Depigmenting activities of kojic acid derivatives without tyrosinase inhibitory activities

被引:18
作者
Cho, Jun-Cheol [2 ]
Rho, Ho Sik [1 ]
Joo, Yung Hyup [1 ]
Lee, Chang Seok [1 ]
Lee, Jaekyoung [1 ]
Ahn, Soo Mi [3 ]
Kim, Jung Eun [4 ]
Shin, Song Seok [1 ]
Park, Young-Ho [1 ]
Suh, Kyung-Do [2 ]
Park, Soo Nam [4 ]
机构
[1] AmorePacific Corp, R&D Ctr, Yongin 446729, South Korea
[2] Hanyang Univ, Coll Engn, Div Chem Engn, Seoul 133791, South Korea
[3] Kyung Hee Univ, Skin Biotechnol Ctr, Suwon 443270, South Korea
[4] Seoul Natl Univ Sci & Technol, Dept Fine Chem, Seoul 139743, South Korea
关键词
Depigmentation; Tyrosinase; Hydroxylbenzoic acid; Kojic acid; KOJYL THIOETHER DERIVATIVES;
D O I
10.1016/j.bmcl.2012.04.046
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
We synthesized benzoate ester derivatives of kojic acid with and without adamantane moiety. Benzoate derivatives 2a-e that did not contain an adamantane moiety showed potent tyrosinase inhibitory activities. However, depigmenting activity was not noted in a cell-based assay. Contrasting results were obtained for benzoate derivatives (3a-e) containing an adamantane moiety. Compounds 3a-e showed potent depigmenting activities without tyrosinase inhibitory activities. To the best of our knowledge, this is the first study showing the depigmenting activities of kojic acid derivatives without tyrosinase inhibitory activities. (C) 2012 Published by Elsevier Ltd.
引用
收藏
页码:4159 / 4162
页数:4
相关论文
共 22 条
[1]   Inhibitory activity of novel kojic acid derivative containing trolox moiety on melanogenesis [J].
Ahn, Soo Mi ;
Rho, Ho Sik ;
Baek, Heung Soo ;
Joo, Yung Hyup ;
Hong, Yong Deog ;
Shin, Song Seok ;
Park, Young-Ho ;
Park, Soo Nam .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (24) :7466-7469
[2]   Identification of a composite enhancer of the human tyrosinase-related protein 2/DOPAchrome tautomerase gene [J].
Amae, S ;
Yasumoto, K ;
Takeda, K ;
Udono, T ;
Takahashi, K ;
Shibahara, S .
BIOCHIMICA ET BIOPHYSICA ACTA-GENE STRUCTURE AND EXPRESSION, 2000, 1492 (2-3) :505-508
[3]  
Baek HS, 2008, B KOREAN CHEM SOC, V29, P43
[4]   Inhibition of the catecholase activity of biomimetic dinuclear copper complexes by kojic acid [J].
Battaini, G ;
Monzani, E ;
Casella, L ;
Santagostini, L ;
Pagliarin, R .
JOURNAL OF BIOLOGICAL INORGANIC CHEMISTRY, 2000, 5 (02) :262-268
[5]   Depigmenting activity of new kojic acid derivative obtained as a side product in the synthesis of cinnamate of kojic acid [J].
Cho, Jun-Cheol ;
Rho, Ho Sik ;
Baek, Heung Soo ;
Ahn, Soo Mi ;
Woo, Byoung Young ;
Hong, Yong Deog ;
Cheon, Jong Woo ;
Heo, Jung Mi ;
Shin, Song Seok ;
Park, Young-Ho ;
Suh, Kyung-Do .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (05) :2004-2007
[6]   TRP-1 EXPRESSION CORRELATES WITH EUMELANOGENESIS IN HUMAN PIGMENT-CELLS IN CULTURE [J].
DELMARMOL, V ;
ITO, S ;
JACKSON, I ;
VACHTENHEIM, J ;
BERR, P ;
GHANEM, G ;
MORANDINI, R ;
WAKAMATSU, K ;
HUEZ, G .
FEBS LETTERS, 1993, 327 (03) :307-310
[7]   Synthesis of kojic acid derivatives containing phenolic hydroxy groups [J].
Kadokawa, J ;
Nishikura, T ;
Muraoka, R ;
Tagaya, H ;
Fukuoka, N .
SYNTHETIC COMMUNICATIONS, 2003, 33 (07) :1081-1086
[8]   Chalcones as potent tyrosinase inhibitors: the importance of a 2,4-substituted resorcinol moiety [J].
Khatib, S ;
Nerya, O ;
Musa, R ;
Shmuel, M ;
Tamir, S ;
Vaya, J .
BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (02) :433-441
[9]   Enhanced cell permeability of kojic acid-phenylalanine amide with metal complex [J].
Kwak, Seon-Yeong ;
Noh, Jin-Mi ;
Park, So-Hee ;
Byun, Jang-Woong ;
Choi, Hye-Ryung ;
Park, Kyoung-Chan ;
Lee, Yoon-Sik .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (02) :738-741
[10]   The entrapment of kojic oleate in bilayer vesicles [J].
Manosroi, A ;
Wongtrakul, P ;
Manosroi, J ;
Midorikawa, U ;
Hanyu, Y ;
Yuasa, M ;
Sugawara, F ;
Sakai, H ;
Abe, A .
INTERNATIONAL JOURNAL OF PHARMACEUTICS, 2005, 298 (01) :13-25