Mechanism-Based Inhibitors of the Human Sirtuin 5 Deacylase: Structure-Activity Relationship, Biostructural, and Kinetic Insight

Angew Chem Int Ed Engl. 2017 Nov 20;56(47):14836-14841. doi: 10.1002/anie.201709050. Epub 2017 Nov 2.

Abstract

The sirtuin enzymes are important regulatory deacylases in a variety of biochemical contexts and may therefore be potential therapeutic targets through either activation or inhibition by small molecules. Here, we describe the discovery of the most potent inhibitor of sirtuin 5 (SIRT5) reported to date. We provide rationalization of the mode of binding by solving co-crystal structures of selected inhibitors in complex with both human and zebrafish SIRT5, which provide insight for future optimization of inhibitors with more "drug-like" properties. Importantly, enzyme kinetic evaluation revealed a slow, tight-binding mechanism of inhibition, which is unprecedented for SIRT5. This is important information when applying inhibitors to probe mechanisms in biology.

Keywords: deacylases; drug discovery; enzyme inhibitors; posttranslational modifications; sirtuins.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Crystallography, X-Ray
  • Drug Discovery
  • Histone Deacetylase Inhibitors / chemistry*
  • Histone Deacetylase Inhibitors / pharmacology*
  • Humans
  • Kinetics
  • Molecular Structure
  • Sirtuins / antagonists & inhibitors*
  • Structure-Activity Relationship
  • Substrate Specificity
  • Zebrafish
  • Zebrafish Proteins / antagonists & inhibitors

Substances

  • Histone Deacetylase Inhibitors
  • Zebrafish Proteins
  • SIRT5 protein, human
  • Sirtuins