Investigation of the interaction of 2-(2’-Hydroxyphenyl)-benzoxazoles and their derivatives with B-DNA by docking and molecular dynamics
Autor(a) principal: | |
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Data de Publicação: | 2015 |
Outros Autores: | , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UFRGS |
Texto Completo: | http://hdl.handle.net/10183/132524 |
Resumo: | In this work we carried out a study covering conformational analysis, docking calculations and molecular dynamics (MD) simulations of six excited state intramolecular proton transfer (ESIPT)-fluorescent 2-(2’-hydroxyphenyl)-benzoxazoles, interacting with the Dickerson-Drew (d(CGCGAATTCGCG)2) dodecamer in B-DNA conformation. In the analysis of the molecular docking calculations, the derivatives with the -NH2 group in the phenolic ring presented the most favorable interaction energies with the DNA, and the scores were even more favorable for the ligands containing the -NO2 group as substituent in the benzoxazolic ring. In the analysis of the MD simulations, the complexes showed stable interactions, with minimal induced structural distortions in the DNA, being the largest increase of the Rise parameter when the ligands were intercalated, and also the unwinding of Twist. During all simulations, the ligands showed stable interactions with the oligonucleotide, without denaturation. Considering these interactions and the peculiar photophysical properties of this class of molecules, they could be used as biological probes. |
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Grasel, Fábio dos SantosOliveira, Tiago Espinosa deNetz, Paulo Augusto2016-01-29T02:48:10Z20150103-5053http://hdl.handle.net/10183/132524000982471In this work we carried out a study covering conformational analysis, docking calculations and molecular dynamics (MD) simulations of six excited state intramolecular proton transfer (ESIPT)-fluorescent 2-(2’-hydroxyphenyl)-benzoxazoles, interacting with the Dickerson-Drew (d(CGCGAATTCGCG)2) dodecamer in B-DNA conformation. In the analysis of the molecular docking calculations, the derivatives with the -NH2 group in the phenolic ring presented the most favorable interaction energies with the DNA, and the scores were even more favorable for the ligands containing the -NO2 group as substituent in the benzoxazolic ring. In the analysis of the MD simulations, the complexes showed stable interactions, with minimal induced structural distortions in the DNA, being the largest increase of the Rise parameter when the ligands were intercalated, and also the unwinding of Twist. During all simulations, the ligands showed stable interactions with the oligonucleotide, without denaturation. Considering these interactions and the peculiar photophysical properties of this class of molecules, they could be used as biological probes.application/pdfengJournal of the Brazilian Chemical Society. São Paulo. Vol. 26, no. 3 (Mar. 2015), p. 420-433BenzazóisDerivados benzazólicosDinâmica molecularDocagem molecularBenzazoles-derivativesMolecular dockingMolecular dynamicsB-DNAInvestigation of the interaction of 2-(2’-Hydroxyphenyl)-benzoxazoles and their derivatives with B-DNA by docking and molecular dynamicsInvestigation of the interaction of 2-(2’-Hydroxyphenyl)-benzoxazoles and their derivatives with B-DNA by docking and molecular dynamics info:eu-repo/semantics/articleinfo:eu-repo/semantics/otherinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UFRGSinstname:Universidade Federal do Rio Grande do Sul (UFRGS)instacron:UFRGSORIGINAL000982471.pdf000982471.pdfTexto completoapplication/pdf4358071http://www.lume.ufrgs.br/bitstream/10183/132524/1/000982471.pdfeaad61320c736b40fd1de8e92402a798MD51TEXT000982471.pdf.txt000982471.pdf.txtExtracted Texttext/plain51439http://www.lume.ufrgs.br/bitstream/10183/132524/2/000982471.pdf.txt90078690eb589454257e67c966b288f2MD52THUMBNAIL000982471.pdf.jpg000982471.pdf.jpgGenerated Thumbnailimage/jpeg1915http://www.lume.ufrgs.br/bitstream/10183/132524/3/000982471.pdf.jpg117df44e91a99260b225e7dcef104388MD5310183/1325242018-10-26 09:37:46.143oai:www.lume.ufrgs.br:10183/132524Repositório de PublicaçõesPUBhttps://lume.ufrgs.br/oai/requestopendoar:2018-10-26T12:37:46Repositório Institucional da UFRGS - Universidade Federal do Rio Grande do Sul (UFRGS)false |
