Imidazolium salts: A mild reducing and antioxidative reagent

Journal of the American Chemical Society

Volumn 130, Issue 38, 2008, Pages 12586-12587

  Zhao, Lan ^a   Zhang, Chunyan ^a   Zhuo, Lang ^a   Zhang, Yugen ^a   Ying, Jackie Y ^a  

^a INSTITUTE OF BIOENGINEERING AND NANOTECHNOLOGY   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIBENZYLIMIDAZOLIUM BROMIDE; ACETYLCYSTEINE; CATALASE; EPIGALLOCATECHIN GALLATE; GLUTATHIONE PEROXIDASE; GOLD; IMIDAZOLE DERIVATIVE; REAGENT; SOLVENT; SUPEROXIDE DISMUTASE; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; CELL FREE SYSTEM; DRUG EFFICACY; ELECTRON TRANSPORT; HUMAN; HUMAN CELL; IC 50; LIVER FIBROSIS; MOISTURE; MOLECULAR STABILITY; OXIDATION REDUCTION REACTION; OXIDATIVE STRESS; REACTION ANALYSIS; TRANSMISSION ELECTRON MICROSCOPY;

ACETYLCYSTEINE; ANIMALS; ANTIOXIDANTS; CATECHIN; DOSE-RESPONSE RELATIONSHIP, DRUG; GOLD; HEPATIC STELLATE CELLS; IMIDAZOLINES; METAL NANOPARTICLES; OXIDATIVE STRESS; RATS; REACTIVE OXYGEN SPECIES; REDUCING AGENTS;

EID: 52449127167     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8037883     Document Type: Article

References (46)

