Evaluation of anti-pigmentary effect of synthetic sulfonylamino chalcone

Eur J Med Chem. 2010 May;45(5):2010-7. doi: 10.1016/j.ejmech.2010.01.049. Epub 2010 Jan 28.

Abstract

The 4'-(p-toluenesulfonylamino)-4-hydroxychalcone (TSAHC), which bears inhibitory chemotypes for both alpha-glucosidase and tyrosinase, was evaluated for tyrosinase activity and depigmenting ability relative to compounds designed to only target tyrosianse activity. TSAHC emerged to be a competitive reversible inhibitor of mushroom tyrosinase. More importantly, it was also able to return the melanin content of alpha-melanocyte stimulated by alpha-MSH to base levels unlike other inhibitors that only targeted tyrosinase. The Western blot for expression levels of proteins involved in melanogenesis showed that TSAHC significantly decreased three main tyrosinase related protein in melanin biosynthesis, tyrosinase, TRP-1 and TRP-2.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chalcone / analogs & derivatives*
  • Chalcone / chemistry
  • Chalcone / pharmacology
  • Drug Design
  • Enzyme Activation / drug effects
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Glycoside Hydrolase Inhibitors*
  • Molecular Structure
  • Monophenol Monooxygenase / antagonists & inhibitors*
  • Monophenol Monooxygenase / metabolism
  • Pigments, Biological / antagonists & inhibitors*
  • Stereoisomerism
  • Structure-Activity Relationship
  • Sulfonamides / chemistry
  • Sulfonamides / pharmacology*
  • alpha-Glucosidases / metabolism

Substances

  • 4'-(4-toluenesulfonylamido)-4-hydroxychalcone
  • Enzyme Inhibitors
  • Glycoside Hydrolase Inhibitors
  • Pigments, Biological
  • Sulfonamides
  • Chalcone
  • Monophenol Monooxygenase
  • alpha-Glucosidases