N,C-Capped dipeptides with selectivity for mycobacterial proteasome over human proteasomes: role of S3 and S1 binding pockets

J Am Chem Soc. 2013 Jul 10;135(27):9968-71. doi: 10.1021/ja400021x. Epub 2013 Jun 25.

Abstract

We identified N,C-capped dipeptides that are selective for the Mycobacterium tuberculosis proteasome over human constitutive and immunoproteasomes. Differences in the S3 and S1 binding pockets appeared to account for the species selectivity. The inhibitors can penetrate mycobacteria and kill nonreplicating M. tuberculosis under nitrosative stress.

Publication types

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

MeSH terms

  • Binding Sites / drug effects
  • Dipeptides / chemistry
  • Dipeptides / pharmacology*
  • Dose-Response Relationship, Drug
  • Humans
  • Models, Molecular
  • Molecular Structure
  • Mycobacterium tuberculosis / chemistry
  • Mycobacterium tuberculosis / drug effects*
  • Proteasome Endopeptidase Complex / metabolism*
  • Structure-Activity Relationship

Substances

  • Dipeptides
  • Proteasome Endopeptidase Complex