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

Hiba Mohamed Ameen, S. Kunsági-Máté, Lajos Szente, Beáta Lemli

Research output: Contribution to journalArticle

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.

Original languageEnglish
Article number117475
JournalSpectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
Volume225
DOIs
Publication statusPublished - Jan 15 2020

Fingerprint

Sulfamethazine
beta-Cyclodextrins
Sulfur Compounds
sulfur compounds
Sulfur compounds
Cyclodextrins
Sulfonamides
Encapsulation
Amides
amides
Hydrogen bonds
hydrogen bonds
dipoles
Molecules
molecules
antibiotics
infectious diseases
microorganisms
Dipole moment
Antibiotics

Keywords

  • Beta-cyclodextrins
  • Host-guest complexes
  • pH-dependent complex formation
  • Sulfamethazine
  • Sulfonamides

ASJC Scopus subject areas

  • Analytical Chemistry
  • Atomic and Molecular Physics, and Optics
  • Instrumentation
  • Spectroscopy

Cite this

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title = "Encapsulation of sulfamethazine by native and randomly methylated β-cyclodextrins: The role of the dipole properties of guests",
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.",
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T1 - Encapsulation of sulfamethazine by native and randomly methylated β-cyclodextrins

T2 - The role of the dipole properties of guests

AU - Mohamed Ameen, Hiba

AU - Kunsági-Máté, S.

AU - Szente, Lajos

AU - Lemli, Beáta

PY - 2020/1/15

Y1 - 2020/1/15

N2 - 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.

AB - 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.

KW - Beta-cyclodextrins

KW - Host-guest complexes

KW - pH-dependent complex formation

KW - Sulfamethazine

KW - Sulfonamides

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