Novel epoxysuccinyl peptides Selective inhibitors of cathepsin B, in vitro
A series of new epoxysuccinyl peptides were designed and synthesized to develop a specific inhibitor of cathepsin B. Of these compounds, N-(L-3- trans-ethoxycarbonyloxirane-2-carbonyl)-L-isoleucyl-L-proline (compound CA-030) and N-(L-3- trans-propylcarbamoyloxirane-2-carbonyl)-L-isoleucyl-L-proline...
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| Veröffentlicht in: | FEBS letters 1991-03, Vol.280 (2), p.307-310 |
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| creator | Murata, Mitsuo Miyashita, Satsuki Yokoo, Chihiro Tamai, Musaharu Hanada, Kazunori Hatayama, Katsuo Towatari, Takae Nikawa, Takeshi Katunuma, Nobuhiko |
| description | A series of new epoxysuccinyl peptides were designed and synthesized to develop a specific inhibitor of cathepsin B. Of these compounds,
N-(L-3-
trans-ethoxycarbonyloxirane-2-carbonyl)-L-isoleucyl-L-proline (compound CA-030) and
N-(L-3-
trans-propylcarbamoyloxirane-2-carbonyl)-L-isoleucyl-L-proline (compound CA-074) were the most potent and specific inhibitors of cathepsin B in vitro. The carboxyl group of proline and the ethyl ester group or
n-propylamide group in the oxirane ring were necessary, the ethyl ester group or the
n-propylamide group being particularly effective for distinguishing cathepsin B from other cysteine proteinases such as cathepsins L and H, and calpains. |
| doi_str_mv | 10.1016/0014-5793(91)80318-W |
| format | Article |
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N-(L-3-
trans-ethoxycarbonyloxirane-2-carbonyl)-L-isoleucyl-L-proline (compound CA-030) and
N-(L-3-
trans-propylcarbamoyloxirane-2-carbonyl)-L-isoleucyl-L-proline (compound CA-074) were the most potent and specific inhibitors of cathepsin B in vitro. The carboxyl group of proline and the ethyl ester group or
n-propylamide group in the oxirane ring were necessary, the ethyl ester group or the
n-propylamide group being particularly effective for distinguishing cathepsin B from other cysteine proteinases such as cathepsins L and H, and calpains.</description><identifier>ISSN: 0014-5793</identifier><identifier>EISSN: 1873-3468</identifier><identifier>DOI: 10.1016/0014-5793(91)80318-W</identifier><identifier>PMID: 2013328</identifier><identifier>CODEN: FEBLAL</identifier><language>eng</language><publisher>Amsterdam: Elsevier B.V</publisher><subject>Analytical, structural and metabolic biochemistry ; Animals ; benzyloxycarbonyl ; Biological and medical sciences ; Calpain - chemistry ; Cathepsin B ; Cathepsin B - antagonists & inhibitors ; Cathepsin H ; Cathepsin L ; Cathepsins - chemistry ; Cysteine Endopeptidases ; Cysteine proteinase ; Dipeptides - pharmacology ; E-64-c (Ep-475) ; E-64-d (EST or Loxistatin) ; Endopeptidases ; Enzymes and enzyme inhibitors ; Epoxysuccinyl peptide ; Fundamental and applied biological sciences. Psychology ; Hydrolases ; In Vitro Techniques ; Leucine - analogs & derivatives ; Leucine - pharmacology ; Liver - drug effects ; Liver - enzymology ; MCA ; methylcoumarylamide ; N-(L-3-trans-Carboxyoxirane-2-carbonyl)-L-leucine-3-methylbutylamide ; N-(L-3-trans-Ethoxycarbonyloxirane-2-carbonyl)-L-leucine-3-methylbutylamide ; Rats ; Specific inhibitor</subject><ispartof>FEBS letters, 1991-03, Vol.280 (2), p.307-310</ispartof><rights>1991</rights><rights>FEBS Letters 280 (1991) 1873-3468 © 2015 Federation of European Biochemical Societies</rights><rights>1991 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c431W-b5c4f7d6ce4d863564b4b8a5d2182ce091643622e8f93b422f19c373304244e73</citedby><cites>FETCH-LOGICAL-c431W-b5c4f7d6ce4d863564b4b8a5d2182ce091643622e8f93b422f19c373304244e73</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/0014-5793(91)80318-W$$EHTML$$P50$$Gelsevier$$Hfree_for_read</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=19591362$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/2013328$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Murata, Mitsuo</creatorcontrib><creatorcontrib>Miyashita, Satsuki</creatorcontrib><creatorcontrib>Yokoo, Chihiro</creatorcontrib><creatorcontrib>Tamai, Musaharu</creatorcontrib><creatorcontrib>Hanada, Kazunori</creatorcontrib><creatorcontrib>Hatayama, Katsuo</creatorcontrib><creatorcontrib>Towatari, Takae</creatorcontrib><creatorcontrib>Nikawa, Takeshi</creatorcontrib><creatorcontrib>Katunuma, Nobuhiko</creatorcontrib><title>Novel epoxysuccinyl peptides Selective inhibitors of cathepsin B, in vitro</title><title>FEBS letters</title><addtitle>FEBS Lett</addtitle><description>A series of new epoxysuccinyl peptides were designed and synthesized to develop a specific inhibitor of cathepsin B. Of these compounds,
