Estudo DFT de propriedades de hipoglicemiantes orais e de suas dispersões sólidas com a trometamina
Autor(a) principal: | |
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Data de Publicação: | 2021 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Biblioteca Digital de Teses e Dissertações da UFMA |
Texto Completo: | https://tedebc.ufma.br/jspui/handle/tede/tede/4123 |
Resumo: | Theoretical chemistry studies performed with the use of computational resources have promoted great advances in the development of materials with applications in many areas. The basis of this powerful combination, beyond of other existing methods, is supported in Density Functional Theory (DFT). The employment of theoretical chemistry foundations in the development of compounds with pharmacological applications allow the study of important physical-chemistry properties and promote, among other advantages, the resources saving in experimental studies. In co-amorphous materials two or more different compounds are combined, in order to obtain a new material with different physical-chemistry properties. The preparation of co-amorphous materials has been one of the most promising strategies to promote an increase in the bioavailability of drugs, with the obtention of these new materials from drugs with low solubility in water with a coformer compound with higher solubility in water. Oral hypoglycemiant drugs derived from sulfonylurea are used for the treatment of diabetes mellitus type II. These drugs have low aqueous solubility and, consequently, low bioavailability in human organism, directly impacting their therapeutic efficacy. In this work, a theoretical study was performed, from the use of the DFT in the investigation of properties of the oral hypoglycemic drugs chlorpropamide (CLP) and tolbutamide (TBM), as well as of interactions of each of these drugs with the coformer tromethamine (TRIS). The study was conducted employing the DFT functional ωB97x-D in association with the 6-311++G(d,p) basis set, as implemented in Gaussian16 software, considering also the use of the continuum solvation model Integral Equation Formalism Polarizable Continuum Model (IEFPCM), for analysis of solvation effects. Geometry optimization calculations, followed by vibrational frequencies calculations, were performed for each one of the compounds and for the systems corresponding to drug-coformer interactions, confirming each optimized geometry as a minimum in potential energy surface, since all vibrational frequencies calculated are positive. Structural, electronic, and thermodynamic properties, as well as reactivity indices were calculated for each compound and the most favorable interactions were identified with a basis on interaction energy values calculated. Hydrogen bonds between drug and coformer were elucidated, in each case, from structural parameters analysis and through theoretical FTIR and Raman spectra, with attribution of the main vibrational modes, confronting these data with experimental results available in the literature. The theoretical findings confirmed the stability of the co-amorphous materials obtained from the hipoglicemiant oral drugs CLP and TBM, using TRIS as a coformer, and contributed for a better understanding of the formation of the co-amorphous materials CLP-TRIS (1:1) and TBM-TRIS (1:1). |
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LAGE, Mateus Ribeirohttp://lattes.cnpq.br/7180752938220497LAGE, Mateus Ribeirohttp://lattes.cnpq.br/7180752938220497RIBEIRO, Paulo Roberto da Silvahttp://lattes.cnpq.br/2485501119507783COSTA, Luciano Tavares dahttp://lattes.cnpq.br/4530528894939472http://lattes.cnpq.br/0361434136105014LIMA, Antonio Douglas da Silva Guedes2022-10-05T01:18:16Z2021-07-30LIMA, Antonio Douglas da Silva Guedes. Estudo DFT de propriedades de hipoglicemiantes orais e de suas dispersões sólidas com a trometamina. 2021. 152 f. Dissertação (Programa de Pós-Graduação em Ciência dos Materiais/CCSST) - Universidade Federal do Maranhão, Imperatriz, 2021.https://tedebc.ufma.br/jspui/handle/tede/tede/4123Theoretical chemistry studies performed with the use of computational resources have promoted great advances in the development of materials with applications in many areas. The basis of this powerful combination, beyond of other existing methods, is supported in Density Functional Theory (DFT). The employment of theoretical chemistry foundations in the development of compounds with pharmacological applications allow the study of important physical-chemistry properties and promote, among other advantages, the resources saving in experimental studies. In co-amorphous materials two or more different compounds are combined, in order to obtain a new material with different physical-chemistry