Please use this identifier to cite or link to this item: http://hdl.handle.net/1822/19590

TitleInteraction of antitumoral fluorescent heteroaromatic compounds, a benzothienopyrrole and two thienoindoles, with DNA and lipid membranes
Author(s)Abreu, Ana S.
Castanheira, Elisabete M. S.
Coutinho, Paulo J. G.
Queiroz, Maria João R. P.
Ferreira, Paula M. T.
Silva, Luís A. Vale
Pinto, Eugénia
KeywordsBenzothienopyrrole
Thienoindole
Antitumor activity
Fluorescence
Lipid membranes
DNA binding
Issue date15-Jul-2012
PublisherElsevier
JournalJournal of photochemistry and photobiology A : chemistry
Abstract(s)Three tricyclic compounds, a benzothieno[2,3-b]pyrrole 1, a thieno[3,2-f]indole 2 and a thieno[2,3-e]indole 3, early synthesized by us, were evaluated for their capacity to inhibit the in vitro growth of three human tumor cell lines, MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer) and SF-268 (CNS cancer) and it was found that compound 1 is the most potent presenting the lowest GI50 values (7.9-14.1 µM). The photophysical properties of the three compounds (absorption and fluorescence) were studied in different solvents and in lipid membranes of dipalmitoyl phosphatidylcholine (DPPC), dioctadecyldimethylammonium bromide (DODAB), phosphatidylcholine from egg yolk (egg lecithin, Egg-PC) and dipalmitoyl phosphatidylglycerol (DPPG), considering future drug delivery applications using liposomes. Fluorescence measurements indicate that all the compounds incorporated in lipid membranes are mainly located in the lipid bilayer. Compounds 1 and 3 clearly detect the gel to liquid-crystalline phase transition, while compound 2 feels a more hydrated environment in DPPG and DODAB vesicles. Due to the antitumoral properties of the three fluorescent compounds, interactions with salmon sperm DNA were investigated using fluorescence techniques which allowed the determination of binding constants (Ki) and binding site sizes (n) for each compound. When compared with the thienoindoles 2 and 3, the benzothienopyrrole 1 showed the highest affinity to DNA. Quenching experiments with iodide ion showed that intercalation is the preferred mode of binding of the three compounds to the DNA molecule.
TypeArticle
URIhttp://hdl.handle.net/1822/19590
DOI10.1016/j.jphotochem.2012.05.009
ISSN1010-6030
Publisher versionwww.sciencedirect.com
Peer-Reviewedyes
AccessRestricted access (UMinho)
Appears in Collections:CDF - FAMO - Artigos/Papers (with refereeing)
CDQuim - Artigos (Papers)

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