Molecular engineering of benzenesulfonyl analogs for visual hydrogen polysulfide fluorescent probes based on Nile red skeleton

Abstract

Hydrogen polysulfide (H2Sn, n > 1) has a valuable function in various aspects of biological regulation. Therefore, it is of great significance to realize the visual monitoring of H2Sn levels in vivo. Herein, a series of fluorescent probes NR-BS were constructed by changing types and positions of substituents on the benzene ring of benzenesulfonyl. Among them, probe NR-BS4 was optimized due to its wide linear range (0 ∼ 350 μM) and little interference from biothiols. In addition, NR-BS4 has a broad pH tolerance range (pH = 4 ∼ 10) and high sensitivity (0.140 μM). In addition, the PET mechanism of probe NR-BS4 and H2Sn was demonstrated by DFT calculations and LC-MS. The intracellular imaging studies indicate that NR-BS4 can be successfully devoted to monitor the levels of exogenous and endogenous H2Sn in vivo.