Pyrene-based fluorescent nitric oxide cheletropic traps (FNOCTs) for the detection of nitric oxide in cell cultures and tissues.
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.
Düppe
Peter M
PM
Institut für Organische Chemie, Universität Duisburg-Essen, Campus Essen, Universitätsstr. 5, 45141 Essen, Germany.
Talbierski
Peter M
PM
Hornig
Frank S
FS
Rauen
Ursula
U
Korth
Hans-Gert
HG
Wille
Timo
T
Boese
Roland
R
Omlor
Thorsten
T
de Groot
Herbert
H
Sustmann
Reiner
R
D000818:Animals; D001011:Aorta / Q000737:chemistry* / Q000378:metabolism; D018929:Cell Culture Techniques; D018360:Crystallography, X-Ray; D004727:Endothelium / Q000737:chemistry* / Q000378:metabolism; D016676:Macrophages, Alveolar / Q000737:chemistry* / Q000378:metabolism; D015394:Molecular Structure; D009569:Nitric Oxide / Q000032:analysis* / Q000737:chemistry*; D011721:Pyrenes / Q000737:chemistry*; D051381:Rats; D017208:Rats, Wistar; D012680:Sensitivity and Specificity; D013050:Spectrometry, Fluorescence / Q000379:methods
D011721:Pyrenes; D009569:Nitric Oxide