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Structure-based design and synthesis of small molecule protein-tyrosine phosphatase 1B inhibitors.

Abstract：

:Protein-tyrosine phosphatase (PTP) inhibitors are attractive as potential signal transduction-directed therapeutics which may be useful in the treatment of a variety of diseases. We have previously reported the X-ray structure of 1,1-difluoro-1-(2-naphthalenyl)methyl] phosphonic acid (4) complexed with the human the protein-tyrosine phosphatase 1B (PTP1B) and its use in the design of an analogue which binds with higher affinity within the catalytic site (Burke, T. R., Jr. et al. Biochemistry 1996, 35, 15989). In the current study, new naphthyldifluoromethyl phosphonic acids were designed bearing acidic functionality intended to interact with the PTP1B Arg47, which is situated just outside the catalytic pocket. This residue has been shown previously to provide key interactions with acidic residues of phosphotyrosyl-containing peptide substrates. Consistent with trends predicted by molecular dynamics calculations, the new analogues bound with 7- to 14-fold higher affinity than the parent 4, in principal validating the design rationale.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Yao ZJ,Ye B,Wu XW,Wang S,Wu L,Zhang ZY,Burke TR Jr

doi

10.1016/s0968-0896(98)00140-0

subject

Has Abstract

pub_date

1998-10-01 00:00:00

pages

1799-810

issue

10

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(98)00140-0

journal_volume

6

pub_type

杂志文章

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