Development of 5-[(3-aminopropyl)phosphinooxy]-2-(hydroxymethyl)-4H-pyran-4-one as a novel whitening agent

被引：29

作者：

Kim, DH ^{[1
]}

Hwang, JS ^{[1
]}

Baek, HS ^{[1
]}

Kim, KJ ^{[1
]}

Lee, BG ^{[1
]}

Chang, I ^{[1
]}

Kang, HH ^{[1
]}

Lee, OS ^{[1
]}

机构：

[1] Amore Pacific Corp, R&D Ctr, Yongin 449729, Kyounggi Do, South Korea

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 2003年 / 51卷 / 02期

关键词：

Kojyl-APPA; kojic acid; tyrosinase inhibition; melanin synthesis;

D O I：

10.1248/cpb.51.113

中图分类号：

R914 [药物化学];

学科分类号：

100701 [药物化学];

摘要：

A stable derivative of kojic acid, 5-[(3-aminopropyl)phosphinooxyl]-2-(hydroxymethyl)-4H-pyran-4-one (Kojyl-APPA), was synthesized in good yield. The effects of Kojyl-APPA on tyrosinase activity and melanin synthesis were investigated. Kojyl-APPA showed tyrosinase inhibition effect (30%) in situ, but not in vitro. Kojyl-APPA inhibited tyrosinase activity significantly at 24 h after treatment in normal human melanocytes. It means that Kojyl-APPA is not a direct inhibitor of tyrosinase itself, but it is converted to a potential inhibitor kojic acid enzymatically in cells. In addition, Kojyl-APPA decreased melanin content to 75% of control in melanoma cells and decreased neomelanin synthesis to 43% of control in normal human melanocytes. Its permeation through skin increased by about 8 times as compared with kojic acid.

引用

页码：113 / 116

页数：4

共 15 条

[1]

ABERDAM E, 1993, J CELL SCI, V106, P1015

[2]

DOOLEY TP, 1994, SKIN PHARMACOL, V7, P188

[3]

HEARING VJ, 1987, METHOD ENZYMOL, V142, P154

[4]

MAMMALIAN TYROSINASE - COMPARISON OF TYROSINE HYDROXYLATION AND MELANIN FORMATION [J].

HEARING, VJ ;

EKEL, TM .

BIOCHEMICAL JOURNAL, 1976, 157 (03) :549-557

[5]

LEE OS, 1998, Patent No. 5723645

[6]

Hydroxy- or methoxy-substituted benzaldoximes and benzaldehyde-O-alkyloximes as tyrosinase inhibitors [J].

Ley, JP ;

Bertram, HJ .

BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (07) :1879-1885

[7]

LOTAN R, 1980, CANCER RES, V40, P3345

[8]

STIMULATION OF TYROSINASE IN HUMAN MELANOCYTES BY PRO-OPIOMELANOCORTIN-DERIVED PEPTIDES [J].

MCLEOD, SD ;

SMITH, C ;

MASON, RS .

JOURNAL OF ENDOCRINOLOGY, 1995, 146 (03) :439-447

[9]

FATE OF L[3,5-H-3] TYROSINE IN CELL-FREE EXTRACTS AND TISSUE-CULTURES OF MELANOMA CELLS - NEW ASSAY METHOD FOR TYROSINASE IN LIVING CELLS [J].

OIKAWA, A ;

NOHARA, M ;

NAKAYASU, M ;

TCHEN, TT .

ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1972, 148 (02) :548-&

[10]

L-TYROSINE3,5-3H ASSAY FOR TYROSINASE DEVELOPMENT IN SKIN OF NEWBORN HAMSTERS [J].

POMERANTZ, SH .

SCIENCE, 1969, 164 (3881) :838-+

← 1 2 →