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TitleSynthesis of the first thieno-delta-carboline: fluorescence studies in solution and in lipid vesicles
Author(s)Queiroz, Maria João R. P.
Castanheira, Elisabete M. S.
Pinto, Ana M. R.
Ferreira, Isabel C. F. R.
Begouin, Agathe
Kirsch, G.
KeywordsPalladium-assisted reactions
Solvatochromic probes
Lipid vesicles
Issue dateJul-2006
JournalJournal of Photochemistry and Photobiology A: Chemistry
Citation"Journal of photochemistry and photobiology A : chemistry". ISSN 1010-6030. 181:2-3 (July 2006) 290-296.
Abstract(s)The first thieno-delta-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 palladium catalyzed 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-delta-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.
Publisher versionThe original publication is available at
AccessOpen access
Appears in Collections:CDF - FAMO - Artigos/Papers (with refereeing)

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