properties. The preparation of co-amorphous materials has been one of the most promising strategies to promote an increase in the bioavailability of drugs, with the obtention of these new materials from drugs with low solubility in water with a coformer compound with higher solubility in water. Oral hypoglycemiant drugs derived from sulfonylurea are used for the treatment of diabetes mellitus type II. These drugs have low aqueous solubility and, consequently, low bioavailability in human organism, directly impacting their therapeutic efficacy. In this work, a theoretical study was performed, from the use of the DFT in the investigation of properties of the oral hypoglycemic drugs chlorpropamide (CLP) and tolbutamide (TBM), as well as of interactions of each of these drugs with the coformer tromethamine (TRIS). The study was conducted employing the DFT functional ωB97x-D in association with the 6-311++G(d,p) basis set, as implemented in Gaussian16 software, considering also the use of the continuum solvation model Integral Equation Formalism Polarizable Continuum Model (IEFPCM), for analysis of solvation effects. Geometry optimization calculations, followed by vibrational frequencies calculations, were performed for each one of the compounds and for the systems corresponding to drug-coformer interactions, confirming each optimized geometry as a minimum in potential energy surface, since all vibrational frequencies calculated are positive. Structural, electronic, and thermodynamic properties, as well as reactivity indices were calculated for each compound and the most favorable interactions were identified with a basis on interaction energy values calculated. Hydrogen bonds between drug and coformer were elucidated, in each case, from structural parameters analysis and through theoretical FTIR and Raman spectra, with attribution of the main vibrational modes, confronting these data with experimental results available in the literature. The theoretical findings confirmed the stability of the co-amorphous materials obtained from the hipoglicemiant oral drugs CLP and TBM, using TRIS as a coformer, and contributed for a better understanding of the formation of the co-amorphous materials CLP-TRIS (1:1) and TBM-TRIS (1:1).Estudos de química teórica realizados com o uso de recursos computacionais tem promovido grandes avanços no desenvolvimento de materiais com aplicações em diversas áreas. A base dessa poderosa combinação, para além de outros métodos existentes, encontra-se apoiada na Teoria do Funcional da Densidade (DFT). O emprego de fundamentos de química teórica no desenvolvimento de compostos com aplicações farmacológicas permite o estudo de propriedades físico-químicas importantes e promove, dentre outras vantagens, economia de recursos em estudos experimentais. Em materiais co-amorfos dois ou mais compostos distintos são combinados, a fim de se obter um novo material com propriedades físico químicas diferentes. A preparação de co-amorfos tem sido uma das estratégias mais promissoras para se conseguir um aumento na biodisponibilidade de fármacos, com a obtenção desses novos materiais a partir de fármacos pouco solúveis, combinados com coformadores com maior solubilidade em água. Hipoglicemiantes orais derivados da sulfoniluréia são utilizados no tratamento de diabetes mellitus tipo II. Esses fármacos apresentam baixa solubilidade em água e, consequente, baixa biodisponibilidade no organismo, impactando diretamente em sua eficácia terapêutica. No presente trabalho, foi realizado um estudo teórico, a partir do uso da DFT na investigação de propriedades dos fármacos hipoglicemiantes orais clorpropamida (CLP) e tolbutamida (TBM), bem como da interação de cada um desses fármacos com o coformador trometamina (TRIS). O estudo foi conduzido empregando-se o funcional DFT ωB97x-D em associação com o conjunto de funções de base 6-311++G(d,p), como implementado no software Gaussian16, considerando ainda o uso do modelo de solvatação contínua Integral Equation Formalism Polarizable Continuum Model (IEFPCM), para análise de efeitos de solvatação. Cálculos de otimização de geometria, seguidos de cálculos de frequências vibracionais, foram realizados para cada um dos compostos e para os sistemas correspondentes às interações fármaco-coformador, confirmando cada geometria obtida como um ponto de mínimo na superfície de energia potencial, já que todas as frequências vibracionais calculadas são positivas. Propriedades estruturais, eletrônicas, termodinâmicas e índices de reatividade foram então calculados e as interações mais favoráveis foram identificadas com base em valores de energia de interação calculados. Ligações de hidrogênio entre fármaco e coformador foram elucidadas, em cada caso, a partir da análise