Pyrene-based fluorescent nitric oxide cheletropic traps (FNOCTs) for the detection of nitric oxide in cell cultures and tissues

Chemistry - A European Journal

Volumn 16, Issue 36, 2010, Pages 11121-11132

  Düppe, Peter M ^a   Talbierski, Peter M ^a   Hornig, Frank S ^a   Rauen, Ursula ^b   Korth, Hans Gert ^a   Wille, Timo ^b   Boese, Roland ^a   Omlor, Thorsten ^a   De Groot, Herbert ^b   Sustmann, Reiner ^a  

^a UNIVERSITY OF DUISBURG ESSEN   (Germany)

^b UNIVERSITY HOSPITAL ESSEN   (Germany)

Author keywords

Bioinorganic chemistry; Cheletropic traps; Fluorescence spectroscopy; Nitrogen oxides; Quinodimethanes

Indexed keywords

ALVEOLAR MACROPHAGES; AQUEOUS SOLUTIONS; BIOINORGANIC CHEMISTRY; BIOLOGICAL APPLICATIONS; CHELETROPIC TRAPS; DIAZENIUMDIOLATES; NANOMOLAR RANGE; PORCINE AORTA; QUINODIMETHANES; SPECTROSCOPIC CHARACTERIZATION; TRAPPING CAPABILITY;

BIOCHEMISTRY; CELL CULTURE; FLUORESCENCE SPECTROSCOPY; NITRIC OXIDE; NITROGEN OXIDES; SOLUTIONS;

FLUORESCENCE;

NITRIC OXIDE; PYRENE DERIVATIVE;

ANIMAL; AORTA; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CULTURE TECHNIQUE; ENDOTHELIUM; LUNG ALVEOLUS MACROPHAGE; METABOLISM; METHODOLOGY; RAT; SENSITIVITY AND SPECIFICITY; SPECTROFLUOROMETRY; WISTAR RAT; X RAY CRYSTALLOGRAPHY;

ANIMALS; AORTA; CELL CULTURE TECHNIQUES; CRYSTALLOGRAPHY, X-RAY; ENDOTHELIUM; MACROPHAGES, ALVEOLAR; MOLECULAR STRUCTURE; NITRIC OXIDE; PYRENES; RATS; RATS, WISTAR; SENSITIVITY AND SPECIFICITY; SPECTROMETRY, FLUORESCENCE;

EID: 77956950704     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201000029     Document Type: Article

References (67)

