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

被引:14
作者
Dueppe, Peter M. [1 ]
Talbierski, Peter M. [1 ]
Hornig, Frank S. [1 ]
Rauen, Ursula [2 ]
Korth, Hans-Gert [1 ]
Wille, Timo [2 ]
Boese, Roland [3 ]
Omlor, Thorsten [3 ]
de Groot, Herbert [2 ]
Sustmann, Reiner [1 ]
机构
[1] Univ Duisburg Essen, Inst Organ Chem, D-45141 Essen, Germany
[2] Univ Klinikum Essen, Inst Physiol Chem, D-45122 Essen, Germany
[3] Univ Duisburg Essen, Inst Anorgan Chem, D-45141 Essen, Germany
关键词
bioinorganic chemistry; cheletropic traps; fluorescence spectroscopy; nitrogen oxides; quinodimethanes; ORTHO-QUINODIMETHANE; ENDOTHELIAL-CELLS; O-QUINODIMETHANES; NO; EFFICIENT; RADICALS; RELEASE; LIVER;
D O I
10.1002/chem.201000029
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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 pyretic 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.
引用
收藏
页码:11121 / 11132
页数:12
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