Abordagem teórica das interações dissacarídeo-protótipo de membrana fosfolipídica
| Autor(a) principal: | |
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| Data de Publicação: | 2022 |
| Tipo de documento: | Tese |
| Idioma: | por |
| Título da fonte: | Biblioteca Digital de Teses e Dissertações da UFRRJ |
| Texto Completo: | https://rima.ufrrj.br/jspui/handle/20.500.14407/10266 |
Resumo: | A presente tese teve como objetivo principal estudar as interações entre uma molécula de dissacarídeo e um protótipo de membrana fosfolipídica, formado por um sistema dimérico composto por duas moléculas de fosfolipídio. Tal estudo foi feito de maneira teórica, utilizando métodos quânticos para a modelagem dos sistemas moleculares de interesse: um método baseado na Teoria do Funcional da Densidade (B97-D/6-31G(d,p)) e um método semi-empírico (PM6). Os dissacarídeos considerados foram trealose, maltose e celobiose. O fosfolipídio considerado foi dioctanoil- fosfatidilcolina. O estudo de tais interações envolveu a construção do protótipo de membrana fosfolipídica e a criação de um protocolo para a aproximação dos dissacarídeos ao protótipo e se deu por meio do cálculo da energia de interação quando na formação dos sistemas interagentes (dissacarídeo-protótipo de membrana fosfolipídica). Com base em critérios geométricos, foram identificados dois tipos de interações entre todos os dissacarídeos e o protótipo de membrana fosfolipídica: interações com grupos fosfato e com grupos trimetil-amônio. Foram obtidos os espectros de absorção no infravermelho para o protótipo de membrana fosfolipídica isolado e para todos os sistemas interagentes – quatro para a trealose, três para a maltose e dois para a celobiose, a fim de comparar o comportamento do sinal correspondente ao estiramento assimétrico do grupo fosfato para agregados fosfolipídicos secos e agregados fosfolipídicos na presença de diferentes carboidratos, indicado na literatura como diferentemente afetado pela presença de diferentes carboidratos. Utilizando uma equação que relaciona o valor da constante de acoplamento de spin heteronuclear à três ligações 3JC1,H1’ ao valor do ângulo diedro definido pela sequência de átomos C1–O–C1’–H1’, ao longo da ligação glicosídica da trealose, foram calculados os respectivos valores de 3JC1,H1’ para todos os quatro sistemas interagentes obtidos. A partir do cálculo de população de Boltzmann para os sistemas interagentes, foi obtido um valor médio para a constante de acoplamento, que foi comparado ao resultado experimental disponível na literatura. Os valores de energia de interação dissacarídeo- protótipo de membrana fosfolipídica não mostraram concordância com o comportamento do sinal correspondente ao estiramento assimétrico do grupo fosfato, isso considerando os sistemas interagentes de mais baixa energia, sem correção de ponto zero. Tal resultado foi compreendido como sendo um forte indício de que as interações com grupos trimetil-amônio também precisam ser consideradas nessa avaliação. Já o valor médio obtido para a constante de acoplamento de spin heteronuclear, comparou-se muito bem ao valor experimental disponível na literatura, sendo um indicativo de que os valores dos ângulos glicosídicos da trealose presentes nos sistemas interagentes obtidos teoricamente comparam-se àqueles assumidos pelo dissacarídeo em sistemas interagentes reais, de forma que o método PM6, utilizado para a modelagem dos sistemas interagentes, pode ser apontado como um método computacional capaz de descrever adequadamente os efeitos estabilizantes da ligação glicosídica da trealose nesse tipo de sistema. |
