Complexos de rutênio contendo lapachol e lausona: síntese, caracterização e suas propriedades quimioterapêuticas

Detalhes bibliográficos
Ano de defesa: 2014
Autor(a) principal: Oliveira, Katia Mara de
Orientador(a): Batista, Alzir Azevedo lattes
Banca de defesa: Não Informado pela instituição
Tipo de documento: Dissertação
Tipo de acesso: Acesso aberto
Idioma: por
Instituição de defesa: Universidade Federal de São Carlos
Câmpus São Carlos
Programa de Pós-Graduação: Programa de Pós-Graduação em Química - PPGQ
Departamento: Não Informado pela instituição
País: Não Informado pela instituição
Palavras-chave em Português:
Naftoquinonas lapachol
Lawsone
Ligantes lapachol
Palavras-chave em Inglês:
Naphthoquinones lapachol
Lawsone
Ligands lapachol
Área do conhecimento CNPq:
CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA
Link de acesso: https://repositorio.ufscar.br/handle/20.500.14289/10245
Resumo: The present work focuses on the synthesis and characterization of new ruthenium complexes containing the naphthoquinones lapachol and lawsone, due to the interesting biological properties exhibited by them. Complexes of general formula [Ru(L)(dppb)(N-N)]PF6, trans-[Ru(L)(PPh3)2(N-N)] PF6 and cis-[Ru(PPh3)2(lap)2] where L refers to the ligands lapachol (lap) or lawsone (lau), N-N corresponds to 2,2'-bipyridine, 4,4'- dimethyl-2,2'-bipyridine, 4,4'-dimethoxy-2,2'-bipyridine and 1,10- phenanthroline, dppb = 1,4-bis(diphenylphosphino)butane and PPh3 = triphenylphosphine. All synthesized compounds were characterized by molar conductivity, elemental analysis, infrared absorption spectroscopy, UV-visible absorption spectroscopy, 31P{1H}, 1H and 13C{1H} nuclear magnetic resonance, cyclic and differential pulse voltammetry, and for some complexes, by X-ray crystallography. The complexes were evaluated with respect their cytotoxic activity in tumor lines cell MCF-7 (breast adenocarcinoma) and L929 (normal mouse fibroblast), which showed very promising results with IC50 values in the range 0.12 to 1.11 μM. In addition, the complexes proved to be more active than the reference drug, cisplatin, which has IC50 μM to 13.98 MCF-7 lineage and 20.14 uM to L929. For the purpose of elucidating the possible mechanism of complex action, studies of interaction with DNA and with bovine serum albumin (BSA) were performed.
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spelling Oliveira, Katia Mara deBatista, Alzir Azevedohttp://lattes.cnpq.br/6469642481998660http://lattes.cnpq.br/8218994148704667bf75888b-4b9b-48da-a0d8-56f6ac8d9cbd2018-07-03T12:00:11Z2018-07-03T12:00:11Z2014-03-21OLIVEIRA, Katia Mara de. Complexos de rutênio contendo lapachol e lausona: síntese, caracterização e suas propriedades quimioterapêuticas. 2014. Dissertação (Mestrado em Química) – Universidade Federal de São Carlos, São Carlos, 2014. Disponível em: https://repositorio.ufscar.br/handle/20.500.14289/10245.https://repositorio.ufscar.br/handle/20.500.14289/10245The present work focuses on the synthesis and characterization of new ruthenium complexes containing the naphthoquinones lapachol and lawsone, due to the interesting biological properties exhibited by them. Complexes of general formula [Ru(L)(dppb)(N-N)]PF6, trans-[Ru(L)(PPh3)2(N-N)] PF6 and cis-[Ru(PPh3)2(lap)2] where L refers to the ligands lapachol (lap) or lawsone (lau), N-N corresponds to 2,2'-bipyridine, 4,4'- dimethyl-2,2'-bipyridine, 4,4'-dimethoxy-2,2'-bipyridine and 1,10- phenanthroline, dppb = 1,4-bis(diphenylphosphino)butane and PPh3 = triphenylphosphine. All synthesized compounds were characterized by molar conductivity, elemental analysis, infrared absorption spectroscopy, UV-visible absorption spectroscopy, 31P{1H}, 1H and 13C{1H} nuclear magnetic resonance, cyclic and differential pulse voltammetry, and for some complexes, by X-ray crystallography. The complexes were evaluated with respect their cytotoxic activity in tumor lines cell MCF-7 (breast adenocarcinoma) and L929 (normal mouse fibroblast), which showed very promising results with IC50 values in the range 0.12 to 1.11 μM. In addition, the complexes proved to be more active than the reference drug, cisplatin, which has IC50 μM to 13.98 MCF-7 lineage and 20.14 uM to L929. For the purpose of elucidating the possible mechanism of complex action, studies of interaction with DNA and with bovine serum albumin (BSA) were performed.O