Fluorescence properties of a potential antitumoral benzothieno[3,2-b]pyrrole in solution and lipid membranes

• Type: Article in International Scientific Journal
• Date: 2009

Authors

Elisabete M S Castanheira (Author) Other; Ana S Abreu (Author) Other; Maria Joao R P Queiroz (Author) Other; Paula M T Ferreira (Author) Other; Paulo J G Coutinho (Author) Other; Nair Nazareth (Author) Other; Sao Jose J Nascimento (Author) FFUP

Journal

Title: Journal of Photochemistry and Photobiology A: Chemistry

Vol. 206

Pages: 220-226

ISSN: 1010-6030

Publisher: Elsevier

Indexing

ISI Web of Knowledge - 5 Citations

Scopus - 5 Citations

Scientific classification

FOS: Natural sciences > Chemical sciences

Other information

Authenticus ID: P-003-GRD

DOI: 10.1016/j.jphotochem.2009.07.007

Abstract (EN): Fluorescence properties of the antitumoral methyl 3-(benzo[b]thien-2-yl)-benzothieno[3,2-b]pyrrole-2-carboxylate (BTP) were studied in solution and in lipid bilayers of dipalmitoyl phosphatidylcholine (DPPC), dioleoyl phosphatidylethanol ami ne (DOPE) and egg yolk phosphatidylcholine (Egg-PC). BTP presents good fluorescence quantum yields in all solvents studied (0.20 <= phi(F) <= 0.32) and a bathochromic shift in polar solvents. The results indicate an ICT character of the excited state, with an estimated dipole moment of mu e = 7.38 D. Fluorescence (steady-state) anisotropy measurements of BTP incorporated in lipid membranes of DPPC, DOPE and Egg-PC indicate that this compound is deeply located in the lipid bilayer, feeling the difference between the rigid gel phase and fluid phases. BTP inhibits the growth of three human tumour cell lines, MCF-7 (breast adenocarcinoma), SF-268 (glioma) and NCI-H460(non-small cell lung cancer), being significantly more potent against the NCI-H460 tumour cells.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 7