Síntese, análise estrutural, luminescência e atividade biológica de complexos de metais de transição com ligantes derivados de benzoilidrazina e feniltiossemicarbazida

Detalhes bibliográficos
Autor(a) principal: Bessega, Tiago
Data de Publicação: 2019
Tipo de documento: Tese
Idioma: por
Título da fonte: Biblioteca Digital de Teses e Dissertações do UFSM
Texto Completo: http://repositorio.ufsm.br/handle/1/17544
Resumo: This work reports the synthesis and characterization of new complexes with 2,6-diacetylpyridine-bis(benzoylidrazone) (L1) and 2,6-diformylpyridine-bis(4-phenylthiosemicarbazone) (L2) ligands. The complexes [(L1)2Ce]Cl3.14H2O (L1Ce), [(L1)2Ln]Cl3.3EtOH.2H2O (L1Ln, where Ln = Sm, Eu, Gd, Tb, Dy, Ho and Er), [L2Zn(MeOH)2](NO3)2 (L2Zn), [L2Pd].MeOH (L2Pd) and [L2Pt].MeOH (L2Pt) was structurally characterized by X-ray diffraction. Lanthanide complexes had their luminescent properties investigated, while Pd, Pt and Zn complexes were studied against DNA and BSA protein interactions. Lanthanide complexes are isostructural. In all the complexes, the atom of Ln is coordinated by two ligatures L1 in a pentadentate mode, being decacoordenated, in a distorted square bipyramidal geometry. In the L2Zn complex, the metal is heptacoordinated, with bipyramidal-pentagonal geometry, with the donor set N3S2 of the ligand at the pentagonal 10 base and two molecules of methanol occupying the axial positions. In the L2Pd and L2Pt complexes, the ligand acts as a dianionic tetradentate donor, coordinating the metal in a planar square geometry. The ability of L2 ligand and its complexes to interact with DNA and bovine serum albumin (BSA) was evaluated. The interactions of the compounds L2, L2Zn, L2Pd and L2Pt with DNA were recorded by UV-vis absorption spectroscopy and the interactions between bovine serum albumin (BSA) and the compounds were quantified by steady-state fluorescence emission measurements. The L2Pd and L2Pt complexes showed strong binding constants to CT-DNA, following the increasing order of Kb values: L2Zn <L2 <L2Pd ≈ L2Pt. Molecular docking calculations were performed in order to elucidate the interaction modes between these compounds and the DNA and BSA structure. The most likely binding sites of each compound with DNA and BSA were estimated, also identifying the amino acid residues involved in the interaction.
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spelling 2019-07-24T11:57:54Z2019-07-24T11:57:54Z2019-01-30http://repositorio.ufsm.br/handle/1/17544This work reports the synthesis and characterization of new complexes with 2,6-diacetylpyridine-bis(benzoylidrazone) (L1) and 2,6-diformylpyridine-bis(4-phenylthiosemicarbazone) (L2) ligands. The complexes [(L1)2Ce]Cl3.14H2O (L1Ce), [(L1)2Ln]Cl3.3EtOH.2H2O (L1Ln, where Ln = Sm, Eu, Gd, Tb, Dy, Ho and Er), [L2Zn(MeOH)2](NO3)2 (L2Zn), [L2Pd].MeOH (L2Pd) and [L2Pt].MeOH (L2Pt) was structurally characterized by X-ray diffraction. Lanthanide complexes had their luminescent properties investigated, while Pd, Pt and Zn complexes were studied against DNA and BSA protein interactions. Lanthanide complexes are isostructural. In all the complexes, the atom of Ln is coordinated by two ligatures L1 in a pentadentate mode, being decacoordenated, in a distorted square bipyramidal geometry. In the L2Zn complex, the metal is heptacoordinated, with bipyramidal-pentagonal geometry, with the donor set N3S2 of the ligand at the pentagonal 10 base and two molecules of methanol occupying the axial positions. In the L2Pd and L2Pt complexes, the ligand acts as a dianionic tetradentate donor, coordinating the metal in a planar square geometry. The ability of L2 ligand and its complexes to interact with DNA and bovine serum albumin (BSA) was evaluated. The interactions of the compounds L2, L2Zn, L2Pd and L2Pt with DNA were recorded by UV-vis absorption spectroscopy