Determinação do coeficiente cromatográfico de partição, log kw, de inibidores da bomba H+/K+ - ATPase
Autor(a) principal: | |
---|---|
Data de Publicação: | 2007 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Repositório Institucional da UFSCAR |
Texto Completo: | https://repositorio.ufscar.br/handle/ufscar/6399 |
Resumo: | The relative retention and enantioselectivity of a homologue series constituted by five benzimidazoles, K+/H+ - ATPase pump inhibitors, was determined for three amylose tris-phenylcarbamate chiral stationary phases (CSP), under reverse and normal phase modes of elution, using ethanol as a organic modifier. It was verified similar retention profiles for the benzimidazoles homologue series on the three evaluated chiral phases, under reversed mode of elution. The switch between reversed to polar organic mode of elution, under same conditions of reversed mode, and even with a percentage of water, in the mobile phase, around 15% it is clearly observed and discussed. Also, the benzimidazoles series retention profiles on three chiral columns were similar when in the normal elution mode. However, a switch from normal to polar organic mode is slow, indicating that retention/separation mechanisms, that operate in both elution modes, are very comparable. The discrimination chiral capacity of these stationary phases was differentiated when ethanol was used as organic modifier on three elution modes. The amylose tris (3,5 dimethylphenylcarbamate) phase (CSP-2) showed high resolution (Rs) power (0.90 ¡Ü Rs ¡Ü 3.46 and 1.25 ¡Ü á ¡Ü 2.24) for omeprazole enantiomers on the three elution modes. The amylose tris [(S)-phenyethyllcarbamate) phase (CSP-3), in turn, display resolution capacity for all series of homologous enantiomers in normal mode of elution. Herein, it was established for first time a relation between normal and reversed elution mode through the isoelution point determination. Under the same percentage of ethanol, in normal mode, and water in reversed mode, the retentions are similar, when polysaccharides phases are used as chiral selectors. The enantiomeric separations of enantiomers series were carried out in multimilligram scale, and the determination of its elution order was evaluated in the three elution modes. The omeprazole enantiomers separation was performed in multimilligram scale, as a model, using the solid-phase injection technique. The results were compared with those obtained from the separation by means of classical volume injection of sample. These results are presented and discussed. |
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Coimbra, MarianaCass, Quezia Bezerrahttp://genos.cnpq.br:12010/dwlattes/owa/prc_imp_cv_int?f_cod=K4781559E6http://lattes.cnpq.br/10503275070498167faa0003-917f-4359-bce4-d880789850252016-06-02T20:36:13Z2008-08-192016-06-02T20:36:13Z2007-03-15COIMBRA, Mariana. Determination of chromatographic partition coefficient, Log kw, of h+/k+- atpase pump inhibitors. 2007. 177 f. Dissertação (Mestrado em Ciências Exatas e da Terra) - Universidade Federal de São Carlos, São Carlos, 2007.https://repositorio.ufscar.br/handle/ufscar/6399The relative retention and enantioselectivity of a homologue series constituted by five benzimidazoles, K+/H+ - ATPase pump inhibitors, was determined for three amylose tris-phenylcarbamate chiral stationary phases (CSP), under reverse and normal phase modes of elution, using ethanol as a organic modifier. It was verified similar retention profiles for the benzimidazoles homologue series on the three evaluated chiral phases, under reversed mode of elution. The switch between reversed to polar organic mode of elution, under same conditions of reversed mode, and even with a percentage of water, in the mobile phase, around 15% it is clearly observed and discussed. Also, the benzimidazoles series retention profiles on three chiral columns were similar when in the normal elution mode. However, a switch from normal to polar organic mode is slow, indicating that retention/separation mechanisms, that operate in both elution modes, are very comparable. The discrimination chiral capacity of these stationary phases was differentiated when ethanol was used as organic modifier on three elution modes. The amylose tris (3,5 dimethylphenylcarbamate) phase (CSP-2) showed high resolution (Rs) power (0.90 ¡Ü Rs ¡Ü 3.46 and 1.25 ¡Ü á ¡Ü 2.24) for omeprazole enantiomers on the three elution modes. The amylose tris [(S)-phenyethyllcarbamate) phase (CSP-3), in turn, display resolution capacity for all series of homologous enantiomers in normal mode of elution. Herein, it was established for first time a relation between normal and reversed elution mode through the isoelution point determination. Under the same percentage of ethanol, in normal mode, and water in reversed mode, the retentions are similar, when polysaccharides phases are used as chiral selectors. The enantiomeric separations of enantiomers series were carried out in multimilligram scale, and the