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

Duck Hee Kim; Jae Sung Hwang; Heung Soo Baek; Kil Joong Kim; Byeong Gon Lee; Ihseop Chang; Hak Hee Kang; Ok Sub Lee

doi:10.1248/cpb.51.113

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

Duck Hee Kim
, Jae Sung Hwang
, Heung Soo Baek
, Kil Joong Kim
, Byeong Gon Lee
, Ihseop Chang
, Hak Hee Kang
, Ok Sub Lee

Research output: Contribution to journal › Article › peer-review

33 Citations (Scopus)

Abstract

A stable derivative of kojic acid, 5-[(3-aminopropyl)phosphinooxy]-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.

Original language	English
Pages (from-to)	113-116
Number of pages	4
Journal	Chemical and Pharmaceutical Bulletin
Volume	51
Issue number	2
DOIs	https://doi.org/10.1248/cpb.51.113
Publication status	Published - Feb 2003

Keywords

Kojic acid
Kojyl-APPA
Melanin synthesis
Tyrosinase inhibition

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@article{8538a3f133f042abba695e4383cd6867,

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

abstract = "A stable derivative of kojic acid, 5-[(3-aminopropyl)phosphinooxy]-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.",

keywords = "Kojic acid, Kojyl-APPA, Melanin synthesis, Tyrosinase inhibition",

author = "Kim, \{Duck Hee\} and Hwang, \{Jae Sung\} and Baek, \{Heung Soo\} and Kim, \{Kil Joong\} and Lee, \{Byeong Gon\} and Ihseop Chang and Kang, \{Hak Hee\} and Lee, \{Ok Sub\}",

year = "2003",

month = feb,

doi = "10.1248/cpb.51.113",

language = "English",

volume = "51",

pages = "113--116",

journal = "Chemical and Pharmaceutical Bulletin",

issn = "0009-2363",

publisher = "Pharmaceutical Society of Japan",

number = "2",

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TY - JOUR

T1 - Development of 5-[(3-aminopropyl)phosphinooxy]-2-(hydroxymethyl)-4H-pyran- 4-one as a novel whitening agent

AU - Kim, Duck Hee

AU - Hwang, Jae Sung

AU - Baek, Heung Soo

AU - Kim, Kil Joong

AU - Lee, Byeong Gon

AU - Chang, Ihseop

AU - Kang, Hak Hee

AU - Lee, Ok Sub

PY - 2003/2

Y1 - 2003/2

N2 - A stable derivative of kojic acid, 5-[(3-aminopropyl)phosphinooxy]-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.

AB - A stable derivative of kojic acid, 5-[(3-aminopropyl)phosphinooxy]-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.

KW - Kojic acid

KW - Kojyl-APPA

KW - Melanin synthesis

KW - Tyrosinase inhibition

UR - https://www.scopus.com/pages/publications/0042522479

U2 - 10.1248/cpb.51.113

DO - 10.1248/cpb.51.113

M3 - Article

C2 - 12576642

AN - SCOPUS:0042522479

SN - 0009-2363

VL - 51

SP - 113

EP - 116

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

IS - 2

ER -

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

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Keywords

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