Please use this identifier to cite or link to this item: http://repositorio.ufla.br/jspui/handle/1/15157
metadata.artigo.dc.title: Theoretical and experimental study of inclusion complexes formed by isoniazid and modified β-cyclodextrins: 1H NMR structural determination and antibacterial activity evaluation
metadata.artigo.dc.creator: Teixeira, Milena G.
Assis, João V. de
Soares, Cássia G. P.
Venâncio, Mateus F.
Lopes, Juliana F.
Nascimento Junior, Clebio S.
Anconi, Cleber P. A.
Carvalho, Guilherme S. L.
Lourenço, Cristina S.
Almeida, Mauro V. de
Fernandes, Sergio A.
Almeida, Wagner B. de
metadata.artigo.dc.subject: Antibacterial activity
Tuberculosis - Treatment
Antituberculosis drug
Atividade antibacteriana
Tuberculose - Tratamento
Droga antituberculose
metadata.artigo.dc.publisher: ACS Publications
metadata.artigo.dc.date.issued: 2014
metadata.artigo.dc.identifier.citation: TEIXEIRA, M. G. et al. Theoretical and experimental study of inclusion complexes formed by isoniazid and modified β-cyclodextrins: 1H NMR structural determination and antibacterial activity evaluation. Journal of Physical Chemistry B, Washington, v. 118, n. 1, p. 81-93, 2014.
metadata.artigo.dc.description.abstract: 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 1H 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 1H NMR chemical shift values for the isoniazid (H6′,8′ and H5′,9′) and cyclodextrins (H3,5) C1H 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.
metadata.artigo.dc.identifier.uri: http://pubs.acs.org/doi/abs/10.1021/jp409579m
http://repositorio.ufla.br/jspui/handle/1/15157
metadata.artigo.dc.language: en_US
Appears in Collections:DQI - Artigos publicados em periódicos

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