title: Experimental and theoretical NMR determination of isoniazid and sodium p-sulfonatocalix[n]arenes inclusion complexes.
abstract: In this work the inclusion complex formation of isoniazid with sodium p-sulfonatocalix[n]arenes is reported aiming to improve the physicochemical and biopharmaceutical properties of isoniazid a first line antibuberculosis drug. The architectures of the complexes were proposed according to NMR data Job plot indicating details on the insertion of the isoniazid in the calix[n]arenes cavities. DFT theoretical NMR calculations were also performed for sodium p-sulfonatocalix[4]arene complex with isoniazid, with various modes of complexation being considered, to provide support for the experimental proposal. A comparison between experimental and theoretical ¹H NMR chemical shifts profiles allowed for the inclusion complex characterization confirming the isoniazid inclusion mode which is preferentially through the hydrazide moiety. The remarkable agreement between experimental and theoretical NMR profiles adds support to their use in the structural characterization of inclusion compounds. Antibacterial activity was evaluated and the results indicated the inclusion complexes as a potential strategy for tuberculosis treatment.
authors: Núcleo Multifuncional de Pesquisas Químicas-NUPEQ, Departamento de Química, Instituto de Ciências Exatas, Universidade Federal de Juiz de Fora-UFJF, 36033-900 Juiz de Fora, MG, Brazil.
authors: João V
authors: JV
authors: de Assis
authors: Milena G
authors: MG
authors: Teixeira
authors: Cássia G P
authors: CG
authors: Soares
authors: Juliana F
authors: JF
authors: Lopes
authors: Guilherme S L
authors: GS
authors: Carvalho
authors: Maria C S
authors: MC
authors: Lourenço
authors: Mauro V
authors: MV
authors: de Almeida
authors: Wagner B
authors: WB
authors: de Almeida
authors: Sergio A
authors: SA
authors: Fernandes
mesh_terms: D000995:Antitubercular Agents / Q000737:chemistry* / Q000494:pharmacology; D047250:Calixarenes / Q000737:chemistry* / Q000494:pharmacology; D016503:Drug Delivery Systems; D007538:Isoniazid / Q000737:chemistry* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D009169:Mycobacterium tuberculosis / Q000187:drug effects / Q000254:growth & development
chemical_list: D000995:Antitubercular Agents; D047250:Calixarenes; D007538:Isoniazid