Biotransformação da diacereína por fungos e avaliação do potencial citotóxico do seu principal metabólito humano
Autor(a) principal: | |
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Data de Publicação: | 2016 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Repositório Institucional da UFG |
Texto Completo: | http://repositorio.bc.ufg.br/tede/handle/tede/6049 |
Resumo: | The study of biotransformation is important in the evaluation of safety and efficacy and for developing of new drug candidates. The "microbial models of mammalian metabolism", in which microbial biotransformation is used for the purpose of predict and obtaining human metabolites, is an alternative method to the use of animals for this study. Several advantages such as lower cost, a greater quantity and variety of derivatives produced, using mild conditions of reaction and decreasing the use of toxic volatile organic solvents are observed. The aim of this study was to produce derivatives of diacerein (1,8-diacetoxy-3-carboxyanthraquinone) by biotransformation using filamentous fungi and to evaluate the cytotoxicity of the main derivatives obtained given the resurgence of interest in this class of compounds. The diacerein is an anthraquinone with a wide range of biological activities, like as anti-osteoarthritis, analgesic, anti-inflammatory, antipyretic, prevention of vascular disease, insulin resistance treatment, anticancer. Analytical methodologies have been developed for monitoring the production of derivatives by thin layer chromatography and high-performance liquid chromatography (HPLC). After screening with seventeen fungal strains, Aspergillus ochraceus ATCC 1009 and Cunninghamella echinulata ATCC 9245 were selected for incubation in semipreparative scale. Of these incubations rhein (the main human metabolite) was obtained, which was characterized using the techniques Nuclear Magnetic Resonance (NMR) 1H e 13C, High Resolution Mass Spectrometry (MS), spectrometry in the UV region and analysed by HPLC. Another derivative was obtained by incubation with Aspergillus ochraceus ATCC 1009 and characterized by MS and analyzed by HPLC being, possibly, glycosylated diacerein. The influence of the addition of cytochrome P450 inhibitor in the production of metabolites was performed and inhibited the production of rhein about 41%, which may indicate the involvement of CYP1A1 and CYP1A2 in the deacetylation reaction. The cytotoxic potential of diacerein and rhein was evaluated by the tetrazolium reduction method (MTT) assay using murine fibroblast cells 3T3 and tumor cell line B16F10 (melanoma). Both the rhein, as diacerein, have demonstrated cytotoxic potential against B16F10 cells. |
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Oliveira, Valéria dehttp://lattes.cnpq.br/6300240031300604Oliveira, Valéria dePaula, José Realino deKato, LucíliaOliveira, Cecília Maria Alves dehttp://lattes.cnpq.br/7137345573529858Ferreira, Júlia Martins Ulhôa2016-08-31T13:05:08Z2016-08-16FERREIRA, Júlia Martins Ulhôa. Biotransformação da diacereína por fungos e avaliação do potencial citotóxico do seu principal metabólito humano. 2016. 99 f. Dissertação (Mestrado em Ciências Farmacêuticas) - Universidade Federal de Goiás,Goiânia, 2016.http://repositorio.bc.ufg.br/tede/handle/tede/6049The study of biotransformation is important in the evaluation of safety and efficacy and for developing of new drug candidates. The "microbial models of mammalian metabolism", in which microbial biotransformation is used for the purpose of predict and obtaining human metabolites, is an alternative method to the use of animals for this study. Several advantages such as lower cost, a greater quantity and variety of derivatives produced, using mild conditions of reaction and decreasing the use of toxic volatile organic solvents are observed. The aim of this study was to produce derivatives of diacerein (1,8-diacetoxy-3-carboxyanthraquinone) by biotransformation using filamentous fungi and to evaluate the cytotoxicity of the main derivatives obtained given the resurgence of interest in this class of compounds. The diacerein is an anthraquinone with a wide range of biological activities, like as anti-osteoarthritis, analgesic, anti-inflammatory, antipyretic, prevention of vascular disease, insulin resistance