de parâmetros estruturais e por meio de espectros teóricos FTIR e Raman, com a atribuição dos principais modos vibracionais, confrontando esses dados com resultados experimentais existentes na literatura. Os achados teóricos confirmam a estabilidade dos materiais co-amorfos obtidos a partir dos fármacos hipoglicemiantes orais CLP e TBM, usando a TRIS como coformador, e contribuem para uma melhor compreensão da formação dos co-amorfos CLP-TRIS (1:1) e TBM-TRIS (1:1).Submitted by Daniella Santos (daniella.santos@ufma.br) on 2022-10-05T01:18:16Z No. of bitstreams: 1 AntonioDouglas.pdf: 5076975 bytes, checksum: cec9487667f9a86bee9913064742eb87 (MD5)Made available in DSpace on 2022-10-05T01:18:16Z (GMT). No. of bitstreams: 1 AntonioDouglas.pdf: 5076975 bytes, checksum: cec9487667f9a86bee9913064742eb87 (MD5) Previous issue date: 2021-07-30CAPESapplication/pdfporUniversidade Federal do MaranhãoPROGRAMA DE PÓS-GRADUAÇÃO EM CIÊNCIA DOS MATERIAIS/CCSSTUFMABrasilDEPARTAMENTO DE QUÍMICA/CCETteoria do funcional da densidade;hipoglicemiantes orais;materiais co-amorfo;density functional theory;oral hypoglycemic agents;co-amorphous materials.QuímicaEstudo DFT de propriedades de hipoglicemiantes orais e de suas dispersões sólidas com a trometaminaDFT study of properties of oral hypoglycemic agents and their solid dispersions with tromethamineinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisinfo:eu-repo/semantics/openAccessreponame:Biblioteca Digital de Teses e Dissertações da UFMAinstname:Universidade Federal do Maranhão (UFMA)instacron:UFMAORIGINALAntonioDouglas.pdfAntonioDouglas.pdfapplication/pdf5076975http://tedebc.ufma.br:8080/bitstream/tede/4123/2/AntonioDouglas.pdfcec9487667f9a86bee9913064742eb87MD52LICENSElicense.txtlicense.txttext/plain; charset=utf-82255http://tedebc.ufma.br:8080/bitstream/tede/4123/1/license.txt97eeade1fce43278e63fe063657f8083MD51tede/41232022-10-04 22:18:16.38oai:tede2: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Biblioteca Digital de Teses e Dissertaçõeshttps://tedebc.ufma.br/jspui/PUBhttp://tedebc.ufma.br:8080/oai/requestrepositorio@ufma.br||repositorio@ufma.bropendoar:21312022-10-05T01:18:16Biblioteca Digital de Teses e Dissertações da UFMA - Universidade Federal do Maranhão (UFMA)false |
dc.title.por.fl_str_mv |
Estudo DFT de propriedades de hipoglicemiantes orais e de suas dispersões sólidas com a trometamina |
dc.title.alternative.eng.fl_str_mv |
DFT study of properties of oral hypoglycemic agents and their solid dispersions with tromethamine |
title |
Estudo DFT de propriedades de hipoglicemiantes orais e de suas dispersões sólidas com a trometamina |
spellingShingle |
Estudo DFT de propriedades de hipoglicemiantes orais e de suas dispersões sólidas com a trometamina LIMA, Antonio Douglas da Silva Guedes teoria do funcional da densidade; hipoglicemiantes orais; materiais co-amorfo; density functional theory; oral hypoglycemic agents; co-amorphous materials. Química |
title_short |
Estudo DFT de propriedades de hipoglicemiantes orais e de suas dispersões sólidas com a trometamina |
title_full |
Estudo DFT de propriedades de hipoglicemiantes orais e de suas dispersões sólidas com a trometamina |
title_fullStr |
Estudo DFT de propriedades de hipoglicemiantes orais e de suas dispersões sólidas com a trometamina |
title_full_unstemmed |
Estudo DFT de propriedades de hipoglicemiantes orais e de suas dispersões sólidas com a trometamina |
title_sort |
Estudo DFT de propriedades de hipoglicemiantes orais e de suas dispersões sólidas com a trometamina |
author |
LIMA, Antonio Douglas da Silva Guedes |
author_facet |
LIMA, Antonio Douglas da Silva Guedes |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
LAGE, Mateus Ribeiro |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/7180752938220497 |
dc.contributor.referee1.fl_str_mv |
LAGE, Mateus Ribeiro |
dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/7180752938220497 |
dc.contributor.referee2.fl_str_mv |
RIBEIRO, Paulo Roberto da Silva |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/2485501119507783 |
dc.contributor.referee3.fl_str_mv |
COSTA, Luciano Tavares da |
dc.contributor.referee3Lattes.fl_str_mv |
http://lattes.cnpq.br/4530528894939472 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/0361434136105014 |
dc.contributor.author.fl_str_mv |
LIMA, Antonio Douglas da Silva Guedes |
contributor_str_mv |
LAGE, Mateus Ribeiro LAGE, Mateus Ribeiro RIBEIRO, Paulo Roberto da Silva COSTA, Luciano Tavares da |
dc.subject.por.fl_str_mv |
teoria do funcional da densidade; hipoglicemiantes orais; materiais co-amorfo; |
topic |
teoria do funcional da densidade; hipoglicemiantes orais; materiais co-amorfo; density functional theory; oral hypoglycemic agents; co-amorphous materials. Química |