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Soares, Cinthia SantosSilva, Clarissa Oliveira da014.109.957-71https://orcid.org/0000-0002-5640-5387http://lattes.cnpq.br/3211933004567550Bauerfeldt, Glauco Favilla069.023.487-23https://orcid.org/0000-0001-5906-7080http://lattes.cnpq.br/1876040291299143Silva, Clarissa Oliveira da014.109.957-71https://orcid.org/0000-0002-5640-5387http://lattes.cnpq.br/3211933004567550Riger, Cristiano Jorgehttps://orcid.org/0000-0002-7579-5958http://lattes.cnpq.br/8756160468801705Pereira, Márcio Soareshttps://orcid.org/0000-0002-7579-5958http://lattes.cnpq.br/8756160468801705Magalhães, Camila Silva de077.313.237-65Baptista, Leonardo053.120.556-89https://orcid.org/0000-0001-9433-3313http://lattes.cnpq.br/2182432135517042099.709.887-27http://lattes.cnpq.br/86301620097994062023-12-21T18:59:48Z2023-12-21T18:59:48Z2022-07-06SOARES, Cinthia Santos. Abordagem teórica das interações dissacarídeo-protótipo de membrana fosfolipídica. 2022. 132 f. Tese (Doutorado em Química) - Instituto de Química, Universidade Federal Rural do Rio de Janeiro, Seropédica, 2022.https://rima.ufrrj.br/jspui/handle/20.500.14407/10266A presente tese teve como objetivo principal estudar as interações entre uma molécula de dissacarídeo e um protótipo de membrana fosfolipídica, formado por um sistema dimérico composto por duas moléculas de fosfolipídio. Tal estudo foi feito de maneira teórica, utilizando métodos quânticos para a modelagem dos sistemas moleculares de interesse: um método baseado na Teoria do Funcional da Densidade (B97-D/6-31G(d,p)) e um método semi-empírico (PM6). Os dissacarídeos considerados foram trealose, maltose e celobiose. O fosfolipídio considerado foi dioctanoil- fosfatidilcolina. O estudo de tais interações envolveu a construção do protótipo de membrana fosfolipídica e a criação de um protocolo para a aproximação dos dissacarídeos ao protótipo e se deu por meio do cálculo da energia de interação quando na formação dos sistemas interagentes (dissacarídeo-protótipo de membrana fosfolipídica). Com base em critérios geométricos, foram identificados dois tipos de interações entre todos os dissacarídeos e o protótipo de membrana fosfolipídica: interações com grupos fosfato e com grupos trimetil-amônio. Foram obtidos os espectros de absorção no infravermelho para o protótipo de membrana fosfolipídica isolado e para todos os sistemas interagentes – quatro para a trealose, três para a maltose e dois para a celobiose, a fim de comparar o comportamento do sinal correspondente ao estiramento assimétrico do grupo fosfato para agregados fosfolipídicos secos e agregados fosfolipídicos na presença de diferentes carboidratos, indicado na literatura como diferentemente afetado pela presença de diferentes carboidratos. Utilizando uma equação que relaciona o valor da constante de acoplamento de spin heteronuclear à três ligações 3JC1,H1’ ao valor do ângulo diedro definido pela sequência de átomos C1–O–C1’–H1’, ao longo da ligação glicosídica da trealose, foram calculados os respectivos valores de 3JC1,H1’ para todos os quatro sistemas interagentes obtidos. A partir do cálculo de população de Boltzmann para os sistemas interagentes, foi obtido um valor médio para a constante de acoplamento, que foi comparado ao resultado experimental disponível na literatura. Os valores de energia de interação dissacarídeo- protótipo de membrana fosfolipídica não mostraram concordância com o comportamento do sinal correspondente ao estiramento assimétrico do grupo fosfato, isso considerando os sistemas interagentes de mais baixa energia, sem correção de ponto zero. Tal resultado foi compreendido como sendo um forte indício de que as interações com grupos trimetil-amônio também precisam ser consideradas nessa avaliação. Já o valor médio obtido para a constante de acoplamento de spin heteronuclear, comparou-se muito bem ao valor experimental disponível na literatura, sendo um indicativo de que os valores dos ângulos glicosídicos da trealose presentes nos sistemas interagentes obtidos teoricamente comparam-se àqueles assumidos pelo dissacarídeo em sistemas interagentes reais, de forma que o método PM6, utilizado para a modelagem dos sistemas interagentes, pode ser apontado como um método computacional capaz de descrever adequadamente os efeitos estabilizantes da ligação glicosídica da trealose nesse tipo de sistema.CAPES - Coordenação de Aperfeiçoamento de