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New pyridoxal based chemosensor for selective detection of Zn2+: Application in live cell imaging and phosphatase activity response
Published in Elsevier BV
2017
Volume: 334
   
Pages: 86 - 100
Abstract

Although a variety of fluorescence based chemosensors have been utilized for selective detection of Zn2+, pyridoxal containing simple Schiff bases still remained less explored. Here, we combine pyridoxal hydrochloride and 1,2-diaminocyclohexane to generate a new sensor molecule, H4PydChda [5-Hydroxymethyl-4-({2-[5-hydroxymethyl-2-methylpyridin-3-hydroxy-4-ylethylene)-amino]-cyclohexylimino}-methyl-2-methylpyridin-3-ol]. Chemosensor H4PydChda exhibits selective turn-on type response in presence of Zn2+ in ethanol-water mixture at physiological pH. Appreciable fluorescence enhancement occurs upon addition of Zn2+ to H4PydChda as a result of inhibited C

double bond

N isomerisation and excited state intramolecular proton transfer (ESIPT) leading to efficient chelation enhanced fluorescence (CHEF). The relevant properties, including reversibility, life time measurements and detection limit have been determined for the sensor system. The experimental and theoretical supports in terms of 1H and 13C NMR spectroscopy and DFT/TDDFT study are provided to establish the binding mode of H4PydChda to Zn2+. H4PydChda was employed as a sensor for detection of Zn2+ in Human gastric adenocarcinoma (AGS) cells. Moreover, the resulting probe-Zn2+complex shows convincing phosphatase activity (kcat = 21.59 s−1), opening a promising avenue for further research.

Graphical abstract

We reported a pyridoxal-based reversible chemosensor, H4PydChda, exhibiting selective turn-on response for Zn2+. The experimental and theoretical supports are provided to establish the binding mode of H4PydChda to Zn2+. The prob-Zn2+ ensemble is capable of showing appreciable phosphatase activity with NPP substrate.

About the journal
JournalData powered by TypesetJournal of Photochemistry and Photobiology A: Chemistry
PublisherData powered by TypesetElsevier BV
ISSN1010-6030
Open AccessNo