Theoretical and experimental studies of the spin trapping of inorganic radicals by 5,5-dimethyl-1-pyrroline N-oxide (DMPO). 3. Sulfur dioxide, sulfite, and sulfate radical anions

Journal of Physical Chemistry A

Volumn 116, Issue 26, 2012, Pages 7210-7218

  Zamora, Pedro L ^a   Villamena, Frederick A ^a  

^a THE OHIO STATE UNIVERSITY COLLEGE OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCHEMICAL PATHWAY; CONJUGATE ACID; DECOMPOSITION PATHWAY; DENSITY FUNCTIONAL THEORIES (DFT); EXPERIMENTAL STUDIES; IN-VIVO; NUCLEOPHILIC ADDITIONS; RADICAL ADDITION; SPIN POPULATION; SPIN TRAP; SPIN TRAPPING; SULFATE RADICALS; THEORETICAL VALUES; THERMODYNAMIC DATA;

ADDITION REACTIONS; DENSITY FUNCTIONAL THEORY; ELECTRON SPIN RESONANCE SPECTROSCOPY; HYDROGEN BONDS; MAGNETIC RESONANCE; PARAMAGNETISM; POPULATION STATISTICS; SULFUR; THERMOCHEMISTRY; THERMODYNAMICS;

SULFUR DIOXIDE;

5,5 DIMETHYL 1 PYRROLINE 1 OXIDE; 5,5-DIMETHYL-1-PYRROLINE-1-OXIDE; AMINE OXIDE; FREE RADICAL; SULFATE; SULFITE; SULFUR DIOXIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; ELECTRON SPIN RESONANCE; SPIN LABELING; THERMODYNAMICS;

CYCLIC N-OXIDES; ELECTRON SPIN RESONANCE SPECTROSCOPY; FREE RADICALS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; SPIN LABELS; SULFATES; SULFITES; SULFUR DIOXIDE; THERMODYNAMICS;

EID: 84863617089     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp3039169     Document Type: Article

References (63)