determination of its elution order was evaluated in the three elution modes. The omeprazole enantiomers separation was performed in multimilligram scale, as a model, using the solid-phase injection technique. The results were compared with those obtained from the separation by means of classical volume injection of sample. These results are presented and discussed.A retenção relativa e a enantiosseletividade de uma séria homóloga de cinco benzimidazóis, inibidores da bomba K+/H+-ATPase, foram determinados em três fases quirais de tris-fenilcarbamatos de amilose, no modo reverso e normal de eluição, utilizando etanol como modificador orgânico. Foram verificados perfis de retenção similares para a série homóloga de benzimidazóis, nas três fases quirais avaliadas no modo reverso de eluição. A passagem do modo reverso para o modo polar-orgânico de eluição, mesmo sob condições de modo reverso, e ainda com porcentagem de água, na fase móvel, em torno de 15% é claramente observada e discutida. Os perfis de retenção da série de benzimidazóis nas três colunas quirais também foram similares quando a eluição foi no modo normal. Entretanto, a mudança do modo normal para o modo polar-orgânico é lenta, indicando que os mecanismos de retenção/separação, que operam nos dois modos de eluição, são mais próximos. A capacidade de discriminação quiral destas fases estacionárias foi diferenciada quando se utilizou etanol como modificador orgânico nos três modos de eluição. A fase tris (3,5 dimetilfenilcarbamato) de amilose (CSP-2) mostrou alto poder de resolução (0,90 . Rs . 3,46 e 1,25 . α . 2,24) para os enantiômeros do omeprazol nos três modos de eluição. A fase tris [(S)-feniletilcarbamato] de amilose (CSP-3.1), por sua vez, apresentou capacidade de resolução para todos os enantiômeros da série homóloga no modo normal de eluição. Neste trabalho, foi estabelecida, pela primeira vez, uma relação entre o modo normal e reverso de eluição através da determinação do ponto de isoeluição. Numa mesma porcentagem de etanol, no modo normal, e de água, no modo reverso, as retenções são similares, quando se utilizam as fases de polissacarídeos como seletores quirais. Foram realizadas as separações enantioméricas dos enantiômeros da série em escala multi-miligramas, e a determinação da ordem de eluição dos mesmos foi avaliada nos três modos de eluição. A separação dos enantiômeros do omeprazol foi feita em escala multi-miligrama, como modelo, usando a técnica de injeção em fase sólida. Os resultados foram comprados com os obtidos da separação utilizando o modo clássico de injeção de amostras. Estes resultados são apresentados e discutidos.Financiadora de Estudos e Projetosapplication/pdfporUniversidade Federal de São CarlosPrograma de Pós-Graduação em Química - PPGQUFSCarBRCromatografia líquida de alta eficiênciaSulfóxidos quiraisColunas de polissacarídeosMultimodalSeletor quiralCIENCIAS EXATAS E DA TERRA::QUIMICADeterminação do coeficiente cromatográfico de partição, log kw, de inibidores da bomba H+/K+ - ATPaseDetermination of chromatographic partition coefficient, Log kw, of h+/k+- atpase pump inhibitorsinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesis-1-1867fc213-f339-49e1-a669-a1e54cf68bf1info:eu-repo/semantics/openAccessreponame:Repositório Institucional da UFSCARinstname:Universidade Federal de São Carlos (UFSCAR)instacron:UFSCARORIGINAL1927.pdfapplication/pdf15439861https://repositorio.ufscar.br/bitstream/ufscar/6399/1/1927.pdfa37ec11edf9b18931913f9fd214dc363MD51THUMBNAIL1927.pdf.jpg1927.pdf.jpgIM Thumbnailimage/jpeg8216https://repositorio.ufscar.br/bitstream/ufscar/6399/2/1927.pdf.jpg36c93f81e1d7326834bb87ff6ae6b43dMD52ufscar/63992023-09-18 18:31:11.402oai:repositorio.ufscar.br:ufscar/6399Repositório InstitucionalPUBhttps://repositorio.ufscar.br/oai/requestopendoar:43222023-09-18T18:31:11Repositório Institucional da UFSCAR - Universidade Federal de São Carlos (UFSCAR)false |
dc.title.por.fl_str_mv |
Determinação do coeficiente cromatográfico de partição, log kw, de inibidores da bomba H+/K+ - ATPase |
dc.title.alternative.eng.fl_str_mv |
Determination of chromatographic partition coefficient, Log kw, of h+/k+- atpase pump inhibitors |
title |
Determinação do coeficiente cromatográfico de partição, log kw, de inibidores da bomba H+/K+ - ATPase |
spellingShingle |
Determinação do coeficiente cromatográfico de partição, log kw, de inibidores da bomba H+/K+ - ATPase Coimbra, Mariana Cromatografia líquida de alta eficiência Sulfóxidos quirais Colunas de polissacarídeos Multimodal Seletor quiral CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Determinação do coeficiente cromatográfico de partição, log kw, de inibidores da bomba H+/K+ - ATPase |
title_full |
Determinação do coeficiente cromatográfico de partição, log kw, de inibidores da bomba H+/K+ - ATPase |
title_fullStr |
Determinação do coeficiente cromatográfico de partição, log kw, de inibidores da bomba H+/K+ - ATPase |
title_full_unstemmed |
