Theoretical and experimental study of inclusion complexes formed by isoniazid and modified β-Cyclodextrins: 1H NMR structural determination and antibacterial activity evaluation
Autor(a) principal: | |
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Data de Publicação: | 2013 |
Outros Autores: | , , , , , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | LOCUS Repositório Institucional da UFV |
Texto Completo: | https://www.ncbi.nlm.nih.gov/pubmed/24321011 http://www.locus.ufv.br/handle/123456789/19079 |
Resumo: | Me-β-cyclodextrin (Me-βCD) and HP-β-cyclodextrin (HP-βCD) inclusion complexes with isoniazid (INH) were prepared with the aim of modulating the physicochemical and biopharmaceutical properties of the guest molecule, a well-known antibuberculosis drug. The architectures of the complexes were initially proposed according to NMR data Job plot and ROESY followed by density functional theory (DFT) calculations of (1)H NMR spectra using the PBE1PBE functional and 6-31G(d,p) basis set, including the water solvent effect with the polarizable continuum model (PCM), for various inclusion modes, providing support for the experimental proposal. An analysis of the (1)H NMR chemical shift values for the isoniazid (H6',8' and H5',9') and cyclodextrins (H3,5) C(1)H hydrogens, which are known to be very adequately described by the DFT methodology, revealed them to be extremely useful, promptly confirming the inclusion complex formation. An included mode which describes Me-βCD partially enclosing the hydrazide group of the INH is predicted as the most favorable supramolecular structure that can be used to explain the physicochemical properties of the encapsulated drug. Antibacterial activity was also evaluated, and the results indicated the inclusion complexes are a potential strategy for tuberculosis treatment. |
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Teixeira, Milena G.Assis, João V. deSoares, Cássia G. P.Venâncio, Mateus F.Lopes, Juliana F.Nascimento Jr, Clebio S.Anconi, Cleber P. A.Carvalho, Guilherme S. L.Lourenço, Cristina S.Almeida, Mauro V. deFernandes, Sergio A.Almeida, Wagner B. de2018-04-24T14:53:50Z2018-04-24T14:53:50Z2013-12-091520-5207https://www.ncbi.nlm.nih.gov/pubmed/24321011http://www.locus.ufv.br/handle/123456789/19079Me-β-cyclodextrin (Me-βCD) and HP-β-cyclodextrin (HP-βCD) inclusion complexes with isoniazid (INH) were prepared with the aim of modulating the physicochemical and biopharmaceutical properties of the guest molecule, a well-known antibuberculosis drug. The architectures of the complexes were initially proposed according to NMR data Job plot and ROESY followed by density functional theory (DFT) calculations of (1)H NMR spectra using the PBE1PBE functional and 6-31G(d,p) basis set, including the water solvent effect with the polarizable continuum model (PCM), for various inclusion modes, providing support for the experimental proposal. An analysis of the (1)H NMR chemical shift values for the isoniazid (H6',8' and H5',9') and cyclodextrins (H3,5) C(1)H hydrogens, which are known to be very adequately described by the DFT methodology, revealed them to be extremely useful, promptly confirming the inclusion complex formation. An included mode which describes Me-βCD partially enclosing the hydrazide group of the INH is predicted as the most favorable supramolecular structure that can be used to explain the physicochemical properties of the encapsulated drug. Antibacterial activity was also evaluated, and the results indicated the inclusion complexes are a potential strategy for tuberculosis treatment.engThe Journal of Physical Chemistry Bv. 118, n. 1, p. 81-93, 2014American Chemical Societyinfo:eu-repo/semantics/openAccessInclusion complexesIsoniazid and modified β-CyclodextrinsStructural determination and Antibacterial activity evaluationTheoretical and experimental study of inclusion complexes formed by isoniazid and modified β-Cyclodextrins: 1H NMR structural determination and antibacterial activity evaluationinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfreponame:LOCUS Repositório Institucional da UFVinstname:Universidade Federal de Viçosa (UFV)instacron:UFVORIGINALartigo.pdfartigo.pdftexto completoapplication/pdf3565388https://locus.ufv.br//bitstream/123456789/19079/1/artigo.pdfb9caef87749f1a50afbb1bb671e7fbfeMD51LICENSElicense.txtlicense.txttext/plain; charset=utf-81748https://locus.ufv.br//bitstream/123456789/19079/2/license.txt8a4605be74aa9ea9d79846c1fba20a33MD52THUMBNAILartigo.pdf.jpgartigo.pdf.jpgIM Thumbnailimage/jpeg6323https://locus.ufv.br//bitstream/123456789/19079/3/artigo.pdf.jpgb53d0fa9847a1e774e03e6769a72f8b6MD53123456789/190792018-04-24 23:00:39.417oai:locus.ufv.br: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Repositório InstitucionalPUBhttps://www.locus.ufv.br/oai/requestfabiojreis@ufv.bropendoar:21452018-04-25T02:00:39LOCUS Repositório Institucional da UFV - Universidade Federal de Viçosa (UFV)false |
dc.title.en.fl_str_mv |
Theoretical and experimental study of inclusion complexes formed by isoniazid and modified β-Cyclodextrins: 1H NMR structural determination and antibacterial activity evaluation |
title |
