Pyrene‐Based Fluorescent Nitric Oxide Cheletropic Traps (FNOCTs) for the Detection of Nitric Oxide in Cell Cultures and Tissues

Abstract

The synthesis and the structural and spectroscopic characterization of nonfluorescent, pyrene-based cyclic o-quinodimethanes are reported. These compounds react efficiently with nitric oxide (NO) in a formal cheletropic manner, by which the fluorescent aromatic pyrene system is regenerated. The NO trapping capabilities and kinetics of the fluorescent nitric oxide cheletropic traps (FNOCTs) are assessed in THF and buffered aqueous solution by ESR, UV/Vis, and fluorescence spectroscopy, by employing NO solutions and NO released from N-diazeniumdiolates (NONOates). Prototypal biological applications include the quantitation of NO production from cultured rat alveolar macrophages and the endothelium of porcine aorta, which demonstrate a sensitivity for NO detection in the nanomolar range.

Recommendations on terminology and experimental best practice associated with plant nitric oxide research

“…As well as DAF‐based probes, there are other fluorescent dyes available for RNS measurements, such as the copper(II) fluorescein (CuFL) complex (Lim et al ., ), the diaminorhodamine‐4M probes (DAR‐4M, Kojima et al ., ), or the Pyrene‐Based Fluorescent Nitric Oxide Cheletropic Traps (FNOCTs, Düppe et al ., ). CuFL complex has the advantage of reacting directly with NO itself rather than a derivative RNS and is an interesting alternative to that of DAF.…”

Nitric Oxide Turn-on Fluorescent Probe Based on Deamination of Aromatic Primary Monoamines

“…In view of its sensitivity, selectivity, spatiotemporal resolution, and experimental feasibility, fluorimetry, which exploits fluorescent probes to monitor analytes of interest under a fluorescence microscope, has been regarded as a most promising method to detect endogenous NO. There have been a number of small-molecule organic or inorganic fluorescent NO sensors reported to date . A two-component system comprised of an NO-reactive moiety coupling to an organic fluorophore has been widely investigated to develop NO-responsive organic molecule based sensors.…”