Inhibiting AMPylation: a novel screen to identify the first small molecule inhibitors of protein AMPylation

ACS Chem Biol. 2014 Feb 21;9(2):433-42. doi: 10.1021/cb4006886. Epub 2013 Nov 25.

Abstract

Enzymatic transfer of the AMP portion of ATP to substrate proteins has recently been described as an essential mechanism of bacterial infection for several pathogens. The first AMPylator to be discovered, VopS from Vibrio parahemolyticus, catalyzes the transfer of AMP onto the host GTPases Cdc42 and Rac1. Modification of these proteins disrupts downstream signaling events, contributing to cell rounding and apoptosis, and recent studies have suggested that blocking AMPylation may be an effective route to stop infection. To date, however, no small molecule inhibitors have been discovered for any of the AMPylators. Therefore, we developed a fluorescence-polarization-based high-throughput screening assay and used it to discover the first inhibitors of protein AMPylation. Herein we report the discovery of the first small molecule VopS inhibitors (e.g., calmidazolium, GW7647, and MK886) with Ki's ranging from 6 to 50 μM and upward of 30-fold selectivity versus HYPE, the only known human AMPylator.

Publication types

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

MeSH terms

  • Adenosine Monophosphate / antagonists & inhibitors
  • Adenosine Monophosphate / metabolism*
  • Adenosine Triphosphate / antagonists & inhibitors
  • Adenosine Triphosphate / metabolism*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Bacterial Proteins / antagonists & inhibitors*
  • Bacterial Proteins / metabolism
  • Drug Discovery
  • High-Throughput Screening Assays
  • Humans
  • Small Molecule Libraries / chemistry
  • Small Molecule Libraries / pharmacology*
  • Vibrio Infections / drug therapy
  • Vibrio Infections / microbiology
  • Vibrio parahaemolyticus / drug effects*
  • Vibrio parahaemolyticus / metabolism*

Substances

  • Anti-Bacterial Agents
  • Bacterial Proteins
  • Small Molecule Libraries
  • Adenosine Monophosphate
  • Adenosine Triphosphate