dc.title.pt_BR.fl_str_mv |
Investigation of the interaction of 2-(2’-Hydroxyphenyl)-benzoxazoles and their derivatives with B-DNA by docking and molecular dynamics |
dc.title.alternative.en.fl_str_mv |
Investigation of the interaction of 2-(2’-Hydroxyphenyl)-benzoxazoles and their derivatives with B-DNA by docking and molecular dynamics |
title |
Investigation of the interaction of 2-(2’-Hydroxyphenyl)-benzoxazoles and their derivatives with B-DNA by docking and molecular dynamics |
spellingShingle |
Investigation of the interaction of 2-(2’-Hydroxyphenyl)-benzoxazoles and their derivatives with B-DNA by docking and molecular dynamics Grasel, Fábio dos Santos Benzazóis Derivados benzazólicos Dinâmica molecular Docagem molecular Benzazoles-derivatives Molecular docking Molecular dynamics B-DNA |
title_short |
Investigation of the interaction of 2-(2’-Hydroxyphenyl)-benzoxazoles and their derivatives with B-DNA by docking and molecular dynamics |
title_full |
Investigation of the interaction of 2-(2’-Hydroxyphenyl)-benzoxazoles and their derivatives with B-DNA by docking and molecular dynamics |
title_fullStr |
Investigation of the interaction of 2-(2’-Hydroxyphenyl)-benzoxazoles and their derivatives with B-DNA by docking and molecular dynamics |
title_full_unstemmed |
Investigation of the interaction of 2-(2’-Hydroxyphenyl)-benzoxazoles and their derivatives with B-DNA by docking and molecular dynamics |
title_sort |
Investigation of the interaction of 2-(2’-Hydroxyphenyl)-benzoxazoles and their derivatives with B-DNA by docking and molecular dynamics |
author |
Grasel, Fábio dos Santos |
author_facet |
Grasel, Fábio dos Santos Oliveira, Tiago Espinosa de Netz, Paulo Augusto |
author_role |
author |
author2 |
Oliveira, Tiago Espinosa de Netz, Paulo Augusto |
author2_role |
author author |
dc.contributor.author.fl_str_mv |
Grasel, Fábio dos Santos Oliveira, Tiago Espinosa de Netz, Paulo Augusto |
dc.subject.por.fl_str_mv |
Benzazóis Derivados benzazólicos Dinâmica molecular Docagem molecular |
topic |
Benzazóis Derivados benzazólicos Dinâmica molecular Docagem molecular Benzazoles-derivatives Molecular docking Molecular dynamics B-DNA |
dc.subject.eng.fl_str_mv |
Benzazoles-derivatives Molecular docking Molecular dynamics B-DNA |
description |
In this work we carried out a study covering conformational analysis, docking calculations and molecular dynamics (MD) simulations of six excited state intramolecular proton transfer (ESIPT)-fluorescent 2-(2’-hydroxyphenyl)-benzoxazoles, interacting with the Dickerson-Drew (d(CGCGAATTCGCG)2) dodecamer in B-DNA conformation. In the analysis of the molecular docking calculations, the derivatives with the -NH2 group in the phenolic ring presented the most favorable interaction energies with the DNA, and the scores were even more favorable for the ligands containing the -NO2 group as substituent in the benzoxazolic ring. In the analysis of the MD simulations, the complexes showed stable interactions, with minimal induced structural distortions in the DNA, being the largest increase of the Rise parameter when the ligands were intercalated, and also the unwinding of Twist. During all simulations, the ligands showed stable interactions with the oligonucleotide, without denaturation. Considering these interactions and the peculiar photophysical properties of this class of molecules, they could be used as biological probes. |
publishDate |
2015 |
dc.date.issued.fl_str_mv |
2015 |
dc.date.accessioned.fl_str_mv |
2016-01-29T02:48:10Z |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article info:eu-repo/semantics/other |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://hdl.handle.net/10183/132524 |
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0103-5053 |
dc.identifier.nrb.pt_BR.fl_str_mv |
000982471 |
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url |
http://hdl.handle.net/10183/132524 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.ispartof.pt_BR.fl_str_mv |
Journal of the Brazilian Chemical Society. São Paulo. Vol. 26, no. 3 (Mar. 2015), p. 420-433 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
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