Encapsulation of sodium nimesulide and precursors in beta-cyclodextrin
authors Braga, SS; Ribeiro-Claro, P; Pillinger, M; Goncalves, IS; Pereira, F; Fernandes, AC; Romao, CC; Correia, PB; Teixeira-Dias, JJC
nationality International
journal ORGANIC & BIOMOLECULAR CHEMISTRY
keywords COMPACT EFFECTIVE POTENTIALS; C-13 CHEMICAL-SHIFTS; EXPONENT BASIS-SETS; INCLUSION COMPLEXES; N-BUTANE; CONFORMATION; DERIVATIVES; EFFICIENT; ENERGY; DRUGS
abstract Crystalline 1 : 1 inclusion complexes with beta-cyclodextrin (beta-CD) and the sodium salt of nimesulide (4-nitro-2phenoxymethanesulfonanilide), and the sodium salt of the derivative 2-phenoxymethanesulfonanilide, have been prepared by co-precipitation from aqueous solution. The presence of true inclusion complexes was supported by elemental analysis, thermogravimetry and powder X-ray diffraction. FTIR and C-13 CP MAS NMR spectroscopy confirmed that no chemical modification of the guests occurred upon formation of inclusion complexes. The reaction of the precursors 2-phenoxynitrobenzene and 2-phenoxyaniline with beta-CD was also studied and crystalline inclusion complexes with a 2 : 1 (host-to-guest) stoichiometry were isolated. The interaction of the different guest species with beta-CD host molecules was studied theoretically by carrying out ab initio calculations. Favourable inclusion geometries were obtained for the four guests mentioned above. On the other hand, it was found that the inclusion of the neutral guests nimesulide and 2-phenoxymethanesulfonanilide was considerably less favourable. This is in agreement with the experimentally observed difficulty in isolating true inclusion complexes containing these guests and beta-CD. The calculated lower stability is attributed to the different steric hindrance arising from the different conformational preferences of neutral and anionic forms.
publisher ROYAL SOC CHEMISTRY
issn 1477-0520
year published 2003
volume 1
issue 5
beginning page 873
ending page 878
digital object identifier (doi) 10.1039/b211295g
web of science category Chemistry, Organic
subject category Chemistry
unique article identifier WOS:000181798400018
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