A Novel Method for Detecting Nitric Oxide (NO) by Formation of Fluorescent Products Based on Cheletropic Spin Traps

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 13-14, 1997, Pages 1501-1503

  Bätz, Michael ^a   Korth, Hans Gert ^a   Sustmann, Reiner ^a  

^a UNIVERSITY OF DUISBURG ESSEN   (Germany)

Author keywords

EPR spectroscopy; Fluorescence spectroscopy; Nitric oxides; Quinodimethanes; Radicals

Indexed keywords

EID: 0030841495     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199715011     Document Type: Article

References (18)

1. a) The Biology of Nitric Oxide, Part 5 (Eds.: S. Moncada, J. Stamler, S. Gross, E. A. Higgs). Portland Press, London, 1996, and preceeding volumes;
2. b) Methods in Nitric Oxide Research (Eds.: M. Feelisch, J. S. Stamler), Wiley, Chichester, 1996.
3. a) T. Paul, M. A. Hassan, H.-G. Korth, R. Sustmann, D. V. Avila, J. Org. Chem. 1996, 61, 6835-6848, and references therein;
4. b) H.-G. Korth, R. Sustmann, Aspects of Nitric Oxide Chemistry in Free Radicals in Biology and Environment (Ed.: F. Minisci), Klüwer, Dordrecht, 1996, p. 63-78.
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6. b) I. Ioannidis, M. Bätz, H.-G. Korth, R. Sustmann, H. de Groot, ibid. 1997, submitted.
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8. b) R. I. Zhdanov, I. B. Kadenatsi, L. E. Kholodov in Bioactive Spin Labels (Ed.: R. I. Zhdanov), Springer, Berlin, 1992, p. 527, and references therein.
9. This methodology is conceptually different from other applications of fluorescence spectroscopy for the detection of free radicals reported so far, see for example S. Pou, A. Bhan, U. S. Bhadti, S. Y. Wu, R. S. Hosmane, G. M. Rosen, FASEB J. 1995, 9, 1085-1090.
10. M. Bätz, Ph.D. thesis, Universität Essen, 1997.
11. W. Dilthey, J. Prakt. Chem. 1935, 143, 189-210.
12. 13C NMR, IR, UV/Vis), mass spectrometry, and elemental analysis.
13. a protons, the nitrogen atom of the imide group, and the N-methyl group for 2b.
14. A. R. Forrester in Landolt-Börnstein, New Series. Magnetic Properties of Free Radicals, Vol. 9, Part c1 (Eds.: H. Fischer, K. H. Hellwege), Springer, Berlin, 1979, p. 524-538.
15. G. G. Guibault, Practical Fluorescence, Marcel Dekker, New York, 1973, p. 84.
16. Preliminary product studies show that, depending on the amount of NO, several (>6) nitroso- and nitro-substituted products are formed from the nitroxides, in part by ring-opening reactions, in addition to the corresponding hydroxylamine derivatives. A detailed product study will be reported.
17. S. A. Green, D. J. Simpson, G. Zhou, P. S. Ho, N. V. Blough, J. Am. Chem. Soc. 1990, 112, 7337-7346.
18. (2)-1-{N-[3-Aminopropyl]-N-[4-{3-aminopropylammonio)butyl]amino}-diazen- 1-ium-1,2-diolate: J. A. Hrabie, J. R. Klose, D. A. Wink, L. K. Keefer, J. Org. Chem. 1993, 58, 1472-1476.