Determinação do coeficiente cromatográfico de partição, log kw, de inibidores da bomba H+/K+ - ATPase |
title_sort |
Determinação do coeficiente cromatográfico de partição, log kw, de inibidores da bomba H+/K+ - ATPase |
author |
Coimbra, Mariana |
author_facet |
Coimbra, Mariana |
author_role |
author |
dc.contributor.authorlattes.por.fl_str_mv |
http://lattes.cnpq.br/1050327507049816 |
dc.contributor.author.fl_str_mv |
Coimbra, Mariana |
dc.contributor.advisor1.fl_str_mv |
Cass, Quezia Bezerra |
dc.contributor.advisor1Lattes.fl_str_mv |
http://genos.cnpq.br:12010/dwlattes/owa/prc_imp_cv_int?f_cod=K4781559E6 |
dc.contributor.authorID.fl_str_mv |
7faa0003-917f-4359-bce4-d88078985025 |
contributor_str_mv |
Cass, Quezia Bezerra |
dc.subject.por.fl_str_mv |
Cromatografia líquida de alta eficiência Sulfóxidos quirais Colunas de polissacarídeos Multimodal Seletor quiral |
topic |
Cromatografia líquida de alta eficiência Sulfóxidos quirais Colunas de polissacarídeos Multimodal Seletor quiral CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.cnpq.fl_str_mv |
CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
The relative retention and enantioselectivity of a homologue series constituted by five benzimidazoles, K+/H+ - ATPase pump inhibitors, was determined for three amylose tris-phenylcarbamate chiral stationary phases (CSP), under reverse and normal phase modes of elution, using ethanol as a organic modifier. It was verified similar retention profiles for the benzimidazoles homologue series on the three evaluated chiral phases, under reversed mode of elution. The switch between reversed to polar organic mode of elution, under same conditions of reversed mode, and even with a percentage of water, in the mobile phase, around 15% it is clearly observed and discussed. Also, the benzimidazoles series retention profiles on three chiral columns were similar when in the normal elution mode. However, a switch from normal to polar organic mode is slow, indicating that retention/separation mechanisms, that operate in both elution modes, are very comparable. The discrimination chiral capacity of these stationary phases was differentiated when ethanol was used as organic modifier on three elution modes. The amylose tris (3,5 dimethylphenylcarbamate) phase (CSP-2) showed high resolution (Rs) power (0.90 ¡Ü Rs ¡Ü 3.46 and 1.25 ¡Ü á ¡Ü 2.24) for omeprazole enantiomers on the three elution modes. The amylose tris [(S)-phenyethyllcarbamate) phase (CSP-3), in turn, display resolution capacity for all series of homologous enantiomers in normal mode of elution. Herein, it was established for first time a relation between normal and reversed elution mode through the isoelution point determination. Under the same percentage of ethanol, in normal mode, and water in reversed mode, the retentions are similar, when polysaccharides phases are used as chiral selectors. The enantiomeric separations of enantiomers series were carried out in multimilligram scale, and the determination of its elution order was evaluated in the three elution modes. The omeprazole enantiomers separation was performed in multimilligram scale, as a model, using the solid-phase injection technique. The results were compared with those obtained from the separation by means of classical volume injection of sample. These results are presented and discussed. |
publishDate |
2007 |
dc.date.issued.fl_str_mv |
2007-03-15 |
dc.date.available.fl_str_mv |
2008-08-19 2016-06-02T20:36:13Z |
dc.date.accessioned.fl_str_mv |
2016-06-02T20:36:13Z |
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 |
COIMBRA, Mariana. Determination of chromatographic partition coefficient, Log kw, of h+/k+- atpase pump inhibitors. 2007. 177 f. Dissertação (Mestrado em Ciências Exatas e da Terra) - Universidade Federal de São Carlos, São Carlos, 2007. |
dc.identifier.uri.fl_str_mv |
https://repositorio.ufscar.br/handle/ufscar/6399 |
identifier_str_mv |
COIMBRA, Mariana. Determination of chromatographic partition coefficient, Log kw, of h+/k+- atpase pump inhibitors. 2007. 177 f. Dissertação (Mestrado em Ciências Exatas e da Terra) - Universidade Federal de São Carlos, São Carlos, 2007. |
url |
https://repositorio.ufscar.br/handle/ufscar/6399 |
dc.language.iso.fl_str_mv |
por |
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por |
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-1 -1 |
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info:eu-repo/semantics/openAccess |
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openAccess |
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application/pdf |
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Universidade Federal de São Carlos |
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Programa de Pós-Graduação em Química - PPGQ |
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UFSCar |
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BR |
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Universidade Federal de São Carlos |
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