Influence of the environment on the protective effects of guaiacol derivatives against oxidative stress: Mechanisms, kinetics, and relative antioxidant activity

Journal of Physical Chemistry B

Volumn 116, Issue 24, 2012, Pages 7129-7137

  Galano, Annia ^a   León Carmona, Jorge Rafael ^a   Alvarez Idaboy, Juan Raúl ^b  

^a DEPARTAMENTO DE QUÍMICA   (Mexico)

^b UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; DENSITY FUNCTIONAL THEORY; FREE RADICAL REACTIONS; HYDROGEN; PH; PHENOLS; SCAVENGING;

ANTIOXIDANT ACTIVITIES; ELECTRON TRANSFER; HYDROGEN TRANSFER; NON-POLAR; NONPOLAR ENVIRONMENT; NONPOLAR MEDIA; PEROXYL RADICAL; PHYSIOLOGICAL PH; PROTECTIVE EFFECTS; SCAVENGING ACTIVITIES; SCAVENGING PROCESS; VANILLIC ACIDS;

SOLUTIONS;

EID: 84862649986     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp302810w     Document Type: Article

References (101)

1. Boyd, N. F.; McGuire, V. Free Radical Biol. Med. 1991, 10, 185-190
2. Nelson, R. L. Free Radical Biol. Med. 1992, 12, 161-168
3. Knekt, P.; Reunanen, A.; Takkunen, H.; Aromaa, A.; Heliovaara, M.; Hakuunen, T. Int. J. Cancer 1994, 56, 379-382
4. Salonen, J. T.; Nyyssoner, K.; Korpela, H.; Tuomilehto, J.; Seppanen, R.; Salonen, R. Circulation 1992, 86, 803-811
5. Street, D. A.; Comstock, G.; Salkeld, R.; Klag, M. Circulation 1994, 90, 1154-1161
6. Stephens, N. G.; Parsons, A.; Brown, M. J.; Schofield, P. M.; Kelly, F.; Cheesman, K.; Mitchinson, M. J. Lancet 1996, 347, 781-786
7. Panasenko, O. M.; Nova, T. V.; Azizova, O. A.; Vladimirov, Y. A. Free Radical Biol. Med. 1991, 10, 137-148
8. Steinberg, D. Circulation 1991, 84, 1420-1425
9. Janero, D. R. Free Radical Biol. Med. 1991, 11, 129-144
10. Hodis, H. N.; Mack, W. J.; LaBree, L.; Cashin-Hemphill, L.; Sevanian, A.; Johnson, R.; Azen, S. J. Am. Med. Asoc. 1995, 273, 1849-1854
11. Braekke, K.; Harsem, N. K.; Staff, A. C. Pediatr. Res. 2006, 60, 560-564
12. Biri, A.; Bozkurt, N.; Turp, A.; Kavutcu, M.; Himmetoglu, O.; Durak, I. Gynecol. Obstet. Invest. 2007, 64, 187-192
13. Hracsko, Z.; Orvos, H.; Novak, Z.; Pal, A.; Varga, I. S. Redox Rep. 2008, 13, 11-16
14. Christen, Y. Am. J. Clin. Nutr. 2000, 71, 621S-629S
15. Halliwell, B. Drugs Aging 2001, 8, 685-716
16. Butterfield, D. A. Free Radical Res. 2002, 36, 1307-1313
17. Halliwell, B. Biochem. Soc. Trans. 2007, 35, 1147-1150
18. Pham-Huy, L. A.; He, H.; Pham-Huy, C. Int. J. Biomed. Sci. 2008, 4, 89-96
19. Willcox, J. K.; Ash, S. L.; Catignani, G. L. Crit. Rev. Food. Sci. Nutr. 2004, 44, 275-295
20. Valko, M.; Morris, H.; Cronin, M. T. D. Curr. Med. Chem. 2005, 12, 1161-1208
21. Pasupathi, P.; Rao, Y. Y.; Farook, J.; Saravanan, G.; Bakthavathsalam, G. Res. J. Med. Med. Sci. 2009, 4, 151-159
22. Reiter, R. J.; Manchester, L. C.; Tan, D. X. Curr. Neuropharmacol. 2010, 8, 194-210
23. Blokhina, O.; Virolainen, E.; Fagerstedt, K. V. Ann. Bot. 2003, 91, 179-194
24. Scalbert, A.; Johnson, I. T.; Saltmarsh, M. Am. J. Clin. Nutr. 2005, 81, 215S-217S
25. Dudonnee, S.; Vitrac, X.; Coutiere, P.; Woillez, M.; Meerillon, J.-M. J. Agric. Food Chem. 2009, 57, 1768-1774
26. Ahmed, S.; Beigh, S. H. J. Med. Biol. Sci. 2009, 3, 1-8
