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Highly selective fluorescence ‘turn off’ sensing of picric acid and efficient cell labelling by water-soluble luminescent anthracene-bridged poly(N-vinyl pyrrolidone)

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Abstract

A novel, water-soluble, luminescent anthracene-bridged AA-type bi-arm poly(N-vinylpyrrolidone) (ATC-PNVP) was synthesized using a click reaction between alkyne-terminated PNVP and 9,10-bis(azidomethyl)anthracene. The resultant anthracene-bridged PNVP (ATC-PNVP) was characterized using 1H NMR, FTIR, UV-Vis, and fluorescence spectroscopic methods and GPC analysis. ATC-PNVP showed effective fluorescence properties in an aqueous medium. It showed highly selective “turn off” sensing behaviour towards picric acid, a common nitro-aromatic explosive, with a wide linear range of detection of 0.01–0.3 mM and LOD value of 0.006 mM in water. ATC-PNVP-based paper sensors also showed very effective detection of picric acid in the concentration range 0.001–1.0 mM. Its binding with bovine serum albumin (BSA) was studied using steady-state, synchronous and 3D fluorescence spectroscopy and this study showed effective quenching of the intrinsic fluorescence of BSA and occurrence of a FRET-type interaction. Furthermore, this luminescent ATC-PNVP was efficiently used as a fluorescence microscopy labelling agent in NIH-3T3 and HeLa cells, and showed greater uptake and hence better fluorescent labelling in the cytosols of the tested cells than free 9,10-bis(azidomethyl) anthracene. The cell viability study also showed a very good biocompatible and non-toxic nature of ATC-PNVP at lower working concentrations towards each of the types of cells tested.

Graphical abstract: Highly selective fluorescence ‘turn off’ sensing of picric acid and efficient cell labelling by water-soluble luminescent anthracene-bridged poly(N-vinyl pyrrolidone)

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Publication details

The article was received on 13 Dec 2018, accepted on 21 Apr 2019 and first published on 25 Apr 2019


Article type: Paper
DOI: 10.1039/C8AN02417K
Analyst, 2019, Advance Article

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    Highly selective fluorescence ‘turn off’ sensing of picric acid and efficient cell labelling by water-soluble luminescent anthracene-bridged poly(N-vinyl pyrrolidone)

    R. Singh, K. Mitra, S. Singh, S. Senapati, V. K. Patel, S. Vishwakarma, A. Kumari, J. Singh, S. K. Sen Gupta, N. Misra, P. Maiti and B. Ray, Analyst, 2019, Advance Article , DOI: 10.1039/C8AN02417K

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