2-Phenylquinoline-Sugar Hybrids as Photoswitchable α-Glucosidase Inhibitors

Chem Asian J. 2019 May 2;14(9):1409-1412. doi: 10.1002/asia.201900203. Epub 2019 Mar 26.

Abstract

Purpose-designed 2-phenylquinoline (PQ)-sugar hybrids 1 and 2 were synthesized and evaluated for their photodegradation activities against an α-glucosidase target. The results indicated that PQ-mannose hybrid 2 selectively and effectively photodegraded α-glucosidase and significantly inhibited its enzymatic activity upon irradiation with long-wavelength UV light in the absence of any additives under neutral and aqueous conditions. Furthermore, 2 selectively and effectively inhibited α-glucosidase activity only with photo-irradiation even in complex cell lysate.

Keywords: 2-phenylquinoline; C-glycosides; hydrolases; photodegradation; α-glucosidase.

MeSH terms

  • 1-Deoxynojirimycin / chemistry
  • Glucosamine / analogs & derivatives
  • Glucosamine / chemistry
  • Glycoside Hydrolase Inhibitors / chemical synthesis
  • Glycoside Hydrolase Inhibitors / chemistry*
  • Glycoside Hydrolase Inhibitors / metabolism
  • Monosaccharides / chemistry*
  • Photolysis / radiation effects
  • Quinolines / chemistry*
  • Ultraviolet Rays
  • alpha-Glucosidases / chemistry
  • alpha-Glucosidases / metabolism*

Substances

  • 2-phenylquinoline
  • Glycoside Hydrolase Inhibitors
  • Monosaccharides
  • Quinolines
  • deoxynojirimycine
  • 1-Deoxynojirimycin
  • alpha-Glucosidases
  • Glucosamine