Síntese, nanoencapsulamento e atividade biológica de compostos triazenos
Ano de defesa: | 2012 |
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Autor(a) principal: | |
Orientador(a): | |
Banca de defesa: | , |
Tipo de documento: | Dissertação |
Tipo de acesso: | Acesso aberto |
Idioma: | por |
Instituição de defesa: |
Universidade Federal de Santa Maria
|
Programa de Pós-Graduação: |
Programa de Pós-Graduação em Química
|
Departamento: |
Química
|
País: |
BR
|
Palavras-chave em Português: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.ufsm.br/handle/1/10498 |
Resumo: | Compounds featuring triazenidic units constitute a versatile class of molecules for the preparation of new inorganic complexes with broad applications that include cancer therapy such as leukemia treatment. Gold-triazenide complexes exhibit recognized versatility in bioinorganic chemistry and medicine, which prompted their development as a basis for anticancer compounds. However, strategies to reduce non-specific cytotoxic effects from the administration of chemotherapy directly into the blood plasma are necessary, as for many other systems. In this regard, the use of polymeric nanoparticles allows not only reduction of side-effects, but also to promote site-specific delivery and controlled release. In this work, the aspects mentioned above have been incorporated into a new polymeric nanoparticles system containing triazenide compounds, and its application to leukemia therapy was investigated. First, the pre-ligand 1-(4-amidophenyl)-3-(4-acetilphenyl)triazene (1) and the complex 1-(4-amidophenyl)-3-(4-acetilphenyl)triazenide-(triphenilphosphine)gold(I) (2) were synthesized and fully characterized by spectroscopic techniques and X-ray diffraction in crystal. Then the compounds were evaluated for their potential antibacterial and antileukemic activities. In vitro studies indicated good antibacterial and antileukemic potential to triazenide complex, while the free ligand showed no biological activity. Subsequently, the pre-ligand (1) and complex (2) were encapsulated in polymeric nanoparticles (15-200 nm) with spherical core-shell micelar morphology, formed by block copolymers. For such compounds, the most efficient encapsulation method is by pre-film, with which encapsulation capabilities of up to 10% mcompound / mpolymer can be achieved for systems featuring poly[methacrylate 2-(dialkylamino) ethyl] or polystyrene cores. Afterwards, nanoencapsulation, loading and release kinetics studies were carried out using PEO-b-PG2MA-b-PDPA and PS-b-PAA copolymers. |
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2017-05-112017-05-112012-02-01FREITAS, Augusto Gonzaga Oliveira de. Synthesis, nanoencapsulation and biological activity of triazenes Compounds. 2012. 158 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2012.http://repositorio.ufsm.br/handle/1/10498Compounds featuring triazenidic units constitute a versatile class of molecules for the preparation of new inorganic complexes with broad applications that include cancer therapy such as leukemia treatment. Gold-triazenide complexes exhibit recognized versatility in bioinorganic chemistry and medicine, which prompted their development as a basis for anticancer compounds. However, strategies to reduce non-specific cytotoxic effects from the administration of chemotherapy directly into the blood plasma are necessary, as for many other systems. In this regard, the use of polymeric nanoparticles allows not only reduction of side-effects, but also to promote site-specific delivery and controlled release. In this work, the aspects mentioned above have been incorporated into a new polymeric nanoparticles system containing triazenide compounds, and its application to leukemia therapy was investigated. First, the pre-ligand 1-(4-amidophenyl)-3-(4-acetilphenyl)triazene (1) and the complex 1-(4-amidophenyl)-3-(4-acetilphenyl)triazenide-(triphenilphosphine)gold(I) (2) were synthesized and fully characterized by spectroscopic techniques and X-ray diffraction in crystal. Then the compounds were evaluated for their potential antibacterial and antileukemic activities. In vitro studies indicated good antibacterial and antileukemic potential to triazenide complex, while the free ligand showed no biological activity. Subsequently, the pre-ligand (1) and complex (2) were encapsulated in polymeric nanoparticles (15-200 nm) with spherical core-shell micelar morphology, formed by block copolymers. For such compounds, the most efficient encapsulation method is by pre-film, with which encapsulation capabilities of up to 10% mcompound / mpolymer can be achieved for systems featuring poly[methacrylate 2-(dialkylamino) ethyl] or polystyrene cores. Afterwards, nanoencapsulation, loading and release kinetics studies were carried out using PEO-b-PG2MA-b-PDPA and PS-b-PAA copolymers.Os compostos contendo unidades triazenídicas constituem uma classe versátil de moléculas para a preparação de novos complexos inorgânicos, cujas aplicações potenciais são amplas e incluem o tratamento de vários tipos de câncer, tal como a leucemia. Quando ligados a centro metálicos de ouro, complexos triazenídicos possuem reconhecida versatilidade na química bioinorgânica e na medicina, e, por isso, vem sendo vastamente estudados atualmente como base para compostos anticancerígenos. Entretanto, à exemplo de outros sistemas, estratégias para redução dos efeitos citotóxicos não específicos oriundos da administração de quimioterápicos diretamente no plasma sanguíneo se fazem necessárias. Neste sentido a utilização de nanopartículas poliméricas permite não somente reduzir os efeitos indesejados, mas também promover a entrega em locais específicos e a liberação controlada. Neste trabalho, um novo sistema de nanopartículas poliméricas contendo compostos triazenídicos, que associou os fatores acima, foi desenvolvido, e sua aplicação para terapia de células leucêmicas foi investigada. Primeiramente, o pré-ligante 1-(4-acetilfenil)-3-(4-amidofenil)triazeno (1) e o complexo [1-(4-amidofenil)-3-(4-acetilfenil)triazenido]-(trifenilfosfina)ouro(I) (2) foram sintetizados e devidamente caracterizados por técnicas espectroscopias e difração de raios-X em monocristal. Em seguida os compostos foram avaliados quanto a seus potenciais antibacterianos e antileucêmicos. Os estudos in vitro indicaram potencialidade antibacteriana e antileucêmica ao triazenido complexo, ao passo que o ligante livre não apresentou atividade biológica. Na seqüência, o pré-ligante (1) e o complexo (2) foram encapsulados em nanopartículas (15 200 nm) poliméricas, com morfologia micelar núcleo-corona, esféricas, formadas por copolímeros em bloco. Para tais compostos, o método de encapsulamento mais eficiente é por pré-filme, o qual permite atingir capacidades de encapsulamento de até 10% mcomposto/mpolímero para sistemas com núcleo hidrofóbico de poli[metacrilato de 2-(dialquilamino)etila] ou poliestireno. Posteriormente foram desenvolvidos estudos de nanoencapsulamento, cinética e mecanismos de carregamento dos compostos, usando os copolímeros PEO-b-PG2MA-b-PDPA e PS-b-PAA.Coordenação de Aperfeiçoamento de Pessoal de Nível Superiorapplication/pdfporUniversidade Federal de Santa MariaPrograma de Pós-Graduação em QuímicaUFSMBRQuímicaQuímicaQuímica orgânicaCompostos triazenosNanopartículasNanoestruturasAtividade biológicaCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese, nanoencapsulamento e atividade biológica de compostos triazenosSynthesis, nanoencapsulation and biological activity of triazenes compoundsinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisGiacomelli, Cristianohttp://lattes.cnpq.br/1429116139250396Back, Davi Fernandohttp://lattes.cnpq.br/3778138554788107Giacomelli, Vanessa Schmidthttp://lattes.cnpq.br/0181326876779784http://lattes.cnpq.br/2698783509266261Freitas, Augusto Gonzaga Oliveira de10060000000040050050030050041f37587-ea61-4b16-a6ef-406dce2bea7077cc29d3-75ce-495f-869a-83c9b0bbfdb719ae3041-d76f-4cf3-846a-de236bea0d3915d28ca0-ebec-4ad8-a76e-683e711eb217info:eu-repo/semantics/openAccessreponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALFREITAS, AUGUSTO GONZAGA DE.pdfapplication/pdf4276603http://repositorio.ufsm.br/bitstream/1/10498/1/FREITAS%2c%20AUGUSTO%20GONZAGA%20DE.pdf15789bab6301f303e3dcb072f43ce842MD51TEXTFREITAS, AUGUSTO GONZAGA DE.pdf.txtFREITAS, AUGUSTO GONZAGA DE.pdf.txtExtracted texttext/plain216729http://repositorio.ufsm.br/bitstream/1/10498/2/FREITAS%2c%20AUGUSTO%20GONZAGA%20DE.pdf.txtbc8f100e8bd47726f6c51698d2d8b164MD52THUMBNAILFREITAS, AUGUSTO GONZAGA DE.pdf.jpgFREITAS, AUGUSTO GONZAGA DE.pdf.jpgIM Thumbnailimage/jpeg4863http://repositorio.ufsm.br/bitstream/1/10498/3/FREITAS%2c%20AUGUSTO%20GONZAGA%20DE.pdf.jpg4b83e028825fbb93b67ab716116e5315MD531/104982022-06-03 12:23:28.925oai:repositorio.ufsm.br:1/10498Biblioteca Digital de Teses e Dissertaçõeshttps://repositorio.ufsm.br/ONGhttps://repositorio.ufsm.br/oai/requestatendimento.sib@ufsm.br||tedebc@gmail.comopendoar:2022-06-03T15:23:28Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.por.fl_str_mv |
Síntese, nanoencapsulamento e atividade biológica de compostos triazenos |
dc.title.alternative.eng.fl_str_mv |
