TY - JOUR
T1 - Fluorescent sensing of Al3+ by benzophenone based Schiff base chemosensor and live cell imaging applications
T2 - Impact of keto-enol tautomerism
AU - Naskar, Barnali
AU - Modak, Ritwik
AU - Sikdar, Yeasin
AU - Maiti, Dilip K.
AU - Bauzá, Antonio
AU - Frontera, Antonio
AU - Katarkar, Atul
AU - Chaudhuri, Keya
AU - Goswami, Sanchita
N1 - Funding Information:
B. Naskar acknowledge UGC, India for fellowship (sanction no. RGNF-2013-14-SC-WES-38844). RFSMS fellowship (Sanction No. UGC/740/RFSMS) to R. Modak and is gratefully acknowledge. DST–FIST is acknowledged for providing Single crystal XRD at department of Chemistry, University of Calcutta. A.B. and A.F. thank DGICYT of Spain (projects CTQ2014-57393-C2-1-P and CONSOLIDER INGENIO CSD2010–00065, FEDER funds) for funding. We thank the CTI (UIB) for free allocation of computer time.
Publisher Copyright:
© 2016
PY - 2017/2/1
Y1 - 2017/2/1
N2 - 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.
AB - 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.
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U2 - 10.1016/j.snb.2016.08.148
DO - 10.1016/j.snb.2016.08.148
M3 - Article
AN - SCOPUS:84983781459
SN - 0925-4005
VL - 239
SP - 1194
EP - 1204
JO - Sensors and Actuators, B: Chemical
JF - Sensors and Actuators, B: Chemical
ER -