Pessoal de Nível SuperiorThe main objective of this thesis was to study the interactions between a disaccharide molecule and a phospholipid membrane prototype, formed by a dimeric system composed of two phospholipid molecules. This study was carried out theoretically, using quantum methods to model the molecular systems of interest: a method based on the Density Functional Theory (B97-D/6-31G(d,p)) and a semi- empirical method (PM6). The disaccharides considered were trehalose, maltose and cellobiose. The phospholipid considered was dioctanoyl-phosphatidylcholine. The study of such interactions involved the construction of the phospholipid membrane prototype and the creation of a protocol for the approximation of the disaccharides to the prototype. Based on geometric criteria, two types of interactions were identified between all disaccharides and the phospholipid membrane prototype: interactions with phosphate groups and with trimethyl-ammonium groups. Infrared absorption spectra were obtained for the isolated phospholipid membrane prototype and for all interacting systems - four for trehalose, three for maltose and two for cellobiose, in order to compare the behavior of the signal corresponding to the asymmetric stretching of the phosphate group for dry phospholipid aggregates and phospholipid aggregates in the presence of different carbohydrates, indicated in the literature as differently affected by the presence of different carbohydrates. Using an equation that relates the value of the heteronuclear spin coupling constant 3JC1,H1' to the value of the dihedral angle defined by the sequence of atoms C1–O–C1'–H1', along the glycosidic bond of trehalose, the respective values of 3JC1,H1' were calculated for all four interacting systems obtained. From the calculation of the Boltzmann population for the interacting systems, an average value for the coupling constant was obtained, which was compared to the experimental result available in the literature. The values of disaccharide-prototype phospholipid membrane interaction energy did not show agreement with the behavior of the signal corresponding to the asymmetric stretching of the phosphate group, considering the lowest energy interacting systems, without zero point correction. This result was understood as a strong indication that interactions with trimethyl-ammonium groups also need to be considered in this evaluation. The average value obtained for the heteronuclear spin coupling constant, compared very well to the experimental value available in the literature, being an indication that the values of the glycosidic angles of trehalose present in the interacting systems theoretically obtained are compared to those assumed by the disaccharide in real interacting systems, so that the PM6 method, used to model the interacting systems, can be pointed out as a computational method capable of adequately describing the stabilizing effects of the trehalose glycosidic bond in this type of system.application/pdfporUniversidade Federal Rural do Rio de JaneiroPrograma de Pós-Graduação em QuímicaUFRRJBrasilInstituto de QuímicaConformação de fosfolipídiosMembrana fosfolipídicaInteração dissacarídeo-membranaPhospholipid conformationPhospholipid membraneDissaccharide- membrane interactionQuímicaAbordagem teórica das interações dissacarídeo-protótipo de membrana fosfolipídicaTheoretical approach of dissaccharide-phospholipid membrane interactionsinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisJAIN, M. 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FT infrared and Raman investigation of saccharide-phosphatidylcholine interactions using novelstructure probes. Spectrochimica Acta Part A, v. 54, p. 1989˗2000. 1998.https://tede.ufrrj.br/retrieve/73869/2022%20-%20Cinthia%20Santos%20Soares.pdf.jpghttps://tede.ufrrj.br/jspui/handle/jspui/6732Submitted by Leticia Schettini (leticia@ufrrj.br) on 2023-07-14T11:51:43Z No. of bitstreams: 1 2022 - Cinthia Santos Soares.pdf: 2995100 bytes, checksum: 45eb6cda77e7db0d56e6a4c20745b2f5 (MD5)Made available in DSpace on 2023-07-14T11:51:43Z (GMT). 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| dc.title.por.fl_str_mv |
