Phenolate-thiazole based reversible "turn-on" chemosensor for the selective detection of carbonate anion: X-ray crystallography, DFT/TDFT, and cell study.

Autor: Pramanik C; Post Graduate Department of Chemistry, Panskura Banamali College (Autonomous) (Vidyasagar University), Panskura R.S, Midnapore (East), West Bengal 721152, India; Department of Chemistry, Dinabandhu Andrews College, Kolkata, West Bengal 700 084, India., Jana A; Post Graduate Department of Chemistry, Panskura Banamali College (Autonomous) (Vidyasagar University), Panskura R.S, Midnapore (East), West Bengal 721152, India., Brandao P; Department of Chemistry, CICECO, University of Aveiro, 3810-193 Aveiro, Portugal., Aher A; Centre for DNA Fingerprinting & Diagnostics (CDFD), Hyderabad, Telangana 500 039, India., Bera P; Post Graduate Department of Chemistry, Panskura Banamali College (Autonomous) (Vidyasagar University), Panskura R.S, Midnapore (East), West Bengal 721152, India; Department of Chemistry, Kandi Raj College, Murshidabad, West Bengal 742137, India., Khatua S; Department of Chemistry, Y.S. Palpara College, Palpara, Midnapore (East), West Bengal 721458, India., Majumdar S; Department of Chemistry, Kandi Raj College, Murshidabad, West Bengal 742137, India., Mandal B; Post Graduate Department of Chemistry, Panskura Banamali College (Autonomous) (Vidyasagar University), Panskura R.S, Midnapore (East), West Bengal 721152, India; Department of Chemistry, Shahid Matangini Hazra Govt. College for Women, Midnapore (East), West Bengal 721 649, India., Kumar Manna S; Centre for DNA Fingerprinting & Diagnostics (CDFD), Hyderabad, Telangana 500 039, India., Bera P; Post Graduate Department of Chemistry, Panskura Banamali College (Autonomous) (Vidyasagar University), Panskura R.S, Midnapore (East), West Bengal 721152, India. Electronic address: pb721152@gmail.com.
Jazyk: angličtina
Zdroj: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy [Spectrochim Acta A Mol Biomol Spectrosc] 2024 Jul 05; Vol. 315, pp. 124233. Date of Electronic Publication: 2024 Mar 31.
DOI: 10.1016/j.saa.2024.124233
Abstrakt: A new phenolate-thiazole derivative (L) has been synthesized and structurally characterized.The chemo-sensing activity of L is detected by the naked eye for the aqueous carbonate anion in the pH range of 4 to 8. The selective 'turn-on' fluorescence occurs through the formation of a stable intermediate L∙CO 3 2- (1) following the PET mechanism. The limit of detection (LOD) is found 0.18 µM based on the absorbance-based assay.The quinonoid form of bromophenol unit binds strongly with CO 3 2- through thiazole nitrogen and hydrazinic nitrogen. Further, the selective holding of CO 3 2- anion over other planar tetranuclear anions (e.g., SO 3 2- , NO 3 - ) happens with several intra and intermolecular hydrogen bonds as envisaged by the DFT/TDFT study. The formation mechanism of L∙CO 3 2- is proposed based on experimental and theoretical studies. The biological experiments (MTT and cell imaging)reveal the non-cytotoxicity nature of L and the biocompatible uptake of L mostly in the cytoplasm at physiological pH.
Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
(Copyright © 2024 Elsevier B.V. All rights reserved.)
Databáze: MEDLINE
Externí odkaz: