fulltext.study @t Gmail

Benzothienoquinolines: New one-pot synthesis and fluorescence studies of their interaction with DNA and polynucleotides

Paper ID Volume ID Publish Year Pages File Format Full-Text
26132 43936 2014 11 PDF Available
Title
Benzothienoquinolines: New one-pot synthesis and fluorescence studies of their interaction with DNA and polynucleotides
Abstract

•A new one-pot procedure for the synthesis of benzothienoquinolines was developed.•The interaction of benzothienoquinolines with nucleic acids was investigated.•Fluorescence and docking studies point to intercalation and groove binding to DNA.

In this work, we were able to obtain the benzothieno[3,2-b]quinoline 1 and benzothieno[2,3-c]quinoline 2 using a new one-pot procedure from the reaction of the commercially available 3-bromobenzo[b]thiophene-2-carbaldehyde with 2-aminophenylpinacolborane under Suzuki coupling conditions using a stereochemically hindered ligand, 2-(cyclohexylphosphane)biphenyl and Ba(OH)2·8H2O as the base.Fluorescence properties of the benzothieno[3,2-b]quinoline 1 and the benzothieno[2,3-c]quinoline 2 were studied in solvents of different polarity. Both compounds exhibit a solvent sensitive emission, compound 1 being less fluorescent (ΦF < 0.05) than compound 2 (0.04 ≤ ΦF ≤ 0.10).The interaction of these compounds with salmon sperm DNA and synthetic double-stranded heteropolynucleotides, poly(dA–dT)·(dA–dT) and poly(dG–dC)·(dG–dC), was studied using spectroscopic methods, allowing the determination of the intrinsic binding constants and binding site sizes. The interaction of both compounds is stronger with adenine–thymine (A–T) base pairs. Compound 1 is the most intercalative in salmon sperm DNA (47%) and polynucleotides (46–49% of intercalated molecules), while for compound 2, 41% is intercalated in salmon sperm DNA and only 8% in poly(dG–dC)·(dG–dC). Docking studies indicate that compound 1 interacts more strongly with DNA than compound 2, with a significant value of binding free energy in the case of intercalation. Minor groove binding is also very favourable and, probably, both mechanisms occur with a preponderance of intercalation in the case of compound 1.Overall, these results indicate that both benzothienoquinolines interact with nucleic acids by both intercalation and groove binding.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide

Keywords
Benzothieno[3,2-b]quinoline; Benzothieno[2,3-c]quinoline; DNA interaction; Polynucleotides; Fluorescence; Docking studies
First Page Preview
Benzothienoquinolines: New one-pot synthesis and fluorescence studies of their interaction with DNA and polynucleotides
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 294, 15 November 2014, Pages 20–30
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