Rate constants for peroxidation of polyunsaturated fatty acids and sterols in solution and in liposomes

Journal of the American Chemical Society

Volumn 131, Issue 36, 2009, Pages 13037-13044

  Xu, Libin ^a   Davis, Todd A ^a,b   Porter, Ned A ^a  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b IDAHO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARACHIDONATE; ARACHIDONIC ACIDS; BENZENE SOLUTION; CARBON CHAINS; DOCOSAHEXAENOATE; DOCOSAHEXAENOIC ACID; EICOSAPENTAENOIC ACID; FREE RADICAL OXIDATION; HYDROGEN ATOM ABSTRACTION; HYDROGEN ATOMS; KINETIC PROPERTIES; LINOLEIC ACID; LIPID MIXTURES; LOCAL ENVIRONMENTS; MOLECULAR SPECIES; MULTILAMELLAR; OXIDATION PRODUCTS; OXIDATION REACTIONS; PEROXIDATION; PEROXIDATION REACTIONS; PEROXYL RADICAL; PHOSPHATIDYLCHOLINE; POLYUNSATURATED FATTY ACIDS; PRODUCT RATIOS; PROPAGATION RATE CONSTANT; RADICAL CLOCKS; SOLVENT POLARITY; UNILAMELLAR LIPOSOMES;

ACIDS; ATOMS; BENZENE; CHOLESTEROL; CLOCKS; ESTERS; FATTY ACIDS; FREE RADICALS; HYDROGEN; LIPID BILAYERS; LIPOSOMES; NANOCAPSULES; OLEFINS; OXIDATION; PHOSPHOLIPIDS; SOLVENTS; SUGAR (SUCROSE);

RATE CONSTANTS;

7 DEHYDROCHOLESTEROL; ALKADIENE; ARACHIDONIC ACID; BENZENE; CARBON; CHOLESTEROL; DOCOSAHEXAENOIC ACID; HYDROGEN; ICOSAPENTAENOIC ACID; LINOLEIC ACID; LIPOSOME; PEROXY RADICAL; PHOSPHATIDYLCHOLINE; POLYUNSATURATED FATTY ACID; STEARIC ACID DERIVATIVE; STEROL;

ARTICLE; AUTOOXIDATION; LIPID BILAYER; OXIDATION; PEROXIDATION;

FATTY ACIDS, UNSATURATED; KINETICS; LIPOSOMES; MODELS, MOLECULAR; OXIDATION-REDUCTION; PHOSPHATIDYLCHOLINES; SOLUTIONS; STEROLS;

EID: 70349116511     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9029076     Document Type: Article

References (63)

