Influence of Conformation on the EPR Spectrum of 5,5-Dimethyl-1-hydroperoxy-1-pyrrolidinyloxyl: A Spin Trapped Adduct of Superoxide

Journal of Organic Chemistry

Volumn 69, Issue 4, 2004, Pages 1321-1330

  Rosen, Gerald M ^a,b,c,d   Beselman, Aleksandra ^a   Tsai, Pei ^a   Pou, Sovitj ^b   Mailer, Colin ^c,d   Ichikawa, Kazuhiro ^c,d,f   Robinson, Bruce H ^e   Nielsen, Robert ^e   Halpern, Howard J ^c,d   MacKerell Jr , Alexander D ^a  

^a UNIVERSITY OF MARYLAND SCHOOL OF PHARMACY   (United States)

^b UNIVERSITY OF MARYLAND BIOTECHNOLOGY INSTITUTE   (United States)

^c UNIVERSITY OF CHICAGO   (United States)

^d UNIVERSITY OF MARYLAND   (United States)

^e UNIVERSITY OF WASHINGTON   (United States)

^f KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRON SPIN RESONANCE SPECTROSCOPY; FREE RADICALS; HYDROGEN; NITROGEN COMPOUNDS;

HYPERFINE SPLITTING; SPIN TRAPPING;

CONFORMATIONS;

5,5 DIMETHYL 1 HYDROPEROXY 1 PYRROLIDINYLOXYL; CARBON; NITRONE; NITROSO DERIVATIVE; PYRROLIDINE DERIVATIVE; SUPEROXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CONFORMATION; ELECTRON SPIN RESONANCE; MOLECULAR MODEL; SPIN TRAPPING; TECHNIQUE;

ELECTRON SPIN RESONANCE SPECTROSCOPY; PYRROLIDINES; SPIN LABELS; SUPEROXIDES;

EID: 10744229627     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0354894     Document Type: Article

References (55)

