Development of 5-[(3-Aminopropyl)phosphinooxy]-2-(hydroxymethyl)-4H-pyran-4-one as a Novel Whitening Agent
| Autor: | Duck Hee Kim, Heung Soo Baek, Kil-Joong Kim, Ih-Seop Chang, Hak Hee Kang, Jae Sung Hwang, Byeong Gon Lee, Ok Sub Lee |
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| Rok vydání: | 2003 |
| Předmět: |
Tyrosinase
Guinea Pigs Skin Pigmentation Melanocyte Chemical synthesis Melanin Mice chemistry.chemical_compound Drug Discovery Tumor Cells Cultured medicine Animals Humans Technology Pharmaceutical Hydroxymethyl Melanoma Skin Melanins biology Chemistry General Chemistry General Medicine Permeation medicine.disease In vitro medicine.anatomical_structure Biochemistry Pyrones Enzyme inhibitor Pyran biology.protein Melanocytes Female Dermatologic Agents Kojic acid Nuclear chemistry |
| Zdroj: | Chemical and Pharmaceutical Bulletin. 51:113-116 |
| ISSN: | 1347-5223 0009-2363 |
| DOI: | 10.1248/cpb.51.113 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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