Síntese e avaliação fotofísica de compostos fulereno[60]-glicoconjugados
Ano de defesa: | 2018 |
---|---|
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/1/15570 |
Resumo: | In the midst of a variety of alternative therapies in the treatment of several diseases, the photodynamic therapy appears as a versatile protocol. This therapy uses the absorptive properties of photoactive molecules, called photosensitizers and light itself, for the treatment some diseases caused by viruses, bacteria and even some type of tumors. The aim of this work is the synthesis of fullerene [60] -glycolonjugates compounds and the evaluation of their photophysical properties for the use as potential photosensitizers in photodynamic therapy. In this context, the synthesis of 10 C60 Fulerene derived compounds, conjugated to different carbohydrate residues, linked through 1,2,3-triazoyl-malonate moieties were obtained through two different types of cycloaddition reactions. The bis (1- (glycosyl) -5H-1,2,3-triazol-4-alkynyl) malonates (3aa-3ae and 3ba-3be) were obtained through a CuAAc 1,3-dipolar cycloaddition between the acetylenic malonates (2a, 2b) and glycosyl azides (1a-1e). The incorporation of bis (1- (glycosyl) -5H-1,2,3-triazol-4-alkynyl) malonates was carried out through a Bingel-Hirsch type cycloaddition with C60 fullerene, using iodine (I2), DBU as base, in monochlorobenzene for 4 h at room temperature, leading to fullerene[60]-glycolonjugates (4aa-4a and 4ba-4b). The singlet oxygen generation capacity of fulerene[60]-glycolonjugates compounds was evaluated by DPBF photodegradation assays. Then the quantum yields of singlet oxygen generation were quantified for the compounds. The results were considered satisfactory when compared to the pure C60 fulerene used as standard. So, these results accredit the fulerene[60]-glycolonjugates synthesized as potential photosensitizers, for the use in photodynamic therapy. |
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2019-02-07T13:21:18Z2019-02-07T13:21:18Z2018-09-19http://repositorio.ufsm.br/handle/1/15570In the midst of a variety of alternative therapies in the treatment of several diseases, the photodynamic therapy appears as a versatile protocol. This therapy uses the absorptive properties of photoactive molecules, called photosensitizers and light itself, for the treatment some diseases caused by viruses, bacteria and even some type of tumors. The aim of this work is the synthesis of fullerene [60] -glycolonjugates compounds and the evaluation of their photophysical properties for the use as potential photosensitizers in photodynamic therapy. In this context, the synthesis of 10 C60 Fulerene derived compounds, conjugated to different carbohydrate residues, linked through 1,2,3-triazoyl-malonate moieties were obtained through two different types of cycloaddition reactions. The bis (1- (glycosyl) -5H-1,2,3-triazol-4-alkynyl) malonates (3aa-3ae and 3ba-3be) were obtained through a CuAAc 1,3-dipolar cycloaddition between the acetylenic malonates (2a, 2b) and glycosyl azides (1a-1e). The incorporation of bis (1- (glycosyl) -5H-1,2,3-triazol-4-alkynyl) malonates was carried out through a Bingel-Hirsch type cycloaddition with C60 fullerene, using iodine (I2), DBU as base, in monochlorobenzene for 4 h at room temperature, leading to fullerene[60]-glycolonjugates (4aa-4a and 4ba-4b). The singlet oxygen generation capacity of fulerene[60]-glycolonjugates compounds was evaluated by DPBF photodegradation assays. Then the quantum yields of singlet oxygen generation were quantified for the compounds. The results were considered satisfactory when compared to the pure C60 fulerene used as standard. So, these results accredit the fulerene[60]-glycolonjugates synthesized as potential photosensitizers, for the use in photodynamic therapy.Em meio ao surgimento de diversos tipos de terapias alternativas no tratamento de doenças, na medicina moderna podemos destacar a terapia fotodinâmica. Esta terapia se utiliza das propriedades absortivas