A rapid oxime linker-based library approach to identification of bivalent inhibitors of the Yersinia pestis protein-tyrosine phosphatase, YopH

Bioorg Med Chem Lett. 2010 May 1;20(9):2813-6. doi: 10.1016/j.bmcl.2010.03.058. Epub 2010 Mar 15.

Abstract

A bivalent tethered approach toward YopH inhibitor development is presented that joins aldehydes with mixtures of bis-aminooxy-containing linkers using oxime coupling. The methodology is characterized by its facility and ease of use and its ability to rapidly identify low micromolar affinity inhibitors. The generality of the approach may potentially make it amenable to the development of bivalent inhibitors directed against other phosphatases.

Publication types

  • Research Support, N.I.H., Intramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Aldehydes / chemical synthesis
  • Aldehydes / chemistry*
  • Aldehydes / pharmacology
  • Bacterial Outer Membrane Proteins / antagonists & inhibitors*
  • Bacterial Outer Membrane Proteins / metabolism
  • Binding Sites
  • Computer Simulation
  • Crystallography, X-Ray
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacology
  • Oximes / chemistry*
  • Protein Tyrosine Phosphatases / antagonists & inhibitors*
  • Protein Tyrosine Phosphatases / metabolism
  • Small Molecule Libraries
  • Yersinia pestis / enzymology*

Substances

  • Aldehydes
  • Bacterial Outer Membrane Proteins
  • Enzyme Inhibitors
  • Oximes
  • Small Molecule Libraries
  • Protein Tyrosine Phosphatases
  • yopH protein, Yersinia