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

Detalhes bibliográficos
Autor(a) principal: Rodrigues, Ana Rita O.
Data de Publicação: 2014
Outros Autores: Carvalho, M. Solange D., Cardoso, J. André V., Calhelha, Ricardo C., Queiroz, Maria João R. P., Coutinho, Paulo J. G., Castanheira, Elisabete M. S.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: https://hdl.handle.net/1822/30740
Resumo: Revised version. "Available online 10 August 2014"
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spelling Benzothienoquinolines: new one-pot synthesis and fluorescence studies of their interaction with DNA and polynucleotidesBenzothieno[3,2-c]quinolineDNA interactionPolynucleotidesFluorescenceDocking studiesBenzothieno[3,2-b]quinolineBenzothieno[2,3-c]quinolineCiências Naturais::Ciências FísicasScience & TechnologyRevised version. "Available online 10 August 2014"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 (quantum yield < 0.05) than compound 2 (quantum yield between 0.04 and 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 favorable 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.Foundation for the Science and Technology (FCT, Portugal), for financial support to the Portuguese NMR network (PTNMR) and also to FEDER and QREN for financial support to the Research Centres, CFUM [Strategic Project PEst-C/FIS/UI0607/2013 (FCOMP-01-0124-FEDER-037291)] and CQ/UM [Strategic Project PEst-C/QUI/UI0686/2013 (FCOMP-01-0124-FEDER-037302)], and to the research project PTDC/QUI-QUI/111060/2009 (F-COMP-01-0124-FEDER-015603) also financed by COMPETE/QREN/EU. FCT, POPH-QREN and FSE are acknowledged for the PhD grants of A.R.O.R. (SFRH/BD/90949/2012) and M.S.D.C. (SFRH/BD/47052/2008), for the Post-Doc. Grant of R.C.C. (SFRH/BPD/68344/2010) and for support to MAP-Fis Doctoral Program.ElsevierUniversidade do MinhoRodrigues, Ana 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.2014-112014-11-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/1822/30740eng1010-603010.1016/j.jphotochem.2014.08.001www.sciencedirect.cominfo:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-07-21T12:23:58ZPortal AgregadorONG
dc.title.none.fl_str_mv Benzothienoquinolines: new one-pot synthesis and fluorescence studies of their interaction with DNA and polynucleotides
title Benzothienoquinolines: new one-pot synthesis and fluorescence studies of their interaction with DNA and polynucleotides
spellingShingle Benzothienoquinolines: new one-pot synthesis and fluorescence studies of their interaction with DNA and polynucleotides
Rodrigues, Ana Rita O.
Benzothieno[3,2-c]quinoline
DNA interaction
Polynucleotides
Fluorescence
Docking studies
Benzothieno[3,2-b]quinoline
Benzothieno[2,3-c]quinoline
Ciências Naturais::Ciências Físicas
Science & Technology
title_short Benzothienoquinolines: new one-pot synthesis and fluorescence studies of their interaction with DNA and polynucleotides
title_full Benzothienoquinolines: new one-pot synthesis and fluorescence studies of their interaction with DNA and polynucleotides
title_fullStr Benzothienoquinolines: new one-pot synthesis and fluorescence studies of their interaction with DNA and polynucleotides
title_full_unstemmed Benzothienoquinolines: new one-pot synthesis and fluorescence studies of their interaction with DNA and polynucleotides
title_sort Benzothienoquinolines: new one-pot synthesis and fluorescence studies of their interaction with DNA and polynucleotides
author Rodrigues, Ana Rita O.
author_facet Rodrigues, Ana 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.
author_role author
author2 Carvalho, M. Solange D.
Cardoso, J. André V.
Calhelha, Ricardo C.
Queiroz, Maria João R. P.
Coutinho, Paulo J. G.
Castanheira, Elisabete M. S.
author2_role author
author
author
author
author
author
dc.contributor.none.fl_str_mv Universidade do Minho
dc.contributor.author.fl_str_mv Rodrigues, Ana 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.
dc.subject.por.fl_str_mv Benzothieno[3,2-c]quinoline
DNA interaction
Polynucleotides
Fluorescence
Docking studies
Benzothieno[3,2-b]quinoline
Benzothieno[2,3-c]quinoline
Ciências Naturais::Ciências Físicas
Science & Technology
topic Benzothieno[3,2-c]quinoline
DNA interaction
Polynucleotides
Fluorescence
Docking studies
Benzothieno[3,2-b]quinoline
Benzothieno[2,3-c]quinoline
Ciências Naturais::Ciências Físicas
Science & Technology
description Revised version. "Available online 10 August 2014"
publishDate 2014
dc.date.none.fl_str_mv 2014-11
2014-11-01T00:00:00Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv https://hdl.handle.net/1822/30740
url https://hdl.handle.net/1822/30740
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 1010-6030
10.1016/j.jphotochem.2014.08.001
www.sciencedirect.com
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron_str RCAAP
institution RCAAP
reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository.name.fl_str_mv
repository.mail.fl_str_mv
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