and the interactions between bovine serum albumin (BSA) and the compounds were quantified by steady-state fluorescence emission measurements. The L2Pd and L2Pt complexes showed strong binding constants to CT-DNA, following the increasing order of Kb values: L2Zn <L2 <L2Pd ≈ L2Pt. Molecular docking calculations were performed in order to elucidate the interaction modes between these compounds and the DNA and BSA structure. The most likely binding sites of each compound with DNA and BSA were estimated, also identifying the amino acid residues involved in the interaction.Este trabalho trata da síntese e caracterização de novos complexos com os ligantes 2,6-diacetilpiridina-bis(benzoilidrazona) (L1) e 2,6-diformilpiridina-bis(4-feniltiossemicarbazona) (L2). Os complexos [(L1)2Ce]Cl3.14H2O (L1Ce), [(L1)2Ln]Cl3.3EtOH.2H2O (L1Ln, onde Ln = Sm, Eu, Gd, Tb, Dy, Ho e Er), [L2Zn(MeOH)2](NO3)2 (L2Zn), [L2Pd].MeOH (L2Pd) e [L2Pt].MeOH (L2Pt) foram caracterizados estruturalmente por difração de raios X de monocristal. Complexos de lantanídeos foram avaliados quanto às propriedades luminescentes, enquanto complexos de Pd, Pt e Zn foram estudados frente a interações com DNA e a proteína BSA. Os complexos de lantanídeos são isoestruturais. Em todos os complexos, o átomo de Ln é coordenado por dois ligantes L1 de modo pentadentado, sendo decacoordenado, com geometria de coordenação bipiramidal quadrática alongada distorcida. No complexo L2Zn o metal é heptacoordenado, com geometria bipiramidal-pentagonal, com o conjunto doador N3S2 do ligante na base pentagonal e duas moléculas de solvente ocupando as posições axiais. Nos complexos de L2Pd e L2Pt, o ligante atua como doador tetradentado dianionico, coordenando ao metal em uma geometria quadrada planar. 8 A capacidade de interação do ligante L2 e seus complexos com o DNA e com albumina de soro bovino (BSA) foi avaliada. As interações dos compostos L2, L2Zn, L2Pd e L2Pt com DNA foram registrados por espectroscopia de absorção na região do UV-vis e as interações entre albumina de soro bovino (BSA) e os compostos foram quantificadas por medições de emissão de fluorescência em estado estacionário. Os complexos L2Pd e L2Pt demonstraram uma forte ligação ao CT-DNA, seguindo a ordem crescente dos valores de Kb: L2Zn < L2< L2Pd ≈ L2Pt. Cálculos de docking molecular foram realizados a fim de elucidar os modos de interação entre estes compostos e a estrutura do DNA e da BSA. Os locais de ligação mais prováveis de cada composto com o DNA e a BSA foram estimados, identificando também os resíduos de aminoácidos envolvidos na interação.porUniversidade Federal de Santa MariaCentro de Ciências Naturais e ExatasPrograma de Pós-Graduação em QuímicaUFSMBrasilQuímicaAttribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessHidrazonasTiossemicarbazonasLantanídeosLuminescênciaPaládioPlatinaDNAHydrazonesThiosemicarbazonesLanthanidesLuminescencePalladiumPlatinumDNACNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese, análise estrutural, luminescência e atividade biológica de complexos de metais de transição com ligantes derivados de benzoilidrazina e feniltiossemicarbazidaSynthesis, structural analysis, luminescence and biological activity of transition metals complexes with ligants derived from benzoylhidrazine and phenylthiosemicarbazideinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisOliveira, Gelson Noe Manzoni dehttp://lattes.cnpq.br/5103552511601104Zancanaro, Aline Machadohttp://lattes.cnpq.br/5586726444452426Faoro, Eliandrohttp://lattes.cnpq.br/2482924502296959Squizani, Fatimahttp://lattes.cnpq.br/1060502818943139Cargnelutti, Robertahttp://lattes.cnpq.br/7099019913953283http://lattes.cnpq.br/9171699676435874Bessega, Tiago100600000000600f18777f7-770b-45dc-b851-ff35cd700dcfc89eb4ef-8d72-4114-ac4d-5570578c0757bb10fd80-272e-44af-8569-a97ed80f3a2795fd8b7a-94a5-42be-9ae0-b2cbda8d971c4ddc4bcd-a704-4703-b2d0-cbad425c775c65b05951-c45c-4e5a-9d19-8289f4839c50reponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALTES_PPGQUIMICA_2019_BESSEGA_TIAGO.pdfTES_PPGQUIMICA_2019_BESSEGA_TIAGO.pdfTese