dc.subject.eng.fl_str_mv |
density functional theory; oral hypoglycemic agents; co-amorphous materials. |
dc.subject.cnpq.fl_str_mv |
Química |
description |
Theoretical chemistry studies performed with the use of computational resources have promoted great advances in the development of materials with applications in many areas. The basis of this powerful combination, beyond of other existing methods, is supported in Density Functional Theory (DFT). The employment of theoretical chemistry foundations in the development of compounds with pharmacological applications allow the study of important physical-chemistry properties and promote, among other advantages, the resources saving in experimental studies. In co-amorphous materials two or more different compounds are combined, in order to obtain a new material with different physical-chemistry properties. The preparation of co-amorphous materials has been one of the most promising strategies to promote an increase in the bioavailability of drugs, with the obtention of these new materials from drugs with low solubility in water with a coformer compound with higher solubility in water. Oral hypoglycemiant drugs derived from sulfonylurea are used for the treatment of diabetes mellitus type II. These drugs have low aqueous solubility and, consequently, low bioavailability in human organism, directly impacting their therapeutic efficacy. In this work, a theoretical study was performed, from the use of the DFT in the investigation of properties of the oral hypoglycemic drugs chlorpropamide (CLP) and tolbutamide (TBM), as well as of interactions of each of these drugs with the coformer tromethamine (TRIS). The study was conducted employing the DFT functional ωB97x-D in association with the 6-311++G(d,p) basis set, as implemented in Gaussian16 software, considering also the use of the continuum solvation model Integral Equation Formalism Polarizable Continuum Model (IEFPCM), for analysis of solvation effects. Geometry optimization calculations, followed by vibrational frequencies calculations, were performed for each one of the compounds and for the systems corresponding to drug-coformer interactions, confirming each optimized geometry as a minimum in potential energy surface, since all vibrational frequencies calculated are positive. Structural, electronic, and thermodynamic properties, as well as reactivity indices were calculated for each compound and the most favorable interactions were identified with a basis on interaction energy values calculated. Hydrogen bonds between drug and coformer were elucidated, in each case, from structural parameters analysis and through theoretical FTIR and Raman spectra, with attribution of the main vibrational modes, confronting these data with experimental results available in the literature. The theoretical findings confirmed the stability of the co-amorphous materials obtained from the hipoglicemiant oral drugs CLP and TBM, using TRIS as a coformer, and contributed for a better understanding of the formation of the co-amorphous materials CLP-TRIS (1:1) and TBM-TRIS (1:1). |
publishDate |
2021 |
dc.date.issued.fl_str_mv |
2021-07-30 |
dc.date.accessioned.fl_str_mv |
2022-10-05T01:18:16Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/masterThesis |
format |
masterThesis |
status_str |
publishedVersion |
dc.identifier.citation.fl_str_mv |
LIMA, Antonio Douglas da Silva Guedes. Estudo DFT de propriedades de hipoglicemiantes orais e de suas dispersões sólidas com a trometamina. 2021. 152 f. Dissertação (Programa de Pós-Graduação em Ciência dos Materiais/CCSST) - Universidade Federal do Maranhão, Imperatriz, 2021. |
dc.identifier.uri.fl_str_mv |
https://tedebc.ufma.br/jspui/handle/tede/tede/4123 |
identifier_str_mv |
LIMA, Antonio Douglas da Silva Guedes. Estudo DFT de propriedades de hipoglicemiantes orais e de suas dispersões sólidas com a trometamina. 2021. 152 f. Dissertação (Programa de Pós-Graduação em Ciência dos Materiais/CCSST) - Universidade Federal do Maranhão, Imperatriz, 2021. |
url |
https://tedebc.ufma.br/jspui/handle/tede/tede/4123 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
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application/pdf |
dc.publisher.none.fl_str_mv |
Universidade Federal do Maranhão |
dc.publisher.program.fl_str_mv |
PROGRAMA DE PÓS-GRADUAÇÃO EM CIÊNCIA DOS MATERIAIS/CCSST |
dc.publisher.initials.fl_str_mv |
UFMA |
dc.publisher.country.fl_str_mv |
Brasil |
dc.publisher.department.fl_str_mv |
DEPARTAMENTO DE QUÍMICA/CCET |
publisher.none.fl_str_mv |
Universidade Federal do Maranhão |
dc.source.none.fl_str_mv |
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Biblioteca Digital de Teses e Dissertações da UFMA |
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