New insight into the discrimination between omeprazole enantiomers by cyclodextrins in aqueous solution
Autor(a) principal: | |
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Data de Publicação: | 2008 |
Outros Autores: | , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/10316/7945 https://doi.org/10.1007/s10847-008-9477-6 |
Resumo: | We report results regarding the use of 1H-NMR spectroscopy in the study of the conformational behaviour and optical activity of omeprazole. Changes in the chemical shifts of chosen atoms reveal that the conformational behaviour of omeprazole is temperature and pH sensitive. Separation and identification of omeprazole enantiomers in the presence of natural and derivative cyclodextrins, such as ß-cyclodextrin (ßCD) and methyl-ß-cyclodextrin (MßCD) are achieved using 1H-NMR spectroscopy, with information from molecular dynamics simulation. This work shows that ßCD includes preferentially R-(–)-omeprazole, acting as a chiral selector. This discrimination of omeprazole enantiomers by cyclodextrins allows development of pharmaceutical formulations with a better bioavailability profile. |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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New insight into the discrimination between omeprazole enantiomers by cyclodextrins in aqueous solutionCyclodextrinEnantiomersMolecular DynamicsNMROmeprazoleSpectroscopyWe report results regarding the use of 1H-NMR spectroscopy in the study of the conformational behaviour and optical activity of omeprazole. Changes in the chemical shifts of chosen atoms reveal that the conformational behaviour of omeprazole is temperature and pH sensitive. Separation and identification of omeprazole enantiomers in the presence of natural and derivative cyclodextrins, such as ß-cyclodextrin (ßCD) and methyl-ß-cyclodextrin (MßCD) are achieved using 1H-NMR spectroscopy, with information from molecular dynamics simulation. This work shows that ßCD includes preferentially R-(–)-omeprazole, acting as a chiral selector. This discrimination of omeprazole enantiomers by cyclodextrins allows development of pharmaceutical formulations with a better bioavailability profile.2008-08-22info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://hdl.handle.net/10316/7945http://hdl.handle.net/10316/7945https://doi.org/10.1007/s10847-008-9477-6engFigueiras, A.Sarraguça, J. M. G.Pais, A. A. C. C.Veiga, J. F.Carvalho, R. A.info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2021-05-25T07:53:46ZPortal AgregadorONG |
dc.title.none.fl_str_mv |
New insight into the discrimination between omeprazole enantiomers by cyclodextrins in aqueous solution |
title |
New insight into the discrimination between omeprazole enantiomers by cyclodextrins in aqueous solution |
spellingShingle |
New insight into the discrimination between omeprazole enantiomers by cyclodextrins in aqueous solution Figueiras, A. Cyclodextrin Enantiomers Molecular Dynamics NMR Omeprazole Spectroscopy |
title_short |
New insight into the discrimination between omeprazole enantiomers by cyclodextrins in aqueous solution |
title_full |
New insight into the discrimination between omeprazole enantiomers by cyclodextrins in aqueous solution |
title_fullStr |
New insight into the discrimination between omeprazole enantiomers by cyclodextrins in aqueous solution |
title_full_unstemmed |
New insight into the discrimination between omeprazole enantiomers by cyclodextrins in aqueous solution |
title_sort |
New insight into the discrimination between omeprazole enantiomers by cyclodextrins in aqueous solution |
author |
Figueiras, A. |
author_facet |
Figueiras, A. Sarraguça, J. M. G. Pais, A. A. C. C. Veiga, J. F. Carvalho, R. A. |
author_role |
author |
author2 |
Sarraguça, J. M. G. Pais, A. A. C. C. Veiga, J. F. Carvalho, R. A. |
author2_role |
author author author author |
dc.contributor.author.fl_str_mv |
Figueiras, A. Sarraguça, J. M. G. Pais, A. A. C. C. Veiga, J. F. Carvalho, R. A. |
dc.subject.por.fl_str_mv |
Cyclodextrin Enantiomers Molecular Dynamics NMR Omeprazole Spectroscopy |
topic |
Cyclodextrin Enantiomers Molecular Dynamics NMR Omeprazole Spectroscopy |
description |
We report results regarding the use of 1H-NMR spectroscopy in the study of the conformational behaviour and optical activity of omeprazole. Changes in the chemical shifts of chosen atoms reveal that the conformational behaviour of omeprazole is temperature and pH sensitive. Separation and identification of omeprazole enantiomers in the presence of natural and derivative cyclodextrins, such as ß-cyclodextrin (ßCD) and methyl-ß-cyclodextrin (MßCD) are achieved using 1H-NMR spectroscopy, with information from molecular dynamics simulation. This work shows that ßCD includes preferentially R-(–)-omeprazole, acting as a chiral selector. This discrimination of omeprazole enantiomers by cyclodextrins allows development of pharmaceutical formulations with a better bioavailability profile. |
publishDate |
2008 |
dc.date.none.fl_str_mv |
2008-08-22 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://hdl.handle.net/10316/7945 http://hdl.handle.net/10316/7945 https://doi.org/10.1007/s10847-008-9477-6 |
url |
http://hdl.handle.net/10316/7945 https://doi.org/10.1007/s10847-008-9477-6 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.source.none.fl_str_mv |
reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação instacron:RCAAP |
instname_str |
Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
instacron_str |
RCAAP |
institution |
RCAAP |
reponame_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
collection |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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1777302613845344256 |