treatment, anticancer. Analytical methodologies have been developed for monitoring the production of derivatives by thin layer chromatography and high-performance liquid chromatography (HPLC). After screening with seventeen fungal strains, Aspergillus ochraceus ATCC 1009 and Cunninghamella echinulata ATCC 9245 were selected for incubation in semipreparative scale. Of these incubations rhein (the main human metabolite) was obtained, which was characterized using the techniques Nuclear Magnetic Resonance (NMR) 1H e 13C, High Resolution Mass Spectrometry (MS), spectrometry in the UV region and analysed by HPLC. Another derivative was obtained by incubation with Aspergillus ochraceus ATCC 1009 and characterized by MS and analyzed by HPLC being, possibly, glycosylated diacerein. The influence of the addition of cytochrome P450 inhibitor in the production of metabolites was performed and inhibited the production of rhein about 41%, which may indicate the involvement of CYP1A1 and CYP1A2 in the deacetylation reaction. The cytotoxic potential of diacerein and rhein was evaluated by the tetrazolium reduction method (MTT) assay using murine fibroblast cells 3T3 and tumor cell line B16F10 (melanoma). Both the rhein, as diacerein, have demonstrated cytotoxic potential against B16F10 cells.O estudo da biotransformação é de fundamental importância na avaliação da segurança e eficácia e para o desenvolvimento de novos candidatos a fármacos. O “Modelo microbiano do metabolismo animal”, no qual a biotransformação microbiana é utilizada com a finalidade de prever e obter metabólitos humanos, representa um método alternativo ao uso de animais para esse estudo, uma vez que são observadas diversas vantagens como menor custo, maior quantidade e variedade de derivados produzidos, utilização de condições brandas de reação e redução da utilização de solventes orgânicos voláteis tóxicos. O objetivo deste estudo foi produzir derivados da diacereína (1,8-diacetoxi-3-carboxiantraquinona) por biotransformação, utilizando fungos filamentosos e avaliar a citotoxicidade dos principais derivados obtidos, em função do ressurgimento do interesse desta classe de compostos. A diacereína é uma antraquinona com ampla gama de atividades biológicas - antiosteoartrósica, analgésica, anti-inflamatória, antipirética, prevenção de doenças vasculares, tratamento de resistência à insulina, anticâncer. Metodologias analíticas foram desenvolvidas para o monitoramento da produção dos derivados por cromatografia em camada delgada e cromatografia líquida de alta eficiência (CLAE). Após triagem com dezessete cepas fúngicas, Aspergillus ochraceus ATCC 1009 e Cunninghamella echinulata ATCC 9245 foram selecionadas para incubações em escala semipreparativa. Dessas incubações obteve-se reína (o principal metabólito humano), a qual foi caracterizada utilizando as técnicas Ressonância Magnética Nuclear de 1H e 13C, Espectrometria de Massas de Alta Resolução (EM), Espectrometria na região do ultravioleta/visível e analisada por CLAE. Outro derivado foi obtido da incubação com Aspergillus ochraceus ATCC 1009 e caracterizado por EM e analisado em CLAE, sendo, possivelmente, a diacereína glicosilada. A influência da adição de inibidor do citocromo P450 na produção dos metabólitos foi realizada e inibiu a produção de reína em cerca de 41%, o que pode indicar o envolvimento do CYP1A1 e CYP1A2 na reação de desacetilação.O potencial citotóxico da diacereína e da reína foi avaliado pelo método de redução do tetrazólio (MTT) utilizando células de fibroblasto murino 3T3 e da linhagem tumoral B16F10 (melanoma). Tanto a reína, quanto a diacereína, demonstraram potencial citotóxico contra células B16F10.Submitted by Marlene Santos (marlene.bc.ufg@gmail.com) on 2016-08-30T17:41:02Z No. of bitstreams: 2 Dissertação - Júlia Martins Ulhôa Ferreira - 2016.pdf: 3148442 bytes, checksum: fc17d72cc71fdebb2a4ec57487e7cd21 (MD5) license_rdf: 0 bytes, checksum: d41d8cd98f00b204e9800998ecf8427e (MD5)Approved for entry into archive by Luciana Ferreira (lucgeral@gmail.com) on 2016-08-31T13:05:08Z (GMT) No. of bitstreams: 2 Dissertação - Júlia Martins Ulhôa Ferreira - 2016.pdf: 3148442 bytes, checksum: fc17d72cc71fdebb2a4ec57487e7cd21 (MD5) license_rdf: 0 bytes, checksum: d41d8cd98f00b204e9800998ecf8427e (MD5)Made available