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CuAAC-Derived Selective Fluorescent Probe as a Recognition Agent for Pb(II) and Hg(II): DFT and Docking Studies

[Image: see text] Copper(I)-catalyzed alkyne–azide cycloaddition (CuAAC) is a resourceful and stereospecific methodology that has considerably yielded promising 1,2,3-triazole-appended “click” scaffolds with the potential for selective metal ion recognition. Based on “click” methodology, this report...

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Autores principales: Singh, Gurleen, George, Nancy, Singh, Riddima, Singh, Gurjaspreet, Kaur, Jashan Deep, Kaur, Gurpreet, Singh, Harminder, Singh, Jandeep
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9631732/
https://www.ncbi.nlm.nih.gov/pubmed/36340062
http://dx.doi.org/10.1021/acsomega.2c05050
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author Singh, Gurleen
George, Nancy
Singh, Riddima
Singh, Gurjaspreet
Kaur, Jashan Deep
Kaur, Gurpreet
Singh, Harminder
Singh, Jandeep
author_facet Singh, Gurleen
George, Nancy
Singh, Riddima
Singh, Gurjaspreet
Kaur, Jashan Deep
Kaur, Gurpreet
Singh, Harminder
Singh, Jandeep
author_sort Singh, Gurleen
collection PubMed
description [Image: see text] Copper(I)-catalyzed alkyne–azide cycloaddition (CuAAC) is a resourceful and stereospecific methodology that has considerably yielded promising 1,2,3-triazole-appended “click” scaffolds with the potential for selective metal ion recognition. Based on “click” methodology, this report presents a chemosensor probe (TCT) based on 4-tert-butylcatechol architecture, via the CuAAC pathway, as a selective and efficient sensor for Pb(II) and Hg(II) ions, categorized as the most toxic and alarming environmental contaminants among the heavy metal ions. The synthesized probe was successfully characterized by spectroscopy [IR and NMR ((1)H and (13)C)] and mass spectrometry. The chemosensing study performed in acetonitrile/water (4:1) solvent media, via UV–vis and fluorescence spectroscopy, established its selective sensitivity for Pb(II) and Hg(II) species among the list of explored metal ions with the limits of detection being 8.6 and 11 μM, respectively. Additionally, the (1)H NMR and IR spectra of the synthesized TCT–metal complex also confirmed the metal–ligand binding. Besides, the effect of time and temperature on the binding ability of TCT with Pb(II) and Hg(II) was also studied via UV–vis spectroscopy. Furthermore, density functional theory studies put forward the structural comprehension of the sensor by availing the hybrid density functional (B3LYP)/6311G++(d,p) basis set of theory which was subsequently utilized for investigating its anti-inflammatory potential by performing docking analysis with human leukotriene b4 protein.
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spelling pubmed-96317322022-11-04 CuAAC-Derived Selective Fluorescent Probe as a Recognition Agent for Pb(II) and Hg(II): DFT and Docking Studies Singh, Gurleen George, Nancy Singh, Riddima Singh, Gurjaspreet Kaur, Jashan Deep Kaur, Gurpreet Singh, Harminder Singh, Jandeep ACS Omega [Image: see text] Copper(I)-catalyzed alkyne–azide cycloaddition (CuAAC) is a resourceful and stereospecific methodology that has considerably yielded promising 1,2,3-triazole-appended “click” scaffolds with the potential for selective metal ion recognition. Based on “click” methodology, this report presents a chemosensor probe (TCT) based on 4-tert-butylcatechol architecture, via the CuAAC pathway, as a selective and efficient sensor for Pb(II) and Hg(II) ions, categorized as the most toxic and alarming environmental contaminants among the heavy metal ions. The synthesized probe was successfully characterized by spectroscopy [IR and NMR ((1)H and (13)C)] and mass spectrometry. The chemosensing study performed in acetonitrile/water (4:1) solvent media, via UV–vis and fluorescence spectroscopy, established its selective sensitivity for Pb(II) and Hg(II) species among the list of explored metal ions with the limits of detection being 8.6 and 11 μM, respectively. Additionally, the (1)H NMR and IR spectra of the synthesized TCT–metal complex also confirmed the metal–ligand binding. Besides, the effect of time and temperature on the binding ability of TCT with Pb(II) and Hg(II) was also studied via UV–vis spectroscopy. Furthermore, density functional theory studies put forward the structural comprehension of the sensor by availing the hybrid density functional (B3LYP)/6311G++(d,p) basis set of theory which was subsequently utilized for investigating its anti-inflammatory potential by performing docking analysis with human leukotriene b4 protein. American Chemical Society 2022-10-20 /pmc/articles/PMC9631732/ /pubmed/36340062 http://dx.doi.org/10.1021/acsomega.2c05050 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Singh, Gurleen
George, Nancy
Singh, Riddima
Singh, Gurjaspreet
Kaur, Jashan Deep
Kaur, Gurpreet
Singh, Harminder
Singh, Jandeep
CuAAC-Derived Selective Fluorescent Probe as a Recognition Agent for Pb(II) and Hg(II): DFT and Docking Studies
title CuAAC-Derived Selective Fluorescent Probe as a Recognition Agent for Pb(II) and Hg(II): DFT and Docking Studies
title_full CuAAC-Derived Selective Fluorescent Probe as a Recognition Agent for Pb(II) and Hg(II): DFT and Docking Studies
title_fullStr CuAAC-Derived Selective Fluorescent Probe as a Recognition Agent for Pb(II) and Hg(II): DFT and Docking Studies
title_full_unstemmed CuAAC-Derived Selective Fluorescent Probe as a Recognition Agent for Pb(II) and Hg(II): DFT and Docking Studies
title_short CuAAC-Derived Selective Fluorescent Probe as a Recognition Agent for Pb(II) and Hg(II): DFT and Docking Studies
title_sort cuaac-derived selective fluorescent probe as a recognition agent for pb(ii) and hg(ii): dft and docking studies
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9631732/
https://www.ncbi.nlm.nih.gov/pubmed/36340062
http://dx.doi.org/10.1021/acsomega.2c05050
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