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

• Published in: Bioorganic & medicinal chemistry letters Vol. 20; no. 2; pp. 738 - 741
• Main Authors: Kwak, Seon-Yeong, Noh, Jin-Mi, Park, So-Hee, Byun, Jang-Woong, Choi, Hye-Ryung, Park, Kyoung-Chan, Lee, Yoon-Sik
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier Ltd 15.01.2010; Elsevier
• Subjects: Animals; Biological and medical sciences; Cell Line, Tumor; Cell Membrane Permeability - drug effects; Cell permeability; Coordination Complexes - chemical synthesis; Coordination Complexes - chemistry; Coordination Complexes - pharmacology; Kojic acid derivatives; Medical sciences; Melanins - metabolism; Melanogenesis inhibition; Metal complex; Mice; Monophenol Monooxygenase - antagonists & inhibitors; Monophenol Monooxygenase - metabolism; Pharmacology. Drug treatments; Phenylalanine - analogs & derivatives; Phenylalanine - chemistry; Pyrones - chemistry; Skin, nail, hair, dermoskeleton; Spectroscopy, Fourier Transform Infrared; Tyrosinase inhibitor; Metal complex; Kojic acid derivatives; Tyrosinase inhibitor; Melanogenesis inhibition; Cell permeability; Fourier transformation; Enzyme; Aminoamide; Melanocyte; Organic ligand; Enzyme inhibitor; 4-Pyranone(5-hydroxy-2-hydroxymethyl); Transition metal Complexes; Monophenol monooxygenase; Melanogenesis; Copper Complexes; In vitro; Biological activity; Infrared spectrometry; α-Aminoacid; Oxidoreductases; Inhibition; Chemical synthesis; Zinc Complexes
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2009.11.069

The metal complexes of kojic acid–phenylalanine amide were prepared to enhance the cell permeability. 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.