de moléculas fotoativas, chamadas fotossensibilizadores e, da própria luz, para o tratamento de doenças causadas por vírus, bactérias e até mesmo o câncer. Desta forma, tem-se como objetivo deste trabalho, a síntese de compostos fulereno[60]-glicoconjugados e a avaliação de suas propriedades fotofísicas para o emprego destes como potenciais fotossensibilizadores em terapia fotodinâmica. Desta maneira, 10 compostos derivados de Fulereno C60, conjugados a diferentes resíduos de carboidratos, ligados através de porções 1,2,3-triazoil-malonatos foram obtidos através de dois diferentes tipos de reações de cicloadição. Os bis(1-(glicosil)-5H-1,2,3-triazol-4-alquinil)malonatos (3aa-3ae,e 3ba-3be) foram obtidos através de uma cicloadição CuAAc 1,3-dipolar, entre os malonatos acetilênicos 2a e 2b e as glicosil azidas 1a – 1e. A incorporação dos bis(1-(glicosil)-5H-1,2,3-triazol-4-alquinil)malonatos foram realizadas através de uma cicloadição do tipo Bingel-Hirsch com o fulereno C60, empregando-se iodo (I2), DBU como base, em monoclorobenzeno durante 4h à temperatura ambiente, levando aos fulereno[60]-glicoconjugados (4aa-4ae e 4ba-4be). A capacidade de geração de oxigênio singlete dos compostos fulereno[60]-glicoconjugados foi avaliada por ensaios de fotodegradação do DPBF. Em que os rendimentos quânticos de geração de oxigênio singlete foram quantificados para os compostos sintetizados. Os resultados foram considerados satisfatórios quando comparados ao fulereno C60 utilizado como padrão. Desta forma credenciando os compostos fulereno[60]-glicoconjugados como potenciais fotossensibilizadores, para uso em terapia fotodinâmica.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESporUniversidade 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/openAccessFulerenoCarboidratosGlicofulerenosFotofísicaFullereneCarbohydratesGlycofullerenesPhotophysicsCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese e avaliação fotofísica de compostos fulereno[60]-glicoconjugadosSynthesis and photophysical evaluation of c60 glicoconjugated fullerenesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisRodrigues, Oscar Endrigo Dorneleshttp://lattes.cnpq.br/6536519955416085Dornelles, Lucianohttp://lattes.cnpq.br/7629319262073140Dalcol, Ionara Irionhttp://lattes.cnpq.br/9769548819312192Iglesias, Bernardo Almeidahttp://lattes.cnpq.br/4402375533322977Appelt, Helmoz Roseniaimhttp://lattes.cnpq.br/5360357766246970Souza, Diego dehttp://lattes.cnpq.br/3561369550388349http://lattes.cnpq.br/4522960269975592Silva, Rafael Santos da10060000000060009fef019-ac43-4d8b-83d3-3565e4686d7b5ff7e2fd-19fd-41e4-b59d-5129b85a618188ff8616-1678-47c5-b3c5-9a8e5085844f2cbacb00-be94-498b-9c77-1d47963baf69bef0481f-6297-4683-a6d3-ce04e5d709e3208c1834-aaa3-42a8-9b15-94470d8775e0f34665e4-34ee-4ecb-8643-15d836621adereponame:Manancial - Repositório Digital da UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALTES_PPGQUIMICA_2018_SILVA_RAFAEL.pdfTES_PPGQUIMICA_2018_SILVA_RAFAEL.pdfTese de Doutoradoapplication/pdf6325081http://repositorio.ufsm.br/bitstream/1/15570/1/TES_PPGQUIMICA_2018_SILVA_RAFAEL.pdf62ea87ccb7e7bd70dc1c538552ac39bbMD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv |
Síntese e avaliação fotofísica de compostos fulereno[60]-glicoconjugados |
dc.title.alternative.eng.fl_str_mv |
Synthesis and photophysical evaluation of c60 glicoconjugated fullerenes |
title |
Síntese e avaliação fotofísica de compostos fulereno[60]-glicoconjugados |
spellingShingle |
Síntese e avaliação fotofísica de compostos fulereno[60]-glicoconjugados Silva, Rafael Santos da Fulereno Carboidratos Glicofulerenos Fotofísica Fullerene Carbohydrates Glycofullerenes Photophysics CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese e avaliação fotofísica de compostos fulereno[60]-glicoconjugados |
title_full |
Síntese e avaliação fotofísica de compostos fulereno[60]-glicoconjugados |
title_fullStr |
Síntese e avaliação fotofísica de compostos fulereno[60]-glicoconjugados |
title_full_unstemmed |
