Development of Active Center-Directed Inhibitors against Plasmin
Active center-directed inhibitors of plasmin were designed based on the structure of specific substrates of plasmin and then synthesized. Their effects on plasmin were examined and the structure-inhibitory activity relationship was studied. Nα-trans-4-Aminomethylcyclohexanecarbonyllysine 4-benzoylan...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1991/09/25, Vol.39(9), pp.2340-2346 |
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| container_title | Chemical & pharmaceutical bulletin |
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| creator | TENO, Naoki WANAKA, Keiko OKADA, Yoshio TSUDA, Yuko OKAMOTO, Utako HIJIKATA-OKUNOMIYA, Akiko NAITO, Taketoshi OKAMOTO, Shosuke |
| description | Active center-directed inhibitors of plasmin were designed based on the structure of specific substrates of plasmin and then synthesized. Their effects on plasmin were examined and the structure-inhibitory activity relationship was studied. Nα-trans-4-Aminomethylcyclohexanecarbonyllysine 4-benzoylanilide (Tra-Lys-BZA) inhibited plasmin activities toward S-2251 and fibrin with IC50 values of 15 and 6.1 μM, respectively and Nα-trans-4-aminomethylcyclohexanecarbonyllysine 4-benzylpiperidine amide (Tra-Lys-BPP) did not show any detectable inhibitory activity. Moreover, it was revealed that Tra-Lys-4-methoxycarbonylanilide inhibited plasma kallikrein more potently than plasmin. |
| doi_str_mv | 10.1248/cpb.39.2340 |
| format | Article |
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Their effects on plasmin were examined and the structure-inhibitory activity relationship was studied. Nα-trans-4-Aminomethylcyclohexanecarbonyllysine 4-benzoylanilide (Tra-Lys-BZA) inhibited plasmin activities toward S-2251 and fibrin with IC50 values of 15 and 6.1 μM, respectively and Nα-trans-4-aminomethylcyclohexanecarbonyllysine 4-benzylpiperidine amide (Tra-Lys-BPP) did not show any detectable inhibitory activity. Moreover, it was revealed that Tra-Lys-4-methoxycarbonylanilide inhibited plasma kallikrein more potently than plasmin.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.39.2340</identifier><identifier>PMID: 1839513</identifier><identifier>CODEN: CPBTAL</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>4-aminomethylcyclohexanecarbonyllysine 4-benzoylanilide ; 4-aminomethylcyclohexanecarbonyllysine 4-benzylpiperdine amide ; Analytical, structural and metabolic biochemistry ; Binding Sites ; Biological and medical sciences ; competitive inhibitor ; design ; Enzymes and enzyme inhibitors ; Fibrinolysin - antagonists & inhibitors ; Fundamental and applied biological sciences. Psychology ; Hydrolases ; Lys derivative ; plasmin ; structure-activity relationship ; synthesis ; Tra-Lys-4-methoxycarbonylanilide</subject><ispartof>Chemical and Pharmaceutical Bulletin, 1991/09/25, Vol.39(9), pp.2340-2346</ispartof><rights>The Pharmaceutical Society of Japan</rights><rights>1992 INIST-CNRS</rights><rights>Copyright Japan Science and Technology Agency 1991</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c666t-d8d508483a17f8d11dace31d1b993b1b2987bbe88a4bdd8c1a060ff59dd4fdd13</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1877,4010,27900,27901,27902</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=5093602$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/1839513$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>TENO, Naoki</creatorcontrib><creatorcontrib>WANAKA, Keiko</creatorcontrib><creatorcontrib>OKADA, Yoshio</creatorcontrib><creatorcontrib>TSUDA, Yuko</creatorcontrib><creatorcontrib>OKAMOTO, Utako</creatorcontrib><creatorcontrib>HIJIKATA-OKUNOMIYA, Akiko</creatorcontrib><creatorcontrib>NAITO, Taketoshi</creatorcontrib><creatorcontrib>OKAMOTO, Shosuke</creatorcontrib><title>Development of Active Center-Directed Inhibitors against Plasmin</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>Active center-directed inhibitors of plasmin were designed based on the structure of specific substrates of plasmin and then synthesized. Their effects on plasmin were examined and the structure-inhibitory activity relationship was studied. Nα-trans-4-Aminomethylcyclohexanecarbonyllysine 4-benzoylanilide (Tra-Lys-BZA) inhibited plasmin activities toward S-2251 and fibrin with IC50 values of 15 and 6.1 μM, respectively and Nα-trans-4-aminomethylcyclohexanecarbonyllysine 4-benzylpiperidine amide (Tra-Lys-BPP) did not show any detectable inhibitory activity. Moreover, it was revealed that Tra-Lys-4-methoxycarbonylanilide inhibited plasma kallikrein more potently than plasmin.