Nitric Oxide Sensing through 1,2,3,4-Oxatriazole Formation from Acylhydrazide: A Kinetic Study

Abstract

A simple molecular probe displays highly selective turnon response toward NO by the unprecedented NO-induced formation of a 1,2,3,4-oxatriazole ring exhibiting no interference from various endogenous biomolecules including DHA, AA, etc. Kinetics of the reactions between NO and the probe provide a mechanistic insight into the formation of 1,2,3,4-oxatriazole which showed that, though initially 1,2,3,4-oxatriazole is formed and extractable in solid form, it exists in equilibrium with the ring opened azide form which ultimately hydrolyzed and converted to carboxylic acid and nitrate. The reaction displays second-order dependence on [NO] and first-order on [Probe]. The probe is water-soluble, cell permeable, and noncytotoxic and appropriates for live cell imaging. This constitutes the first report where there is a direct evidence of NO-induced ring closing reaction of an acyl hydrazide moiety leading to the formation of 1,2,3,4-oxatriazole.

Phenazine-Embedded Copper(II) Complex as a Fluorescent Probe for the Detection of NO and HNO with a Bioimaging Application

“…A549 cells and murine macrophages cells (Raw 264.7) were grown in Dulbecco's modified Eagle's (DMEM) medium provided with 10% FBS and 1% antibiotic at 37 °C with 5% CO 2 . 69 The cell viability of the probe [(PIP)Cu II (Cl)] in A549 and Raw 264.7 cells was analyzed with a gradual increase in concentration of the PIP−Cu 2+ ([(PIP)Cu II (Cl)]) complex, in the range 10−100 μM/mL for 24 h by an MTT assay. 33 Cell Incubation, Imaging, and Flow Cytometry Analysis.…”

Rapid Visual Detection of Amines by Pyrylium Salts for Food Spoilage Taggant

“…In past few years, much effort has been invested for developing chromogenic molecular and supramolecular sensors that can rapidly change their color in the presence of specific stimuli. , Among the different types of optical sensors, fluorescent detectors attract special attention because of rapid and very sensitive response to a diverse range of liquid or gaseous analytes by changing fluorescence intensity or wavelength. − Particularly, organic fluorophore that can selectively detect liquid or gaseous analyte have immense practical importance in the area of microfluidic medical diagnostics for health monitoring, safety sensors and many other technological applications. − ·…”

Tetrazole Azasydnone (C2N7O2H) And Its Salts: High‐Performing Zwitterionic Energetic Materials Containing A Unique Explosophore

“…Recently,s ome beautiful work by Sheremetev et al [35] has pioneered the use of this unique heterocyclic system in energetic materials.W hile published studies on the energetic properties of azasydnones are relativelyl imited compared to other heterocyclic energetic backbones [35,36,45,[37][38][39][40][41][42][43][44] they have been explored as nitric oxide donors in pharmaceuticals. [46][47][48] Furthermore, the azasydnone ring, like the tetrazole ring can form its detonation products by pushing electrons, without needing to move atoms, an importantc riteria in the development of primary explosives. [49] In this work we synthesized anazasydnone ring on the 5-position of the tetrazole ring giving tetrazoleazasydnone.…”