Fluorescent sensing of Al³⁺ by benzophenone based Schiff base chemosensor and live cell imaging applications: Impact of keto-enol tautomerism

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• 作者：Barnali Naskar^aAuthor Vitae ; Ritwik Modak^aAuthor Vitae ; Yeasin Sikdar^aAuthor Vitae ; Dilip K. Maiti^aAuthor Vitae ; Antonio Bauzá ; ^bAuthor Vitae ; Antonio Frontera^bAuthor Vitae ; Atul Katarkar^cAuthor Vitae ; Keya Chaudhuri^cAuthor Vitae ; Sanchita Goswami^a ; ^{sgchem@caluniv.ac.in" class="auth_mail" title="E-mail the corresponding author} ; ^{sgoswamicu@gmail.com" class="auth_mail" title="E-mail the corresponding author}Author Vitae
• 关键词：Fluorimetric sensor ; Al3+ detection ; Benzophenone Schiff base ; Keto&ndash ; enol tautomerism ; DFT/TDDFT ; Biological studies
• 刊名：Sensors & Actuators: B. Chemical
• 出版年：2017
• 出版时间：February 2017
• 年：2017
• 卷：239
• 期：Complete
• 页码：1194-1204
• 全文大小：3496 K

文摘

Developing simple probes to sense Al³⁺in vivo and in vitro in real time is highly desirable as Al³⁺ imbalance has been linked to a variety of diseases in human being. Here, we introduce a new, highly selective and sensitive Schiff base chemosensor, H₂bpet, based on benzophenone that can detect Al³⁺ in a 0.01% ethanol in 50 mM HEPES buffer medium by fluorimetric sensing. The structure of the probe, H₂bpet involves existence of keto−–enol tautomerism. Single crystal X-ray diffraction study reveals prevalence of keto form of H₂bpet in the solid state. The binding properties of H₂bpet with Al³⁺ was thoroughly investigated by fluorescence spectroscopy and ESI–MS analyses. The binding of Al³⁺ to the probe H₂bpet, induces distinct ¹H and ¹³C NMR shifts in favour of H₂bpet (keto form):Al³⁺ aggregate. The sensing mechanism of H₂bpet toward Al³⁺ and composition of H₂bpet:Al³⁺ aggregate was proposed and established by DFT/TDDFT calculations. Its application in fluorescent imaging in HepG2 cells was also tested. This report demonstrates an advancement in detection of Al³⁺ with the introduction of a new benzophenone containing Schiff base chemosensor.