title: alpha-Ketocarboxylic acid-based inhibitors of protein tyrosine phosphatases.
abstract: A series of aryl alpha-ketocarboxylic acids was synthesized and investigated as inhibitors for the protein tyrosine phosphatase from Yersinia enterocolitica. IC(50) values for these compounds range from 79 to 2700 microM. Larger aromatic groups, and aromatic groups with high electron density, lead to more potent inhibitors. In general, the related aryl alpha-hydroxycarboxylic acids show lower activity.
authors.affiliation: Department of Chemistry, Brown University, 02912, Providence, RI, USA.
authors.forename: Y T
authors.initials: YT
authors.lastname: Chen
authors.forename: M B
authors.initials: MB
authors.lastname: Onaran
authors.forename: C J
authors.initials: CJ
authors.lastname: Doss
authors.forename: C T
authors.initials: CT
authors.lastname: Seto
mesh_terms: D001665:Binding Sites / Q000502:physiology; D002264:Carboxylic Acids / Q000138:chemical synthesis / Q000494:pharmacology; D015195:Drug Design; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D020128:Inhibitory Concentration 50; D007659:Ketones / Q000737:chemistry; D010084:Oxidation-Reduction; D019000:Phosphotyrosine / Q000737:chemistry; D017027:Protein Tyrosine Phosphatases / Q000037:antagonists & inhibitors*; D015008:Yersinia enterocolitica / Q000201:enzymology*
chemical_list: D002264:Carboxylic Acids; D004791:Enzyme Inhibitors; D007659:Ketones; D019000:Phosphotyrosine; D017027:Protein Tyrosine Phosphatases