Enhanced cell permeability of kojic acid-phenylalanine amide with metal complex

Bioorg Med Chem Lett. 2010 Jan 15;20(2):738-41. doi: 10.1016/j.bmcl.2009.11.069. Epub 2009 Dec 3.

Abstract

Kojic acid-phenylalanine amide (KA-F-NH(2)), which showed an excellent tyrosinase inhibitory activity, did not inhibit melanogenesis in melanocyte due to its low cell permeability. To enhance its cell permeability by increasing lipophilicity, we prepared metal coordination compounds of KA-F-NH(2) and characterized them by FT-IR and ICP analysis. The metal complex of KA-F-NH(2) inhibited mushroom tyrosinase activity as much as KA-F-NH(2) and reduced melanin contents in melanocyte efficiently.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Line, Tumor
  • Cell Membrane Permeability / drug effects
  • Coordination Complexes / chemical synthesis
  • Coordination Complexes / chemistry*
  • Coordination Complexes / pharmacology
  • Melanins / metabolism
  • Mice
  • Monophenol Monooxygenase / antagonists & inhibitors*
  • Monophenol Monooxygenase / metabolism
  • Phenylalanine / analogs & derivatives*
  • Phenylalanine / chemistry
  • Pyrones / chemistry*
  • Spectroscopy, Fourier Transform Infrared

Substances

  • Coordination Complexes
  • Melanins
  • Pyrones
  • Phenylalanine
  • phenylalanine amide
  • kojic acid
  • Monophenol Monooxygenase