Synthesis, nanoencapsulation and biological activity of triazenes compounds |
title |
Síntese, nanoencapsulamento e atividade biológica de compostos triazenos |
spellingShingle |
Síntese, nanoencapsulamento e atividade biológica de compostos triazenos Freitas, Augusto Gonzaga Oliveira de Química Química orgânica Compostos triazenos Nanopartículas Nanoestruturas Atividade biológica CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese, nanoencapsulamento e atividade biológica de compostos triazenos |
title_full |
Síntese, nanoencapsulamento e atividade biológica de compostos triazenos |
title_fullStr |
Síntese, nanoencapsulamento e atividade biológica de compostos triazenos |
title_full_unstemmed |
Síntese, nanoencapsulamento e atividade biológica de compostos triazenos |
title_sort |
Síntese, nanoencapsulamento e atividade biológica de compostos triazenos |
author |
Freitas, Augusto Gonzaga Oliveira de |
author_facet |
Freitas, Augusto Gonzaga Oliveira de |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Giacomelli, Cristiano |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/1429116139250396 |
dc.contributor.referee1.fl_str_mv |
Back, Davi Fernando |
dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/3778138554788107 |
dc.contributor.referee2.fl_str_mv |
Giacomelli, Vanessa Schmidt |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/0181326876779784 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/2698783509266261 |
dc.contributor.author.fl_str_mv |
Freitas, Augusto Gonzaga Oliveira de |
contributor_str_mv |
Giacomelli, Cristiano Back, Davi Fernando Giacomelli, Vanessa Schmidt |
dc.subject.por.fl_str_mv |
Química Química orgânica Compostos triazenos Nanopartículas Nanoestruturas Atividade biológica |
topic |
Química Química orgânica Compostos triazenos Nanopartículas Nanoestruturas Atividade biológica CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
Compounds featuring triazenidic units constitute a versatile class of molecules for the preparation of new inorganic complexes with broad applications that include cancer therapy such as leukemia treatment. Gold-triazenide complexes exhibit recognized versatility in bioinorganic chemistry and medicine, which prompted their development as a basis for anticancer compounds. However, strategies to reduce non-specific cytotoxic effects from the administration of chemotherapy directly into the blood plasma are necessary, as for many other systems. In this regard, the use of polymeric nanoparticles allows not only reduction of side-effects, but also to promote site-specific delivery and controlled release. In this work, the aspects mentioned above have been incorporated into a new polymeric nanoparticles system containing triazenide compounds, and its application to leukemia therapy was investigated. First, the pre-ligand 1-(4-amidophenyl)-3-(4-acetilphenyl)triazene (1) and the complex 1-(4-amidophenyl)-3-(4-acetilphenyl)triazenide-(triphenilphosphine)gold(I) (2) were synthesized and fully characterized by spectroscopic techniques and X-ray diffraction in crystal. Then the compounds were evaluated for their potential antibacterial and antileukemic activities. In vitro studies indicated good antibacterial and antileukemic potential to triazenide complex, while the free ligand showed no biological activity. Subsequently, the pre-ligand (1) and complex (2) were encapsulated in polymeric nanoparticles (15-200 nm) with spherical core-shell micelar morphology, formed by block copolymers. For such compounds, the most efficient encapsulation method is by pre-film, with which encapsulation capabilities of up to 10% mcompound / mpolymer can be achieved for systems featuring poly[methacrylate 2-(dialkylamino) ethyl] or polystyrene cores. Afterwards, nanoencapsulation, loading and release kinetics studies were carried out using PEO-b-PG2MA-b-PDPA and PS-b-PAA copolymers. |
publishDate |
2012 |
dc.date.issued.fl_str_mv |
2012-02-01 |
dc.date.accessioned.fl_str_mv |
2017-05-11 |
dc.date.available.fl_str_mv |
2017-05-11 |
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 |
FREITAS, Augusto Gonzaga Oliveira de. Synthesis, nanoencapsulation and biological activity of triazenes Compounds. 2012. 158 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2012. |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/10498 |
identifier_str_mv |
FREITAS, Augusto Gonzaga Oliveira de. Synthesis, nanoencapsulation and biological activity of triazenes Compounds. 2012. 158 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2012. |
url |
http://repositorio.ufsm.br/handle/1/10498 |
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