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

• Published in: Journal of inclusion phenomena and macrocyclic chemistry Vol. 80; no. 1-2; pp. 113 - 124
• Main Authors: Tačić, Ana, Savić, Ivan, Nikolić, Vesna, Savić, Ivana, Ilić-Stojanović, Snežana, Ilić, Dušica, Petrović, Slobodan, Popsavin, Mirjana, Kapor, Agnes
• Format: Journal Article
• Language: English
• Published: Dordrecht Springer Netherlands 01.10.2014
• Subjects: Chemistry; Chemistry and Materials Science; Crystallography and Scattering Methods; Food Science; Organic Chemistry; Original Article; 2-Hydroxypropyl-β-cyclodextrin; β-Cyclodextrin; Inclusion complexes; Phase-solubility and photostability; Sulfanilamide
• ISSN: 1388-3127; 1573-1111
• DOI: 10.1007/s10847-014-0410-x

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, 1 H-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.