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1,2,5-Thiadiazolidin-3-one 1,1 dioxide: a powerful scaffold for probing the S' subsites of (chymo)trypsin-like serine proteases

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dc.contributor Wichita State University. Department of Chemistry en_US
dc.contributor.author Groutas, William C. en_US
dc.contributor.author Epp, Jeffrey B. en_US
dc.contributor.author Kuang, Rongze en_US
dc.contributor.author Ruan, Sumei en_US
dc.contributor.author Chong, Lee S. en_US
dc.contributor.author Venkataraman, Radhika en_US
dc.contributor.author Tu, Juan en_US
dc.contributor.author He, Shu en_US
dc.contributor.author Yu, Hongyi en_US
dc.contributor.author Fu, Qingfong en_US
dc.contributor.author Li, Yue He en_US
dc.contributor.author Truong, Tien M. en_US
dc.contributor.author Vu, Nga T. en_US
dc.date.accessioned 2012-02-06T17:15:22Z
dc.date.available 2012-02-06T17:15:22Z
dc.date.issued 2001-01-01 en_US
dc.identifier 11361013 en_US
dc.identifier 0372430 en_US
dc.identifier S0003-9861(00)92139-8 en_US
dc.identifier HL57788 en_US
dc.identifier.citation Archives of biochemistry and biophysics. 2001 Jan 1; 385(1): 162-9. en_US
dc.identifier.issn 0003-9861 en_US
dc.identifier.uri http://dx.doi.org/10.1006/abbi.2000.2139 en_US
dc.identifier.uri http://hdl.handle.net/10057/4231
dc.description Click on the DOI link below to access the article (may not be free). en_US
dc.description.abstract The 1,2,5-thiadiazolidin-3-one 1,1 dioxide scaffold (I) embodies a motif that allows it to dock to the active site of (chymo)trypsin-like proteases in a predictable and substrate-like fashion. Consequently, inhibitors derived from this heterocyclic scaffold interact with both the S and S' subsites of an enzyme. Exploitation of binding interactions with both the S and S' subsites of a target enzyme may lead to compounds with greatly enhanced enzyme selectivity and inhibitory potency. This preliminary report describes the use of a series of compounds having the heterocyclic scaffold linked to various amino acids to probe the S' subsites of human leukocyte elastase (HLE), proteinase 3 (PR 3), and cathepsin G (Cat G). For comparative purposes, a series of compounds derived from a related scaffold, isothiazolidin-3-one 1,1 dioxide (II), was also generated. Several of the compounds were found to be highly potent and selective time-dependent inhibitors of HLE, PR 3, and Cat G. en_US
dc.description.sponsorship NHLBI NIH HHS en_US
dc.format.extent 162-9 en_US
dc.language.iso eng en_US
dc.publisher Elsevier en_US
dc.relation.ispartofseries Archives of biochemistry and biophysics en_US
dc.relation.ispartofseries Arch. Biochem. Biophys. en_US
dc.source NLM en_US
dc.subject Research Support, Non-U.S. Gov't en_US
dc.subject Research Support, U.S. Gov't, P.H.S. en_US
dc.subject.mesh Cathepsin G en_US
dc.subject.mesh Cathepsins/chemistry en_US
dc.subject.mesh Chymotrypsin/chemistry en_US
dc.subject.mesh Cyclic S-Oxides/chemistry en_US
dc.subject.mesh Humans en_US
dc.subject.mesh Kinetics en_US
dc.subject.mesh Leukocyte Elastase/chemistry en_US
dc.subject.mesh Models, Chemical en_US
dc.subject.mesh Molecular Probes/chemistry en_US
dc.subject.mesh Myeloblastin en_US
dc.subject.mesh Protein Binding en_US
dc.subject.mesh Serine Endopeptidases/chemistry en_US
dc.subject.mesh Temperature en_US
dc.subject.mesh Thiazoles/chemistry en_US
dc.subject.mesh Time Factors en_US
dc.subject.mesh Cathepsins/metabolism en_US
dc.subject.mesh Leukocyte Elastase/metabolism en_US
dc.subject.mesh Serine Endopeptidases/metabolism en_US
dc.title 1,2,5-Thiadiazolidin-3-one 1,1 dioxide: a powerful scaffold for probing the S' subsites of (chymo)trypsin-like serine proteases en_US
dc.type Article en_US
dc.coverage.spacial United States en_US
dc.description.version peer reviewed en_US
dc.rights.holder Copyright © 2001, Elsevier en_US

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