Síntese e avaliação fotofísica de compostos fulereno[60]-glicoconjugados
Autor(a) principal: | |
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Data de Publicação: | 2018 |
Tipo de documento: | Tese |
Idioma: | por |
Título da fonte: | Manancial - Repositório Digital da UFSM |
Texto Completo: | 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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Síntese e avaliação fotofísica de compostos fulereno[60]-glicoconjugadosSynthesis and photophysical evaluation of c60 glicoconjugated fullerenesFulerenoCarboidratosGlicofulerenosFotofísicaFullereneCarbohydratesGlycofullerenesPhotophysicsCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICAIn 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.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESEm 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.Universidade Federal de Santa MariaBrasilQuímicaUFSMPrograma de Pós-Graduação em QuímicaCentro de Ciências Naturais e ExatasRodrigues, 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/3561369550388349Silva, Rafael Santos da2019-02-07T13:21:18Z2019-02-07T13:21:18Z2018-09-19info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisapplication/pdfhttp://repositorio.ufsm.br/handle/1/15570porAttribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessreponame:Manancial - Repositório Digital da UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSM2019-02-08T05:02:20Zoai:repositorio.ufsm.br:1/15570Biblioteca Digital de Teses e Dissertaçõeshttps://repositorio.ufsm.br/ONGhttps://repositorio.ufsm.br/oai/requestatendimento.sib@ufsm.br||tedebc@gmail.comopendoar:2019-02-08T05:02:20Manancial - Repositório Digital da UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.none.fl_str_mv |
Síntese e avaliação fotofísica de compostos fulereno[60]-glicoconjugados 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.none.fl_str_mv |
Rodrigues, Oscar Endrigo Dorneles http://lattes.cnpq.br/6536519955416085 Dornelles, Luciano http://lattes.cnpq.br/7629319262073140 Dalcol, Ionara Irion http://lattes.cnpq.br/9769548819312192 Iglesias, Bernardo Almeida http://lattes.cnpq.br/4402375533322977 Appelt, Helmoz Roseniaim http://lattes.cnpq.br/5360357766246970 Souza, Diego de http://lattes.cnpq.br/3561369550388349 |
dc.contributor.author.fl_str_mv |
Silva, Rafael Santos da |
dc.subject.por.fl_str_mv |
Fulereno Carboidratos Glicofulerenos Fotofísica Fullerene Carbohydrates Glycofullerenes Photophysics CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
topic |
Fulereno Carboidratos Glicofulerenos Fotofísica Fullerene Carbohydrates Glycofullerenes Photophysics 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.none.fl_str_mv |
2018-09-19 2019-02-07T13:21:18Z 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 |
url |
http://repositorio.ufsm.br/handle/1/15570 |
dc.language.iso.fl_str_mv |
por |
language |
por |
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.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
Universidade Federal de Santa Maria Brasil Química UFSM Programa de Pós-Graduação em Química Centro de Ciências Naturais e Exatas |
publisher.none.fl_str_mv |
Universidade Federal de Santa Maria Brasil Química UFSM Programa de Pós-Graduação em Química Centro de Ciências Naturais e Exatas |
dc.source.none.fl_str_mv |
reponame:Manancial - Repositório Digital da UFSM instname:Universidade Federal de Santa Maria (UFSM) instacron:UFSM |
instname_str |
Universidade Federal de Santa Maria (UFSM) |
instacron_str |
UFSM |
institution |
UFSM |
reponame_str |
Manancial - Repositório Digital da UFSM |
collection |
Manancial - Repositório Digital da UFSM |
repository.name.fl_str_mv |
Manancial - Repositório Digital da UFSM - Universidade Federal de Santa Maria (UFSM) |
repository.mail.fl_str_mv |
atendimento.sib@ufsm.br||tedebc@gmail.com |
_version_ |
1805922152254275584 |