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

Radhakrishnan Venkatasamy, Laura Faas, Antony R. Young, Amala Raman, Robert C. Hider

Research output: Contribution to journalArticle

64 Scopus citations

Abstract

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-2E,4E-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.

Original languageEnglish (US)
Pages (from-to)1905-1920
Number of pages16
JournalBioorganic and Medicinal Chemistry
Volume12
Issue number8
DOIs
StatePublished - Apr 15 2004

Keywords

  • 12-O-Tetradecanoyl phorbol-13-acetate
  • CT
  • Cholera toxin
  • D
  • DCM
  • DMSO
  • Dendricity
  • Dicholormethane
  • Dimethyl sulfoxide
  • Distribution coefficient at pH 7.4
  • Melanocytes
  • Melanogenesis
  • Piperine analogues
  • SRB
  • Sulphorhodamine B
  • TCA
  • TPA
  • Vitiligo

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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