1. a.)Nitric Oxide (Eds.: B. Tota, B. Trimmer), Elsevier, Amsterdam, 2007;
2. b) Pathophysiology and Clinical Applications of Nitric Oxide (Ed.: G. M. Rubanyi), Harwood Academic Publishers, Amsterdam, 1999;
3. c) S. Lamas, E. Cardenas, Nitric Oxide, Cell Signaling, and Gene Expression, CRC Press, Boca Raton, 2006;
4. d) A. R. Butler, R. Nicholson, Life, Death and Nitric Oxide, RSC, Cambridge, 2003;
5. e) Nitric Oxide: Biology and Pathobiology (Ed.: L. J. Ignarro), Academic Press, San Diego, 2000;
6. f) Nitric Oxide. Principles and Actions (Ed.: J. Lancaster, Jr.), Academic Press, San Diego, 1996.
7. a) R. F. Furchgott, Angew. Chem. 1999, 111, 1990-2000;
8. Angew. Chem. Int. Ed. 1999, 38, 1870-1880;
9. b) L. J. Ignarro, Angew. Chem. 1999, 111, 2002-2013;
10. Angew. Chem. Int. Ed. 1999, 38, 1882-1892;
11. c) F. Murad, Angew. Chem. 1999, 111, 1976-1989;
12. Angew. Chem. Int. Ed. 1999, 38, 1856-1868.
13. a) Special issue on: "Nitric Oxide, Part A: Sources and Detection of NO; NO Synthase": Methods Enzymol. 1996, 268;
14. b) Special issue on: "Nitric Oxide, Part B: Physiological and Pathological Processes": Methods Enzymol. 1996, 269;
15. Special issue on: "Nitric Oxide, Part C: Biological and Antioxidant Activities": Methods Enzymol 1999, 301;
16. Special issue on: "Nitric Oxide, Part D: Oxide Detection, Mitochondria and Cell Functions, and Peroxynitrite Reactions": Methods Enzymol. 2002, 359;
17. e) Special issue on: "Nitric Oxide, Part E": Methods Enzymol. 2005, 396;
18. f) Special issue on: "Nitric Oxide, Part F": Methods Enzymol. 2008, 440;
19. g) Special issue on: "Nitric Oxide, Part G: Oxidative and Nitrosative Stress in Redox Regulation of Cell Signaling": Methods Enzymol 2008, 441.
20. a)Biology of Nitric Oxide (Ed.: S. Moneada), Portland Press, London, 2000;
21. b)Nitric Oxide Protocols (Ed.: M. A. Titheradge), Humana Press, Totowa, 1998;
22. c) Nitric Oxide Protocols (Ed.: A. Hassid), Humana Press, Totowa, 2004;
23. d) Methods in Nitric Oxide Research (Eds.: M. Feelisch, J. S. Stamler), Wiley, New York, 1996.
24. a) C. W. G. Fishwick, D. W. Jones in The Chemistry of Quinoid Compounds, Vol.2 (Eds.: S. Patai, Z. Rappoport), Wiley, New York, 1988, pp. 403-453;
25. b)N. Martin, C. Seoane, M. Hanack, Org. Prep. Proced. 1991, 23, 237-272;
26. J. L. Segura, N. Martin, Chem. Rev. 1999, 99, 3199-3246.
27. H. G. Korth, K. U. Ingold, R. Sustmann, H. De Groot, H. Sies, Angew. Chem. 1992, 104, 915-917;
28. Angew. Chem. Int. Ed. Engl. 1992, 31, 891-893.
29. H.-G. Korth, R. Sustmann, P. Lommes, T. Paul, A. Ernst, H. de Groot, L. Hughes, K. U. Ingold, J. Am. Chem. Soc. 1994, 116, 2767-2777.
30. T. Paul, M. A. Hassan, H.-G. Korth, R. Sustmann, D. V. Avila, J. Org. Chem. 1996, 61, 6835-6848.
31. a) T. Paul, R. Boese, I. Steller, H. Bandmann, G. Gescheidt, H.-G. Korth, R. Sustmann, Eur. J. Org. Chem. 1999, 551-563;
32. -1 endothermic: W. R. Roth, B. P. Scholz, Chem. Ber. 1981, 114, 3741-3750;
33. W. R. Roth, V. Rekowski, S. Borner, M. Quast, Liebigs Ann. Chem. 1996, 409-430.
34. D. W. Jones, A. Pomfret, J. Chem. Soc. Perkin Trans. 1 1991, 263-267.
35. I, Ioannidis, M, Bätz, T. Paul, H.-G. Korth, R. Sustmann, H. de Groot, Biochem. J. 1996, 318, 789-795.
36. M. Bätz, H.-G. Korth, R. Sustmann, Angew. Chem. 1997, 109, 1555-1557;
37. Angw. Chem. Int. Ed. Engl. 1997, 36, 1501-1503.
38. S. A. Green, D. J. Simpson, G. Zhou, P. S. Ho, N. V. Blough, J. Am. Chem. Soc. 1990, 112, 7337-7346.
39. P. Meineke, U. Rauen, H. de Groot, H.-G. Korth, R. Sustmann, Chem. Eur. J. 1999, 5, 1738-1747.
40. P. Meineke, U. Rauen, H. de Groot, H.-G. Korth, R. Sustmann, Biol. Chem. 2000, 381, 575-582.
41. F. S. Hornig, H.-G. Korth, U. Rauen, H. de Groot, R. Sustmann, Helv. Chim. Acta 2006, 89, 2281-2296.
42. F. S. Hornig, Dissertation, Universität Duisburg-Essen (Germany), 2007.
43. J. Hu, D. Zhang, F. W. Harris, J. Org. Chem. 2005, 70, 707-708.
44. D. W. Jones, J. Chem. Soc. Perkin Trans. 1 1977, 980-987.
