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Advisor(s)
Abstract(s)
The first thieno-δ-carboline (6,8,9-trimethyl-5H-pyrido[3,2-b]thieno[3,2-f]indole) was prepared in good yield (70%) by intramolecular
palladium-assisted cyclization of an ortho-chlorodiarylamine. The latter was in turn selectively synthesized in high yield (90%) by C–N palladiumcatalyzed
cross-coupling of 3-bromo-2-chloropyridine with, the also prepared, 6-amino-2,3,7-trimethylbenzo[b]thiophene. Fluorescence studies
in solution show that thieno-δ-carboline has a solvatochromic behaviour. Despite the low fluorescence quantum yields in solution, studies of its
incorporation in lipid vesicles of DPPC, DOPE and DODAB indicate that thienocarboline is located mainly inside the lipid bilayer, exhibiting different
behaviours in gel or liquid-crystalline phases. Our studies are useful for the incorporation of thienocarboline in liposomes and for controlled
drug release assays, due to its biological activity.
Description
Keywords
Palladium-assisted reactions Thieno-δ-carboline Fluorescence Solvatochromic probes Lipid vesicles
Citation
Queiroz, Maria João R.P.; Castanheira, Elisabete M.S.; Pinto, Ana M.R.; Ferreira, Isabel C.F.R.; Begouin, Agathe; Kirsch, Gilbert (2006). Synthesis of the first thieno-δ-carboline. Fluorescence studies in solution and in lipid vesicles. Journal of Photochemistry and Photobiology A: Chemistry. ISSN 1010-6030. 181:2-3, p. 290-296
Publisher
Elsevier