N-(L-3-
trans-ethoxycarbonyloxirane-2-carbonyl)-L-isoleucyl-L-proline (compound CA-030) and
N-(L-3-
trans-propylcarbamoyloxirane-2-carbonyl)-L-isoleucyl-L-proline (compound CA-074) were the most potent and specific inhibitors of cathepsin B in vitro. The carboxyl group of proline and the ethyl ester group or
n-propylamide group in the oxirane ring were necessary, the ethyl ester group or the
n-propylamide group being particularly effective for distinguishing cathepsin B from other cysteine proteinases such as cathepsins L and H, and calpains.</description><subject>Analytical, structural and metabolic biochemistry</subject><subject>Animals</subject><subject>benzyloxycarbonyl</subject><subject>Biological and medical sciences</subject><subject>Calpain - chemistry</subject><subject>Cathepsin B</subject><subject>Cathepsin B - antagonists & inhibitors</subject><subject>Cathepsin H</subject><subject>Cathepsin L</subject><subject>Cathepsins - chemistry</subject><subject>Cysteine Endopeptidases</subject><subject>Cysteine proteinase</subject><subject>Dipeptides - pharmacology</subject><subject>E-64-c (Ep-475)</subject><subject>E-64-d (EST or Loxistatin)</subject><subject>Endopeptidases</subject><subject>Enzymes and enzyme inhibitors</subject><subject>Epoxysuccinyl peptide</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Hydrolases</subject><subject>In Vitro Techniques</subject><subject>Leucine - analogs & derivatives</subject><subject>Leucine - pharmacology</subject><subject>Liver - drug effects</subject><subject>Liver - enzymology</subject><subject>MCA</subject><subject>methylcoumarylamide</subject><subject>N-(L-3-trans-Carboxyoxirane-2-carbonyl)-L-leucine-3-methylbutylamide</subject><subject>N-(L-3-trans-Ethoxycarbonyloxirane-2-carbonyl)-L-leucine-3-methylbutylamide</subject><subject>Rats</subject><subject>Specific inhibitor</subject><issn>0014-5793</issn><issn>1873-3468</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1991</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkUFP3DAQha0KRBfoPwApFyoqEfDYTmJfKgHaLa1WcKDVHq3EmQhX2TjY2aX77-uwK3qrOFme9-aN5zMhJ0AvgUJ-RSmINCsUP1fwRVIOMl18IBOQBU-5yOUembxZPpLDEH7TeJegDsgBo8A5kxPy496tsU2wd382YWWM7TZt0mM_2BpD8ogtmsGuMbHdk63s4HxIXJOYcnjCPtguubmIUrK2g3fHZL8p24CfducR-TWb_ry9S-cP377fXs9TIzgs0iozoinq3KCoZc6zXFSikmVWM5DMIFWQC54zhrJRvBKMNaAMLzinggmBBT8in7e5vXfPKwyDXtpgsG3LDt0qaEkzmuVURaPYGo13IXhsdO_tsvQbDVSPCPXIR498tAL9ilAvYtvpLn9VLbF-a9oxi_rZTi-DKdvGl52x4V-2yhTEBaJvtvW92BY375qtZ9MbNgpjXcFrdXzQ120QRqpri14HY7EzWFsfv0fXzv5_o7-12J-p</recordid><startdate>19910325</startdate><enddate>19910325</enddate><creator>Murata, Mitsuo</creator><creator>Miyashita, Satsuki</creator><creator>Yokoo, Chihiro</creator><creator>Tamai, Musaharu</creator><creator>Hanada, Kazunori</creator><creator>Hatayama, Katsuo</creator><creator>Towatari, Takae</creator><creator>Nikawa, Takeshi</creator><creator>Katunuma, Nobuhiko</creator><general>Elsevier B.V</general><general>Elsevier</general><scope>6I.</scope><scope>AAFTH</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>19910325</creationdate><title>Novel epoxysuccinyl peptides Selective inhibitors of cathepsin B, in vitro</title><author>Murata, Mitsuo ; Miyashita, Satsuki ; Yokoo, Chihiro ; Tamai, Musaharu ; Hanada, Kazunori ; Hatayama, Katsuo ; Towatari, Takae ; Nikawa, Takeshi ; Katunuma, Nobuhiko</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c431W-b5c4f7d6ce4d863564b4b8a5d2182ce091643622e8f93b422f19c373304244e73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1991</creationdate><topic>Analytical, structural and metabolic biochemistry</topic><topic>Animals</topic><topic>benzyloxycarbonyl</topic><topic>Biological and medical sciences</topic><topic>Calpain - chemistry</topic><topic>Cathepsin B</topic><topic>Cathepsin B - antagonists & inhibitors</topic><topic>Cathepsin H</topic><topic>Cathepsin