N-(2-formylphenyl)-4-methylbenzenesulfonamide: A simple endoplasmic reticulum-targetable probe for the ratiometric fluorescent detection of hydrazine in environmental and biological systems

Abstract

Hydrazine (N2H4) is widely used in the industry; however, it is highly toxic to the environment and humans. Detection of N2H4 at the specific subcellular organelle, e.g., endoplasmic reticulum (ER), helps elucidate its toxicological mechanism in the biological systems. In this study, a simple aldehyde-based probe with methylbenzenesulfonamide as an ER-targeting group was designed for the fluorescent ratiometric detection of N2H4. The green fluorescence of probe 1 was quenched by N2H4, emitting a blue emission. This process was highly selective and sensitive toward N2H4, as characterized by nuclear magnetic resonance, mass spectrometry, single crystal X-ray diffraction, and density functional theory calculation analysis. Moreover, probe 1 was used to detect N2H4 in water and soil samples, and the 1-loaded test trip was fabricated for conveniently monitoring N2H4 in aqueous solution and gas states. The probe was confirmed as an excellent tool for monitoring N2H4 in the ER of living cells, plants, and animals.