1. Gerschman, R.; Gilbert, D. L.; Nye, S. W.; Dwyer, P.; Fenn, W. O. Science 1954, 119, 623-626.
2. McCord, J. M.; Fridovich, I. J. Biol. Chem. 1969, 244, 6049-6055.
3. (a) Carlioz, A.; Touati, D. EMBO J. 1986, 5, 623-630.
4. (b) Natvig, D. O.; Imlay, K.; Touati, D.; Hallewell, R. A. J. Biol. Chem. 1987, 262, 14697-1701.
5. (c) Storz, G.; Christman, M. F.; Sies, H.; Ames, B. N. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 8917-8921.
6. (d) Nakayama, K. J. Bacteriol. 1992, 174, 4928-4934.
7. (e) Nakayama, K. J. Bacteriol. 1994, 176, 1939-1943.
8. (f) Longo, V. D.; Gralla, E. B.; Valetine, J. S. J. Biol. Chem. 1996, 271, 12275-12280.
9. (a) Babior, B. M.; Kipnes, R. S.; Curnutte, J. T. J. Clin. Invest. 1973, 52, 741-744.
10. (b) Malech, H. L.; Nauseef, W. M. Semin. Hematol. 1997, 34, 279-290.
11. (a) Finkel, T. J. Leukocyte Biol. 1999, 65, 33-340.
12. (b) Wolin, M. S. Arterioscler. Thromb. Vasc. Biol. 2000, 20, 1430-1442.
13. (c) Droge, W. Physiol. Rev. 2002, 82, 47-95.
14. Iwamura, M.; Inamoto, N. Bull. Chem. Soc. Jpn. 1967, 40, 703.
15. (a) Janzen, E. G.; Blackburn, B. J. J. Am. Chem. Soc. 1968, 90, 5909-5910.
16. (b) Janzen, E. G.; Blackburn, B. J. J. Am. Chem Soc. 1969, 91, 4481-4490.
17. (a) Janzen, E. G. Acc. Chem. Res. 1971, 4, 31-40.
18. (b) Janzen, E. G. In Free Radicals in Biology; Pryor, W. A., Ed.; Academic Press: New York, 1980; Vol. 4, pp 116-154.
19. (c) Finkelstein, E.; Rosen, G. M.; Rauckman, E. J. Arch. Biochem. Biophys. 1980, 200, 1-16.
20. (a) Janzen, E. G.; Evans, C. A.; Liu, J. I.-P. J. Magn. Reson. 1973, 9, 513-516.
21. (b) Janzen, E. G.; Liu, J. I.-P. J. Magn. Reson. 1973, 9, 510-512.
22. (c) Engström M.; Vaara, J.; Schimmellpfennig, B.; Agren, H. J. Phys. Chem. B. 2002, 106, 12354-12360.
23. (a) Buettner, G. R. Free Radicals Biol. Med. 1987, 3, 259-303.
24. (b) Anson, S. W. L.; deHaas, A. H.; Buettner, G. R.; Chignell, C. F. A Database for Spin. Trapping Implemented on the IBM PC; Laboratory of Molecular Biophysics, National Institute of Environmental Health Sciences, 1989.
25. (a) Britigan, B. E.; Rosen, G. M.; Chai, Y.; Cohen, M. S. J. Biol. Chem. 1986, 261, 4426-4431.
26. (b) Pou, S.; Cohen, M. S.; Britigan, B. E.; Rosen, G. M. J. Biol. Chem. 1989, 264, 12299-12302.
27. (c) Ramos, C. L.; Pou, S.; Britigan, B. E.; Cohen, M. S.; Rosen, G. M. J. Biol. Chem. 1992, 267, 8307-8312.
28. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; John Wiley & Sons: New York, 1986.
29. Harbour, J. R.; Chow, V.; Bolton, J. R. Can. J. Chem. 1974, 52, 3549-3553.
30. (a) Finkelstein, E.; Rosen, G. M.; Rauckman, E. J. Mol. Pharmacol. 1979, 16, 676-685.
31. (b) Kalyanaraman, B.; Perez-Reyes, E.; Mason, R. P. Biochem. Biophys. Acta 1980, 630, 119-130.
32. (c) Mottley, C.; Connor, H. D.; Mason, R. P. Biochem. Biophys. Res. Commun. 1986, 141, 622-628.
33. (a) Rosen, G. M.; Turner, J. M., III J. Med. Chem. 1988, 31, 428-432.
34. (b) Buettner, G. R.; Britigan, B. E. Free Radicals Biol. Med. 1990, 8, 57-60.
35. Kotake, Y.; Kuwata, K.; Janzen, E. G. J. Phys. Chem. 1979, 83, 3024-3029.
36. Kong, S.; Evanseck, J. D. J. Am. Chem. Soc. 2000, 122, 10418-10427.
37. (a) Dalhgren, G., Jr.; Long, F. A. J. Am. Chem. Soc. 1960, 82, 1303-1308.
38. (b) Creswell, C. J.; Allred, A. L. J. Am. Chem. Soc. 1962, 84, 3966-3967.
39. Halpern, H. J.; Pou, S.; Peric, M.; Yu, C.; Barth, E.; Rosen, G. M. J. Am. Chem. Soc. 1993, 115, 218-223.
40. (a) McQuarrie, D. A. Statistical Mechanics; Harper & Row: New York, 1976,
41. (b) Yang, B.; Wright, J.; Eldefrawi, M. E.; Pou, S.; MacKerell, A. D., Jr. J. Am. Chem, Soc. 1994, 116, 8722-8732.
42. (a) Robinson, B. H.; Mailer, C.; Reese, A. W. J. Magn. Reson. 1999, 138, 199-200.
43. (b) Robinson, B. H.; Mailer, C.; Reese, A. W. J. Magn. Reson. 1999, 138, 210-219.
44. (c) Mailer, C.; Robinson, B. H.; Williams, B. B.; Halpern, H. J. Magn. Reson. Med. 2003, 49, 1175-1180.
45. Tsai, P.; Ichikawa, K.; Mailer, C.; Pou, S.; Halpern, H. J.; Robinson, B. H.; Nielsen, R.; Rosen, G. M. J. Org. Chem. 2003, 60, 7811-7817.
46. Frejaville, C.; Karoui, H.; Tuccio, B.; Le Moigne, F.; Culcasi, M.; Pietri, S.; Lauricella, R.; Tordo, P. J. Med. Chem. 1995, 38, 258-265.
47. Owenius, R.; Engström, M.; Lindgren, M.; Huber, M. J. Phys. Chem. A 2001, 105, 10967-10977.
48. Steinhoff, H. J.; Savitsky, A.; Wegener, C.; Pfeiffer, M.; Plato, M.; Möbius, K. Biochim. Biophys. Acta 2000, 1457, 253-262.
49. Marsh, D. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 7777-7782.
50. Bales, B. L.; Blum, R. A.; Mareno, D.; Peric, M.; Halpern, H. J. J. Magn. Reson. 1992, 98, 299-307.
51. Bales, B. L.; Peric, M.; Lamy-Freund, M. T. J. Magn. Reson. 1998, 132, 279-286.
52. Bonnett, R.; Brown, R. F. C.; Clark, V. M.; Sutherland, I. O.; Todd, A. J. Chem. Soc. 1959, 2094-2102.
53. Gutteridge, J. M. C. FEB Lett. 1987, 214, 362-364.
54. Kuthan, H.; Ullrich, V.; Estabrook, R. W. Biochem. J. 1982, 203, 551-558.
55. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J. ; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Head-Gordon, M. ; Gonzalez, C.; Pople, J. A. Gaussian 94, C.3 ed.; Gaussian, Inc.: Pittsburgh, PA, 1996.