L</topic><topic>Cathepsins - chemistry</topic><topic>Cysteine Endopeptidases</topic><topic>Cysteine proteinase</topic><topic>Dipeptides - pharmacology</topic><topic>E-64-c (Ep-475)</topic><topic>E-64-d (EST or Loxistatin)</topic><topic>Endopeptidases</topic><topic>Enzymes and enzyme inhibitors</topic><topic>Epoxysuccinyl peptide</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Hydrolases</topic><topic>In Vitro Techniques</topic><topic>Leucine - analogs & derivatives</topic><topic>Leucine - pharmacology</topic><topic>Liver - drug effects</topic><topic>Liver - enzymology</topic><topic>MCA</topic><topic>methylcoumarylamide</topic><topic>N-(L-3-trans-Carboxyoxirane-2-carbonyl)-L-leucine-3-methylbutylamide</topic><topic>N-(L-3-trans-Ethoxycarbonyloxirane-2-carbonyl)-L-leucine-3-methylbutylamide</topic><topic>Rats</topic><topic>Specific inhibitor</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Murata, Mitsuo</creatorcontrib><creatorcontrib>Miyashita, Satsuki</creatorcontrib><creatorcontrib>Yokoo, Chihiro</creatorcontrib><creatorcontrib>Tamai, Musaharu</creatorcontrib><creatorcontrib>Hanada, Kazunori</creatorcontrib><creatorcontrib>Hatayama, Katsuo</creatorcontrib><creatorcontrib>Towatari, Takae</creatorcontrib><creatorcontrib>Nikawa, Takeshi</creatorcontrib><creatorcontrib>Katunuma, Nobuhiko</creatorcontrib><collection>ScienceDirect Open Access Titles</collection><collection>Elsevier:ScienceDirect:Open Access</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>FEBS letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Murata, Mitsuo</au><au>Miyashita, Satsuki</au><au>Yokoo, Chihiro</au><au>Tamai, Musaharu</au><au>Hanada, Kazunori</au><au>Hatayama, Katsuo</au><au>Towatari, Takae</au><au>Nikawa, Takeshi</au><au>Katunuma, Nobuhiko</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Novel epoxysuccinyl peptides Selective inhibitors of cathepsin B, in vitro</atitle><jtitle>FEBS letters</jtitle><addtitle>FEBS Lett</addtitle><date>1991-03-25</date><risdate>1991</risdate><volume>280</volume><issue>2</issue><spage>307</spage><epage>310</epage><pages>307-310</pages><issn>0014-5793</issn><eissn>1873-3468</eissn><coden>FEBLAL</coden><abstract>A series of new epoxysuccinyl peptides were designed and synthesized to develop a specific inhibitor of cathepsin B. Of these compounds,
N-(L-3-
trans-ethoxycarbonyloxirane-2-carbonyl)-L-isoleucyl-L-proline (compound CA-030) and
N-(L-3-
trans-propylcarbamoyloxirane-2-carbonyl)-L-isoleucyl-L-proline (compound CA-074) were the most potent and specific inhibitors of cathepsin B in vitro. The carboxyl group of proline and the ethyl ester group or
n-propylamide group in the oxirane ring were necessary, the ethyl ester group or the
n-propylamide group being particularly effective for distinguishing cathepsin B from other cysteine proteinases such as cathepsins L and H, and calpains.</abstract><cop>Amsterdam</cop><pub>Elsevier B.V</pub><pmid>2013328</pmid><doi>10.1016/0014-5793(91)80318-W</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0014-5793 |
| ispartof | FEBS letters, 1991-03, Vol.280 (2), p.307-310 |
| issn | 0014-5793 1873-3468 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_80505609 |
| source | MEDLINE; ScienceDirect Journals (5 years ago - present); EZB-FREE-00999 freely available EZB journals; Alma/SFX Local Collection |
| subjects | Analytical, structural and metabolic biochemistry Animals benzyloxycarbonyl Biological and medical sciences Calpain - chemistry Cathepsin B Cathepsin B - antagonists & inhibitors Cathepsin H Cathepsin L Cathepsins - chemistry Cysteine Endopeptidases Cysteine proteinase Dipeptides - pharmacology E-64-c (Ep-475) E-64-d (EST or Loxistatin) Endopeptidases Enzymes and enzyme inhibitors Epoxysuccinyl peptide Fundamental and applied biological sciences. Psychology Hydrolases In Vitro Techniques Leucine - analogs & derivatives Leucine - pharmacology Liver - drug effects Liver - enzymology MCA methylcoumarylamide N-(L-3-trans-Carboxyoxirane-2-carbonyl)-L-leucine-3-methylbutylamide N-(L-3-trans-Ethoxycarbonyloxirane-2-carbonyl)-L-leucine-3-methylbutylamide Rats Specific inhibitor |
| title | Novel epoxysuccinyl peptides Selective inhibitors of cathepsin B, in vitro |
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