fulltext.study @t Gmail

Interaction of antitumoral fluorescent heteroaromatic compounds, a benzothienopyrrole and two thienoindoles, with DNA and lipid membranes

Paper ID Volume ID Publish Year Pages File Format Full-Text
27063 43998 2012 12 PDF Available
Title
Interaction of antitumoral fluorescent heteroaromatic compounds, a benzothienopyrrole and two thienoindoles, with DNA and lipid membranes
Abstract

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.

► The fluorescence properties of a benzothienopyrrole and two thienoindoles were studied. ► The compounds were incorporated in lipid membranes of DPPC, DPPG, egg lecithin and DODAB. ► All compounds exhibited a growth inhibitory effect on three human tumor cell lines. ► The benzothienopyrrole showed a higher affinity to DNA than the two thienoindoles.

Keywords
DPPC, dipalmitoyl phosphatidylcholine; Egg-PC, phosphatidylcholine from egg yolk; DPPG, dipalmitoyl phosphatidylglycerol; DODAB, dioctadecyl-dimethylammonium bromide; PC, phosphatidylcholine; PG, phosphatidylglycerolBenzothienopyrrole; Thienoindole; Antit
First Page Preview
Interaction of antitumoral fluorescent heteroaromatic compounds, a benzothienopyrrole and two thienoindoles, with DNA and lipid membranes
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
Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 240, 15 July 2012, Pages 14–25
Authors
, , , , , , ,
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