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Synthesis of the first thieno-δ-carboline: Fluorescence studies in solution and in lipid vesicles

Paper ID Volume ID Publish Year Pages File Format Full-Text
28546 44080 2006 7 PDF Available
Title
Synthesis of the first thieno-δ-carboline: Fluorescence studies in solution and in lipid vesicles
Abstract

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 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-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.

Keywords
Palladium-assisted reactions; Thieno-δ-carboline; Fluorescence; Solvatochromic probes; Lipid vesicles
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 181, Issues 2–3, 31 July 2006, Pages 290–296
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us