Estudos de modelagem molecular para previsão In Silico dos prováveis metabólitos de fase I de flavonóides
Autor(a) principal: | |
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Data de Publicação: | 2012 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Repositório Institucional da UFG |
Texto Completo: | http://repositorio.bc.ufg.br/tede/handle/tede/4259 |
Resumo: | Flavonoids are an important class of natural products candidate drugs, and low molecular weight polyphenols, widely distributed throughout the plant kingdom. Investigations on its activities over the past 30 years, demonstrated a potential to prevent several diseases, among them cardiovascular diseases, inflammatory disorders, viral infections, diabetes and neurological disorders, in addition to its known antioxidant. The family of cytochrome P450 (CYP) is composed of monooxygenases, which play a crucial role in the metabolism of endogenous and exogenous substances, and participates in the metabolism of flavonoids. In this paper we describe the application of a methodology for exploring combined in silico prediction of sites of metabolism of quercetin, rutin, naringin and naringenin, found in abundance in nature. A methodology used was ligand based drug design (LBDD) to predict the sites of metabolism (SOM) and the program MetaPrint2D most likely estimate of the metabolites, combined with the method structure based drug design (SBDD) by using molecular docking and energy minimization, to predict the interaction of quercetin, rutin, naringin and naringenin with the isoforms CYP2C9 and CYP1A2. Metabolites were found several Phase I with catalytically active distance (<5 Å) and interaction sites described in the literature, with hydroxylation reactions of aliphatic, aromatic hydroxylation, dealkylation and O-dealkylation. The proposed in silico metabolic hydroxylation at the position corresponding to the C3' were consistent with studies in vitro and in vivo experiments described in the literature for naringin and naringenin. Amino acids of the active site of CYP isoforms have been identified as important in the positioning of the flavonoids quercetin, rutin, naringin and naringenin toward the heme, confirming the involvement of these isoforms in the metabolism of flavonoids. |
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Andrade, Carolina Hortahttp://lattes.cnpq.br/2018317447324228Andrade, Carolina HortaSilva, Vinícius Barreto daSabino, José RicardoOliveira, Valéria deCV: http://lattes.cnpq.br/0458976053220883Sousa, Mariana Côrtes de2015-03-06T18:30:44Z2012-02-28SOUSA, M. C. Estudos de modelagem molecular para previsão In Silico dos prováveis metabólitos de fase I de flavonóides. 2012. 53 f. Dissertação (Mestrado em Ciências Farmacêuticas)–Universidade Federal de Goiás, Goiânia, 2012.http://repositorio.bc.ufg.br/tede/handle/tede/4259ark:/38995/0013000005n9hFlavonoids are an important class of natural products candidate drugs, and low molecular weight polyphenols, widely distributed throughout the plant kingdom. Investigations on its activities over the past 30 years, demonstrated a potential to prevent several diseases, among them cardiovascular diseases, inflammatory disorders, viral infections, diabetes and neurological disorders, in addition to its known antioxidant. The family of cytochrome P450 (CYP) is composed of monooxygenases, which play a crucial role in the metabolism of endogenous and exogenous substances, and participates in the metabolism of flavonoids. In this paper we describe the application of a methodology for exploring combined in silico prediction of sites of metabolism of quercetin, rutin, naringin and naringenin, found in abundance in nature. A methodology used was ligand based drug design (LBDD) to predict the sites of metabolism (SOM) and the program MetaPrint2D most likely estimate of the metabolites, combined with the method structure based drug design (SBDD) by using molecular docking and energy minimization, to predict the interaction of quercetin, rutin, naringin and naringenin with the isoforms CYP2C9 and CYP1A2. Metabolites were found several Phase I with catalytically active distance (<5 Å) and interaction sites described in the literature, with hydroxylation reactions of aliphatic, aromatic hydroxylation, dealkylation and O-dealkylation. The proposed in silico metabolic hydroxylation at the position corresponding to the C3' were consistent with studies in vitro and in vivo experiments described in the literature for naringin and naringenin. Amino acids of the active site of CYP isoforms have been identified as important in the positioning of the flavonoids quercetin, rutin, naringin and naringenin toward the heme, confirming the involvement of these isoforms in the metabolism of flavonoids.Os flavonóides representam uma importante classe de produtos naturais