Abordagem teórica das interações dissacarídeo-protótipo de membrana fosfolipídica |
| dc.title.alternative.eng.fl_str_mv |
Theoretical approach of dissaccharide-phospholipid membrane interactions |
| title |
Abordagem teórica das interações dissacarídeo-protótipo de membrana fosfolipídica |
| spellingShingle |
Abordagem teórica das interações dissacarídeo-protótipo de membrana fosfolipídica Soares, Cinthia Santos Conformação de fosfolipídios Membrana fosfolipídica Interação dissacarídeo-membrana Phospholipid conformation Phospholipid membrane Dissaccharide- membrane interaction Química |
| title_short |
Abordagem teórica das interações dissacarídeo-protótipo de membrana fosfolipídica |
| title_full |
Abordagem teórica das interações dissacarídeo-protótipo de membrana fosfolipídica |
| title_fullStr |
Abordagem teórica das interações dissacarídeo-protótipo de membrana fosfolipídica |
| title_full_unstemmed |
Abordagem teórica das interações dissacarídeo-protótipo de membrana fosfolipídica |
| title_sort |
Abordagem teórica das interações dissacarídeo-protótipo de membrana fosfolipídica |
| author |
Soares, Cinthia Santos |
| author_facet |
Soares, Cinthia Santos |
| author_role |
author |
| dc.contributor.author.fl_str_mv |
Soares, Cinthia Santos |
| dc.contributor.advisor1.fl_str_mv |
Silva, Clarissa Oliveira da |
| dc.contributor.advisor1ID.fl_str_mv |
014.109.957-71 https://orcid.org/0000-0002-5640-5387 |
| dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/3211933004567550 |
| dc.contributor.advisor-co1.fl_str_mv |
Bauerfeldt, Glauco Favilla |
| dc.contributor.advisor-co1ID.fl_str_mv |
069.023.487-23 https://orcid.org/0000-0001-5906-7080 |
| dc.contributor.advisor-co1Lattes.fl_str_mv |
http://lattes.cnpq.br/1876040291299143 |
| dc.contributor.referee1.fl_str_mv |
Silva, Clarissa Oliveira da |
| dc.contributor.referee1ID.fl_str_mv |
014.109.957-71 https://orcid.org/0000-0002-5640-5387 |
| dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/3211933004567550 |
| dc.contributor.referee2.fl_str_mv |
Riger, Cristiano Jorge |
| dc.contributor.referee2ID.fl_str_mv |
https://orcid.org/0000-0002-7579-5958 |
| dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/8756160468801705 |
| dc.contributor.referee3.fl_str_mv |
Pereira, Márcio Soares |
| dc.contributor.referee3ID.fl_str_mv |
https://orcid.org/0000-0002-7579-5958 |
| dc.contributor.referee3Lattes.fl_str_mv |
http://lattes.cnpq.br/8756160468801705 |
| dc.contributor.referee4.fl_str_mv |
Magalhães, Camila Silva de |
| dc.contributor.referee4ID.fl_str_mv |
077.313.237-65 |
| dc.contributor.referee5.fl_str_mv |
Baptista, Leonardo |
| dc.contributor.referee5ID.fl_str_mv |
053.120.556-89 https://orcid.org/0000-0001-9433-3313 |
| dc.contributor.referee5Lattes.fl_str_mv |
http://lattes.cnpq.br/2182432135517042 |
| dc.contributor.authorID.fl_str_mv |
099.709.887-27 |
| dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/8630162009799406 |
| contributor_str_mv |
Silva, Clarissa Oliveira da Bauerfeldt, Glauco Favilla Silva, Clarissa Oliveira da Riger, Cristiano Jorge Pereira, Márcio Soares Magalhães, Camila Silva de Baptista, Leonardo |
| dc.subject.por.fl_str_mv |
Conformação de fosfolipídios Membrana fosfolipídica Interação dissacarídeo-membrana |
| topic |
Conformação de fosfolipídios Membrana fosfolipídica Interação dissacarídeo-membrana Phospholipid conformation Phospholipid membrane Dissaccharide- membrane interaction Química |
| dc.subject.eng.fl_str_mv |
Phospholipid conformation Phospholipid membrane Dissaccharide- membrane interaction |
| dc.subject.cnpq.fl_str_mv |
Química |
| description |
