Benzothienoquinolines: new one-pot synthesis and fluorescence studies of their interaction with DNA and polynucleotides
Autor(a) principal: | |
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Data de Publicação: | 2014 |
Outros Autores: | , , , , , |
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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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:RCAAP2023-07-21T12:23:58Zoai:repositorium.sdum.uminho.pt:1822/30740Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T19:17:50.039834Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse |
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 |
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Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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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 |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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1799132632095653888 |