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Imidazo[1,5-α]pyridine-derived fluorescent turn-on probe for cellular thiols imaging with a large Stokes shift

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Abstract We presented the design, synthesis and preliminary evaluation of the 2,4-dinitrobenzenesulfonate (DNBS) of imidazo[1,5- α ]pyridine derivative, NIPY-DNBS , as a turn-on fluorescent probe for the detection of thiols… Click to show full abstract

Abstract We presented the design, synthesis and preliminary evaluation of the 2,4-dinitrobenzenesulfonate (DNBS) of imidazo[1,5- α ]pyridine derivative, NIPY-DNBS , as a turn-on fluorescent probe for the detection of thiols in aqueous solution. The reaction mechanism was confirmed by means of fluorescence, absorption and HRMS. The large Stokes shift (201 nm), high sensitivity (the detection limit for Cys was calculated to be as low as 0.17 μM) and fast response (10 min) of NIPY-DNBS make it a practical and reliable method for fluorescence imaging. Furthermore, application of NIPY-DNBS for the selective detection of intracellular thiols has been successfully demonstrated in living A549 cells.

Keywords: probe; large stokes; imidazo pyridine; nipy dnbs; stokes shift

Journal Title: Tetrahedron Letters
Year Published: 2017

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