Kojic acid-amino acid amide metal complexes and their melanogenesis inhibitory activities

J Pept Sci. 2011 Dec;17(12):791-7. doi: 10.1002/psc.1404. Epub 2011 Sep 29.

Abstract

Tyrosinase plays a critical role in the early stages of the melanin synthetic pathway by catalyzing the oxidation of the substrate. Therefore, tyrosinase inhibitors have been intensively studied in both cosmetic and food industries to develop hypopigmentary agents and prevent enzymatic browning in food. Previously, we reported that kojic acid-amino acid amide (KA-AA-NH(2)) showed enhanced tyrosinase inhibitory activity compared with kojic acid alone, but this was not observed in a cell test because of poor cell permeability. To enhance cell permeability, we prepared copper and zinc complexes of KA-AA-NH(2) and characterized them using FT-IR spectroscopy, ESI-MS spectrometry, and inductively coupled plasma analysis. We then showed that KA-AA-NH(2) copper complexes exhibited melanogenesis inhibitory activity in Mel-Ab cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemical synthesis*
  • Amino Acids / pharmacology
  • Animals
  • Cell Line
  • Coordination Complexes / chemical synthesis*
  • Coordination Complexes / pharmacology
  • Copper / chemistry
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / pharmacology
  • Melanins / biosynthesis
  • Melanocytes / drug effects
  • Melanocytes / metabolism
  • Mice
  • Monophenol Monooxygenase / antagonists & inhibitors*
  • Monophenol Monooxygenase / metabolism
  • Pyrones / chemical synthesis*
  • Pyrones / pharmacology
  • Zinc / chemistry

Substances

  • Amino Acids
  • Coordination Complexes
  • Enzyme Inhibitors
  • Melanins
  • Pyrones
  • kojic acid
  • Copper
  • Monophenol Monooxygenase
  • Zinc