Investigação das propriedades fotofísicas e estudo da interação com biomoléculas de porfirinas meso-substituídas em posição meta contendo complexos de PdII, PtII e RuII
Ano de defesa: | 2022 |
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Autor(a) principal: | |
Orientador(a): | |
Banca de defesa: | , , , |
Tipo de documento: | Tese |
Tipo de acesso: | Acesso aberto |
Idioma: | por |
Instituição de defesa: |
Universidade Federal de Santa Maria
Centro de Ciências Naturais e Exatas |
Programa de Pós-Graduação: |
Programa de Pós-Graduação em Química
|
Departamento: |
Química
|
País: |
Brasil
|
Palavras-chave em Português: | |
Palavras-chave em Inglês: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.ufsm.br/handle/1/24109 |
Resumo: | This work aimed at the synthesis of porphyrins: meso-tetra(3-pyridyl)porphyrin (3-H2TPyP), meso-tetra [(3- pyridyl)-chlor-(2,2'-bipyridyl)-palladium(II) ]porphyrin (3-Pd(bpy)TPyP), meso-tetra[(3-pyridyl)-chloro-(1,10- phenanthroline)-palladium(II)]porphyrin (3-Pd(phen)TPyP), meso-tetra[(3-pyridyl)-chloro-(2,2'-bipyridyl)- platinum(II)]porphyrin (3-Pt(bpy)TPyP), meso-tetra[(3-pyridyl)-chloro-(1,10-phenanthroline)-platinum(II)] porphyrin (3-Pt(phen)TPyP), meso-tetra[(3-pyridyl)-chloro-bis(2,2'-bipyridyl)-ruthenium(II)]porphyrin (3- Ru(bpy)TPyP) and meso-tetra[(3-pyridyl)-chloro-bis(1,10-phenanthroline)-ruthenium(II)]porphyrin (3- Ru(phen)TPyP). The compounds were characterized by elemental analysis of CHN%, electronic spectroscopy in the ultraviolet-visible and infrared regions, fluorescence emission spectroscopy. In addition, aggregation tests in solution were performed, its photophysical properties, such as photostability and singlet oxygen generation, were investigated. The interactions of these compounds with the biomolecule were also investigated, through interactive studies with calf thymus deoxyribonucleic acid (CT-DNA) and studies with human serum albumin (HSA). To analyze and understand the interactions of these compounds, experiments were performed via UV-Vis spectroscopy. The compounds showed good photo-stability, in the studied light irradiation range, but low quantum yields of singlet oxygen. The assays of interactions with CT-DNA showed results with low values for binding constants (Kb), they also presented low to moderate values of Stern-Volmer suppression constants (Ksv) in the assays of competitors with different dyes, on the other hand, the Gibbs free energy values suggest spontaneous processes. In addition, docking molecular suggests that the greatest interaction is through the smallest groove in the DNA. In relation to the interaction assays with the HSA protein, the constants of Ksv and Ka were in the order of 104 L mol−1 and with the help of theoretical calculations, it was identified that the preference for their interaction is the IB subdomain. |
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2022-04-19T20:08:44Z2022-04-19T20:08:44Z2022-01-19http://repositorio.ufsm.br/handle/1/24109This work aimed at the synthesis of porphyrins: meso-tetra(3-pyridyl)porphyrin (3-H2TPyP), meso-tetra [(3- pyridyl)-chlor-(2,2'-bipyridyl)-palladium(II) ]porphyrin (3-Pd(bpy)TPyP), meso-tetra[(3-pyridyl)-chloro-(1,10- phenanthroline)-palladium(II)]porphyrin (3-Pd(phen)TPyP), meso-tetra[(3-pyridyl)-chloro-(2,2'-bipyridyl)- platinum(II)]porphyrin (3-Pt(bpy)TPyP), meso-tetra[(3-pyridyl)-chloro-(1,10-phenanthroline)-platinum(II)] porphyrin (3-Pt(phen)TPyP), meso-tetra[(3-pyridyl)-chloro-bis(2,2'-bipyridyl)-ruthenium(II)]porphyrin (3- Ru(bpy)TPyP) and meso-tetra[(3-pyridyl)-chloro-bis(1,10-phenanthroline)-ruthenium(II)]porphyrin (3- Ru(phen)TPyP). The compounds were characterized by elemental analysis of CHN%, electronic spectroscopy in the ultraviolet-visible and infrared regions, fluorescence emission spectroscopy. In addition, aggregation tests in solution were performed, its photophysical properties, such as photostability and singlet oxygen generation, were investigated. The interactions of these compounds with the biomolecule were also investigated, through interactive studies with calf thymus deoxyribonucleic acid (CT-DNA) and studies with human serum albumin (HSA). To analyze and understand the interactions of these compounds, experiments were performed via UV-Vis spectroscopy. The compounds showed good photo-stability, in the studied light irradiation range, but low quantum yields of singlet oxygen. The assays of interactions with CT-DNA showed results with low values for binding constants (Kb), they also presented low to moderate values of Stern-Volmer suppression constants (Ksv) in the assays of competitors with different dyes, on the other hand, the Gibbs free energy values suggest spontaneous processes. In addition, docking molecular suggests that the greatest interaction is through the smallest groove in the DNA. In relation to the interaction assays with the HSA protein, the constants of Ksv and Ka were in the order of 104 L mol−1 and with the help of theoretical calculations, it was identified that the preference for their interaction is the IB subdomain.Este trabalho consiste nas sínteses das porfirinas: meso-tetra(3-piridil)porfirina (3-H2TPyP), meso-tetra[(3- piridil)-cloro-(2,2’-bipiridil)-paládio(II)]porfirina (3-Pd(bpy)TPyP), meso-tetra[(3-piridil)-cloro-(1,10- fenantrolina)-paládio(II)]porfirina (3-Pd(phen)TPyP), meso-tetra[(3-piridil)-cloro-(2,2’-bipiridil)- platina(II)]porfirina (3-Pt(bpy)TPyP), meso-tetra[(3-piridil)-cloro-(1,10-fenantrolina)-platina(II)]porfirina (3- Pt(phen)TPyP), meso-tetra[(3-piridil)-cloro-bis(2,2’-bipiridil)-rutênio(II)]porfirina (3-Ru(bpy)TPyP) e mesotetra[( 3-piridil)-cloro-bis(1,10-fenantrolina)-rutênio(II)]porfirina (3-Ru(phen)TPyP). Os compostos foram caracterizados por análise elementar de porcentagem de carbono, nitrogênio e hidrogênio, ponto de fusão, espectroscopia eletrônica nas regiões do ultravioleta-visível (UV-Vis) e do infravermelho, e espectroscopia por emissão de fluorescência. Além disso, ensaios de agregação em solução foram realizados, suas propriedades fotofísicas, como fotoestabilidade e geração de oxigênio singleto, foram investigadas. Também foram investigadas as interações desses compostos com biomolécula, através de estudos interativos com o ácido desoxirribonucleico de timo de bezerro (CT-DNA) e estudos com a albumina do soro humano (HSA). Para analisar e compreender as interações desses compostos, foram realizados experimentos via espectroscopia UV-Vis e fluorescência. Os compostos apresentaram boa fotoestabilidade, na faixa de irradiação de luz estudada, porém baixos rendimentos quânticos de oxigênio singleto. Os ensaios das interações com o CT-DNA demonstraram resultados com valores baixos para as constantes de ligação (Kb), também apresentaram valores baixos a moderados de constantes de supressão de Stern-Volmer (Ksv) nos ensaios de competidores com diferentes corantes. Por outro lado, os valores de energia livre de Gibbs sugerem processos espontâneos. Em complemento, a modelagem computacional sugere que a maior interação é pelo sulco menor do DNA. Em relação aos ensaios de interação com a proteína HSA, as constantes de Ksv e Ka ficaram na ordem de 104 L mol−1 e com o auxílio dos cálculos teóricos, identificou-se que a preferência da interação com as mesmas é o subdomínio IB.Conselho Nacional de Pesquisa e Desenvolvimento Científico e Tecnológico - CNPqporUniversidade 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/openAccessPorfirinasDNAHSAFotofísicaPorphyrinPhotophysicsCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICAInvestigação das propriedades fotofísicas e estudo da interação com biomoléculas de porfirinas meso-substituídas em posição meta contendo complexos de PdII, PtII e RuIIInvestigation of photophysical properties and study of the interaction with biomolecules of meso-replaced porphyrines in meta position containing complexes of PdII, PtII e RuIIinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisIglesias, Bernardo Almeidahttp://lattes.cnpq.br/4402375533322977Lang, Ernesto SchulzTirloni, BarbaraCargnelutti, RobertaCosta, Luiz Antônio SodréDeflon, Victor Marcelohttp://lattes.cnpq.br/4074800603218979Silveira, Carolina Hahn da1006000000006006006006006006006006003140bdfe-ad7b-478b-8ebd-065c1627c13275a3b310-bdd8-4cb9-9a9c-cc1a60fa244fcfa390bb-f563-4e62-bb23-a71c8c15168fc0fdbcac-0be4-42a7-87f7-7d98df7c1dfb3eeb3eee-6d33-4bda-9f45-562ae0474d9f9fe5b23a-94d3-429b-89b9-a7cddab546da91cd8068-c6ef-4ee9-a8c8-eb8fb60839a2reponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMCC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv |
Investigação das propriedades fotofísicas e estudo da interação com biomoléculas de porfirinas meso-substituídas em posição meta contendo complexos de PdII, PtII e RuII |
dc.title.alternative.eng.fl_str_mv |
Investigation of photophysical properties and study of the interaction with biomolecules of meso-replaced porphyrines in meta position containing complexes of PdII, PtII e RuII |
title |
Investigação das propriedades fotofísicas e estudo da interação com biomoléculas de porfirinas meso-substituídas em posição meta contendo complexos de PdII, PtII e RuII |
spellingShingle |
Investigação das propriedades fotofísicas e estudo da interação com biomoléculas de porfirinas meso-substituídas em posição meta contendo complexos de PdII, PtII e RuII Silveira, Carolina Hahn da Porfirinas DNA HSA Fotofísica Porphyrin Photophysics CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Investigação das propriedades fotofísicas e estudo da interação com biomoléculas de porfirinas meso-substituídas em posição meta contendo complexos de PdII, PtII e RuII |
