Bioimaging application of a novel anion selective chemosensor derived from vitamin B6 cofactor

•Vitamin B6 cofactor derived anion selective chemosensor L was reported.•L showed F− and AcO− selective ‘turn-on’ fluorescence at 500 nm.•L can detect cytoplasmic fluoride in HeLa cells through fluorescence imaging.•Experimental results were complemented with DFT study.

The detection of intracellular fluoride was achieved by a novel Schiff base chemosensor derived from vitamin B6 cofactor (L) using fluorescence imaging technique. The sensor L was synthesized by condensation of pyridoxal phosphate with 2-aminothiophenol. The anion recognition ability of L was explored by UV–Vis and fluorescence methods in DMSO and mixed DMSO-H2O system. The sensor L showed both naked-eye detectable color change from colorless to light green and remarkable fluorescence enhancement at 500 nm in the presence of F− and AcO−. The anion recognition was occurred through the formation of hydrogen bonded complexes between these anions and L, followed by the partial deprotonation of L. The detection limit of L for the analysis of F− and AcO− was calculated to be 1.88 μM and 9.10 μM, respectively. Finally, the detection of cytoplasmic fluoride was tested using human cancer cell HeLa through fluorescence imaging.

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