</description><subject>4-aminomethylcyclohexanecarbonyllysine 4-benzoylanilide</subject><subject>4-aminomethylcyclohexanecarbonyllysine 4-benzylpiperdine amide</subject><subject>Analytical, structural and metabolic biochemistry</subject><subject>Binding Sites</subject><subject>Biological and medical sciences</subject><subject>competitive inhibitor</subject><subject>design</subject><subject>Enzymes and enzyme inhibitors</subject><subject>Fibrinolysin - antagonists & inhibitors</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Hydrolases</subject><subject>Lys derivative</subject><subject>plasmin</subject><subject>structure-activity relationship</subject><subject>synthesis</subject><subject>Tra-Lys-4-methoxycarbonylanilide</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1991</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkM1r3DAQxUVpSTfbnnouGFp6Kd5oLFuWbg27aRsINIf2LPQxTrT4YytpA_nvK-MlgV5ymWF4P-bxHiEfgG6gqsWFPZgNk5uK1fQVWQGr27KpKvaarCilsqwYZ2_JeYx7SquGtuyMnIFgsgG2It92-ID9dBhwTMXUFZc2-QcstvnEUO58QJvQFdfjvTc-TSEW-k77Mabittdx8OM78qbTfcT3p70mf75f_d7-LG9-_bjeXt6UlnOeSidcQ0UtmIa2Ew7AaYsMHBgpmQFTSdEag0Lo2jgnLGjKadc10rm6cw7YmnxZ_h7C9PeIManBR4t9r0ecjlG1FZc5qHgRBA6UMUYz-Ok_cD8dw5hDKKg5zXXWwDP1daFsmGIM2KlD8IMOjwqomutXuX7FpJrrz_TH08-jGdA9s0vfWf980nW0uu-CHq2PT1hDc4bsvCa7BdvHpO_wSdchedvjbAmyEbOtXMbs_izf66BwZP8A6n-j3A</recordid><startdate>1991</startdate><enddate>1991</enddate><creator>TENO, Naoki</creator><creator>WANAKA, Keiko</creator><creator>OKADA, Yoshio</creator><creator>TSUDA, Yuko</creator><creator>OKAMOTO, Utako</creator><creator>HIJIKATA-OKUNOMIYA, Akiko</creator><creator>NAITO, Taketoshi</creator><creator>OKAMOTO, Shosuke</creator><general>The Pharmaceutical Society of Japan</general><general>Maruzen</general><general>Japan Science and Technology Agency</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>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope><scope>7QL</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>M81</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>1991</creationdate><title>Development of Active Center-Directed Inhibitors against Plasmin</title><author>TENO, Naoki ; WANAKA, Keiko ; OKADA, Yoshio ; TSUDA, Yuko ; OKAMOTO, Utako ; HIJIKATA-OKUNOMIYA, Akiko ; NAITO, Taketoshi ; OKAMOTO, Shosuke</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c666t-d8d508483a17f8d11dace31d1b993b1b2987bbe88a4bdd8c1a060ff59dd4fdd13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1991</creationdate><topic>4-aminomethylcyclohexanecarbonyllysine 4-benzoylanilide</topic><topic>4-aminomethylcyclohexanecarbonyllysine 4-benzylpiperdine amide</topic><topic>Analytical, structural and metabolic biochemistry</topic><topic>Binding Sites</topic><topic>Biological and medical sciences</topic><topic>competitive inhibitor</topic><topic>design</topic><topic>Enzymes and enzyme inhibitors</topic><topic>Fibrinolysin - antagonists & inhibitors</topic><topic>Fundamental and applied biological sciences. 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Pharm. Bull.</addtitle><date>1991</date><risdate>1991</risdate><volume>39</volume><issue>9</issue><spage>2340</spage><epage>2346</epage><pages>2340-2346</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>Active center-directed inhibitors of plasmin were designed based on the structure of specific substrates of plasmin and then synthesized. Their effects on plasmin were examined and the structure-inhibitory activity relationship was studied. Nα-trans-4-Aminomethylcyclohexanecarbonyllysine 4-benzoylanilide (Tra-Lys-BZA) inhibited plasmin activities toward S-2251 and fibrin with IC50 values of 15 and 6.1 μM, respectively and Nα-trans-4-aminomethylcyclohexanecarbonyllysine 4-benzylpiperidine amide (Tra-Lys-BPP) did not show any detectable inhibitory activity. 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| identifier | ISSN: 0009-2363 |
| ispartof | Chemical and Pharmaceutical Bulletin, 1991/09/25, Vol.39(9), pp.2340-2346 |
| issn | 0009-2363 1347-5223 |
| language | eng |
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| source | J-STAGE Free; MEDLINE; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | 4-aminomethylcyclohexanecarbonyllysine 4-benzoylanilide 4-aminomethylcyclohexanecarbonyllysine 4-benzylpiperdine amide Analytical, structural and metabolic biochemistry Binding Sites Biological and medical sciences competitive inhibitor design Enzymes and enzyme inhibitors Fibrinolysin - antagonists & inhibitors Fundamental and applied biological sciences. Psychology Hydrolases Lys derivative plasmin structure-activity relationship synthesis Tra-Lys-4-methoxycarbonylanilide |
| title | Development of Active Center-Directed Inhibitors against Plasmin |
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