Structure activity relationships of human galactokinase inhibitors

Bioorg Med Chem Lett. 2015 Feb 1;25(3):721-7. doi: 10.1016/j.bmcl.2014.11.061. Epub 2014 Dec 13.

Abstract

Classic Galactosemia is a rare inborn error of metabolism that is caused by deficiency of galactose-1-phosphate uridyltransferase (GALT), an enzyme within the Leloir pathway that is responsible for the conversion of galactose-1-phosphate (gal-1-p) and UDP-glucose to glucose-1-phosphate and UDP-galactose. This deficiency results in elevated intracellular concentrations of its substrate, gal-1-p, and this increased concentration is believed to be the major pathogenic mechanism in Classic Galactosemia. Galactokinase (GALK) is an upstream enzyme of GALT in the Leloir pathway and is responsible for conversion of galactose and ATP to gal-1-p and ADP. Therefore, it was hypothesized that the identification of a small-molecule inhibitor of human GALK would act to prevent the accumulation of gal-1-p and offer a novel entry therapy for this disorder. Herein we describe a quantitative high-throughput screening campaign that identified a single chemotype that was optimized and validated as a GALK inhibitor.

Keywords: Galactokinase; Galactosemia; Structure–activity relationships.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Animals
  • Benzoxazoles / chemical synthesis
  • Benzoxazoles / chemistry
  • Benzoxazoles / metabolism
  • Crystallography, X-Ray
  • Galactokinase / antagonists & inhibitors*
  • Galactokinase / genetics
  • Galactokinase / metabolism
  • Galactosephosphates / metabolism
  • High-Throughput Screening Assays
  • Humans
  • Kinetics
  • Mice
  • Microsomes, Liver / metabolism
  • Molecular Conformation
  • Protein Binding
  • Rats
  • Recombinant Proteins / biosynthesis
  • Recombinant Proteins / chemistry
  • Recombinant Proteins / genetics
  • Spiro Compounds / chemistry
  • Structure-Activity Relationship

Substances

  • Benzoxazoles
  • Galactosephosphates
  • Recombinant Proteins
  • Spiro Compounds
  • galactose-1-phosphate
  • Galactokinase