1. Gunnison, A. F.; Jacobsen, D. W. Crit. Rev. Toxicol. 1987, 17, 185
2. Utell, M. J.; Marrow, P. E.; Speers, D. M.; Darling, J.; Hyde, R. W. Am. Rev. Respir. Dis. 1983, 128, 444
3. Pelltier, M.; Lavastre, V.; Girard, D. Toxicol. Sci. 2002, 69, 210
4. Reist, M.; Marshall, K.; Jenner, P.; Halliwell, B. J. Neurochem. 1998, 71, 2431
5. Thomas, D.; Yolande, S.-K. Microbiol. Mol. Biol. Rev. 1997, 61, 503
6. Karakas, E.; Wilson, H. L.; Graf, T. N.; Xiang, S.; Jaramillo-Busquets, S.; Rajagopalan, K. V.; Kisker, C. J. Biol. Chem. 2005, 280, 33506
7. Brown, G. K.; Scholem, R. D.; Croll, H. B.; Wraith, J. E.; McGill, J. J. Neurology 1989, 39, 252
8. Shih, V. E.; Abroms, I. F.; Johnson, J. L.; Carney, M.; Mandell, R.; Robb, R. M.; Clotherty, J. P.; Rajagopalan, K. V. N. Engl. J. Med. 1977, 297, 1022
9. Ranguelova, K.; Chatterjee, S.; Ehrendhaft, M.; Ramirez, D. C.; Summers, F. A.; Kasiiska, M. B.; Mason, R. P. Photochem. Photobiol. 2010, 32, 563
10. Chignell, C. F.; Kalyanaraman, B.; Mason, R. P.; Sik, R. H. Photochem. Photobiol. 1980, 32, 563
11. Mottley, C.; Mason, R. P.; Chignell, C. F.; Sivarajah, K.; Eling, T. E. J. Biol. Chem. 1982, 257, 5050
12. Covello, P. S.; Thompson, J. E. Biochem. Biophys. Acta 1985, 843, 150
13. Shi, X. J. Inorg. Biochem. 1994, 56, 155
14. Alipazaga, M. V.; Moreno, R. G. M.; Linares, E.; Medeiros, M. H. G.; Coichev, N. J. Chem. Soc., Dalton. Trans. 2008, 5636
15. Niknahad, H.; O'Brien, P. J. Chem.-Biol. Interact. 2008, 174, 147
16. Neta, P.; Huie, R. E.; Ross, A. B. J. Phys. Chem. Ref. Data 1988, 17, 1027
17. Ohya-Nishiguchi, H.; Packer, L. Bioradicals Detected by ESR Spectroscopy; Birkhäuser: Berlin, Germany, 1995.
18. Ranguelova, K.; Mason, R. P. Free Radical Biol. Med. 2009, 47, 128
19. Elias, R. J.; Andersen, M. L.; Skibsted, L. H.; Waterhouse, A. L. J. Agric. Food. Chem. 2009, 57, 4359
20. Zalibera, M.; Rapta, P.; Stasko, A.; Brindzova, L.; Brezova, V. Free Radical Res. 2009, 43, 457
21. Potapenko, D. I.; Bagryanskaya, E. G.; Reznikov, V. V.; Clanton, T. L.; Khramtsov, V. V. Magn. Reson. Chem. 2003, 41, 603
22. Potapenko, D. I.; Clanton, T. L.; Bagryanskaya, E. G.; Gritsan, N. P.; Reznikov, V. A.; Khramtsov, V. V. Free Radical Biol. Med. 2003, 34, 196
23. Villamena, F. A.; Zweier, J. L. Antioxid. Redox Signaling 2004, 6, 619
24. Burgett, R. A.; Bao, X.; Villamena, F. A. J. Phys. Chem. A 2008, 112, 2447
25. Locigno, E. J.; Zweier, J. L.; Villamena, F. A. Org. Biomol. Chem. 2005, 3, 3220
26. Villamena, F. A. J. Phys. Chem. A 2010, 114, 1153
27. Villamena, F. A.; Hadad, C. M.; Zweier, J. L. J. Phys. Chem. A 2005, 109, 1662
28. Villamena, F. A.; Locigno, E. J.; Rockenbauer, A.; Hadad, C. M.; Zweier, J. L. J. Phys. Chem. A 2006, 110, 13253
29. Villamena, F. A.; Locigno, E. J.; Rockenbauer, A.; Hadad, C. M.; Zweier, J. L. J. Phys. Chem. A 2007, 111, 384
30. Villamena, F. A.; Merle, J. K.; Hadad, C. M.; Zweier, J. L. J. Phys. Chem. A 2007, 111, 9995
31. Villamena, F. A.; Xia, S.; Merle, J. K.; Lauricella, R.; Tuccio, B.; Hadad, C. M.; Zweier, J. L. J. Am. Chem. Soc. 2007, 129, 8177
32. Villamena, F. A.; Das, A.; Nash, K. M. Future Med. Chem. 2012, 4, 1171
33. Floyd, R. A.; Kopke, R. D.; Choi, C.-H.; Foster, S. B.; Doblas, S.; Towner, R. A. Free Radical Biol. Med. 2008, 45, 1361
34. Labanowski, J. W.; Andzelm, J. Density Functional Methods in Chemistry; Springer: New York, 1991.
35. Parr, R. G.; Yang, W. Density Functional Theory in Atoms and Molecules; Oxford University Press: New York, 1989.
36. Becke, A. D. Phys. Rev. 1988, 38, 3098
37. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785
38. Becke, A. D. J. Chem. Phys. 1993, 98, 1372
39. Hehre, W. J.; Radom, L.; Schleyer, P. V.; Pople, J. A. Ab Initio Molecular Orbital Theory; John Wiley & Sons: New York, 1986.
40. Tomasi, J.; Persico, M. Chem. Rev. 1994, 94, 2027
41. Cossi, M.; Barone, V.; Cammi, R.; Tomasi, J. Chem. Phys. Lett. 1996, 255, 327
42. Barone, V.; Cossi, M.; Tomasi, J. J. Chem. Phys. 1997, 107, 3210
43. Barone, V.; Cossi, M.; Tomasi, J. J. Comput. Chem. 1998, 19, 404
44. Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999
45. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, revision A.01; Gaussian, Inc.: Wallingford, CT, 2009.
46. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899
47. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502
48. Cirujeda, J.; Vidal-Gancedo, J.; Jurgens, O.; Mota, F.; Novoa, J. J.; Rovira, C.; Veciana, J. J. Am. Chem. Soc. 2000, 122, 11393
49. Pavone, M.; Cimino, P.; De Angelis, F.; Barone, V. J. Am. Chem. Soc. 2006, 128, 4338
50. Saracino, G. A. A.; Tedeschi, A.; D'Errico, G.; Improta, R.; Franco, L.; Ruzzi, M.; Corvaia, C.; Barone, V. J. Phys. Chem. A 2002, 106, 10700
51. Barone, V. In Recent Advances in Density Functional Theory, Part 1; Cong, D. P., Ed.; World Scientific Publishing Co.: Singapore, 1995; p 287.
52. Woon, D. E.; Dunning, T. H. J. Chem. Phys. 1995, 103, 4572
53. Villamena, F. A.; Merle, J. K.; Hadad, C. M.; Zweier, J. L. J. Phys. Chem. A 2005, 109, 6089
54. National Institute of Environmental Health Sciences. http://www.niehs. nih.gov/research/resources/software/tools/index.cfm.
55. Percec, V.; Popov, A. V.; Ramirez-Castillo, E.; Coelho, J. F. J.; Hinojosa-Falcon, L. A. J. Polym. Sci. 2004, 42, 6267
56. Ozawa, T.; Hanaki, A. Biochem. Biophys. Res. Commun. 1987, 142, 410
57. Schomaker, V.; Stevenson, D. P. J. Am. Chem. Soc. 1940, 62, 1270
58. Guthrie, J. P. Can. J. Chem. 1978, 56, 2342
59. Guthrie, J. P. J. Am. Chem. Soc. 1980, 102, 5177
60. Silver, B. L.; Luz, Z.; Peller, S.; Reuben, J. J. Phys. Chem. 1966, 70, 1434
61. Mottley, C.; Connor, H. D.; Mason, R. P. Biochem. Biophys. Res. Commun. 1986, 141, 622
62. Ranguelova, K.; Mason, R. P. Magn. Reson. Chem. 2011, 49, 152
63. Davies, M. J.; Gilbert, B. C.; Stell, J. K.; Witwood, A. C. J. Chem. Soc., Perkin Trans. 1992, 2, 333