in DSpace on 2016-08-31T13:05:08Z (GMT). No. of bitstreams: 2 Dissertação - Júlia Martins Ulhôa Ferreira - 2016.pdf: 3148442 bytes, checksum: fc17d72cc71fdebb2a4ec57487e7cd21 (MD5) license_rdf: 0 bytes, checksum: d41d8cd98f00b204e9800998ecf8427e (MD5) Previous issue date: 2016-08-16Conselho Nacional de Pesquisa e Desenvolvimento Científico e Tecnológico - CNPqapplication/pdfporUniversidade Federal de GoiásPrograma de Pós-graduação em Ciências Farmacêuticas (FF)UFGBrasilFaculdade Farmácia - FF (RG)http://creativecommons.org/licenses/by/4.0/info:eu-repo/semantics/openAccessBiotransformaçãoDiacereínaAspergillus ochraceusGlicosilaçãoCunninghamella echinulataCitotoxicidadeBiotransformationDiacereinglycosylationCytotoxicityCIENCIAS BIOLOGICAS::FARMACOLOGIABiotransformação da diacereína por fungos e avaliação do potencial citotóxico do seu principal metabólito humanoBiotransformation of diacerein by fungi and evaluation of the cytotoxic potential of its main human metaboliteinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesis8249369881961524126006006006006010281161524209375700814650651154363-2555911436985713659reponame:Repositório Institucional da UFGinstname:Universidade Federal de Goiás (UFG)instacron:UFGLICENSElicense.txtlicense.txttext/plain; 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dc.title.por.fl_str_mv |
Biotransformação da diacereína por fungos e avaliação do potencial citotóxico do seu principal metabólito humano |
dc.title.alternative.eng.fl_str_mv |
Biotransformation of diacerein by fungi and evaluation of the cytotoxic potential of its main human metabolite |
title |
Biotransformação da diacereína por fungos e avaliação do potencial citotóxico do seu principal metabólito humano |
spellingShingle |
Biotransformação da diacereína por fungos e avaliação do potencial citotóxico do seu principal metabólito humano Ferreira, Júlia Martins Ulhôa Biotransformação Diacereína Aspergillus ochraceus Glicosilação Cunninghamella echinulata Citotoxicidade Biotransformation Diacerein glycosylation Cytotoxicity CIENCIAS BIOLOGICAS::FARMACOLOGIA |
title_short |
Biotransformação da diacereína por fungos e avaliação do potencial citotóxico do seu principal metabólito humano |
title_full |
Biotransformação da diacereína por fungos e avaliação do potencial citotóxico do seu principal metabólito humano |
title_fullStr |
Biotransformação da diacereína por fungos e avaliação do potencial citotóxico do seu principal metabólito humano |
title_full_unstemmed |
Biotransformação da diacereína por fungos e avaliação do potencial citotóxico do seu principal metabólito humano |
title_sort |
Biotransformação da diacereína por fungos e avaliação do potencial citotóxico do seu principal metabólito humano |
author |
Ferreira, Júlia Martins Ulhôa |
author_facet |
Ferreira, Júlia Martins Ulhôa |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Oliveira, Valéria de |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/6300240031300604 |
dc.contributor.referee1.fl_str_mv |
Oliveira, Valéria de |
dc.contributor.referee2.fl_str_mv |
Paula, José Realino de |
dc.contributor.referee3.fl_str_mv |
Kato, Lucília |
dc.contributor.referee4.fl_str_mv |
Oliveira, Cecília Maria Alves de |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/7137345573529858 |
dc.contributor.author.fl_str_mv |
Ferreira, Júlia Martins Ulhôa |
contributor_str_mv |
Oliveira, Valéria de Oliveira, Valéria de Paula, José Realino de Kato, Lucília Oliveira, Cecília Maria Alves de |
dc.subject.por.fl_str_mv |
Biotransformação Diacereína Aspergillus ochraceus Glicosilação Cunninghamella echinulata Citotoxicidade |
topic |
Biotransformação Diacereína Aspergillus ochraceus Glicosilação Cunninghamella echinulata Citotoxicidade Biotransformation Diacerein glycosylation Cytotoxicity CIENCIAS BIOLOGICAS::FARMACOLOGIA |
dc.subject.eng.fl_str_mv |
Biotransformation Diacerein glycosylation Cytotoxicity |
dc.subject.cnpq.fl_str_mv |
CIENCIAS BIOLOGICAS::FARMACOLOGIA |
description |
