Cargando…

Binding Study of Antibacterial Drug Ciprofloxacin with Imidazolium-Based Ionic Liquids Having Different Halide Anions: A Spectroscopic and Density Functional Theory Analysis

[Image: see text] Herein, we have shown the interaction of an antibiotic drug ciprofloxacin (CIP) with three surface-active ionic liquids (ILs), having the same cation and different anions, namely, 1-decyl-3-methylimidazoliumtetrafluoroborate [C(10)mim][BF(4)], 1-decyl-3-methylimidazolium bromide [C...

Descripción completa

Detalles Bibliográficos
Autores principales: Siddiquee, Abrar, Parray, Zahoor, Anand, Aashima, Tasneem, Shadma, Hasan, Nazim, Alamier, Waleed M., Ageeli, Abeer A., Wani, Farooq Ahmad, Singh, Prashant, Patel, Rajan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10653064/
https://www.ncbi.nlm.nih.gov/pubmed/38024745
http://dx.doi.org/10.1021/acsomega.3c05100
_version_ 1785136342352527360
author Siddiquee, Abrar
Parray, Zahoor
Anand, Aashima
Tasneem, Shadma
Hasan, Nazim
Alamier, Waleed M.
Ageeli, Abeer A.
Wani, Farooq Ahmad
Singh, Prashant
Patel, Rajan
author_facet Siddiquee, Abrar
Parray, Zahoor
Anand, Aashima
Tasneem, Shadma
Hasan, Nazim
Alamier, Waleed M.
Ageeli, Abeer A.
Wani, Farooq Ahmad
Singh, Prashant
Patel, Rajan
author_sort Siddiquee, Abrar
collection PubMed
description [Image: see text] Herein, we have shown the interaction of an antibiotic drug ciprofloxacin (CIP) with three surface-active ionic liquids (ILs), having the same cation and different anions, namely, 1-decyl-3-methylimidazoliumtetrafluoroborate [C(10)mim][BF(4)], 1-decyl-3-methylimidazolium bromide [C(10)mim][Br], and 1-decyl-3-methylimidazolium chloride [C(10)mim][Cl]. This study has been performed by exploiting various spectroscopic techniques such as steady-state fluorescence, time-resolved fluorescence, and UV–visible spectroscopy. The fluorescence emission study of CIP with ILs was performed at various concentrations of all the three ILs. The emission spectra of CIP decreased in the presence of ILs, suggesting complex formation between CIP–IL. The effect of different concentrations of ILs on the emission spectra of CIP was exploited in terms of quenching and binding parameters. Further, fluorescence emission study was validated by the time-resolved fluorescence technique by measuring the average lifetime (τ(avg)) of CIP in the presence of all the three ILs. The τ(avg) value of the drug changed with the addition of ILs, which suggests complex formation between the drug and ILs. This complex formation was also confirmed by UV–visible spectroscopy results of CIP with all the three ILs. Further, for evaluating the thermodynamic parameters of the CIP–IL interactions, isothermal titration calorimetry (ITC) was performed. The ITC experiment yielded the thermodynamic parameters, ΔH (change in the enthalpy of association), ΔG (Gibbs free energy change), ΔS (entropy change), and binding constant (K(a)). The binding parameters driven by ITC revealed that CIP–IL interactions are spontaneous in nature and enthalpy-driven, involving hydrophobic forces. Further, the classical density functional theory (DFT) calculations were performed, which provided deep insight for CIP–IL complex formation.
format Online
Article
Text
id pubmed-10653064
institution National Center for Biotechnology Information
language English
publishDate 2023
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-106530642023-11-01 Binding Study of Antibacterial Drug Ciprofloxacin with Imidazolium-Based Ionic Liquids Having Different Halide Anions: A Spectroscopic and Density Functional Theory Analysis Siddiquee, Abrar Parray, Zahoor Anand, Aashima Tasneem, Shadma Hasan, Nazim Alamier, Waleed M. Ageeli, Abeer A. Wani, Farooq Ahmad Singh, Prashant Patel, Rajan ACS Omega [Image: see text] Herein, we have shown the interaction of an antibiotic drug ciprofloxacin (CIP) with three surface-active ionic liquids (ILs), having the same cation and different anions, namely, 1-decyl-3-methylimidazoliumtetrafluoroborate [C(10)mim][BF(4)], 1-decyl-3-methylimidazolium bromide [C(10)mim][Br], and 1-decyl-3-methylimidazolium chloride [C(10)mim][Cl]. This study has been performed by exploiting various spectroscopic techniques such as steady-state fluorescence, time-resolved fluorescence, and UV–visible spectroscopy. The fluorescence emission study of CIP with ILs was performed at various concentrations of all the three ILs. The emission spectra of CIP decreased in the presence of ILs, suggesting complex formation between CIP–IL. The effect of different concentrations of ILs on the