Síntese e avaliação fotofísica de compostos fulereno[60]-glicoconjugados |
title_sort |
Síntese e avaliação fotofísica de compostos fulereno[60]-glicoconjugados |
author |
Silva, Rafael Santos da |
author_facet |
Silva, Rafael Santos da |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Rodrigues, Oscar Endrigo Dorneles |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/6536519955416085 |
dc.contributor.advisor-co1.fl_str_mv |
Dornelles, Luciano |
dc.contributor.advisor-co1Lattes.fl_str_mv |
http://lattes.cnpq.br/7629319262073140 |
dc.contributor.referee1.fl_str_mv |
Dalcol, Ionara Irion |
dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/9769548819312192 |
dc.contributor.referee2.fl_str_mv |
Iglesias, Bernardo Almeida |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/4402375533322977 |
dc.contributor.referee3.fl_str_mv |
Appelt, Helmoz Roseniaim |
dc.contributor.referee3Lattes.fl_str_mv |
http://lattes.cnpq.br/5360357766246970 |
dc.contributor.referee4.fl_str_mv |
Souza, Diego de |
dc.contributor.referee4Lattes.fl_str_mv |
http://lattes.cnpq.br/3561369550388349 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/4522960269975592 |
dc.contributor.author.fl_str_mv |
Silva, Rafael Santos da |
contributor_str_mv |
Rodrigues, Oscar Endrigo Dorneles Dornelles, Luciano Dalcol, Ionara Irion Iglesias, Bernardo Almeida Appelt, Helmoz Roseniaim Souza, Diego de |
dc.subject.por.fl_str_mv |
Fulereno Carboidratos Glicofulerenos Fotofísica |
topic |
Fulereno Carboidratos Glicofulerenos Fotofísica Fullerene Carbohydrates Glycofullerenes Photophysics CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Fullerene Carbohydrates Glycofullerenes Photophysics |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
In the midst of a variety of alternative therapies in the treatment of several diseases, the photodynamic therapy appears as a versatile protocol. This therapy uses the absorptive properties of photoactive molecules, called photosensitizers and light itself, for the treatment some diseases caused by viruses, bacteria and even some type of tumors. The aim of this work is the synthesis of fullerene [60] -glycolonjugates compounds and the evaluation of their photophysical properties for the use as potential photosensitizers in photodynamic therapy. In this context, the synthesis of 10 C60 Fulerene derived compounds, conjugated to different carbohydrate residues, linked through 1,2,3-triazoyl-malonate moieties were obtained through two different types of cycloaddition reactions. The bis (1- (glycosyl) -5H-1,2,3-triazol-4-alkynyl) malonates (3aa-3ae and 3ba-3be) were obtained through a CuAAc 1,3-dipolar cycloaddition between the acetylenic malonates (2a, 2b) and glycosyl azides (1a-1e). The incorporation of bis (1- (glycosyl) -5H-1,2,3-triazol-4-alkynyl) malonates was carried out through a Bingel-Hirsch type cycloaddition with C60 fullerene, using iodine (I2), DBU as base, in monochlorobenzene for 4 h at room temperature, leading to fullerene[60]-glycolonjugates (4aa-4a and 4ba-4b). The singlet oxygen generation capacity of fulerene[60]-glycolonjugates compounds was evaluated by DPBF photodegradation assays. Then the quantum yields of singlet oxygen generation were quantified for the compounds. The results were considered satisfactory when compared to the pure C60 fulerene used as standard. So, these results accredit the fulerene[60]-glycolonjugates synthesized as potential photosensitizers, for the use in photodynamic therapy. |
publishDate |
2018 |
dc.date.issued.fl_str_mv |
2018-09-19 |
dc.date.accessioned.fl_str_mv |
2019-02-07T13:21:18Z |
dc.date.available.fl_str_mv |
2019-02-07T13:21:18Z |
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/1/15570 |
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http://repositorio.ufsm.br/handle/1/15570 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.cnpq.fl_str_mv |
100600000000 |
dc.relation.confidence.fl_str_mv |
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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