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Open AccessArticle

Thermodynamic Characterization of the Interaction between the Antimicrobial Drug Sulfamethazine and Two Selected Cyclodextrins

1
Department of General and Physical Chemistry, Faculty of Sciences, University of Pécs, Ifjúság 6, H-7624 Pécs, Hungary
2
Institute of Organic and Medicinal Chemistry, Medical School, University of Pécs, Szigeti 12, H-7624 Pécs, Hungary
3
János Szentágothai Research Center, University of Pécs, Ifjúság 20, H-7624 Pécs, Hungary
4
CycloLab Cyclodextrin Research & Development Laboratory, Ltd., Illatos 7, H-1097 Budapest, Hungary
5
Department of Pharmacology, Faculty of Pharmacy, University of Pécs, Szigeti 12, H-7624 Pécs, Hungary
*
Author to whom correspondence should be addressed.
Academic Editors: Marina Isidori, Margherita Lavorgna and Rosa Iacovino
Molecules 2019, 24(24), 4565; https://doi.org/10.3390/molecules24244565
Received: 17 October 2019 / Revised: 5 December 2019 / Accepted: 11 December 2019 / Published: 13 December 2019
(This article belongs to the Special Issue Cyclodextrin Chemistry and Toxicology)
Sulfamethazine is a representative member of the sulfonamide antibiotic drugs; it is still used in human and veterinary therapy. The protonation state of this drug affects its aqueous solubility, which can be controlled by its inclusion complexes with native or chemically-modified cyclodextrins. In this work, the temperature-dependent (298–313 K) interaction of sulfamethazine with native and randomly methylated β-cyclodextrins have been investigated at acidic and neutral pH. Surprisingly, the interaction between the neutral and anionic forms of the guest molecule and cyclodextrins with electron rich cavity are thermodynamically more favorable compared to the cationic guest. This property probably due to the enhanced formation of zwitterionic form of sulfamethazine in the hydrophobic cavities of cyclodextrins. Spectroscopic measurements and molecular modeling studies indicated the possible driving forces (hydrophobic interaction, hydrogen bonding, and electrostatic interaction) of the complex formation, and highlighted the importance of the reorganization of the solvent molecules during the entering of the guest molecule into the host’s cavity. View Full-Text
Keywords: cyclodextrin; sulfamethazine; zwitterion; host-guest complex; thermodynamics cyclodextrin; sulfamethazine; zwitterion; host-guest complex; thermodynamics
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MDPI and ACS Style

Mohamed Ameen, H.; Kunsági-Máté, S.; Bognár, B.; Szente, L.; Poór, M.; Lemli, B. Thermodynamic Characterization of the Interaction between the Antimicrobial Drug Sulfamethazine and Two Selected Cyclodextrins. Molecules 2019, 24, 4565.

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