de Doutoradoapplication/pdf5158834http://repositorio.ufsm.br/bitstream/1/17544/1/TES_PPGQUIMICA_2019_BESSEGA_TIAGO.pdf16bf099b87eff7068781d21922bc3092MD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv Síntese, análise estrutural, luminescência e atividade biológica de complexos de metais de transição com ligantes derivados de benzoilidrazina e feniltiossemicarbazida
dc.title.alternative.eng.fl_str_mv Synthesis, structural analysis, luminescence and biological activity of transition metals complexes with ligants derived from benzoylhidrazine and phenylthiosemicarbazide
title Síntese, análise estrutural, luminescência e atividade biológica de complexos de metais de transição com ligantes derivados de benzoilidrazina e feniltiossemicarbazida
spellingShingle Síntese, análise estrutural, luminescência e atividade biológica de complexos de metais de transição com ligantes derivados de benzoilidrazina e feniltiossemicarbazida
Bessega, Tiago
Hidrazonas
Tiossemicarbazonas
Lantanídeos
Luminescência
Paládio
Platina
DNA
Hydrazones
Thiosemicarbazones
Lanthanides
Luminescence
Palladium
Platinum
DNA
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
title_short Síntese, análise estrutural, luminescência e atividade biológica de complexos de metais de transição com ligantes derivados de benzoilidrazina e feniltiossemicarbazida
title_full Síntese, análise estrutural, luminescência e atividade biológica de complexos de metais de transição com ligantes derivados de benzoilidrazina e feniltiossemicarbazida
title_fullStr Síntese, análise estrutural, luminescência e atividade biológica de complexos de metais de transição com ligantes derivados de benzoilidrazina e feniltiossemicarbazida
title_full_unstemmed Síntese, análise estrutural, luminescência e atividade biológica de complexos de metais de transição com ligantes derivados de benzoilidrazina e feniltiossemicarbazida
title_sort Síntese, análise estrutural, luminescência e atividade biológica de complexos de metais de transição com ligantes derivados de benzoilidrazina e feniltiossemicarbazida
author Bessega, Tiago
author_facet Bessega, Tiago
author_role author
dc.contributor.advisor1.fl_str_mv Oliveira, Gelson Noe Manzoni de
dc.contributor.advisor1Lattes.fl_str_mv http://lattes.cnpq.br/5103552511601104
dc.contributor.referee1.fl_str_mv Zancanaro, Aline Machado
dc.contributor.referee1Lattes.fl_str_mv http://lattes.cnpq.br/5586726444452426
dc.contributor.referee2.fl_str_mv Faoro, Eliandro
dc.contributor.referee2Lattes.fl_str_mv http://lattes.cnpq.br/2482924502296959
dc.contributor.referee3.fl_str_mv Squizani, Fatima
dc.contributor.referee3Lattes.fl_str_mv http://lattes.cnpq.br/1060502818943139
dc.contributor.referee4.fl_str_mv Cargnelutti, Roberta
dc.contributor.referee4Lattes.fl_str_mv http://lattes.cnpq.br/7099019913953283
dc.contributor.authorLattes.fl_str_mv http://lattes.cnpq.br/9171699676435874
dc.contributor.author.fl_str_mv Bessega, Tiago
contributor_str_mv Oliveira, Gelson Noe Manzoni de
Zancanaro, Aline Machado
Faoro, Eliandro
Squizani, Fatima
Cargnelutti, Roberta
dc.subject.por.fl_str_mv Hidrazonas
Tiossemicarbazonas
Lantanídeos
Luminescência
Paládio
Platina
DNA
topic Hidrazonas
Tiossemicarbazonas
Lantanídeos
Luminescência
Paládio
Platina
DNA
Hydrazones
Thiosemicarbazones
Lanthanides
Luminescence
Palladium
Platinum
DNA
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
dc.subject.eng.fl_str_mv Hydrazones
Thiosemicarbazones
Lanthanides
Luminescence
Palladium
Platinum
DNA
dc.subject.cnpq.fl_str_mv CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
