M. Elastase and trypsin were not inhibited at concentrations less-than-or-equal-to 10(-5) M. A number of aranciamycin derivatives 2-13 were prepared and tested for collagenase inhibition. While loss of activity was found for derivatives modified in the sugar ring or rings B and D of the aglycone, increased potency was found when the tertiary alcohol at C-9 was esterified. All compounds 1-13 were found to inhibit DNA synthesis of Yoshida sarcoma tumor cells.</description><subject>Alicyclic compounds</subject><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids</subject><subject>Animals</subject><subject>Anthracyclines</subject><subject>Antibiotics, Antineoplastic - chemistry</subject><subject>Antibiotics, Antineoplastic - pharmacology</subject><subject>Chemistry</subject><subject>Chemistry, Medicinal</subject><subject>Exact sciences and technology</subject><subject>Life Sciences & Biomedicine</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Microbial Collagenase - antagonists & inhibitors</subject><subject>Organic chemistry</subject><subject>Pancreatic Elastase - antagonists & inhibitors</subject><subject>Pharmacology & Pharmacy</subject><subject>Preparations and properties</subject><subject>Rats</subject><subject>Sarcoma, Experimental</subject><subject>Science & Technology</subject><subject>Streptomyces - chemistry</subject><subject>Trypsin Inhibitors - pharmacology</subject><subject>Tumor Cells, Cultured</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1992</creationdate><recordtype>article</recordtype><sourceid>EZCTM</sourceid><sourceid>EIF</sourceid><recordid>eNqNkc1v1DAQxS0EKtvCiTNSDogeUIo_skl8rFZd6IcEokVIXKyJPQYvG7vYScv-97jNagsSB06WPb83b_yGkBeMHjHK2dtVTymVAihtH5EZm3NaVi2tHpMZpZyXvObiKdlPaZUxwbjYI3tMcC7bekaWp_6769zggi-CLXRYr-EbekhYdJsCInjtoN9o5wvw5u8Hg9HdwOBuMD0jTyysEz7fngfk8_LkavG-vPjw7nRxfFGCaMVQmqq1Us6Z7aAxlaYckGFdC9Z1xgqGRhiksrVgrEbNoRN5yLY2UrfWmnw9IK-nvtcx_BwxDap3SWMe2mMYk2oElU3-dAbfTKCOIaWIVl1H10PcKEbVXWrqj9Qy_XLbdux6NA_sFFOuv9rWIWlY2_sU0g6bV6KmonowvcUu2KQdeo076phJyc-Wlayz8b1p-__0wg1wt6RFGP2QpeUkdWnAXzsNxB-qbkQzV1cfLxWtzr-yL58u1VnmDycedFKrMEafl_TPJH4D_LWypQ</recordid><startdate>19920701</startdate><enddate>19920701</enddate><creator>Bols, Mikael</creator><creator>Binderup, Lise</creator><creator>Hansen, Jytte</creator><creator>Rasmussen, Poul</creator><general>American Chemical Society</general><general>Amer Chemical Soc</general><scope>BSCLL</scope><scope>BLEPL</scope><scope>DTL</scope><scope>EZCTM</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></search><sort><creationdate>19920701</creationdate><title>Inhibition of collagenase by aranciamycin and aranciamycin derivatives</title><author>Bols, Mikael ; Binderup, Lise ; Hansen, Jytte ; Rasmussen, Poul</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a383t-d48f9951fba7d4c02ae1e6631bbdf31ed3de098fadfcec2ab398686d9c8ffdab3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1992</creationdate><topic>Alicyclic compounds</topic><topic>Alicyclic compounds, terpenoids, prostaglandins, steroids</topic><topic>Animals</topic><topic>Anthracyclines</topic><topic>Antibiotics, Antineoplastic - chemistry</topic><topic>Antibiotics, Antineoplastic - pharmacology</topic><topic>Chemistry</topic><topic>Chemistry, Medicinal</topic><topic>Exact sciences and technology</topic><topic>Life Sciences & Biomedicine</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Microbial Collagenase - antagonists & inhibitors</topic><topic>Organic chemistry</topic><topic>Pancreatic Elastase - antagonists & inhibitors</topic><topic>Pharmacology & Pharmacy</topic><topic>Preparations and properties</topic><topic>Rats</topic><topic>Sarcoma, Experimental</topic><topic>Science & Technology</topic><topic>Streptomyces - chemistry</topic><topic>Trypsin Inhibitors - pharmacology</topic><topic>Tumor Cells, Cultured</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bols, Mikael</creatorcontrib><creatorcontrib>Binderup, Lise</creatorcontrib><creatorcontrib>Hansen, Jytte</creatorcontrib><creatorcontrib>Rasmussen, Poul</creatorcontrib><collection>Istex</collection><collection>Web of Science Core Collection</collection><collection>Science Citation Index Expanded</collection><collection>Web of Science - Science Citation Index Expanded - 1992</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><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bols, Mikael</au><au>Binderup, Lise</au><au>Hansen, Jytte</au><au>Rasmussen, Poul</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Inhibition of collagenase by aranciamycin and aranciamycin derivatives</atitle><jtitle>Journal of medicinal chemistry</jtitle><stitle>J MED CHEM</stitle><addtitle>J. Med. Chem</addtitle><date>1992-07-01</date><risdate>1992</risdate><volume>35</volume><issue>15</issue><spage>2768</spage><epage>2771</epage><pages>2768-2771</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>Aranciamycin (1), an anthracycline antibiotic, was found to be an inhibitor of Clostridium histolyticum collagenase, with an IC50 = 3.7 x 10(-7) M. Elastase and trypsin were not inhibited at concentrations less-than-or-equal-to 10(-5) M. A number of aranciamycin derivatives 2-13 were prepared and tested for collagenase inhibition. While loss of activity was found for derivatives modified in the sugar ring or rings B and D of the aglycone, increased potency was found when the tertiary alcohol at C-9 was esterified. All compounds 1-13 were found to inhibit DNA synthesis of Yoshida sarcoma tumor cells.</abstract><cop>WASHINGTON</cop><pub>American Chemical Society</pub><pmid>1322986</pmid><doi>10.1021/jm00093a008</doi><tpages>4</tpages></addata></record> |
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| ispartof | Journal of medicinal chemistry, 1992-07, Vol.35 (15), p.2768-2771 |
| issn | 0022-2623 1520-4804 |
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| source | Web of Science - Science Citation Index Expanded - 1992<img src="https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg" />; MEDLINE; American Chemical Society Journals |
| subjects | Alicyclic compounds Alicyclic compounds, terpenoids, prostaglandins, steroids Animals Anthracyclines Antibiotics, Antineoplastic - chemistry Antibiotics, Antineoplastic - pharmacology Chemistry Chemistry, Medicinal Exact sciences and technology Life Sciences & Biomedicine Magnetic Resonance Spectroscopy Microbial Collagenase - antagonists & inhibitors Organic chemistry Pancreatic Elastase - antagonists & inhibitors Pharmacology & Pharmacy Preparations and properties Rats Sarcoma, Experimental Science & Technology Streptomyces - chemistry Trypsin Inhibitors - pharmacology Tumor Cells, Cultured |
| title | Inhibition of collagenase by aranciamycin and aranciamycin derivatives |
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