Water-soluble Hantzsch ester as switch-on fluorescent probe for efficiently detecting nitric oxide

• DHPS showed sensitively and selectively fluorescent detection of NO in water, the limitation of the detection is 18 nM.
• The NO-induced aromatization of dihydropyridine in DHPS is responsible for the fluorescent switch-on mechanism.
• The probe was successfully applied in the field of cell imaging for detecting the endogenously generated NO.

A water soluble Hantzsch ester derivative of coumarin, DHPS, was synthesized and successfully applied in the fluorescent sensing nitric oxide (NO) in aqueous solution. The fluorescence of probe DHPS is extremely weak, while its fluorescence was greatly switched on upon the addition of NO solution and showed high selectivity and sensitivity to NO. The limitation of the detection was calculated to be 18 nM. The NO-induced aromatization of dihydropyridine in DHPS to pyridine derivative (PYS) proved to be the switching mechanism for the fluorescent sensing process, which was confirmed through spectra characterization and computation study. Cytotoxicity assay demonstrated both DHPS and PYS are biocompatible, the DHPS was successfully applied to track the endogenously produced NO in the RAW 264.7 cells.

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