Synthesis of novel psoralen analogues and their in vitro antitumor activity

Detalhes bibliográficos
Autor(a) principal: Francisco, Carla Santana
Data de Publicação: 2013
Outros Autores: Rodrigues, L. R., Cerqueira, N. M. F. S. A., Campos, Ana M. F. Oliveira, Rodrigues, Lígia M., Esteves, Ana Paula
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/1822/25551
Resumo: New tetracyclic benzofurocoumarin (benzopsoralen) analogues were synthesized and their inhibitory effect on the growth of tumor cell lines was evaluated. The human tumor cell lines used were MDA MB231 (breast adenocarcinoma), HeLa (cervix adenocarcinoma) and TCC-SUP (bladder transitional cell carcinoma). The in vitro antitumor activity of the new benzopsoralens was discussed in terms of structure–activity relationship. Molecular docking studies with human-CYP2A6 enzymes were also carried out with the synthesized compounds in order to evaluate the potential of these compounds to interact with the heme group of the enzymes. The results have demonstrated that the linear compounds have the most pronounced activity against tumor cell lines and this might be related to the better accessibility that these compounds have to the active site in relation to the angular ones that have shown in the majority of the cases multiple binding poses in the active site of CYP2A6.
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spelling Synthesis of novel psoralen analogues and their in vitro antitumor activityBenzofurocoumarinsBenzopsoralen analoguesAntitumor activityDockingComputational studiesScience & TechnologyNew tetracyclic benzofurocoumarin (benzopsoralen) analogues were synthesized and their inhibitory effect on the growth of tumor cell lines was evaluated. The human tumor cell lines used were MDA MB231 (breast adenocarcinoma), HeLa (cervix adenocarcinoma) and TCC-SUP (bladder transitional cell carcinoma). The in vitro antitumor activity of the new benzopsoralens was discussed in terms of structure–activity relationship. Molecular docking studies with human-CYP2A6 enzymes were also carried out with the synthesized compounds in order to evaluate the potential of these compounds to interact with the heme group of the enzymes. The results have demonstrated that the linear compounds have the most pronounced activity against tumor cell lines and this might be related to the better accessibility that these compounds have to the active site in relation to the angular ones that have shown in the majority of the cases multiple binding poses in the active site of CYP2A6.To the Foundation for the Science and Technology (FCT, Portugal) for financial support to the NMR portuguese network (PTNMR, Bruker Avance III 400-Univ. Minho). FCT and FEDER (European Fund for Regional Development)-COMPETE-QREN-EU for financial support to the Research Centre, CQ/UM [PEst-C/QUI/UI0686/2011 (FCOMP-01-0124-FEDER-022716)], (Pest-C/EQB/LA0006/2011) and the PhD grant to C.S.F. (SFRH/BD/48636/2008). The authors also acknowledge the Institute of Molecular Pathology and Immunology of the University of Porto (IPATIMUP, Porto, Portugal) for kindly providing the breast cancer cell line used in this work.ElsevierUniversidade do MinhoFrancisco, Carla SantanaRodrigues, L. R.Cerqueira, N. M. F. S. A.Campos, Ana M. F. OliveiraRodrigues, Lígia M.Esteves, Ana Paula20132013-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/1822/25551eng0968-08960968-089610.1016/j.bmc.2013.06.04923886808www.elsevier.com/locate/bmcinfo: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:RCAAP2024-05-11T05:30:30Zoai:repositorium.sdum.uminho.pt:1822/25551Portal AgregadorONGhttps://www.rcaap.pt/oai/openairemluisa.alvim@gmail.comopendoar:71602024-05-11T05:30:30Repositório 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 Synthesis of novel psoralen analogues and their in vitro antitumor activity
title Synthesis of novel psoralen analogues and their in vitro antitumor activity
spellingShingle Synthesis of novel psoralen analogues and their in vitro antitumor activity
Francisco, Carla Santana
Benzofurocoumarins
Benzopsoralen analogues
Antitumor activity
Docking
Computational studies
Science & Technology
title_short Synthesis of novel psoralen analogues and their in vitro antitumor activity
title_full Synthesis of novel psoralen analogues and their in vitro antitumor activity
title_fullStr Synthesis of novel psoralen analogues and their in vitro antitumor activity
title_full_unstemmed Synthesis of novel psoralen analogues and their in vitro antitumor activity
title_sort Synthesis of novel psoralen analogues and their in vitro antitumor activity
author Francisco, Carla Santana
author_facet Francisco, Carla Santana
Rodrigues, L. R.
Cerqueira, N. M. F. S. A.
Campos, Ana M. F. Oliveira
Rodrigues, Lígia M.
Esteves, Ana Paula
author_role author
author2 Rodrigues, L. R.
Cerqueira, N. M. F. S. A.
Campos, Ana M. F. Oliveira
Rodrigues, Lígia M.
Esteves, Ana Paula
author2_role author
author
author
author
author
dc.contributor.none.fl_str_mv Universidade do Minho
dc.contributor.author.fl_str_mv Francisco, Carla Santana
Rodrigues, L. R.
Cerqueira, N. M. F. S. A.
Campos, Ana M. F. Oliveira
Rodrigues, Lígia M.
Esteves, Ana Paula
dc.subject.por.fl_str_mv Benzofurocoumarins
Benzopsoralen analogues
Antitumor activity
Docking
Computational studies
Science & Technology
topic Benzofurocoumarins
Benzopsoralen analogues
Antitumor activity
Docking
Computational studies
Science & Technology
description New tetracyclic benzofurocoumarin (benzopsoralen) analogues were synthesized and their inhibitory effect on the growth of tumor cell lines was evaluated. The human tumor cell lines used were MDA MB231 (breast adenocarcinoma), HeLa (cervix adenocarcinoma) and TCC-SUP (bladder transitional cell carcinoma). The in vitro antitumor activity of the new benzopsoralens was discussed in terms of structure–activity relationship. Molecular docking studies with human-CYP2A6 enzymes were also carried out with the synthesized compounds in order to evaluate the potential of these compounds to interact with the heme group of the enzymes. The results have demonstrated that the linear compounds have the most pronounced activity against tumor cell lines and this might be related to the better accessibility that these compounds have to the active site in relation to the angular ones that have shown in the majority of the cases multiple binding poses in the active site of CYP2A6.
publishDate 2013
dc.date.none.fl_str_mv 2013
2013-01-01T00:00:00Z
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 http://hdl.handle.net/1822/25551
url http://hdl.handle.net/1822/25551
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 0968-0896
0968-0896
10.1016/j.bmc.2013.06.049
23886808
www.elsevier.com/locate/bmc
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 Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
repository.mail.fl_str_mv mluisa.alvim@gmail.com
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