BIOMAT Database Logo BIOMAT Database Logo

Kojic acid-amino acid conjugates as tyrosinase inhibitors. 2009

Jin-Mi Noh, and Seon-Yeong Kwak, and Hyo-Suk Seo, and Joo-Hyun Seo, and Byung-Gee Kim, and Yoon-Sik Lee
School of Chemical and Biological Engineering, Seoul National University, Seoul 151-744, Republic of Korea.

Kojic acid (KA), a well known tyrosinase inhibitor, has insufficient inhibitory activity and stability. We modified KA with amino acids and screened their tyrosinase inhibitory activity. Among them, kojic acid-phenylalanine amide (KA-F-NH(2)) showed the strongest inhibitory activity, which was maintained for over 3 months at 50 degrees C, and acted as a noncompetitive inhibitor as determined by kinetic analysis. It also exhibited dopachrome reducing activity. We also propose a new tyrosinase inhibition mechanism based on the docking simulation data.

UI MeSH Term Description Entries
D007700 Kinetics The rate dynamics in chemical or physical systems.
D011753 Pyrones Keto-pyrans.
D003198 Computer Simulation Computer-based representation of physical systems and phenomena such as chemical processes. Computational Modeling,Computational Modelling,Computer Models,In silico Modeling,In silico Models,In silico Simulation,Models, Computer,Computerized Models,Computer Model,Computer Simulations,Computerized Model,In silico Model,Model, Computer,Model, Computerized,Model, In silico,Modeling, Computational,Modeling, In silico,Modelling, Computational,Simulation, Computer,Simulation, In silico,Simulations, Computer
D004791 Enzyme Inhibitors Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. Enzyme Inhibitor,Inhibitor, Enzyme,Inhibitors, Enzyme
D000596 Amino Acids Organic compounds that generally contain an amino (-NH2) and a carboxyl (-COOH) group. Twenty alpha-amino acids are the subunits which are polymerized to form proteins. Amino Acid,Acid, Amino,Acids, Amino
D014442 Monophenol Monooxygenase An enzyme of the oxidoreductase class that catalyzes the reaction between L-tyrosine, L-dopa, and oxygen to yield L-dopa, dopaquinone, and water. It is a copper protein that acts also on catechols, catalyzing some of the same reactions as CATECHOL OXIDASE. EC 1.14.18.1. Dopa Oxidase,Phenoloxidase,Tyrosinase,Cresolase,Phenol Oxidase,Phenoloxidase A,Phenoloxidase B,Monooxygenase, Monophenol,Oxidase, Dopa,Oxidase, Phenol

Related Publications

Jin-Mi Noh, and Seon-Yeong Kwak, and Hyo-Suk Seo, and Joo-Hyun Seo, and Byung-Gee Kim, and Yoon-Sik Lee
Kojic acid-natural product conjugates as mushroom tyrosinase inhibitors.
September 2020, European journal of medicinal chemistry,
Jin-Mi Noh, and Seon-Yeong Kwak, and Hyo-Suk Seo, and Joo-Hyun Seo, and Byung-Gee Kim, and Yoon-Sik Lee
Combined kinetic studies and computational analysis on kojic acid analogous as tyrosinase inhibitors.
July 2014, Molecules (Basel, Switzerland),
Jin-Mi Noh, and Seon-Yeong Kwak, and Hyo-Suk Seo, and Joo-Hyun Seo, and Byung-Gee Kim, and Yoon-Sik Lee
Analysis of Kojic Acid Derivatives as Competitive Inhibitors of Tyrosinase: A Molecular Modeling Approach.
May 2021, Molecules (Basel, Switzerland),
Jin-Mi Noh, and Seon-Yeong Kwak, and Hyo-Suk Seo, and Joo-Hyun Seo, and Byung-Gee Kim, and Yoon-Sik Lee
1,2,3-Triazole-based kojic acid analogs as potent tyrosinase inhibitors: Design, synthesis and biological evaluation.
February 2019, Bioorganic chemistry,
Jin-Mi Noh, and Seon-Yeong Kwak, and Hyo-Suk Seo, and Joo-Hyun Seo, and Byung-Gee Kim, and Yoon-Sik Lee
Synthesis and biological evaluation of kojic acid derivatives containing 1,2,4-triazole as potent tyrosinase inhibitors.
November 2015, Chemical biology & drug design,
Jin-Mi Noh, and Seon-Yeong Kwak, and Hyo-Suk Seo, and Joo-Hyun Seo, and Byung-Gee Kim, and Yoon-Sik Lee
Design, synthesis, in vitro, and in silico evaluations of kojic acid derivatives linked to amino pyridine moiety as potent tyrosinase inhibitors.
November 2023, Heliyon,
Jin-Mi Noh, and Seon-Yeong Kwak, and Hyo-Suk Seo, and Joo-Hyun Seo, and Byung-Gee Kim, and Yoon-Sik Lee
Synthesis, anti-browning effect and mechanism research of kojic acid-coumarin derivatives as anti-tyrosinase inhibitors.
March 2024, Food chemistry: X,
Jin-Mi Noh, and Seon-Yeong Kwak, and Hyo-Suk Seo, and Joo-Hyun Seo, and Byung-Gee Kim, and Yoon-Sik Lee
Synthesis and biological evaluation of novel hydroxybenzaldehyde-based kojic acid analogues as inhibitors of mushroom tyrosinase.
February 2017, Bioorganic & medicinal chemistry letters,
Jin-Mi Noh, and Seon-Yeong Kwak, and Hyo-Suk Seo, and Joo-Hyun Seo, and Byung-Gee Kim, and Yoon-Sik Lee
Synthesis of tyrosinase inhibitory kojic acid derivative.
March 2006, Archiv der Pharmazie,
Jin-Mi Noh, and Seon-Yeong Kwak, and Hyo-Suk Seo, and Joo-Hyun Seo, and Byung-Gee Kim, and Yoon-Sik Lee
Application of kojic acid scaffold in the design of non-tyrosinase enzyme inhibitors.
August 2022, Chemical biology & drug design,
Copied contents to your clipboard!