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Discovery and structure-activity relationship of oxalylarylaminobenzoic acids as inhibitors of protein tyrosine phosphatase 1B.

Liu G, Szczepankiewicz BG, Pei Z, Janowick DA, Xin Z, Hajduk PJ, Abad-Zapatero C, Liang H, Hutchins CW, Fesik SW, Ballaron SJ, Stashko MA, Lubben T, Mika AK, Zinker BA, Trevillyan JM, Jirousek MR
J Med Chem 46 2093-103 (2003)
Cited: 29 times
EuropePMC logo PMID: 12747781

Abstract

Protein Tyrosine phosphatase 1B (PTP1B) has been implicated as a key negative regulator of both insulin and leptin signaling pathways. Using an NMR-based screening approach with 15N- and 13C-labeled PTP1B, we have identified 2,3-dimethylphenyloxalylaminobenzoic acid (1) as a general, reversible, and competitive PTPase inhibitor. Structure-based approach guided by X-ray crystallography facilitated the development of 1 into a novel series of potent and selective PTP1B inhibitors occupying both the catalytic site and a portion of the noncatalytic, second phosphotyrosine binding site. Interestingly, oral biovailability has been observed in rats for some compounds. Furthermore, we demonstrated in vivo plasma glucose lowering effects with compound 12d in ob/ob mice.

Articles - 1onz mentioned but not cited (3)

  1. Protein pockets: inventory, shape, and comparison. Coleman RG, Sharp KA. J Chem Inf Model 50 589-603 (2010)
  2. Synthesis, In Vitro, and Computational Studies of PTP1B Phosphatase Inhibitors Based on Oxovanadium(IV) and Dioxovanadium(V) Complexes. Kostrzewa T, Jończyk J, Drzeżdżon J, Jacewicz D, Górska-Ponikowska M, Kołaczkowski M, Kuban-Jankowska A. Int J Mol Sci 23 7034 (2022)
  3. research-article Native dynamics and allosteric responses in PTP1B probed by high-resolution HDX-MS. Woods VA, Abzalimov RR, Keedy DA. bioRxiv 2023.07.12.548582 (2023)


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