presente trabalho centra-se na síntese e caracterização de novos complexos de rutênio contendo as naftoquinonas lapachol e lausona, devido as interessantes propriedades biológicas que elas apresentam. Complexos de fórmula geral [Ru(L)(dppb)(N-N)]PF6, trans-[Ru(lau)(PPh3)2(N-N)]PF6 e cis-[Ru(PPh3)2(lap)2] em que L refere-se aos ligantes lapachol (lap) ou lausona (lau), N-N corresponde a 2,2’-bipiridina, 4,4’-dimetil-2,2’-bipiridina, 4,4’- dimetoxi-2,2’-bipiridina e 1,10-fenantrolina, dppb = 1,4- bis(difenilfosfina)butano e PPh3 = trifenilfosfina. Todos os complexos sintetizados foram caracterizados por condutividade molar, análise elementar, espectroscopia de absorção na região do infravermelho e na região do UVvisível, ressonância magnética nuclear de 31P{1H}, 1H e 13C{1H}, voltametria cíclica e de pulso diferencial, e alguns complexos, por difração de raios X de monocristal. Os complexos foram avaliados quanto à atividade citotóxica na linhagem tumoral MCF-7 (adenocarcinoma de mama) e na linhagem normal L929 (fibroblasto de camundongo), os quais apresentaram resultados muito promissores com valores de IC50 na faixa de 0,12 a 1,11 μM. Além disso, os complexos mostraram-se muito mais ativos do que o fármaco de referência, o cisplatina, o qual apresenta IC50 de 13,98 μM para a linhagem MCF-7 e 20,14 μM para L929. Para fins de elucidação do possível mecanismo de ação dos complexos, estudos de interação com o ct-DNA e com a albumina de soro bovino (BSA) foram realizados.Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)porUniversidade Federal de São CarlosCâmpus São CarlosPrograma de Pós-Graduação em Química - PPGQUFSCarNaftoquinonas lapacholLawsoneLigantes lapacholNaphthoquinones lapacholLawsoneLigands lapacholCIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICAComplexos de rutênio contendo lapachol e lausona: síntese, caracterização e suas propriedades quimioterapêuticasRuthenium complexes containing lapachol and lawsone: synthesis, characterization and chemotherapeutic propertiesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisOnline600600e62fb48f-fa23-4158-8d60-0b17f006946cinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UFSCARinstname:Universidade Federal de São Carlos (UFSCAR)instacron:UFSCARLICENSElicense.txtlicense.txttext/plain; charset=utf-81957https://repositorio.ufscar.br/bitstreams/a7bf2962-52f0-4dd9-ad4c-81a27eacbde7/downloadae0398b6f8b235e40ad82cba6c50031dMD52falseAnonymousREADORIGINALDissKMO.pdfDissKMO.pdfapplication/pdf4099573https://repositorio.ufscar.br/bitstreams/c4998dde-dd02-40ee-8ecd-37fa2fc1410b/download34219ffd416a196075eea75e60054b27MD53trueAnonymousREADTEXTDissKMO.pdf.txtDissKMO.pdf.txtExtracted texttext/plain205835https://repositorio.ufscar.br/bitstreams/c4f4de8c-fbf1-4938-a742-d6f7eaa0d0f7/download83ad5bf759f0283a386f1ffa67f9776eMD56falseAnonymousREADTHUMBNAILDissKMO.pdf.jpgDissKMO.pdf.jpgIM Thumbnailimage/jpeg7348https://repositorio.ufscar.br/bitstreams/591c7213-76f2-4d88-a133-7a073bcaf829/download4fce3eec36ab0abf6e1dc6ead814a5ceMD57falseAnonymousREAD20.500.14289/102452025-02-05 17:55:44.95Acesso abertoopen.accessoai:repositorio.ufscar.br:20.500.14289/10245https://repositorio.ufscar.brRepositório InstitucionalPUBhttps://repositorio.ufscar.br/oai/requestrepositorio.sibi@ufscar.bropendoar:43222025-02-05T20:55:44Repositório Institucional da UFSCAR - Universidade Federal de São Carlos (UFSCAR)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
dc.title.por.fl_str_mv Complexos de rutênio contendo lapachol e lausona: síntese, caracterização e suas propriedades quimioterapêuticas
dc.title.alternative.eng.fl_str_mv Ruthenium complexes containing lapachol and lawsone: synthesis, characterization and chemotherapeutic properties
title Complexos de rutênio contendo lapachol e lausona: síntese, caracterização e suas propriedades quimioterapêuticas
spellingShingle Complexos de rutênio contendo lapachol e lausona: síntese, caracterização e suas propriedades quimioterapêuticas
Oliveira, Katia Mara de
Naftoquinonas lapachol
Lawsone
Ligantes lapachol
Naphthoquinones lapachol
Lawsone
Ligands lapachol
CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA
title_short Complexos de rutênio contendo lapachol e lausona: síntese, caracterização e suas propriedades quimioterapêuticas
title_full Complexos de rutênio contendo lapachol e lausona: síntese, caracterização e suas propriedades quimioterapêuticas
