Inclusion complexes of sulfanilamide with β-cyclodextrin and 2-hydroxypropyl-β-cyclodextrin

被引:0
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作者
Ana Tačić
Ivan Savić
Vesna Nikolić
Ivana Savić
Snežana Ilić-Stojanović
Dušica Ilić
Slobodan Petrović
Mirjana Popsavin
Agnes Kapor
机构
[1] University of Niš,Faculty of Technology
[2] University of Belgrade,Faculty of Technology and Metallurgy
[3] University of Novi Sad,Department of Chemistry, Faculty of Sciences
[4] University of Novi Sad,Faculty of Sciences, Institute of Physics
关键词
Sulfanilamide; Inclusion complexes; β-Cyclodextrin; 2-Hydroxypropyl-β-cyclodextrin; Phase-solubility and photostability;
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摘要
Sulfanilamide belongs to the group of drugs that have a bacteriostatic effect on different pathogenic microorganisms. This activity originates from the competitive antagonism with p-aminobenzoic acid, which is an integral part of folic acid. The safe use of sulfanilamide is limited due to poor solubility in the aqueous medium. Therefore, the aim of this paper is the synthesis of sulfanilamide, as well as preparing and structural characterization of its inclusion complexes with cyclodextrins. The crude sulfanilamide was obtained in the synthesis between acetanilide and chlorosulfonic acid according to the standard procedure. The synthesized sulfanilamide was recrystallized from water in order to obtain the satisfactory purity of the substance. Sufanilamide was complexed with β-cyclodextrin and 2-hydroxypropyl-β-cyclodextrin by the co-precipitation method. A molecular encapsulation of sulfanilamide was confirmed by using FTIR, 1H-NMR, XRD and DSC methods. Phase-solubility techniques were used to assess the formation of the inclusion complex between sulfanilamide and cyclodextrins. The photostability of sulfanilamide and its inclusion complexes was estimated by UVB irradiation in a photochemical reactor by applying the UV–Vis method. Based on the UV–Vis analysis, sulfanilamide:2-hydroxypropyl-β-cyclodextrin complex was presented as more photostable than sulfanilamide:β-cyclodextrin complex and sulfanilamide. The obtained results enable the potential use of these inclusion complexes for the preparation of oral formulations due to the enhanced solubility of sulfanilamide.
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页码:113 / 124
页数:11
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