Highly efficient H(2)S scavengers via thiolysis of positively-charged NBD amines

H(2)S is a well-known toxic gas and also a gaseous signaling molecule involved in many biological processes. Advanced chemical tools that can regulate H(2)S levels in vivo are useful for understanding H(2)S biology as well as its potential therapeutic effects. To this end, we have developed a series of 7-nitro-1,2,3-benzoxadiazole (NBD) amines as potential H(2)S scavengers. The kinetic studies of thiolysis reactions revealed that incorporation of positively-charged groups onto the NBD amines greatly increased the rate of the H(2)S-specific thiolysis reaction. We demonstrate that these reactions proceed effectively, with second order rate constants (k(2)) of >116 M(−1) s(−1) at 37 °C for NBD-S8. Additionally, we demonstrate that NBD-S8 can effectively scavenge enzymatically-produced and endogenous H(2)S in live cells. Furthering the biological significance, we demonstrate NBD-S8 mediates scavenging of H(2)S in mice.