1. Esterbauer, H.; Gebicki, J.; Puhl, H.; Jurgens, G. Free Radical Biol. Med. 1992, 13, 341-390.
2. Berliner, J. A.; Heinecke, J. W. Free Radical Biol. Med. 1996, 20, 707-727.
3. Antczak, A.; Nowak, D.; Shariati, B.; Krol, M.; Piasecka, G.; Kurmanowska, Z. Eur. Respir. J. 1997, 10, 1235-1241.
4. Montuschi, P.; Corradi, M.; Ciabattoni, G.; Nightingale, J.; Kharitonov, S. A.; Barnes, P. J. Am. J. Respir. Crit. Care. Med. 1999, 160, 216-220.
5. Simonian, N. A.; Coyle, J. T. Annu. Rev. Pharmacol. Toxicol. 1996, 36, 83-106.
6. Sayre, L. M.; Zelasko, D. A.; Harris, P. L. R.; Perry, G.; Salomon, R. G.; Smith, M. A. J. Neurochem. 1997, 68, 2092-2097.
7. Fahn, S.; Cohen, G. Ann. Neurol. 1992, 32, 804-812.
8. Yoritaka, A.; Hattori, N.; Uchida, K.; Tanaka, M.; Stadtman, E. R.; Mizuno, Y. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 2696-2701.
9. Gaoua, W.; Chevy, F.; Roux, C.; Wolf, C. J. Lipid. Res. 1999, 40, 456-463.
10. Richards, M. J.; Nagel, B. A.; Fliesler, S. J. Exp. Eye. Res. 2006, 82, 538-541.
11. Valencia, A.; Rajadurai, A.; Carle, A. B.; Kochevar, I. E. Free Radical Biol. Med. 2006, 41, 1704-1718.
12. Valencia, A.; Kochevar, I. E. Free Radical Biol. Med. 2006, 40, 641-650.
13. Smith, L. L. Cholesterol Autoxidation; Plenum Press: New York, 1981.
14. Murphy, R. C.; Johnson, K. M. J. Biol. Chem. 2008, 283, 15521-15525.
15. Girotti, A. W. J. Lipid Res. 1998, 39, 1529-1542.
16. Kresge, N.; Simoni, R. D.; Hill, R. L. J. Biol. Chem. 2005, 280, e7.
17. Javitt, N. B. Steroids 2008, 73, 149-157
18. Herman, G. E. Hum. Mol. Genet. 2003, 12 (Spec No 1), R75-88.
19. Roschek, B.; Tallman, K. A.; Rector, C. L.; Gillmore, J. G.; Pratt, D. A.; Punta, C.; Porter, N. A. J. Org. Chem. 2006, 71, 3527-3532.
20. Porter, N. A.; Weber, B. A.; Weenen, H.; Khan, J. A. J. Am. Chem. Soc. 1980, 102, 5597-5601.
21. Porter, N. A.; Lehman, L. S.; Weber, B. A.; Smith, K. J. J. Am. Chem. Soc. 1981, 103, 6447-6455.
22. Tallman, K. A.; Roschek, B.; Porter, N. A. J. Am. Chem. Soc. 2004, 126, 9240-9247.
23. Pajunen, T. I.; Johansson, M. P.; Hase, T.; Hopia, A. Lipids 2008, 43, 599-610.
24. Davis, T. A.; Gao, L.; Yin, H.; Morrow, J.; Porter, N. A. J. Am. Chem. Soc. 2006, 128, 14897-14904.
25. Antunes, F.; Barclay, L. R. C.; Vinqvist, M. R.; Pinto, R. E. Int. J. Chem. Kinet. 1998, 30, 753-767.
26. Barclay, L. R. C.; Baskin, K. A.; Kong, D.; Locke, S. J. Can. J. Chem. 1987, 65, 2541-2550.
27. Barclay, L. R. C. Can. J. Chem. 1993, 71, 1-16.
28. Barclay, L. R. C.; Ingold, K. U. J. Am. Chem. Soc. 1980, 102, 7792-7794.
29. Barclay, L. R. C.; Ingold, K. U. J. Am. Chem. Soc. 1981, 103, 6478-6485.
30. Barclay, L. R. C.; Locke, S. J.; Macneil, J. M.; Vankessel, J.; Burton, G. W.; Ingold, K. U. J. Am. Chem. Soc. 1984, 106, 2479-2481.
31. Barclay, L. R. C.; Vinqvist, M. R.; Antunes, F.; Pinto, R. E. J. Am. Chem. Soc. 1997, 119, 5764-5765.
