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Analogues of N-hydroxycinnamoylphenalkylamides as inhibitors of human melanocyte-tyrosinase
- Source :
- Bioorganic & Medicinal Chemistry Letters. 16:2252-2255
- Publication Year :
- 2006
- Publisher :
- Elsevier BV, 2006.
-
Abstract
- Melanin play a major role in human skin protection and their biosynthesis is vital. Due to their color, they contribute to the skin pigmentation. Tyrosinase is a key enzyme involved in the first stage of melanin synthesis, catalyzing the transformation of tyrosine to l-dopaquinone. The aim of the present study was to study molecules able to inhibit melanin synthesis through inhibition of tyrosinase and their potential use in treating pigmentation-related disorders. We targeted amides obtained from coupling p-hydroxycinnamic acid derivatives with phenylalkylamines. The biological activity was evaluated on human melanocytes by an assay which measures tyrosine-catalyzed L-Dopa oxidation. The most active amides were: trans-N-caffeoyltyramine, N-dihydrocaffeoyltyramine, and trans-N-dihydro-p-hydroxycinnamoyltyramine which induce complete inhibition at 0.1mM. At the latter concentration, kojic acid, which was used as the reference inhibitor, was inactive.
- Subjects :
- Tyrosinase
Clinical Biochemistry
Tyramine
Pharmaceutical Science
Human skin
Melanocyte
Biochemistry
Catalysis
Levodopa
Melanin
Structure-Activity Relationship
chemistry.chemical_compound
Caffeic Acids
Drug Discovery
Benzoquinones
medicine
Humans
Enzyme Inhibitors
Molecular Biology
Cells, Cultured
Pigmentation disorder
Skin
Melanins
integumentary system
biology
Monophenol Monooxygenase
Organic Chemistry
Biological activity
medicine.disease
Amides
Dihydroxyphenylalanine
medicine.anatomical_structure
chemistry
Pyrones
Enzyme inhibitor
biology.protein
Melanocytes
Tyrosine
Molecular Medicine
Kojic acid
Oxidation-Reduction
Pigmentation Disorders
Subjects
Details
- ISSN :
- 0960894X
- Volume :
- 16
- Database :
- OpenAIRE
- Journal :
- Bioorganic & Medicinal Chemistry Letters
- Accession number :
- edsair.doi.dedup.....6b83002c4879041bbbeffb69d4686a4f