Bioevaluation of sixteen ADMDP stereoisomers toward alpha-galactosidase A: Development of a new pharmacological chaperone for the treatment of Fabry disease and potential enhancement of enzyme replacement therapy efficiency

Eur J Med Chem. 2016 Nov 10:123:14-20. doi: 10.1016/j.ejmech.2016.07.025. Epub 2016 Jul 15.

Abstract

A unique molecular library consisting of all sixteen synthetic ADMDP (1-aminodeoxy-DMDP) stereoisomers has been prepared and evaluated for inhibitory activity against α-Gal A, and ability to impart thermal stabilization of this enzyme. The results of this testing led us to develop a novel pharmacological chaperone for the treatment of Fabry disease. 3-Epimer ADMDP was found to be an effective pharmacological chaperone, able to rescue α-Gal A activity in the lymphoblast of the N215S Fabry patient-derived cell line, without impairment of cellular β-galactosidase activity. When 3-epimer ADMDP was administered with rh-α-Gal A (enzyme replacement therapy) for the treatment of Fabry patient-derived cell lines, improvements in the efficacy of rh-α-Gal A was observed, which suggests this small molecule can also provide clinical benefit of enzyme replacement therapy in Fabry disease.

Keywords: Enzyme replacement therapy; Fabry disease; Lysosomal storage diseases; Lysosomal α-galactosidase A; Pharmacological chaperone; Pyrrolidine-based iminosugar.

MeSH terms

  • Cell Line, Tumor
  • Enzyme Inhibitors / chemistry
  • Enzyme Replacement Therapy / methods*
  • Enzyme Stability / drug effects
  • Fabry Disease / drug therapy*
  • Humans
  • Imino Pyranoses / chemistry
  • Imino Pyranoses / pharmacology
  • Imino Pyranoses / therapeutic use
  • Imino Sugars / chemical synthesis
  • Imino Sugars / pharmacology*
  • Imino Sugars / therapeutic use
  • Mannitol / analogs & derivatives
  • Mannitol / chemistry
  • Mannitol / pharmacology
  • Mannitol / therapeutic use
  • Pyrrolidines / chemical synthesis
  • Pyrrolidines / pharmacology*
  • Pyrrolidines / therapeutic use
  • Small Molecule Libraries / chemistry
  • Small Molecule Libraries / pharmacology
  • Stereoisomerism
  • alpha-Galactosidase / drug effects*

Substances

  • 1-aminodeoxy-2,5-dideoxy-2,5-iminomannitol
  • Enzyme Inhibitors
  • Imino Pyranoses
  • Imino Sugars
  • Pyrrolidines
  • Small Molecule Libraries
  • Mannitol
  • alpha-Galactosidase