A highly selective and sensitive hydrogen sulfide scavenger along with its imaging in cells and zebrafish

Abstract

Hydrogen sulfide (H2S) is widely considered to be an endogenous signaling molecule that plays a crucial role in metabolic processes. Effective chemical tools that can modulate H2S levels in vivo contribute to understanding of H2S related biology as well as its potential therapeutic effects. As a consequence, we designed and synthesized a series of scavengers based on the 7-nitro-1,2,3-benzoxadiazole-piperazine conjugates from NBD-P1 to NBD-P5 were investigated to determine the down regulation of H2S levels. Among them, scavenger NBD-P5 permits a superior kinetic reaction ratio (55.43 M−1s−1), rapid response time (3 min), and a broad linear concentration range of H2S (200−600 μM). Notably, NBD-P5 displayed excellent selectivity of H2S and avoided interference from other competing physiological nucleophiles (Cys, GSH, and Hcy), reactive oxygen species (SO32-, ·OH, and ClO-), and biologically related ions (NO3-, NO2-, and PO43-). Furthermore, it is able to efficiently scavenge exogenous and endogenous H2S in living cells and zebrafish, which will provide the necessary improvements for design of diverse specific scavengers in complex biological systems.