description This work reports the synthesis and characterization of new complexes with 2,6-diacetylpyridine-bis(benzoylidrazone) (L1) and 2,6-diformylpyridine-bis(4-phenylthiosemicarbazone) (L2) ligands. The complexes [(L1)2Ce]Cl3.14H2O (L1Ce), [(L1)2Ln]Cl3.3EtOH.2H2O (L1Ln, where Ln = Sm, Eu, Gd, Tb, Dy, Ho and Er), [L2Zn(MeOH)2](NO3)2 (L2Zn), [L2Pd].MeOH (L2Pd) and [L2Pt].MeOH (L2Pt) was structurally characterized by X-ray diffraction. Lanthanide complexes had their luminescent properties investigated, while Pd, Pt and Zn complexes were studied against DNA and BSA protein interactions. Lanthanide complexes are isostructural. In all the complexes, the atom of Ln is coordinated by two ligatures L1 in a pentadentate mode, being decacoordenated, in a distorted square bipyramidal geometry. In the L2Zn complex, the metal is heptacoordinated, with bipyramidal-pentagonal geometry, with the donor set N3S2 of the ligand at the pentagonal 10 base and two molecules of methanol occupying the axial positions. In the L2Pd and L2Pt complexes, the ligand acts as a dianionic tetradentate donor, coordinating the metal in a planar square geometry. The ability of L2 ligand and its complexes to interact with DNA and bovine serum albumin (BSA) was evaluated. The interactions of the compounds L2, L2Zn, L2Pd and L2Pt with DNA were recorded by UV-vis absorption spectroscopy and the interactions between bovine serum albumin (BSA) and the compounds were quantified by steady-state fluorescence emission measurements. The L2Pd and L2Pt complexes showed strong binding constants to CT-DNA, following the increasing order of Kb values: L2Zn <L2 <L2Pd ≈ L2Pt. Molecular docking calculations were performed in order to elucidate the interaction modes between these compounds and the DNA and BSA structure. The most likely binding sites of each compound with DNA and BSA were estimated, also identifying the amino acid residues involved in the interaction.
publishDate 2019
dc.date.accessioned.fl_str_mv 2019-07-24T11:57:54Z
dc.date.available.fl_str_mv 2019-07-24T11:57:54Z
dc.date.issued.fl_str_mv 2019-01-30
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/doctoralThesis
format doctoralThesis
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://repositorio.ufsm.br/handle/1/17544
url http://repositorio.ufsm.br/handle/1/17544
dc.language.iso.fl_str_mv por
language por
dc.relation.cnpq.fl_str_mv 100600000000
dc.relation.confidence.fl_str_mv 600
dc.relation.authority.fl_str_mv f18777f7-770b-45dc-b851-ff35cd700dcf
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dc.rights.driver.fl_str_mv Attribution-NonCommercial-NoDerivatives 4.0 International
http://creativecommons.org/licenses/by-nc-nd/4.0/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Attribution-NonCommercial-NoDerivatives 4.0 International
http://creativecommons.org/licenses/by-nc-nd/4.0/
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Universidade Federal de Santa Maria
Centro de Ciências Naturais e Exatas
dc.publisher.program.fl_str_mv Programa de Pós-Graduação em Química
dc.publisher.initials.fl_str_mv UFSM
dc.publisher.country.fl_str_mv Brasil
dc.publisher.department.fl_str_mv Química
publisher.none.fl_str_mv Universidade Federal de Santa Maria
Centro de Ciências Naturais e Exatas
dc.source.none.fl_str_mv reponame:Biblioteca Digital de Teses e Dissertações do UFSM
instname:Universidade Federal de Santa Maria (UFSM)
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instname_str Universidade Federal de Santa Maria (UFSM)
instacron_str UFSM
institution UFSM
reponame_str Biblioteca Digital de Teses e Dissertações do UFSM
collection Biblioteca Digital de Teses e Dissertações do UFSM
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MD5
repository.name.fl_str_mv Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM)
repository.mail.fl_str_mv atendimento.sib@ufsm.br||tedebc@gmail.com
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