A presente tese teve como objetivo principal estudar as interações entre uma molécula de dissacarídeo e um protótipo de membrana fosfolipídica, formado por um sistema dimérico composto por duas moléculas de fosfolipídio. Tal estudo foi feito de maneira teórica, utilizando métodos quânticos para a modelagem dos sistemas moleculares de interesse: um método baseado na Teoria do Funcional da Densidade (B97-D/6-31G(d,p)) e um método semi-empírico (PM6). Os dissacarídeos considerados foram trealose, maltose e celobiose. O fosfolipídio considerado foi dioctanoil- fosfatidilcolina. O estudo de tais interações envolveu a construção do protótipo de membrana fosfolipídica e a criação de um protocolo para a aproximação dos dissacarídeos ao protótipo e se deu por meio do cálculo da energia de interação quando na formação dos sistemas interagentes (dissacarídeo-protótipo de membrana fosfolipídica). Com base em critérios geométricos, foram identificados dois tipos de interações entre todos os dissacarídeos e o protótipo de membrana fosfolipídica: interações com grupos fosfato e com grupos trimetil-amônio. Foram obtidos os espectros de absorção no infravermelho para o protótipo de membrana fosfolipídica isolado e para todos os sistemas interagentes – quatro para a trealose, três para a maltose e dois para a celobiose, a fim de comparar o comportamento do sinal correspondente ao estiramento assimétrico do grupo fosfato para agregados fosfolipídicos secos e agregados fosfolipídicos na presença de diferentes carboidratos, indicado na literatura como diferentemente afetado pela presença de diferentes carboidratos. Utilizando uma equação que relaciona o valor da constante de acoplamento de spin heteronuclear à três ligações 3JC1,H1’ ao valor do ângulo diedro definido pela sequência de átomos C1–O–C1’–H1’, ao longo da ligação glicosídica da trealose, foram calculados os respectivos valores de 3JC1,H1’ para todos os quatro sistemas interagentes obtidos. A partir do cálculo de população de Boltzmann para os sistemas interagentes, foi obtido um valor médio para a constante de acoplamento, que foi comparado ao resultado experimental disponível na literatura. Os valores de energia de interação dissacarídeo- protótipo de membrana fosfolipídica não mostraram concordância com o comportamento do sinal correspondente ao estiramento assimétrico do grupo fosfato, isso considerando os sistemas interagentes de mais baixa energia, sem correção de ponto zero. Tal resultado foi compreendido como sendo um forte indício de que as interações com grupos trimetil-amônio também precisam ser consideradas nessa avaliação. Já o valor médio obtido para a constante de acoplamento de spin heteronuclear, comparou-se muito bem ao valor experimental disponível na literatura, sendo um indicativo de que os valores dos ângulos glicosídicos da trealose presentes nos sistemas interagentes obtidos teoricamente comparam-se àqueles assumidos pelo dissacarídeo em sistemas interagentes reais, de forma que o método PM6, utilizado para a modelagem dos sistemas interagentes, pode ser apontado como um método computacional capaz de descrever adequadamente os efeitos estabilizantes da ligação glicosídica da trealose nesse tipo de sistema. |
| publishDate |
2022 |
| dc.date.issued.fl_str_mv |
2022-07-06 |
| dc.date.accessioned.fl_str_mv |
2023-12-21T18:59:48Z |
| dc.date.available.fl_str_mv |
2023-12-21T18:59:48Z |
| 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.citation.fl_str_mv |
SOARES, Cinthia Santos. Abordagem teórica das interações dissacarídeo-protótipo de membrana fosfolipídica. 2022. 132 f. Tese (Doutorado em Química) - Instituto de Química, Universidade Federal Rural do Rio de Janeiro, Seropédica, 2022. |
| dc.identifier.uri.fl_str_mv |
https://rima.ufrrj.br/jspui/handle/20.500.14407/10266 |
| identifier_str_mv |
SOARES, Cinthia Santos. Abordagem teórica das interações dissacarídeo-protótipo de membrana fosfolipídica. 2022. 132 f. Tese (Doutorado em Química) - Instituto de Química, Universidade Federal Rural do Rio de Janeiro, Seropédica, 2022. |
| url |
https://rima.ufrrj.br/jspui/handle/20.500.14407/10266 |
| dc.language.iso.fl_str_mv |
por |
| language |
por |
| dc.relation.references.por.fl_str_mv |
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