32. Culbertson, S. M.; Antunes, F.; Havrilla, C. M.; Milne, G. L.; Porter, N. A. Chem. Res. Toxicol. 2002, 15, 870-876.
33. Weenen, H.; Porter, N. A. J. Am. Chem. Soc. 1982, 104, 5216-5221.
34. Howard, J. A.; Ingold, K. U. Can. J. Chem. 1967, 45, 793-802.
35. -1.
36. Cosgrove, J. P.; Church, D. F.; Pryor, W. A. Lipids 1987, 22, 299-304.
37. Korcek, S.; Chenier, J. H. B.; Howard, J. A.; Ingold, K. U. Can. J. Chem. 1972, 50, 2285-2897.
38. Porter, N. A.; Mills, K. A.; Carter, R. L. J. Am. Chem. Soc. 1994, 116, 6690-6696.
39. R-H).
40. Jha, M.; Pratt, D. A. Chem. Commun. 2008, 1252-1254.
41. Mugnaini, V.; Lucarini, M. Org. Lett. 2007, 9, 2725-2728.
42. Barclay, L. R. C.; Crowe, E.; Edwards, C. D. Lipids 1997, 32, 237-245.
43. Haas, D.; Kelley, R. I.; Hoffmann, G. F. Neuropediatrics 2001, 32, 113-122
44. Waterham, H. R. Clin. Genet. 2002, 61, 393-403.
45. Opitz, J. M.; Gilbert-Barness, E.; Ackerman, J.; Lowichik, A. Pediatr. Pathol. Mol. Med. 2002, 21, 153-181
46. Kelley, R. I. Adv. Pediatr. 2000, 47, 1-53.
47. Kelley, R. I.; Hennekam, R. C. J. Med. Genet. 2000, 37, 321-335
48. Gaoua, W.; Chevy, F.; Roux, C.; Wolf, C. J. Lipid Res. 1999, 40, 456-463
49. Javitt, N. B. Curr. Opin. Lipidol. 2007, 18, 283-288
50. Töröcsik, D.; Szanto, A.; Nagy, L. Mol. Aspects Med. 2009, electronic ahead of print.
51. Akihisa, T.; Franzblau, S. G.; Tokuda, H.; Tagata, M.; Ukiya, M.; Matsuzawa, T.; Metori, K.; Kimura, Y.; Suzuki, T.; Yasukawa, K. Biol. Pharm. Bull. 2005, 28, 1117-1119.
52. Akihisa, T.; Nakamura, Y.; Tagata, M.; Tokuda, H.; Yasukawa, K.; Uchiyama, E.; Suzuki, T.; Kimura, Y. Chem. Biodiversity 2007, 4, 224-231.
53. Ishizuka, T.; Yaoita, Y.; Kikuchi, M. Chem. Pharm. Bull. 1997, 45, 1756-1760.
54. Kawagishi, H.; Katsumi, R.; Sazawa, T.; Mizuno, T.; Hagiwara, T.; Nakamura, T. Phytochemistry 1988, 27, 2777-2779.
55. Luo, X.; Li, F.; Shinde, P. B.; Hong, J.; Lee, C.-O.; Im, K. S.; Jung, J. H. J. Nat. Prod. 2006, 69, 1760-1768.
56. Mansoor, T. A.; Hong, J.; Lee, C. O.; Bae, S. J.; Im, K. S.; Jung, J. H. J. Nat. Prod. 2005, 68, 331-336.
57. Mansoor, T. A.; Lee, Y. M.; Hong, J.; Lee, C.-O.; Im, K. S.; Jung, J. H. J. Nat. Prod. 2006, 69, 131-134.
58. Yaoita, Y.; Amemiya, K.; Ohnuma, H.; Furumura, K.; Masaki, A.; Matsuki, T.; Kikuchi, M. Chem. Pharm. Bull. 1998, 46, 944-950.
59. Yaoita, Y.; Endo, M.; Tani, Y.; Machida, K.; Amemiya, K.; Furumura, K.; Kikuchi, M. Chem. Pharm. Bull. 1999, 47, 847-851.
60. Yaoita, Y.; Matsuki, K.; Iijima, T.; Nakano, S.; Kakuda, R.; Machida, K.; Kikuchi, M. Chem. Pharm. Bull. 2001, 49, 589-594.
61. Yaoita, Y.; Yoshihara, Y.; Kakuda, R.; Machida, K.; Kikuchi, M. Chem. Pharm. Bull. 2002, 50, 551-553.
62. Yue, J. M.; Chen, S. N.; Lin, Z. W.; Sun, H. D. Phytochemistry 2001, 56, 801-806.
63. Albro, P. W.; Bilski, P.; Corbett, J. T.; Schroeder, J. L.; Chignell, C. F. Photochem. Photobiol. 1997, 66, 316-325.