Prenylated derivatives of baicalein and 3,7-dihydroxyflavone: Synthesis and study of their effects on tumor cell lines growth, cell cycle and apoptosis

• Type: Article in International Scientific Journal
• Date: 2011

Authors

Marta Perro Neves (Author) Other; Honorina Cidade (Author) FFUP; Madalena Pinto (Author) FFUP; Artur M S Silva (Author) Other; Luis Gales (Author) ICBAS; Ana Margarida Damas (Author) ICBAS; Raquel T Lima (Author) Other; Helena Vasconcelos, MH (Author) FFUP; Maria de Sao Jose Nascimento (Author) FFUP

Journal

Title: European Journal of Medicinal Chemistry

Vol. 46 No. 1

Pages: 2562-2574

ISSN: 0223-5234

Publisher: Elsevier

Indexing

ISI Web of Knowledge - 55 Citations

Scopus - 62 Citations

Scientific classification

FOS: Medical and Health sciences > Basic medicine

Other information

Authenticus ID: P-002-QXN

DOI: 10.1016/j.ejmech.2011.03.047

Abstract (EN): Fourteen baicalein and 3,7-dihydroxyflavone derivatives were synthesized and evaluated for their inhibitory activity against the in vitro growth of three human tumor cell lines. The synthetic approaches were based on the reaction with prenyl or geranyl bromide in alkaline medium, followed by cyclization of the respective monoprenylated derivative. Dihydropyranoflavonoids were also obtained by one-pot synthesis, using Montmorillonite K10 clay as catalyst combined with microwave irradiation. In vitro screening of the compounds for cell growth inhibitory activity revealed that the presence of one geranyl group was associated with a remarkable increase in the inhibitory activity. Moreover, for the 3,7-dihydroxyflavone derivatives a marked increase in growth inhibitory effect was also observed for compounds with furan and pyran fused rings. The most active compounds were also studied regarding their effect on cell cycle profile and induction of apoptosis. Overall the results point to the relevant role of the prenylation of flavone scaffold in the growth inhibitory activity of cancer cells.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 13