16597-09-4

Basic information

• Product Name: 7-nitrobenzo[c][1,2,5]oxadiazole-4-thiol
• Synonyms: 7-nitrobenzo[c][1,2,5]oxadiazole-4-thiol
• CAS NO: 16597-09-4
• Molecular Weight: 197.174
• Mol File: 16597-09-4.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: 7-nitrobenzo[c][1,2,5]oxadiazole-4-thiol(CAS DataBase Reference)
• NIST Chemistry Reference: 7-nitrobenzo[c][1,2,5]oxadiazole-4-thiol(16597-09-4)
• EPA Substance Registry System: 7-nitrobenzo[c][1,2,5]oxadiazole-4-thiol(16597-09-4)

Safety Data

• Hazardous Substances Data: 16597-09-4(Hazardous Substances Data)

Upstream product

• 16322-23-9 4-nitro-7-(phenylthio)benzo[c][1,2,5]oxadiazole 
• 882289-35-2 4-(4-fluorophenylthio)-7-nitrobenzo[c][1,2,5]oxadiazole 
• 53619-62-8 4-(4-methoxyphenylthio)-7-nitrobenzo[c][1,2,5]oxadiazole 
• 1477524-94-9 C₁₂H₇N₃O₃Se 
• 1558669-85-4 C₁₅H₇N₃O₆ 

Relevant articles and documents

Erratum: Colorimetric signaling of hydrogen sulfide by reduction of a phenylseleno-nitrobenzoxadiazole derivative (Dyes and Pigments (2013) 99 (748-752))

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A NBD-S-rhodamine dyad for dual-color discriminative imaging of biothiols and Cys/Hcy

Biothiols are essential biomolecules in sustaining intracellular redox homeostasis. Abnormal levels of Cys, Hcy, GSH and H2S are linked to different diseases, respectively. Although many fluorescent probes are successfully applied in the detection of these biothiols in living biological samples, probes with high selectivity to discriminatively detect biothiols are underdeveloped. Herein, we designed and synthesized a new dual-color NBD-S-rhodamine fluorescent probe based on fast thiolysis of NBD thioether, a non-thiol-consuming receptor. This probe could react with GSH/H2S to give red fluorescence, and with Cys/Hcy to give both green and red fluorescence for discriminative detection of biothiols and Cys/Hcy. The results revealed that this probe exhibited good selectivity and high sensitivity toward biothiols, and could be used in bioimaging. Based on the probe tool, we could selectively detect Cys/Hcy in the presence of GSH in living mammalian cells.

A highly selective and sensitive 3-hydroxyflavone-based colorimetric and fluorescent probe for hydrogen sulfide with a large Stokes shift

A 3-hydroxyflavone-based colorimetric and fluorescence probe for hydrogen sulfide (H2S) has been developed with high sensitivity and excellent selectivity. This probe was designed based on the mechanism that H2S selectively cleaved the NBD (7-nitro-2,1,3-benzoxadiazole) ether moiety in this probe and therefore release the fluorophore, 3-hydroxyflavone. The addition of H2S to the solution of probe 1 resulted in a green fluorescence and an obvious color change from colorless to pink, indicating that this probe can serve as a colorimetric and fluorescent dual probe for H2S. Furthermore, this probe displays a rapid response and reaches to a plateau within 5 min. It also exhibits a 146 nm Stokes shift and a low detection limit (20 nM, based on S/N=3) in detecting H2S. Importantly, practical utility of this probe for the selective detection of H2S in living cells has been successfully demonstrated.

Reaction-based colorimetric and fluorogenic signaling of hydrogen sulfide using a 7-nitro-2,1,3-benzoxadiazole-coumarin conjugate

A novel reaction-based probe for the dual signaling of hydrogen sulfide (H2S) was investigated. The selective H2S-induced cleavage of the ether linkage of the 7-nitro-2,1,3-benzoxadiazole (NBD) and 7-hydroxycoumarin conjugate resulted in a dual signaling behavior. The colorimetric and fluorogenic signaling behaviors were attributed to the H 2S-induced generation of 7-nitrobenzo-2,1,3-oxadiazole-4-thiol (NBD-SH) and 7-hydroxycoumarin, respectively. The signaling behavior was analyzed by ratiometry. The selective signaling of H2S over other common metal ions and anions was possible with a detection limit of 1.6 × 10-6 M in an aqueous DMSO solution.

A fluorogenic H2S-triggered prodrug based on thiolysis of the NBD amine

Based on thiolysis of the NBD amine, a H2S-triggered prodrug has been designed and synthesized for localized production of ciprofloxacin under micromolar H2S. Activation of the prodrug can be monitored through fluorescence in real-time. We envision that thiolysis of the NBD amine could be readily used for development of other H2S-triggered prodrugs in the future.