45. A. Mohr, P. Talbiersky, H.-G. Korth, R. Sustmann, R. Boese, B. Bläser, H. Rehage, J. Phys. Chem. B 2007, 111, 12985-12992.
46. Only one other isomer (10-20%) of 13a-c could be detected in the NMR spectra of the raw reaction products. According to the chemical shifts of the methylene bridge protons (δ = 1.7-1.8 and 0.9-1.0 ppm), these minor isomers were attributed to the syn-(exo-exo) diastereomer (see the Supporting Information, Scheme S1), by comparison with literature data on decahydro-1,4-exo-endo-5,8-dimethanonaphthalen-9-one (1.74 and 0.94 ppm) and related compounds: T. Svensson, S. Winstein, J Am. Chem. Soc. 1972, 94, 2336-2347. No attempts were made to isolate these isomers in the pure form.
47. We use notations like "exo-endo" etc. to indicate Diels-Alder addition to the exo side of the norbomene in the endo orientation of the diene. The additional syn-anti notation refers to the relative orientation of the two bridges.
48. Only two X-ray structures of o-quinodimethanes have been reported so far: in the monocyclic 7,7,8,8-tetraaryl-o-qui.nodimethane reported by .Iwashita et al. (S. Iwashita, E. Ohta, H. Higuchi, H. Kawai, K. Fujiwara, K. Ono, M. Takenaka, T. Suzuki, Chem. Commun. 2004, 2076-2077) the conjugated o-quinoid system is strongly distorted due to the steric interaction of the four phenyl groups. Very recently, Ghereg et al.
49. (D. Ghereg, S. E.-C. El Kettani, M. Lazraq, H. Ranaivonjatovo, W.W. Schoeller, J. Escudie, H. Gornitzka, Chem. Commun. 2009, 4821-4823) reported on a planar o-quinodimethane stabilized by germyloxyl rings at the terminal positions.
50. R. Allmann, Z. Kristallogr. Kristallgeom. Kristatlphys. Kristallchem. 1970, 132, 129-151.
51. CCDC-757257 (8 b) and 757258 (13 b) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.
52. I. Morishima, K. Yoshikawa, K. Bekki, M. Kohne, K. Arita, J. Am. Chem. Soc. 1973, 95, 5815-5817.
53. -1; see: L. Horný, F. Mariotti, M. Quack, Chimia 2008, 62, 256-259;
54. I. Komaromi, J. M. J. Tronchei, J. Phys. Chem. 1995, 99, 10213-10220.
55. J. A. Hrabie, J. R. Klose, D. A. Wink, L. K, Keefer, J. Org. Chem. 1993, 55, 1472-1476.
56. L. K. Keefer, R. W. Nims, K. M. Davies, D. A. Wink in Methods in Enzymology, Vol. 268 (Ed. : L. Packer), Academic Press, San Diego, 1996, pp. 281-293.
57. V. Stenert, Dissertation, Universität Essen (Germany), 2003.
58. a) D. L. Mooradian, T. C. Hutsell, L. K. Keefer, J. Cardiovasc. Pharmacol 1995, 25, 674-678;
59. b) K. M. Davies, D. A. Wink, J. E. Saavedra, L. K. Keefer, J. Am. Chem. Soc. 2001, 123, 5473-5481.
60. Because the decomposition, of N-diazeniumdiolates is a proton-catalyzed process that can be enhanced by incorporation, in micelles of anionic surfactants like SDS (see: A. Mohr, T. Pozo Vila, H.-G. Korth, H. Rehage, R. Sustmann, ChemPhysChem 2008, 9, 2397-2405), the lower rate constant for MAHMA/NO decomposition in the presence of the nonionic surfactant Plutonic F127 suggests a slightly diminished local proton concentration in the vicinity of the NONOate group of the NO donor by association with the surfactant. This phenomenon is currently under investigation. Note that the applied concentrations of Pluronic and SDS are above the cmc values of these surfactants,
61. see: P. Alexandridis, IF. Holzwarth, T. A. Hatten, Macromolecules 1994, 27, 2414-2425 (Pluronic F127) and ref. [20] (SDS).
62. a) WinSim, D. R. Duling, Laboratory of Molecular Biophysics, Research Triangle Park, North. Carolina, 1994;
63. b) D. R. Duling, J. Magn. Reson. Ser. B 1994, 104, 105-110.
64. Gaussian 03, Revision E.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, J. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B, B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc., Wallingford CT, 2004.
65. J.-F. Wang, P. Komarov, H. de Groot, Arch. Biochem. Biophys. 1993, 304, 189-196.
66. U. Rauen, B. Polzar, H. Stephan, H. G. Mannherz, H. de Groot, FASEB J. 1999, 13, 155-168.
67. U. Rauen, M. Hanßen, W. Lauchart, H. D. Becker, H. de Groot, Transplantation 1993, 55, 469-473.