Encapsulation of sulfamethazine by native and randomly methylated β-cyclodextrins: The role of the dipole properties of guests

Hiba Mohamed Ameen; Sándor Kunsági-Máté; Lajos Szente; Beáta Lemli

doi:10.1016/j.saa.2019.117475

Encapsulation of sulfamethazine by native and randomly methylated β-cyclodextrins: The role of the dipole properties of guests

Spectrochim Acta A Mol Biomol Spectrosc. 2020 Jan 15:225:117475. doi: 10.1016/j.saa.2019.117475. Epub 2019 Aug 17.

Authors

Hiba Mohamed Ameen¹, Sándor Kunsági-Máté², Lajos Szente³, Beáta Lemli⁴

Affiliations

¹ Department of General and Physical Chemistry, Faculty of Sciences, University of Pécs, H-7624 Pécs, Ifjúság 6, Hungary.
² Department of General and Physical Chemistry, Faculty of Sciences, University of Pécs, H-7624 Pécs, Ifjúság 6, Hungary; Institute of Organic and Medicinal Chemistry, Medical School, University of Pécs, H-7624 Pécs, Szigeti 12, Hungary; János Szentágothai Research Center, University of Pécs, H-7624 Pécs, Ifjúság 20, Hungary.
³ CycloLab Cyclodextrin Research & Development Laboratory, Ltd., H-1097 Budapest, Illatos 7, Hungary.
⁴ Department of General and Physical Chemistry, Faculty of Sciences, University of Pécs, H-7624 Pécs, Ifjúság 6, Hungary; Institute of Organic and Medicinal Chemistry, Medical School, University of Pécs, H-7624 Pécs, Szigeti 12, Hungary; János Szentágothai Research Center, University of Pécs, H-7624 Pécs, Ifjúság 20, Hungary. Electronic address: lemli.beata@gytk.pte.hu.

PMID: 31472423
DOI: 10.1016/j.saa.2019.117475

Abstract

Sulfonamides are preventive and therapeutic agents for certain infections caused by gram-positive and gram-negative microorganisms. In this work the interactions of sulfamethazine, a representative of sulfonamide antibiotics, with two β-cyclodextrin derivatives were investigated at different pH. Results show formation of stable sulfamethazine - β-cyclodextrin complexes and reflect importance of the competition of the hydrogen bonding and electrostatic interactions. The complex geometry formed is affected by the orientation of the pH-dependent dipole moment of sulfamethazine molecule and prolonged prior the sulfamethazine molecule enters into the β-cyclodextrin's cavity. Functionalization of the β-cyclodextrin molecule doesn't affect considerably the complex stabilities, therefore the native β-cyclodextrin molecule looks the simplest and most effective inclusion host to design selective and sensitive tool for sulfamethazine sensing.

Keywords: Beta-cyclodextrins; Host-guest complexes; Sulfamethazine; Sulfonamides; pH-dependent complex formation.