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

•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...

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Bibliographic Details
Published in:Journal of photochemistry and photobiology. A, Chemistry. Chemistry., 2014-11, Vol.294, p.20-30
Main Authors: Rodrigues, A. Rita O., Carvalho, M. Solange D., Cardoso, J. André V., Calhelha, Ricardo C., Queiroz, Maria-João R.P., Coutinho, Paulo J.G., Castanheira, Elisabete M.S.
Format: Article
Language:English
Subjects:
Benzothieno[2,3-c]quinoline
Benzothieno[3,2-b]quinoline
DNA interaction
Docking studies
Fluorescence
Polynucleotides
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Summary:•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
ISSN:1010-6030
1873-2666
DOI:10.1016/j.jphotochem.2014.08.001