α-Ketocarboxylic acid-based inhibitors of protein tyrosine phosphatases

被引：28

作者：

Chen, YT ^{[1
]}

Onaran, MB ^{[1
]}

Doss, CJ ^{[1
]}

Seto, CT ^{[1
]}

机构：

[1] Brown Univ, Dept Chem, Providence, RI 02912 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2001年 / 11卷 / 14期

关键词：

D O I：

10.1016/S0960-894X(01)00325-0

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of aryl alpha -ketocarboxylic acids was synthesized and investigated as inhibitors for the protein tyrosine phosphatase from Yersinia enrerocolitica. IC50 values for these compounds range from 79 to 2700 muM. 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. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：1935 / 1938

页数：4

共 26 条

[1] 2-(Oxalylamino)-benzoic acid is a general, competitive inhibitor of protein-tyrosine phosphatases [J].

Andersen, HS ;

Iversen, LF ;

Jeppesen, CB ;

Branner, S ;

Norris, K ;

Rasmussen, HB ;

Moller, KB ;

Moller, NPH .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2000, 275 (10) :7101-7108

[2] ALPHA-DIKETONE AND ALPHA-KETO ESTER DERIVATIVES OF N-PROTECTED AMINO-ACIDS AND PEPTIDES AS NOVEL INHIBITORS OF CYSTEINE AND SERINE PROTEINASES [J].

ANGELASTRO, MR ;

MEHDI, S ;

BURKHART, JP ;

PEET, NP ;

BEY, P .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (01) :11-13

[3] Ligands for the tyrosine kinase p56lck SH2 domain:: Discovery of potent dipeptide derivatives with monocharged, nonhydrolyzable phosphate replacements [J].

Beaulieu, PL ;

Cameron, DR ;

Ferland, JM ;

Gauthier, J ;

Ghiro, E ;

Gillard, J ;

Gorys, V ;

Poirier, M ;

Rancourt, J ;

Wernic, D ;

Llinas-Brunet, M ;

Betageri, R ;

Cardozo, M ;

Hickey, ER ;

Ingraham, R ;

Jakes, S ;

Kabcenell, A ;

Kirrane, T ;

Lukas, S ;

Patel, U ;

Proudfoot, J ;

Sharma, R ;

Tong, L ;

Moss, N .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (10) :1757-1766

[4]

Burke TR, 1998, BIOPOLYMERS, V47, P225, DOI 10.1002/(SICI)1097-0282(1998)47:3<225::AID-BIP3>3.0.CO

[5]

2-O

[6] 4'-O-[2-(2-fluoromalonyl)]-L-tyrosine: A phosphotyrosyl mimic for the preparation of signal transduction inhibitory peptides [J].

Burke, TR ;

Ye, B ;

Akamatsu, M ;

Ford, H ;

Yan, XJ ;

Kole, HK ;

Wolf, G ;

Shoelson, SE ;

Roller, PP .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (05) :1021-1027

[7] Protein-tyrosine phosphatase-1B acts as a negative regulator of insulin signal transduction [J].

Byon, JCH ;

Kusari, AB ;

Kusari, J .

MOLECULAR AND CELLULAR BIOCHEMISTRY, 1998, 182 (1-2) :101-108

[8] Peptide ligands of pp60(c-src) SH2 domains: A thermodynamic and structural study [J].

Charifson, PS ;

Shewchuk, LM ;

Rocque, W ;

Hummel, CW ;

Jordan, SR ;

Mohr, C ;

Pacofsky, GJ ;

Peel, MR ;

Rodriguez, M ;

Sternbach, DD ;

Consler, TG .

BIOCHEMISTRY, 1997, 36 (21) :6283-6293

[9]

DIMICO A, 1995, TETRAHEDRON LETT, V36, P2679

[10] Increased insulin sensitivity and obesity resistance in mice lacking the protein tyrosine phosphatase-1B gene [J].

Elchebly, M ;

Payette, P ;

Michaliszyn, E ;

Cromlish, W ;

Collins, S ;

Loy, AL ;

Normandin, D ;

Cheng, A ;

Himms-Hagen, J ;

Chan, CC ;

Ramachandran, C ;

Gresser, MJ ;

Tremblay, ML ;

Kennedy, BP .

SCIENCE, 1999, 283 (5407) :1544-1548

← 1 2 3 →