Theoretical and experimental study of inclusion complexes formed by isoniazid and modified β-Cyclodextrins: 1H NMR structural determination and antibacterial activity evaluation |
spellingShingle |
Theoretical and experimental study of inclusion complexes formed by isoniazid and modified β-Cyclodextrins: 1H NMR structural determination and antibacterial activity evaluation Teixeira, Milena G. Inclusion complexes Isoniazid and modified β-Cyclodextrins Structural determination and Antibacterial activity evaluation |
title_short |
Theoretical and experimental study of inclusion complexes formed by isoniazid and modified β-Cyclodextrins: 1H NMR structural determination and antibacterial activity evaluation |
title_full |
Theoretical and experimental study of inclusion complexes formed by isoniazid and modified β-Cyclodextrins: 1H NMR structural determination and antibacterial activity evaluation |
title_fullStr |
Theoretical and experimental study of inclusion complexes formed by isoniazid and modified β-Cyclodextrins: 1H NMR structural determination and antibacterial activity evaluation |
title_full_unstemmed |
Theoretical and experimental study of inclusion complexes formed by isoniazid and modified β-Cyclodextrins: 1H NMR structural determination and antibacterial activity evaluation |
title_sort |
Theoretical and experimental study of inclusion complexes formed by isoniazid and modified β-Cyclodextrins: 1H NMR structural determination and antibacterial activity evaluation |
author |
Teixeira, Milena G. |
author_facet |
Teixeira, Milena G. Assis, João V. de Soares, Cássia G. P. Venâncio, Mateus F. Lopes, Juliana F. Nascimento Jr, Clebio S. Anconi, Cleber P. A. Carvalho, Guilherme S. L. Lourenço, Cristina S. Almeida, Mauro V. de Fernandes, Sergio A. Almeida, Wagner B. de |
author_role |
author |
author2 |
Assis, João V. de Soares, Cássia G. P. Venâncio, Mateus F. Lopes, Juliana F. Nascimento Jr, Clebio S. Anconi, Cleber P. A. Carvalho, Guilherme S. L. Lourenço, Cristina S. Almeida, Mauro V. de Fernandes, Sergio A. Almeida, Wagner B. de |
author2_role |
author author author author author author author author author author author |
dc.contributor.author.fl_str_mv |
Teixeira, Milena G. Assis, João V. de Soares, Cássia G. P. Venâncio, Mateus F. Lopes, Juliana F. Nascimento Jr, Clebio S. Anconi, Cleber P. A. Carvalho, Guilherme S. L. Lourenço, Cristina S. Almeida, Mauro V. de Fernandes, Sergio A. Almeida, Wagner B. de |
dc.subject.pt-BR.fl_str_mv |
Inclusion complexes Isoniazid and modified β-Cyclodextrins Structural determination and Antibacterial activity evaluation |
topic |
Inclusion complexes Isoniazid and modified β-Cyclodextrins Structural determination and Antibacterial activity evaluation |
description |
Me-β-cyclodextrin (Me-βCD) and HP-β-cyclodextrin (HP-βCD) inclusion complexes with isoniazid (INH) were prepared with the aim of modulating the physicochemical and biopharmaceutical properties of the guest molecule, a well-known antibuberculosis drug. The architectures of the complexes were initially proposed according to NMR data Job plot and ROESY followed by density functional theory (DFT) calculations of (1)H NMR spectra using the PBE1PBE functional and 6-31G(d,p) basis set, including the water solvent effect with the polarizable continuum model (PCM), for various inclusion modes, providing support for the experimental proposal. An analysis of the (1)H NMR chemical shift values for the isoniazid (H6',8' and H5',9') and cyclodextrins (H3,5) C(1)H hydrogens, which are known to be very adequately described by the DFT methodology, revealed them to be extremely useful, promptly confirming the inclusion complex formation. An included mode which describes Me-βCD partially enclosing the hydrazide group of the INH is predicted as the most favorable supramolecular structure that can be used to explain the physicochemical properties of the encapsulated drug. Antibacterial activity was also evaluated, and the results indicated the inclusion complexes are a potential strategy for tuberculosis treatment. |
publishDate |
2013 |
dc.date.issued.fl_str_mv |
2013-12-09 |
dc.date.accessioned.fl_str_mv |
2018-04-24T14:53:50Z |
dc.date.available.fl_str_mv |
2018-04-24T14:53:50Z |
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 |
https://www.ncbi.nlm.nih.gov/pubmed/24321011 http://www.locus.ufv.br/handle/123456789/19079 |
dc.identifier.issn.none.fl_str_mv |
1520-5207 |
identifier_str_mv |
1520-5207 |
url |
https://www.ncbi.nlm.nih.gov/pubmed/24321011 http://www.locus.ufv.br/handle/123456789/19079 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.ispartofseries.pt-BR.fl_str_mv |
v. 118, n. 1, p. 81-93, 2014 |
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American Chemical Society info:eu-repo/semantics/openAccess |
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American Chemical Society |
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openAccess |
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The Journal of Physical Chemistry B |
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The Journal of Physical Chemistry B |
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