Dual-mode recognition of biogenic amine tryptamine and fluoride ion by naphthyl hydrazone platform: Application in fluorescence imaging of HeLa cells and Zebrafish embryos
A novel, selective and sensitive naphthyl hydrazone anchored Schiff base derivative 1-(1, 3-diphenyl-1H-pyrazol-4-yl)methylene)hydrazono) methyl) naphthalen-2-ol (PYNA) has been fabricated, synthesized and efficiently applied to the fluorogenic and chromogenic recognition of both tryptamine (TryptA) and F ions. The probe PYNA disclosed strong ratiometric absorbance to TryptA amidst the other tested amines and anions. Moreover, the fluorescence data suggest that inhibition of excited state intramolecular proton transfer (ESIPT) takes place through the fluorescence enhancement in the presence of TryptA and F¯ ion for the probe PYNA. The 1:1 binding stoichiometry of PYNA with TryptA/F ions have been determined from Job`s plot based on UV-visible and fluorescence method. In addition, the binding sites of PYNA-TryptA/F have been established from ESI-MS (Electrospray Ionization Mass), 1H NMR titration, 19F NMR and DFT calculations. In-vivo analysis of both TryptA/F in zebrafish embryos and intracellular detection of F- in HeLa cells indicates that PYNA has a good cell permeability and biocompatibility and could act as excellent biologically potent chemical device.