Citation: Wang Shiyu, Li Minghua, Xue Shanshan, Huang Yanru, He Wei. Progress in Application of Nitroxide Radicals[J]. Chemistry, ;2017, 80(11): 1002-1008. shu

Progress in Application of Nitroxide Radicals

Department of Chemistry, School of Pharmacy, Fourth Military Medical University, Xi'an 710032

Corresponding author: He Wei, weihechem@fmmu.edu.cn
Received Date: 24 March 2017
Accepted Date: 28 August 2017

Figures(5)

Nitroxide radical compounds are organic compounds containing carbon, nitrogen, oxygen, hydrogen, and spin-on-one electrons, and are used in many fields because of their special properties. In this review, the characteristics of nitroxides and their application in biology, magnetism, organic catalysis and polymerization were summarized. The development trend of nitroxide radical compounds were discussed.
- Nitroxyl radicals,
- Molecular functional materials,
- Biology activity,
- Organic catalysis
1. [1]
  (a) E Fremy. Ann. Chim. Phys., 1845, 15: 408; (b) H Zimmer, D C Lankin, S W Horgan. Chem. Rev., 1971, 71: 229~246.
2. [2]
  (a) O Piloty, B G Schwerin. Ber. Dtsch. Chem. Ges., 1901, 34(2): 1863~1870; (b) H Wieland, M Offenbächer. Ber. Dtsch. Chem. Ges., 1914, 47(2): 2111~2115; (c) O L Lebedev, S N Kazarnovsky. Tr. Khim. Khim. Tekhnol., 1959, 3: 649~653.
3. [3]
  H M Swartz, J R Booton, D C Borg. Biological applications of electron spin resonance. Wiley-Interacience New York, 1972.
4. [4]
  O H Griffith, P C Jost, L J Berliner. Spin labeling: theory and applications. Academic Press., New York, 1976.
5. [5]
6. [6]
  B K Sinha, R L Cysyk, D B Millar et al. J. Med. Chem., 1976, 19(8): 994~998.
7. [7]
  J Ilas, S Pecar, J Hockemeyer et al. J. Med. Chem., 2005, 48(6): 2108~2114.
8. [8]
  M Zhao, J L Liu, C Wang et al. J. Med. Chem., 2005, 48(13): 4285~4292.
9. [9]
  G Vendemiale, I Grattagliano, E Altomare. Int. J. Clin. Lab. Res., 1999, 29: 49~55.
10. [10]
  M S Cooke, M D Evans, M Dizdaroglu et al. FASEB J., 2003, 17: 1195~1214.
11. [11]
  C W Olanow. Ann. Neurol., 1992, 32: S2~S9.
12. [12]
  R Terranova, R Sorace, A Romeo et al. Minerva. Med., 2001, 92: 405~410.
13. [13]
  D D Bankson, M Kestin, N Rifai et al. Clin. Lab. Med., 1993, 13: 463~480.
14. [14]
  S Jaswal, H C Mehta, A K Sood et al. Clin. Chim. Acta, 2003, 338: 123~129.
15. [15]
  J C W Mak, M M Chan-Yeung. Curr. Opin. Pulm. Med., 2006, 12: 7~11.
16. [16]
  S S Sheu, D Nauduri, M W Anders. Biochim. Biophys. Acta, 2006, 1762: 256~265.
17. [17]
  R E Anderson, F L Kretzer, L M Rapp. Adv. Exp. Med. Biol., 1994, 366: 73~86.
18. [18]
  J H Osiecki, E F Ullman. J. Am. Chem. Soc., 1968, 90: 1078~1079.
19. [19]
  R F Haseloff, S Zollner, I A Kirilyuk et al. Free Radical Res., 1997, 26: 7~17.
20. [20]
  I E Blasig, K Mertsch, R F Haseloff. Neuropharmacology, 2002, 43: 1006~1014.
21. [21]
  A Samuni, C M Krishna, P Riesz et al. J. Biol. Chem., 1988, 263(34): 17921~17924.
22. [22]
  N Kocherginsky, H Swartz. Nitroxide spin labels: reactions in biology and chemistry. New York: CRC Press, 1995.
23. [23]
  R A Floyd, R D Kopke, C H Choi. Free Radical Bio. Med., 2008, 45(10): 1361~1374.
24. [24]
25. [25]
  J B Mitchell, W De Graff, D Kaufman et al. Arch. Biochem. Biophys., 1991, 289(1): 62~70.
26. [26]
27. [27]
28. [28]
29. [29]
30. [30]
31. [31]
  M C Krishna, A Russo, J B Mitchell et al. J. Biol. Chem., 1996, 271(420): 26026~26031.
32. [32]
  M C Krishna, W Degraf, O H Hankovszky et al. J. Med. Chem., 1998, 41(18): 3477~3492.
33. [33]
  G L Wen, Y Z Xiao, J W Yong et al. J. Pharm. Pharmacol., 2006, 58(7): 941~949.
34. [34]
  J B Mitchell, S Xavier, A M Deluca et al. Free Radical Biol. Med., 2003, 34(1): 93~102.
35. [35]