title_full |
Investigação das propriedades fotofísicas e estudo da interação com biomoléculas de porfirinas meso-substituídas em posição meta contendo complexos de PdII, PtII e RuII |
title_fullStr |
Investigação das propriedades fotofísicas e estudo da interação com biomoléculas de porfirinas meso-substituídas em posição meta contendo complexos de PdII, PtII e RuII |
title_full_unstemmed |
Investigação das propriedades fotofísicas e estudo da interação com biomoléculas de porfirinas meso-substituídas em posição meta contendo complexos de PdII, PtII e RuII |
title_sort |
Investigação das propriedades fotofísicas e estudo da interação com biomoléculas de porfirinas meso-substituídas em posição meta contendo complexos de PdII, PtII e RuII |
author |
Silveira, Carolina Hahn da |
author_facet |
Silveira, Carolina Hahn da |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Iglesias, Bernardo Almeida |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/4402375533322977 |
dc.contributor.advisor-co1.fl_str_mv |
Lang, Ernesto Schulz |
dc.contributor.referee1.fl_str_mv |
Tirloni, Barbara |
dc.contributor.referee2.fl_str_mv |
Cargnelutti, Roberta |
dc.contributor.referee3.fl_str_mv |
Costa, Luiz Antônio Sodré |
dc.contributor.referee4.fl_str_mv |
Deflon, Victor Marcelo |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/4074800603218979 |
dc.contributor.author.fl_str_mv |
Silveira, Carolina Hahn da |
contributor_str_mv |
Iglesias, Bernardo Almeida Lang, Ernesto Schulz Tirloni, Barbara Cargnelutti, Roberta Costa, Luiz Antônio Sodré Deflon, Victor Marcelo |
dc.subject.por.fl_str_mv |
Porfirinas DNA HSA Fotofísica |
topic |
Porfirinas DNA HSA Fotofísica Porphyrin Photophysics CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Porphyrin Photophysics |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
This work aimed at the synthesis of porphyrins: meso-tetra(3-pyridyl)porphyrin (3-H2TPyP), meso-tetra [(3- pyridyl)-chlor-(2,2'-bipyridyl)-palladium(II) ]porphyrin (3-Pd(bpy)TPyP), meso-tetra[(3-pyridyl)-chloro-(1,10- phenanthroline)-palladium(II)]porphyrin (3-Pd(phen)TPyP), meso-tetra[(3-pyridyl)-chloro-(2,2'-bipyridyl)- platinum(II)]porphyrin (3-Pt(bpy)TPyP), meso-tetra[(3-pyridyl)-chloro-(1,10-phenanthroline)-platinum(II)] porphyrin (3-Pt(phen)TPyP), meso-tetra[(3-pyridyl)-chloro-bis(2,2'-bipyridyl)-ruthenium(II)]porphyrin (3- Ru(bpy)TPyP) and meso-tetra[(3-pyridyl)-chloro-bis(1,10-phenanthroline)-ruthenium(II)]porphyrin (3- Ru(phen)TPyP). The compounds were characterized by elemental analysis of CHN%, electronic spectroscopy in the ultraviolet-visible and infrared regions, fluorescence emission spectroscopy. In addition, aggregation tests in solution were performed, its photophysical properties, such as photostability and singlet oxygen generation, were investigated. The interactions of these compounds with the biomolecule were also investigated, through interactive studies with calf thymus deoxyribonucleic acid (CT-DNA) and studies with human serum albumin (HSA). To analyze and understand the interactions of these compounds, experiments were performed via UV-Vis spectroscopy. The compounds showed good photo-stability, in the studied light irradiation range, but low quantum yields of singlet oxygen. The assays of interactions with CT-DNA showed results with low values for binding constants (Kb), they also presented low to moderate values of Stern-Volmer suppression constants (Ksv) in the assays of competitors with different dyes, on the other hand, the Gibbs free energy values suggest spontaneous processes. In addition, docking molecular suggests that the greatest interaction is through the smallest groove in the DNA. In relation to the interaction assays with the HSA protein, the constants of Ksv and Ka were in the order of 104 L mol−1 and with the help of theoretical calculations, it was identified that the preference for their interaction is the IB subdomain. |
publishDate |
2022 |
dc.date.accessioned.fl_str_mv |
2022-04-19T20:08:44Z |
dc.date.available.fl_str_mv |
2022-04-19T20:08:44Z |
dc.date.issued.fl_str_mv |
2022-01-19 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/doctoralThesis |
format |
doctoralThesis |
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publishedVersion |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/24109 |
url |
http://repositorio.ufsm.br/handle/1/24109 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.cnpq.fl_str_mv |
100600000000 |
dc.relation.confidence.fl_str_mv |
600 600 600 600 600 600 600 600 |
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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 |
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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 |
_version_ |
1793240166028017664 |