Click-generated triazole ureas as ultrapotent in vivo-active serine hydrolase inhibitors

Nat Chem Biol. 2011 May 15;7(7):469-78. doi: 10.1038/nchembio.579.

Abstract

Serine hydrolases are a diverse enzyme class representing ∼1% of all human proteins. The biological functions of most serine hydrolases remain poorly characterized owing to a lack of selective inhibitors to probe their activity in living systems. Here we show that a substantial number of serine hydrolases can be irreversibly inactivated by 1,2,3-triazole ureas, which show negligible cross-reactivity with other protein classes. Rapid lead optimization by click chemistry-enabled synthesis and competitive activity-based profiling identified 1,2,3-triazole ureas that selectively inhibit enzymes from diverse branches of the serine hydrolase class, including peptidases (acyl-peptide hydrolase, or APEH), lipases (platelet-activating factor acetylhydrolase-2, or PAFAH2) and uncharacterized hydrolases (α,β-hydrolase-11, or ABHD11), with exceptional potency in cells (sub-nanomolar) and mice (<1 mg kg(-1)). We show that APEH inhibition leads to accumulation of N-acetylated proteins and promotes proliferation in T cells. These data indicate 1,2,3-triazole ureas are a pharmacologically privileged chemotype for serine hydrolase inhibition, combining broad activity across the serine hydrolase class with tunable selectivity for individual enzymes.

Publication types

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

MeSH terms

  • Animals
  • Brain / enzymology
  • Cell Line, Tumor
  • Click Chemistry / methods*
  • Humans
  • Mice
  • Molecular Structure
  • Myocardium / enzymology
  • Serine Proteases / genetics
  • Serine Proteases / metabolism*
  • Serine Proteinase Inhibitors / chemical synthesis*
  • Serine Proteinase Inhibitors / chemistry
  • Serine Proteinase Inhibitors / pharmacology
  • T-Lymphocytes / drug effects
  • T-Lymphocytes / enzymology
  • Transfection
  • Triazoles / chemical synthesis*
  • Triazoles / chemistry
  • Triazoles / pharmacology
  • Urea / analogs & derivatives*
  • Urea / pharmacology

Substances

  • Serine Proteinase Inhibitors
  • Triazoles
  • Urea
  • Serine Proteases

Associated data

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