Inhibitor selectivity between aldo-keto reductase superfamily members AKR1B10 and AKR1B1: role of Trp112 (Trp111)

FEBS Lett. 2013 Nov 15;587(22):3681-6. doi: 10.1016/j.febslet.2013.09.031. Epub 2013 Oct 4.

Abstract

The antineoplastic target aldo-keto reductase family member 1B10 (AKR1B10) and the critical polyol pathway enzyme aldose reductase (AKR1B1) share high structural similarity. Crystal structures reported here reveal a surprising Trp112 native conformation stabilized by a specific Gln114-centered hydrogen bond network in the AKR1B10 holoenzyme, and suggest that AKR1B1 inhibitors could retain their binding affinities toward AKR1B10 by inducing Trp112 flip to result in an "AKR1B1-like" active site in AKR1B10, while selective AKR1B10 inhibitors can take advantage of the broader active site of AKR1B10 provided by the native Trp112 side-chain orientation.

Keywords: AKR1A1; AKR1B1; AKR1B10; Crystal structure; FLF; Inhibitor selectivity; aldehyde reductase; aldose reductase aldo–keto reductase family1 member1; aldo–keto reductase family1 member10; flufenamic acid.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehyde Reductase / antagonists & inhibitors
  • Aldehyde Reductase / chemistry*
  • Aldo-Keto Reductases
  • Benzothiazoles / chemistry
  • Catalytic Domain
  • Crystallography, X-Ray
  • Enzyme Inhibitors / chemistry
  • Flufenamic Acid / chemistry
  • Hydrogen Bonding
  • Imidazolidines / chemistry
  • Models, Molecular
  • Naphthalenes / chemistry
  • Oleanolic Acid / chemistry
  • Phthalazines / chemistry
  • Protein Binding
  • Protein Structure, Secondary
  • Rhodanine / analogs & derivatives
  • Rhodanine / chemistry
  • Structural Homology, Protein
  • Thiazolidines / chemistry
  • Tryptophan / chemistry*

Substances

  • Benzothiazoles
  • Enzyme Inhibitors
  • Imidazolidines
  • Naphthalenes
  • Phthalazines
  • Thiazolidines
  • tolrestat
  • zopolrestat
  • epalrestat
  • Flufenamic Acid
  • Oleanolic Acid
  • Rhodanine
  • Tryptophan
  • fidarestat
  • AKR1B10 protein, human
  • Aldo-Keto Reductases
  • AKR1B1 protein, human
  • Aldehyde Reductase

Associated data

  • PDB/4GQG
  • PDB/4I5X
  • PDB/4JIH
  • PDB/4JII
  • PDB/4JIR