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Fluorescence studies on potential antitumor 6-(hetero)arylthieno[3,2-b]pyridine derivatives in solution and in nanoliposomes

Paper ID Volume ID Publish Year Pages File Format Full-Text
27508 44027 2013 11 PDF Available
Title
Fluorescence studies on potential antitumor 6-(hetero)arylthieno[3,2-b]pyridine derivatives in solution and in nanoliposomes
Abstract

•The fluorescence properties of four thienopyridine derivatives were studied.•The compounds were incorporated in lipid membranes of neat DPPC, DPPG, egg lecithin and DODAB.•The most promising antitumor compounds were encapsulated in nanoliposome formulations for future drug delivery applications.

The photophysical properties (absorption and fluorescence) of four 6-(hetero)arylthieno[3,2-b]pyridine derivatives, the methyl 3-amino-6-(thien-3-yl)thieno[3,2-b]pyridine-2-carboxylate 1, the methyl 3-amino-6-(2,2′-bithienyl-5-yl)thieno[3,2-b]pyridine-2-carboxylate 2, the methyl 3-amino-6-(thien-2-yl)thieno[3,2-b]pyridine-2-carboxylate 3 and the methyl 3-amino-6-(fur-3-yl)thieno[3,2-b]pyridine-2-carboxylate 4, evaluated previously as potential antitumor compounds, were studied in solvents of different polarity. All compounds have reasonable fluorescence quantum yields and exhibit a solvatochromic behaviour.The thienopyridine derivatives were incorporated in lipid membranes of neat egg-yolk phosphatidylcholine (egg-PC), dipalmitoyl phosphatidylcholine (DPPC), dipalmitoyl phosphatidylglycerol (DPPG) and dioctadecyldimethylammonium bromide (DODAB). Fluorescence measurements indicate that all compounds are mainly located in the lipid bilayer, feeling the transition from the rigid gel phase to the liquid-crystalline phase.The most promising antitumor compounds, the thien-3-yl and the 2,2′-bithienyl-5-yl thienopyridine derivatives 1 and 2, were encapsulated in different nanoliposome formulations, considering future drug delivery applications using liposomes as carriers. Almost all the liposomes with incorporated compounds have diameters lower than 165 nm and generally low polydispersity. The formulation DPPC:DMPG:DSPE-PEG (1:1:0.1) exhibits a small diameter (below 100 nm), low polydispersity and reasonable negative zeta-potential values for both thienopyridines 1 and 2.

Keywords
Thienopyridine derivatives; Antitumor compounds; Fluorescence anisotropy; Nanoliposomes
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Fluorescence studies on potential antitumor 6-(hetero)arylthieno[3,2-b]pyridine derivatives in solution and in nanoliposomes
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 264, 15 July 2013, Pages 56–66
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
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