title_fullStr Complexos de rutênio contendo lapachol e lausona: síntese, caracterização e suas propriedades quimioterapêuticas
title_full_unstemmed Complexos de rutênio contendo lapachol e lausona: síntese, caracterização e suas propriedades quimioterapêuticas
title_sort Complexos de rutênio contendo lapachol e lausona: síntese, caracterização e suas propriedades quimioterapêuticas
author Oliveira, Katia Mara de
author_facet Oliveira, Katia Mara de
author_role author
dc.contributor.authorlattes.por.fl_str_mv http://lattes.cnpq.br/8218994148704667
dc.contributor.author.fl_str_mv Oliveira, Katia Mara de
dc.contributor.advisor1.fl_str_mv Batista, Alzir Azevedo
dc.contributor.advisor1Lattes.fl_str_mv http://lattes.cnpq.br/6469642481998660
dc.contributor.authorID.fl_str_mv bf75888b-4b9b-48da-a0d8-56f6ac8d9cbd
contributor_str_mv Batista, Alzir Azevedo
dc.subject.por.fl_str_mv Naftoquinonas lapachol
Lawsone
Ligantes lapachol
topic Naftoquinonas lapachol
Lawsone
Ligantes lapachol
Naphthoquinones lapachol
Lawsone
Ligands lapachol
CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA
dc.subject.eng.fl_str_mv Naphthoquinones lapachol
Lawsone
Ligands lapachol
dc.subject.cnpq.fl_str_mv CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA
description The present work focuses on the synthesis and characterization of new ruthenium complexes containing the naphthoquinones lapachol and lawsone, due to the interesting biological properties exhibited by them. Complexes of general formula [Ru(L)(dppb)(N-N)]PF6, trans-[Ru(L)(PPh3)2(N-N)] PF6 and cis-[Ru(PPh3)2(lap)2] where L refers to the ligands lapachol (lap) or lawsone (lau), N-N corresponds to 2,2'-bipyridine, 4,4'- dimethyl-2,2'-bipyridine, 4,4'-dimethoxy-2,2'-bipyridine and 1,10- phenanthroline, dppb = 1,4-bis(diphenylphosphino)butane and PPh3 = triphenylphosphine. All synthesized compounds were characterized by molar conductivity, elemental analysis, infrared absorption spectroscopy, UV-visible absorption spectroscopy, 31P{1H}, 1H and 13C{1H} nuclear magnetic resonance, cyclic and differential pulse voltammetry, and for some complexes, by X-ray crystallography. The complexes were evaluated with respect their cytotoxic activity in tumor lines cell MCF-7 (breast adenocarcinoma) and L929 (normal mouse fibroblast), which showed very promising results with IC50 values in the range 0.12 to 1.11 μM. In addition, the complexes proved to be more active than the reference drug, cisplatin, which has IC50 μM to 13.98 MCF-7 lineage and 20.14 uM to L929. For the purpose of elucidating the possible mechanism of complex action, studies of interaction with DNA and with bovine serum albumin (BSA) were performed.
publishDate 2014
dc.date.issued.fl_str_mv 2014-03-21
dc.date.accessioned.fl_str_mv 2018-07-03T12:00:11Z
dc.date.available.fl_str_mv 2018-07-03T12:00:11Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/masterThesis
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dc.identifier.citation.fl_str_mv OLIVEIRA, Katia Mara de. Complexos de rutênio contendo lapachol e lausona: síntese, caracterização e suas propriedades quimioterapêuticas. 2014. Dissertação (Mestrado em Química) – Universidade Federal de São Carlos, São Carlos, 2014. Disponível em: https://repositorio.ufscar.br/handle/20.500.14289/10245.
dc.identifier.uri.fl_str_mv https://repositorio.ufscar.br/handle/20.500.14289/10245
identifier_str_mv OLIVEIRA, Katia Mara de. Complexos de rutênio contendo lapachol e lausona: síntese, caracterização e suas propriedades quimioterapêuticas. 2014. Dissertação (Mestrado em Química) – Universidade Federal de São Carlos, São Carlos, 2014. Disponível em: https://repositorio.ufscar.br/handle/20.500.14289/10245.
url https://repositorio.ufscar.br/handle/20.500.14289/10245
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language por
dc.relation.confidence.fl_str_mv 600
600
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dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Universidade Federal de São Carlos
Câmpus São Carlos
dc.publisher.program.fl_str_mv Programa de Pós-Graduação em Química - PPGQ
dc.publisher.initials.fl_str_mv UFSCar
publisher.none.fl_str_mv Universidade Federal de São Carlos
Câmpus São Carlos
dc.source.none.fl_str_mv reponame:Repositório Institucional da UFSCAR
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