  R Schubert, L Erker, C Barlow et al. Hum. Mol. Genet., 2004, 13(16): 1793~1802.
36. [36]
  O Augusto, D F Trindade, E Linares et al. An. Acad. Bras. Cienc., 2008, 80(1): 179~189.
37. [37]
  C S Wilcox. Pharmacol. Ther., 2010, 126(3): 119~145.
38. [38]
  D Gelvan, P Saltman, S R Powell. PNAS, 1991, 88(11): 4680~4684.
39. [39]
  M C McDonald, K Zacharowski, J Bowes et al. Free Radical Biol. Med., 1999, 27(5-6): 493~503.
40. [40]
  S Cuzzocrea, M C McDonald, E Mazzon et al. Brain Res., 2000, 875(1-2): 96~106.
41. [41]
  M G Abou, J A Johnson, L Jin et al. J. Pharmacol. Exp. Ther., 2004, 308(1): 289~299.
42. [42]
  W Bi, J H Cai, P Xue et al. Bioorg. Med. Chem. Lett., 2008, 18: 1788~1794.
43. [43]
  A Blaise, H Lemaire, J Pilon et al. C. R. Acda. Sci. Paris, Ser. B, 1972, 274: 157~162.
44. [44]
  A Caneschi, D Gatteschi, R Sessoli. Acc. Chem. Res., 1989, 22(11): 392~398.
45. [45]
  (a) J S Miller, A J Epstein. Angew. Chem. Int. Ed., 1994, 33: 385~415; (b) D Gatteschi. Curr. Opin. Solid State Mater. Sci., 1996, 1: 192~198.
46. [46]
  M Tamura, Y Nakazawa, D Shiomi et al. Chem. Phys. Lett., 1991, 186(1-2): 401~404.
47. [47]
  Y Nakazawa, M Tamura, M Kinoshita et al. Phys. Rev. B., 1992, 46(14): 8906~8914.
48. [48]
  K Awaga, T Inabe, Y Maruyama. Chem. Phys. Lett., 1992, 190(3-4): 349~352.
49. [49]
  T Sugano, M Kurmoo, F L Pratt et al. Mol. Cryst. Liq. Cryst., 1995, 271: 107~114.
50. [50]
  T Sugawara, M M Matsushita, A Izuoka et al. J. Am. Chem. Soc., 1997, 119(19): 4369~4379.
51. [51]
  J Cirujeda, M Mas, E Molins et al. Chem. Commun., 1995, (7): 709~710.
52. [52]
  A Caneschi, F Ferraro, D Gatteschi et al. Adv. Mater., 1995, 7(5): 476~478.
53. [53]
  S Nakatsuji, M Saiga, N Haga et al. New J. Chem., 1998, 22(3): 275~280.
54. [54]
  S Nakatsuji, H Morimoto, H Anzai et al. Chem. Phys. Lett., 1998, 296(1-2): 159~166.
55. [55]
56. [56]
57. [57]
  (a) J Foricher, K Furbriner. EP: 0198351, 1986; (b) J Foricher, C Furbringer, K Pfoertner. USP: 5030739, 1991.
58. [58]
  Y Ishii, K Nakayama, M Takeno et al. J. Org. Chem., 1995, 60(13): 3934~3935.
59. [59]
  V A Golubev, E G Rozantsev, M B Neiman et al. Sci. USSR Chem. Ser., 1965, 4: 1898~1904.
60. [60]
  (a) M F Semmelhack, C R Schmid, D A Cortes et al. J. Am. Chem. Soc., 1984, 106(11): 3374~3376; (b) P L Anelli, C Biffi, F Montanari et al. J. Org. Chem., 1987, 52(12): 2559~2562.
61. [61]
  A Dijksman, A M Gonzalez, A M Payeras et al. J. Am. Chem. Soc., 2001, 123(8): 6826~6833.
62. [62]
  R Liu, X Liang, C Dong et al. J. Am. Chem. Soc., 2004, 126(13): 4112~4113.
63. [63]
  X L Wang, R H Liu, Y Jin et al. Chem. Eur. J., 2008, 14(9): 2679~2685.
64. [64]
  (a) M S Maji, T Pfeifer, A Studer. Angew. Chem. Int. Ed., 2008, 47(49): 9547~9550; (b) M S Maji, A Studer. Synthesis, 2009, (14): 2467~2470; (c) M S Maji, S Murarka, A Studer. Org. Lett., 2010, 12(17): 3878~3881.
65. [65]
  J O Denis, J S David. DEP: 2060645, 1972; D J O'sullivan, D J Stamper. USP: 3682875, 1972.
66. [66]
67. [67]
68. [68]
  J R Harbour, J R Bolton. Biochem. Bioph. Res. Co., 1975, 64(3): 803~807.
69. [69]
  G I Likhtenshtein, J Yamauchi, S Nakatsuji et al. Nitroxides: applications in chemistry biomedicine, and materials science. Wiley-VCH, Weinheim, 2008, 371.
70. [70]
  C Michaut, L Ouahab, P Bergerat et al. J. Am. Chem. Soc., 1996, 118(15): 3610~3616.
71. [71]
  E Damiani, R Castagna, L Greci. Free Radical Biol. Med., 2002, 33(1): 128~136.
72. [72]
  J L Viñas, A Sola, M Gensecà et al. Free Radical Biol. Med., 2006, 40(6): 992~1003.
73. [73]
  T H Kwon, D L Chao, K Malloy et al. J. Neurotraum., 2003, 20(4): 337~345.
74. [74]
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