Effects of piperine analogues on stimulation of melanocyte proliferation and melanocyte differentiation

A wide range of piperine analogues has been synthesised in order to undertake a structure–activity study of their ability to stimulate melanocyte proliferation. Results demonstrate that an aromatic ring containing at least one ether function and a carbonyl group containing side chain is essential fo...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2004-04, Vol.12 (8), p.1905-1920
Main Authors: Venkatasamy, Radhakrishnan, Faas, Laura, Young, Antony R, Raman, Amala, Hider, Robert C
Format: Article
Language:English
Subjects:
Alkaloids
Animals
Benzodioxoles
Biological and medical sciences
Cell Differentiation - drug effects
Cell Differentiation - physiology
Cell Division - drug effects
Cell Division - physiology
Cells, Cultured
Dendricity
Dose-Response Relationship, Drug
Medical sciences
Melanocytes
Melanocytes - cytology
Melanocytes - drug effects
Melanogenesis
Mice
Mice, Inbred C57BL
Pharmacology. Drug treatments
Piperidines - chemistry
Piperidines - pharmacology
Piperine analogues
Polyunsaturated Alkamides
Skin, nail, hair, dermoskeleton
Vitiligo
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Summary:A wide range of piperine analogues has been synthesised in order to undertake a structure–activity study of their ability to stimulate melanocyte proliferation. Results demonstrate that an aromatic ring containing at least one ether function and a carbonyl group containing side chain is essential for this activity. A number of highly active piperine analogues have been identified, for instance 1-(3,4-methylenedioxyphenyl)-penta-2 E,4 E-dienoic acid methyl ester ( 5a), 1- E,E-piperinoyl-isobutylamine ( 4f) and 1-(3,4-methylenedioxyphenyl)-pentanoic acid cyclohexyl amide ( 20). A selection of analogues has also been evaluated for their effect on melanocyte morphology and melanogenesis. The piperine analogues altered cell morphology by increasing dendrite formation leading to bi-, tri- and quadripolar cells. These same analogues were found to increase total melanin in cell cultures, although melanin content per cell was not significantly altered from control in the presence of these compounds. Graphic
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2004.01.036