1. (a) Welton, T. Chem. Rev. 1999, 99, 2071.
2. (b) Visser, A. E.; Swatloski, R. P.; Rogers, R. D. Green Chem. 2002, 2, 1.
3. For recent reviews on NHC organo-catalysis, see: (a) Marion, N.; Diez-Gonzalez, S.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 2988.
4. (b) N-Heterocyclic Carbenes in Synthesis; Nolan, S. P., Ed.; Wiley-VCH: Weinheim, Germany, 2006.
5. For recent reviews on NHC-ligated organometallic catalysis, see: (a) Crudden, C. M.; Allen, D. P. Coord. Chem. Rev. 2004, 248, 2247.
6. (b) Peris, E.; Crabtree, R. H. Coord. Chem. Rev. 2004, 248, 2247.
7. (c) Cesar, V.; Bellemin-Laponnaz, S.; Gade, L. H. Chem. Soc. Rev. 2004, 33, 619.
8. (d) Hahn, F. E. Angew. Chem., Int. Ed. 2006, 45, 1384.
9. (e) Diez-Gonzalez, S.; Nolan, S. P. Coord. Chem. Rev. 2007, 251, 874.
10. Benzoin reaction can be run in aqueous medium: Iwamoto, K.-I.; Hayama, M.; Hashimoto, N.; Kimura, H.; Suzuki, Y.; Sato, M. Tetrahedron Lett. 2006, 47, 7175.
11. (a) Modern Nutrition in Health and Disease, 9th ed.; Shils, M.; Olson, J. A.; Shike, M.; Ross, A. C., Eds.; Williams & Wilkins: Baltimore, MD, 1999; p 381-389.
12. (b) Brody, T. Nutritional Biochemistry, 2nd ed.; Academic Press: San Diego, CA, 1999.
13. (a) Rollet, A.-L.; Porten, P.; Vaultier, M.; Billard, I.; Deschamps, M.; Bessada, C.; Jouvensal, L. J. Phys. Chem. B 2007, 111, 11888.
14. (b) Mele, A.; Tran, C. D.; De Paoli Lacerda, S. H. Angew. Chem., Int. Ed. 2003, 42, 4363.
15. Amyes, T. L.; Diver, S. T.; Richard, J. P.; Rivas, F. M.; Toth, K. J. Am. Chem. Soc. 2004, 126, 4366.
16. (a) Schoenebeck, F.; Murphy, J. A.; Zhou, S.-z.; Uenoyama, Y.; Miclo, Y.; Tuttle, T. J. Am. Chem. Soc. 2007, 129, 13368.
17. (b) Ames, J. R.; Houghtaling, M. A.; Terrian, D. L.; Mitchell, T. A. Can. J. Chem. 1997, 75, 28.
18. (c) Thummel, R. P.; Goulle, V.; Chen, B. J. Org. Chem. 1989, 54, 3057.
19. (d) Taton, T. A.; Chen, P. Angew. Chem., Int. Ed. 1996, 35, 1011.
20. (e) Goldwhite, H.; Kaminski, J.; Millhauser, G.; Ortiz, J.; Vargas, M.; Vertal, L.; Lappert, M. F.; Smith, S. J. J. Organomet. Chem. 1986, 310, 21.
21. (f) Cetinkaya, B.; Cetinkaya, E.; Chamizo, J. A.; Hitchcock, P. B.; Jasim, H. A.; Kucukbay, H.; Lappert, M. F. J. Chem. Soc., Perkin Trans. 1 1998, 2047.
22. (g) Mery, D.; Aranzaes, J. R.; Astruc, D. J. Am. Chem. Soc. 2006, 128, 5602.
23. See Supporting Information for details.
24. Zheng, N.; Fan, J.; Stucky, G. D. J. Am. Chem. Soc. 2006, 128, 6550.
25. (a) Daniel, M. C.; Astruc, D. Chem. Rev. 2004, 104, 293.
26. (b) Astruc, D.; Lu, F.; Aranzaes, J. R. Angew. Chem., Int. Ed. 2005, 44, 7852.
27. (a) Brust, M.; Walker, M.; Bethell, D.; Schiffrin, D. J.; Whyman, R. Chem. Commun. 1994, 801.
28. (b) Schmid, G. Nanoparticles: From Theory to Application; Wiley-VCH: Weinheim, Germany, 2004.
29. (c) Stoeva, S.; Klabunde, K. J.; Sorensen, C. M.; Dragieva, I. J. Am. Chem. Soc. 2002, 124, 2305.
30. (d) Jana, N. R.; Peng, X. G. J. Am. Chem. Soc. 2003, 125, 14280.
31. (e) Tsunoyama, H.; Negishi, Y.; Tsukuda, T. J. Am. Chem. Soc. 2006, 128, 6036.
32. (f) Templeton, A. C.; Wuelfing, M. P.; Murray, R. W. Acc. Chem. Res. 2000, 33, 27.
33. (g) Schaaff, T. G.; Whetten, R. L. J. Phys. Chem. B 2000, 104, 2630.
34. (a) Tumanski, B.; Sheberla, D.; Molev, G.; Apeloig, Y. Angew. Chem., Int. Ed. 2007, 46, 7408.
35. (b) Mckenzie, I.; Brodovitch, J.-C.; Percival, P. W.; Ramnial, T.; Clyburne, J. A. C. J. Am. Chem. Soc. 2003, 125, 11565.
36. (c) Gorodetsky, B.; Ramnial, T.; Branda, N. R.; Clyburne, J. A. C. Chem. Commun. 2004, 1972.
37. Floyd, R. A. Aging Cell 2006, 5, 51.
38. Todd, K.; Butterworth, R. F. Ann. N.Y. Acad. Sci. 1999, 893, 404.
39. (a) Baker, M. V.; Barnard, P. J.; Berners-Price, S. J.; Brayshaw, S. K.; Hickey, J. L.; Skelton, B. W.; White, A. H. Dalton Trans. 2006, 3708.
40. (b) Barnard, P. J.; Baker, M. V.; Berners-Price, S. J.; Day, D. A. J. Inorg. Biochem. 2004, 98, 1642.
41. (c) Kascatan-Nebioglu, A.; Panzner, M. J.; Tessier, C. A.; Cannon, C. L.; Youngs, W. J. Coord. Chem. Rev. 2007, 251, 884.
42. Galli, A.; Svegliati-Baroni, G.; Ceni, E.; Milani, S.; Ridolfi, F.; Salzano, R.; Tarocchi, M.; Grappone, C.; Pellegrini, G.; Benedetti, A.; Surrenti, G.; Casini, A. Hepatologv 2005, 41, 1074.
43. (a) Fu, Y.; Zhou, Y.; Zheng, S.; Chen, A. Lab. Invest. 2006, 86, 697.
44. (b) Meurer, S. K.; Lahme, B.; Tihaa, L.; Weiskirchen, R.; Gressner, A. M. Biochem. Pharmacol. 2005, 70, 1026.
45. (a) Zhang, C. Y.; Zhuo, L. Int. J. Mol. Med. 2006, 18, 1141.
46. (b) Zhang, C. Y.; Zhang, Y.; Ying, J. Y.; Zhuo, L. Manuscript in preparation.