emission spectra of CIP was exploited in terms of quenching and binding parameters. Further, fluorescence emission study was validated by the time-resolved fluorescence technique by measuring the average lifetime (τ(avg)) of CIP in the presence of all the three ILs. The τ(avg) value of the drug changed with the addition of ILs, which suggests complex formation between the drug and ILs. This complex formation was also confirmed by UV–visible spectroscopy results of CIP with all the three ILs. Further, for evaluating the thermodynamic parameters of the CIP–IL interactions, isothermal titration calorimetry (ITC) was performed. The ITC experiment yielded the thermodynamic parameters, ΔH (change in the enthalpy of association), ΔG (Gibbs free energy change), ΔS (entropy change), and binding constant (K(a)). The binding parameters driven by ITC revealed that CIP–IL interactions are spontaneous in nature and enthalpy-driven, involving hydrophobic forces. Further, the classical density functional theory (DFT) calculations were performed, which provided deep insight for CIP–IL complex formation. American Chemical Society 2023-11-01 /pmc/articles/PMC10653064/ /pubmed/38024745 http://dx.doi.org/10.1021/acsomega.3c05100 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Siddiquee, Abrar
Parray, Zahoor
Anand, Aashima
Tasneem, Shadma
Hasan, Nazim
Alamier, Waleed M.
Ageeli, Abeer A.
Wani, Farooq Ahmad
Singh, Prashant
Patel, Rajan
Binding Study of Antibacterial Drug Ciprofloxacin with Imidazolium-Based Ionic Liquids Having Different Halide Anions: A Spectroscopic and Density Functional Theory Analysis
title Binding Study of Antibacterial Drug Ciprofloxacin with Imidazolium-Based Ionic Liquids Having Different Halide Anions: A Spectroscopic and Density Functional Theory Analysis
title_full Binding Study of Antibacterial Drug Ciprofloxacin with Imidazolium-Based Ionic Liquids Having Different Halide Anions: A Spectroscopic and Density Functional Theory Analysis
title_fullStr Binding Study of Antibacterial Drug Ciprofloxacin with Imidazolium-Based Ionic Liquids Having Different Halide Anions: A Spectroscopic and Density Functional Theory Analysis
title_full_unstemmed Binding Study of Antibacterial Drug Ciprofloxacin with Imidazolium-Based Ionic Liquids Having Different Halide Anions: A Spectroscopic and Density Functional Theory Analysis
title_short Binding Study of Antibacterial Drug Ciprofloxacin with Imidazolium-Based Ionic Liquids Having Different Halide Anions: A Spectroscopic and Density Functional Theory Analysis
title_sort binding study of antibacterial drug ciprofloxacin with imidazolium-based ionic liquids having different halide anions: a spectroscopic and density functional theory analysis
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10653064/
https://www.ncbi.nlm.nih.gov/pubmed/38024745
http://dx.doi.org/10.1021/acsomega.3c05100
work_keys_str_mv AT siddiqueeabrar bindingstudyofantibacterialdrugciprofloxacinwithimidazoliumbasedionicliquidshavingdifferenthalideanionsaspectroscopicanddensityfunctionaltheoryanalysis
AT parrayzahoor bindingstudyofantibacterialdrugciprofloxacinwithimidazoliumbasedionicliquidshavingdifferenthalideanionsaspectroscopicanddensityfunctionaltheoryanalysis
AT anandaashima bindingstudyofantibacterialdrugciprofloxacinwithimidazoliumbasedionicliquidshavingdifferenthalideanionsaspectroscopicanddensityfunctionaltheoryanalysis
AT tasneemshadma bindingstudyofantibacterialdrugciprofloxacinwithimidazoliumbasedionicliquidshavingdifferenthalideanionsaspectroscopicanddensityfunctionaltheoryanalysis
AT hasannazim bindingstudyofantibacterialdrugciprofloxacinwithimidazoliumbasedionicliquidshavingdifferenthalideanionsaspectroscopicanddensityfunctionaltheoryanalysis
AT alamierwaleedm bindingstudyofantibacterialdrugciprofloxacinwithimidazoliumbasedionicliquidshavingdifferenthalideanionsaspectroscopicanddensityfunctionaltheoryanalysis
AT ageeliabeera bindingstudyofantibacterialdrugciprofloxacinwithimidazoliumbasedionicliquidshavingdifferenthalideanionsaspectroscopicanddensityfunctionaltheoryanalysis
AT wanifarooqahmad bindingstudyofantibacterialdrugciprofloxacinwithimidazoliumbasedionicliquidshavingdifferenthalideanionsaspectroscopicanddensityfunctionaltheoryanalysis
AT singhprashant bindingstudyofantibacterialdrugciprofloxacinwithimidazoliumbasedionicliquidshavingdifferenthalideanionsaspectroscopicanddensityfunctionaltheoryanalysis
AT patelrajan bindingstudyofantibacterialdrugciprofloxacinwithimidazoliumbasedionicliquidshavingdifferenthalideanionsaspectroscopicanddensityfunctionaltheoryanalysis