candidatos à fármacos, sendo polifenóis de baixo peso molecular, amplamente distribuídos no reino vegetal. Investigações sobre suas atividades, nos últimos 30 anos, demonstraram uma prevenção potencial de diversas patologias, dentre elas doenças cardiovasculares, desordens inflamatórias, infecções virais, diabetes e desordens neurológicas, além de sua conhecida ação antioxidante. A família do citocromo P450 (CYP) é composta de monooxigenases, que desempenham um papel crucial no metabolismo de substâncias endógenas e exógenas, e participa do metabolismo de flavonóides. Neste trabalho, descrevemos a aplicação de uma metodologia in silico combinada para explorar a previsão dos sítios de metabolismo dos flavonóides quercetina, rutina, naringenina e naringina, encontrados em abundância na natureza. Utilizou-se uma metodologia baseada nos ligantes (LBDD) para previsão dos sítios de metabolismo (SOM) pelo programa MetaPrint2D e previsão dos metabólitos mais prováveis, combinado à metodologia baseada na estrutura do receptor (SBDD) através da utilização de docking molecular e minimização de energia, para prever a interação de quercetina, rutina, naringenina e naringina com as isoformas CYP2C9 e CYP1A2. Foram encontrados diversos metabólitos de Fase I, com distâncias cataliticamente ativas (< 5 Å) e sítios de interação descritos na literatura, apresentando reações de hidroxilação alifática, hidroxilação aromática, desalquilação e O-desalquilação. Os metabólitos propostos in silico correspondentes à hidroxilação na posição C3’ foram com coerentes com estudos in vitro e in vivo descritos na literatura para naringenina e naringina. Aminoácidos do sítio ativo das isoformas de CYP foram identificados como importantes no posicionamento dos flavonóides quercetina, rutina, naringenina e naringina em direção ao heme, confirmando a participação dessas isoformas no metabolismo de flavonóides.Submitted by Luanna Matias (lua_matias@yahoo.com.br) on 2015-03-06T18:25:28Z No. of bitstreams: 2 Dissertação - Mariana Côrtes de Sousa - 2012.pdf: 1542160 bytes, checksum: 797a42ca723c95277c56015ce09b4be1 (MD5) license_rdf: 23148 bytes, checksum: 9da0b6dfac957114c6a7714714b86306 (MD5)Approved for entry into archive by Luanna Matias (lua_matias@yahoo.com.br) on 2015-03-06T18:30:44Z (GMT) No. of bitstreams: 2 Dissertação - Mariana Côrtes de Sousa - 2012.pdf: 1542160 bytes, checksum: 797a42ca723c95277c56015ce09b4be1 (MD5) license_rdf: 23148 bytes, checksum: 9da0b6dfac957114c6a7714714b86306 (MD5)Made available in DSpace on 2015-03-06T18:30:44Z (GMT). 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dc.title.eng.fl_str_mv |
Estudos de modelagem molecular para previsão In Silico dos prováveis metabólitos de fase I de flavonóides |
dc.title.alternative.eng.fl_str_mv |
Studies of molecular modeling to in silico prediction of probalby phase 1 metabolites of flavonoids |
title |
Estudos de modelagem molecular para previsão In Silico dos prováveis metabólitos de fase I de flavonóides |
spellingShingle |
Estudos de modelagem molecular para previsão In Silico dos prováveis metabólitos de fase I de flavonóides Sousa, Mariana Côrtes de Metabolismo Flavonóides Citocromo P450 Estudos de docking Metabolism Flavonoids Cytochrome P450 Docking studies CIENCIAS DA SAUDE::FARMACIA |
title_short |
Estudos de modelagem molecular para previsão In Silico dos prováveis metabólitos de fase I de flavonóides |
title_full |
Estudos de modelagem molecular para previsão In Silico dos prováveis metabólitos de fase I de flavonóides |
title_fullStr |
Estudos de modelagem molecular para previsão In Silico dos prováveis metabólitos de fase I de flavonóides |
title_full_unstemmed |
Estudos de modelagem molecular para previsão In Silico dos prováveis metabólitos de fase I de flavonóides |
title_sort |
Estudos de modelagem molecular para previsão In Silico dos prováveis metabólitos de fase I de flavonóides |
author |
Sousa, Mariana Côrtes de |
author_facet |
Sousa, Mariana Côrtes de |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Andrade, Carolina Horta |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/2018317447324228 |
dc.contributor.referee1.fl_str_mv |
Andrade, Carolina Horta |
dc.contributor.referee2.fl_str_mv |
Silva, Vinícius Barreto da |
dc.contributor.referee3.fl_str_mv |
Sabino, José Ricardo |
dc.contributor.referee4.fl_str_mv |
Oliveira, Valéria de |
dc.contributor.authorLattes.fl_str_mv |
CV: http://lattes.cnpq.br/0458976053220883 |
dc.contributor.author.fl_str_mv |
Sousa, Mariana Côrtes de |
contributor_str_mv |
Andrade, Carolina Horta Andrade, Carolina Horta Silva, Vinícius Barreto da Sabino, José Ricardo Oliveira, Valéria de |
dc.subject.por.fl_str_mv |
Metabolismo Flavonóides Citocromo P450 Estudos de docking |
topic |
Metabolismo Flavonóides Citocromo P450 Estudos de docking Metabolism Flavonoids Cytochrome P450 Docking studies CIENCIAS DA SAUDE::FARMACIA |