The study of biotransformation is important in the evaluation of safety and efficacy and for developing of new drug candidates. The "microbial models of mammalian metabolism", in which microbial biotransformation is used for the purpose of predict and obtaining human metabolites, is an alternative method to the use of animals for this study. Several advantages such as lower cost, a greater quantity and variety of derivatives produced, using mild conditions of reaction and decreasing the use of toxic volatile organic solvents are observed. The aim of this study was to produce derivatives of diacerein (1,8-diacetoxy-3-carboxyanthraquinone) by biotransformation using filamentous fungi and to evaluate the cytotoxicity of the main derivatives obtained given the resurgence of interest in this class of compounds. The diacerein is an anthraquinone with a wide range of biological activities, like as anti-osteoarthritis, analgesic, anti-inflammatory, antipyretic, prevention of vascular disease, insulin resistance treatment, anticancer. Analytical methodologies have been developed for monitoring the production of derivatives by thin layer chromatography and high-performance liquid chromatography (HPLC). After screening with seventeen fungal strains, Aspergillus ochraceus ATCC 1009 and Cunninghamella echinulata ATCC 9245 were selected for incubation in semipreparative scale. Of these incubations rhein (the main human metabolite) was obtained, which was characterized using the techniques Nuclear Magnetic Resonance (NMR) 1H e 13C, High Resolution Mass Spectrometry (MS), spectrometry in the UV region and analysed by HPLC. Another derivative was obtained by incubation with Aspergillus ochraceus ATCC 1009 and characterized by MS and analyzed by HPLC being, possibly, glycosylated diacerein. The influence of the addition of cytochrome P450 inhibitor in the production of metabolites was performed and inhibited the production of rhein about 41%, which may indicate the involvement of CYP1A1 and CYP1A2 in the deacetylation reaction. The cytotoxic potential of diacerein and rhein was evaluated by the tetrazolium reduction method (MTT) assay using murine fibroblast cells 3T3 and tumor cell line B16F10 (melanoma). Both the rhein, as diacerein, have demonstrated cytotoxic potential against B16F10 cells. |
publishDate |
2016 |
dc.date.accessioned.fl_str_mv |
2016-08-31T13:05:08Z |
dc.date.issued.fl_str_mv |
2016-08-16 |
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 |
FERREIRA, Júlia Martins Ulhôa. Biotransformação da diacereína por fungos e avaliação do potencial citotóxico do seu principal metabólito humano. 2016. 99 f. Dissertação (Mestrado em Ciências Farmacêuticas) - Universidade Federal de Goiás,Goiânia, 2016. |
dc.identifier.uri.fl_str_mv |
http://repositorio.bc.ufg.br/tede/handle/tede/6049 |
identifier_str_mv |
FERREIRA, Júlia Martins Ulhôa. Biotransformação da diacereína por fungos e avaliação do potencial citotóxico do seu principal metabólito humano. 2016. 99 f. Dissertação (Mestrado em Ciências Farmacêuticas) - Universidade Federal de Goiás,Goiânia, 2016. |
url |
http://repositorio.bc.ufg.br/tede/handle/tede/6049 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.program.fl_str_mv |
824936988196152412 |
dc.relation.confidence.fl_str_mv |
600 600 600 600 |
dc.relation.department.fl_str_mv |
6010281161524209375 |
dc.relation.cnpq.fl_str_mv |
700814650651154363 |
dc.relation.sponsorship.fl_str_mv |
-2555911436985713659 |
dc.rights.driver.fl_str_mv |
http://creativecommons.org/licenses/by/4.0/ info:eu-repo/semantics/openAccess |
rights_invalid_str_mv |
http://creativecommons.org/licenses/by/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) |
instacron_str |
UFG |
institution |
UFG |
reponame_str |
Repositório Institucional da UFG |
collection |
Repositório Institucional da UFG |
bitstream.url.fl_str_mv |
http://repositorio.bc.ufg.br/tede/bitstreams/7218cdd2-7837-4d3c-9ca7-e81de79ffe2b/download http://repositorio.bc.ufg.br/tede/bitstreams/2fc390f4-f755-4dba-ae5f-840d63f97c1b/download http://repositorio.bc.ufg.br/tede/bitstreams/fe4c658b-d969-4808-b229-99e734ffa50f/download http://repositorio.bc.ufg.br/tede/bitstreams/2367e2be-f2c6-4cc8-99e0-9d62601f476e/download http://repositorio.bc.ufg.br/tede/bitstreams/7ef536fb-8a22-4021-a555-b69af94627c7/download |
bitstream.checksum.fl_str_mv |
bd3efa91386c1718a7f26a329fdcb468 321f3992dd3875151d8801b773ab32ed d41d8cd98f00b204e9800998ecf8427e d41d8cd98f00b204e9800998ecf8427e fc17d72cc71fdebb2a4ec57487e7cd21 |
bitstream.checksumAlgorithm.fl_str_mv |
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_ |
1798044324197302272 |