Investigation of thiolysis of NBD amines for the development of H 2 S probes and evaluating the stability of NBD dyes

• Published in: Organic & biomolecular chemistry Vol. 14; no. 47; pp. 11117 - 11124
• Main Authors: Song, Fanbo, Li, Zhifei, Li, Jiayuan, Wu, Shuai, Qiu, Xianbo, Xi, Zhen, Yi, Long
• Format: Journal Article
• Language: English
• Published: England 29.11.2016
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/C6OB02354A

In order to evaluate the thiolysis of NBD (7-nitro-1,2,3-benzoxadiazole) amines for development of H S probes, herein we investigated the reactivity and selectivity of a series of NBD amines for the first time. The piperazinyl- and piperidyl-based NBD probes could react efficiently with micromolar H S in buffer (pH 7.4), while such NBD(S) (nitrobenzothiadiazole) derivatives showed much slow thiolysis even in the presence of millimolar H S. Low reactivity was also observed for thiolysis of these ethylamino-, ethanolamino- and anilino-based NBD probes. Therefore, almost all NBD amines used in bioimaging should be stable, in consideration of the presence of only micromolar endogenous H S in vivo. Moreover, the piperazinyl-NBD derivatives could be efficient in the development of fluorescent H S probes and for directly visualizing H S by paper-based detection.