dc.subject.eng.fl_str_mv |
Metabolism Flavonoids Cytochrome P450 Docking studies |
dc.subject.cnpq.fl_str_mv |
CIENCIAS DA SAUDE::FARMACIA |
description |
Flavonoids are an important class of natural products candidate drugs, and low molecular weight polyphenols, widely distributed throughout the plant kingdom. Investigations on its activities over the past 30 years, demonstrated a potential to prevent several diseases, among them cardiovascular diseases, inflammatory disorders, viral infections, diabetes and neurological disorders, in addition to its known antioxidant. The family of cytochrome P450 (CYP) is composed of monooxygenases, which play a crucial role in the metabolism of endogenous and exogenous substances, and participates in the metabolism of flavonoids. In this paper we describe the application of a methodology for exploring combined in silico prediction of sites of metabolism of quercetin, rutin, naringin and naringenin, found in abundance in nature. A methodology used was ligand based drug design (LBDD) to predict the sites of metabolism (SOM) and the program MetaPrint2D most likely estimate of the metabolites, combined with the method structure based drug design (SBDD) by using molecular docking and energy minimization, to predict the interaction of quercetin, rutin, naringin and naringenin with the isoforms CYP2C9 and CYP1A2. Metabolites were found several Phase I with catalytically active distance (<5 Å) and interaction sites described in the literature, with hydroxylation reactions of aliphatic, aromatic hydroxylation, dealkylation and O-dealkylation. The proposed in silico metabolic hydroxylation at the position corresponding to the C3' were consistent with studies in vitro and in vivo experiments described in the literature for naringin and naringenin. Amino acids of the active site of CYP isoforms have been identified as important in the positioning of the flavonoids quercetin, rutin, naringin and naringenin toward the heme, confirming the involvement of these isoforms in the metabolism of flavonoids. |
publishDate |
2012 |
dc.date.issued.fl_str_mv |
2012-02-28 |
dc.date.accessioned.fl_str_mv |
2015-03-06T18:30:44Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/masterThesis |
format |
masterThesis |
status_str |
publishedVersion |
dc.identifier.citation.fl_str_mv |
SOUSA, M. C. Estudos de modelagem molecular para previsão In Silico dos prováveis metabólitos de fase I de flavonóides. 2012. 53 f. Dissertação (Mestrado em Ciências Farmacêuticas)–Universidade Federal de Goiás, Goiânia, 2012. |
dc.identifier.uri.fl_str_mv |
http://repositorio.bc.ufg.br/tede/handle/tede/4259 |
dc.identifier.dark.fl_str_mv |
ark:/38995/0013000005n9h |
identifier_str_mv |
SOUSA, M. C. Estudos de modelagem molecular para previsão In Silico dos prováveis metabólitos de fase I de flavonóides. 2012. 53 f. Dissertação (Mestrado em Ciências Farmacêuticas)–Universidade Federal de Goiás, Goiânia, 2012. ark:/38995/0013000005n9h |
url |
http://repositorio.bc.ufg.br/tede/handle/tede/4259 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.program.fl_str_mv |
824936988196152412 |
dc.relation.confidence.fl_str_mv |
600 600 600 |
dc.relation.department.fl_str_mv |
6010281161524209375 |
dc.relation.cnpq.fl_str_mv |
6997636413449754996 |
dc.rights.driver.fl_str_mv |
http://creativecommons.org/licenses/by-nc-nd/4.0/ info:eu-repo/semantics/openAccess |
rights_invalid_str_mv |
http://creativecommons.org/licenses/by-nc-nd/4.0/ |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
Universidade Federal de Goiás |
dc.publisher.program.fl_str_mv |
Programa de Pós-graduação em Ciências Farmacêuticas (FF) |
dc.publisher.initials.fl_str_mv |
UFG |
dc.publisher.country.fl_str_mv |
Brasil |
dc.publisher.department.fl_str_mv |
Faculdade Farmácia - FF (RG) |
publisher.none.fl_str_mv |
Universidade Federal de Goiás |
dc.source.none.fl_str_mv |
reponame:Repositório Institucional da UFG instname:Universidade Federal de Goiás (UFG) instacron:UFG |
instname_str |
Universidade Federal de Goiás (UFG) |
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UFG |
institution |
UFG |
reponame_str |
Repositório Institucional da UFG |
collection |
Repositório Institucional da UFG |
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bitstream.checksum.fl_str_mv |
6dfc32d7bf5a8db1ef2c9b1a977ab477 a90f3c64cd3211083c02f93ad0a93f82 4afdbb8c545fd630ea7db775da747b2f b292a83e42bd8ad62533bba1395b83ff 9da0b6dfac957114c6a7714714b86306 797a42ca723c95277c56015ce09b4be1 bd3efa91386c1718a7f26a329fdcb468 |
bitstream.checksumAlgorithm.fl_str_mv |
MD5 MD5 MD5 MD5 MD5 MD5 MD5 |
repository.name.fl_str_mv |
Repositório Institucional da UFG - Universidade Federal de Goiás (UFG) |
repository.mail.fl_str_mv |
tasesdissertacoes.bc@ufg.br |
_version_ |
1811721403885420544 |