27. Firuzi, O.; Javidnia, K.; Gholami, M.; Soltani, M.; Miri, R. Nat. Prod. Commun. 2010, 5, 261-264
28. Fu, L.; Xu, B.-T.; Xu, X.-R.; Qin, X.-S.; Gan, R.-Y.; Li, H.-B. Molecules 2010, 15, 8602-8617
29. Fu, L.; Xu, B.-T.; Gan, R.-Y.; Zhang, Y.; Xu, X.-R.; Xia, E.-Q.; Li, H.-B. Int. J. Mol. Sci. 2011, 12, 2112-2124
30. Anouar, E.; Calliste, C. A.; Kosinova, P.; Di Meo, F.; Duroux, J. L.; Champavier, Y.; Marakchi, K.; Trouillas, P. J. Phys. Chem. A 2009, 113, 13881-13891
31. Burri, J.; Graf, M.; Lambelet, P.; Loliger, J. J. Sci. Food Agric. 1989, 48, 49-56
32. Nagababu, E.; Lakshmaia, N. Biochem. Pharmacol. 1992, 43, 2393-2400
33. Tsujimoto, Y.; Hashizume, H.; Yamazaki, M. Int. J. Biochem. 1993, 25, 491-494
34. Ogata, M.; Hoshi, M.; Shimotohno, K.; Urano, S.; Endo, T. J. Am. Oil Chem. Soc. 1997, 74, 557-562
35. Anklam, E.; Gaglione, S.; Muller, A. Food Chem. 1997, 60, 43-51
36. Kamat, J. P.; Ghosh, A.; Devasagayam, T. P. A. Mol. Cell. Biochem. 2000, 209, 47-53
37. Guha, S. N.; Priyadarsini, K. I. Int. J. Chem. Kinet. 2000, 32, 17-23
38. Mahal, H. S.; Badheka, L. P.; Mukherjee, T. Res. Chem. Intermed. 2001, 27, 595-604
39. Fujisawa, S.; Atsumi, T.; Kadoma, Y.; Ishihara, M.; Okada, N.; Nagasaki, M.; Yokoe, I.; Sakagami, H. Mol. Toxicol. 2001, 13, 269-279
40. Fujisawa, S.; Atsumi, T.; Kadoma, Y.; Sakagami, H. Toxicology 2002, 177, 39-54
41. Mimura, T.; Yazaki, K.; Sawaki, K.; Ozawa, T.; Kawaguchi, M. Biomed. Res. 2005, 26, 139-145
42. Ordoudi, S. A.; Tsimidou, M. Z.; Vafiadis, A. P.; Bakalbassis, E. G. J. Agric. Food Chem. 2006, 54, 5763-5768
43. Shyamala, B. N.; Naidu, M. M.; Sulochanamma, G.; Srinivas, P. J. Agric. Food Chem. 2007, 55, 7738-7743
44. Mourtzinos, I.; Konteles, S.; Kalogeropoulos, N.; Karathanos, V. T. Food Chem. 2009, 114, 791-797
45. Baskaran, Y.; Periyasamy, V.; Venkatraman, A. C. Toxicology 2010, 268, 204-212
46. Chou, T.-H.; Ding, H.-Y.; Hung, W. J.; Liang, C.-H. Exp. Dermatol. 2010, 19, 742-750
47. Makni, M.; Chtourou, Y.; Fetoui, H.; Garoui, E. M.; Boudawara, T.; Zeghal, N. Eur. J. Pharmacol. 2011, 668, 133-139
48. Prince, P. S. M.; Rajakumar, S.; Dhanasekar, K. Eur. J. Pharmacol. 2011, 668, 233-240
49. Tai, A.; Sawano, T.; Yazama, F.; Ito, H. Biochim. Biophys. Acta 2011, 1810, 170-177
50. Terpinc, P.; Abramovic, H. Food Chem. 2010, 121, 366-371
51. Sies, H. Exp. Physiol. 1997, 82, 291-295
52. Itagaki, S.; Kurokawa, T.; Nakata, C.; Saito, Y.; Oikawa, S.; Kobayashi, M.; Hirano, T.; Iseki, K. Food Chem. 2009, 114, 466-471
53. Valko, M.; Rhodes, C. J.; Moncola, J.; Izakovic, M.; Mazur, M. Chem.-Biol. Interact. 2006, 160, 1-40
54. Masuda, T.; Yamada, K.; Maekawa, T.; Takeda, Y.; Yamaguchi, H. Food Sci. Technol. Res. 2006, 12, 173-177
55. Masuda, T.; Yamada, K.; Maekawa, T.; Takeda, Y.; Yamaguchi, H. J. Agric. Food Chem. 2006, 54, 6069-6074
56. De Grey, A. D. N. J. DNA Cell Biol. 2002, 21, 251-257
57. Rose, R. C.; Bode, A. M. FASEB J. 1993, 7, 1135-1142
58. Galano, A.; Tan, D. X.; Reiter, R. J. J. Pineal Res. 2011, 51, 1-16
59. Zhao, Y.; Schultz, N. E.; Truhlar, D. G. J. Chem. Theory Comput. 2006, 2, 364-382
60. Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2009, 113, 6378-6396
61. Velez, E.; Quijano, J.; Notario, R.; Pabón, E.; Murillo, J.; Leal, J.; Zapata, E.; Alarcon, G. J. Phys. Org. Chem. 2009, 22, 971-977
62. Galano, A.; Alvarez-Idaboy, J. R. Org. Lett. 2009, 11, 5114-5117
63. Black, G.; Simmie, J. M. J. Comput. Chem. 2010, 31, 1236-1248
64. Furuncuoglu, T.; Ugur, I.; Degirmenci, I.; Aviyente, V. Macromolecules 2010, 43, 1823-1835
65. Zhao, Y.; Truhlar, D. G. J. Phys. Chem. A 2008, 112, 1095-1099
66. 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.; Gaussian 09, revision A.08; Gaussian, Inc.: Wallingford, CT, 2009.
67. Okuno, Y. Chem.-Eur. J. 1997, 3, 212-218
68. Benson, S. W. The Foundations of Chemical Kinetics; McGraw-Hill: New York, 1960; Chapter XV, pp 504-508.
69. Eyring, H. J. Chem. Phys. 1935, 3, 107-115
70. Evans, M. G.; Polanyi, M. Trans. Faraday Soc. 1935, 31, 875-894
71. Truhlar, D. G.; Hase, W. L.; Hynes, J. T. J. Phys. Chem. 1983, 87, 2664-2682
72. Truhlar, D. G.; Kuppermann, A. J. Am. Chem. Soc. 1971, 93, 1840-1851
73. Marcus, R. A. Annu. Rev. Phys. Chem. 1965, 16, 155-196
74. Marcus, R. A. Rev. Mod. Phys. 1993, 65, 599-610
75. Marcus, R. A. Pure Appl. Chem. 1997, 69, 13-30
76. Collins, F. C.; Kimball, G. E. J. Colloid Sci. 1949, 4, 425-437
77. Smoluchowski, M. Z. Phys. Chem. 1917, 92, 129-168
78. Truhlar, D. G. J. Chem. Educ. 1985, 62, 104-106
79. Einstein, A. Ann. Phys. (Leipzig) 1905, 17, 549-560
80. Stokes, G. G. Mathematical and Physical Papers; Cambridge University Press: Cambridge, U.K., 1903; Vol. 3, p 55.
81. Shorina, N. V.; Kosyakov, D. S.; Bogolitsyn, K. G. Russ. J. Appl. Chem. 2005, 78, 125-129
82. From SciFinder, Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (© 1994-2012 ACD/Labs).
83. Beltran, J. L.; Sanli, N.; Fonrodona, G.; Barron, D.; Ozkan, G.; Barbosa, J. Anal. Chim. Acta 2003, 484, 253-264
84. Erdemgil, F. Z.; Sanli, S.; Sanli, N.; Ozkan, G.; Barbosa, J.; Guiteras, J.; Beltran, J. L. Talanta 2007, 72, 489-496
85. Belcastro, M.; Marino, T.; Russo, N.; Toscano, M. Theor. Chem. Acc. 2006, 115, 361-369
86. Leopoldini, M.; Russo, N.; Chiodo, S.; Toscano, M. J. Agric. Food Chem. 2006, 54, 6343-6351
87. Leopoldini, M.; Rondinelli, F.; Russo, N.; Toscano, M. J. Agric. Food Chem. 2010, 58, 8862-8871
88. Leopoldini, M.; Russo, N.; Toscano, M. Food Chem. 2011, 125, 288-306
89. Perez-Gonzalez, A.; Galano, A. J. Phys. Chem. B 2011, 115, 1306-1314
90. Chiodo, S. G.; Leopoldini, M.; Russo, N.; Toscano, M. Phys. Chem. Chem. Phys. 2010, 12, 7662-7670
91. León-Carmona, J. R.; Galano, A. J. Phys. Chem. B 2011, 115, 4538-4546
92. Galano, A.; Francisco-Márquez, M. J. Phys. Chem. B 2009, 113, 11338-11345
93. Martínez, A.; Vargas, R.; Galano, A. Theor. Chem. Acc. 2010, 127, 595-603
94. Galano, A.; Francisco-Márquez, M.; Alvarez-Idaboy, J. R. J. Phys. Chem. B 2011, 115, 8590-8596
95. Galano, A.; Alvarez-Idaboy, J. R.; Francisco-Marquez, M.; Medina, M. E. Theor. Chem. Acc. 2012, 131, 1173
96. Galano, A.; Alvarez-Idaboy, J. R.; Francisco-Marquez, M. J. Phys. Chem. B 2011, 115, 13101-13109
97. Galano, A.; Francisco-Marquez, M.; Alvarez-Idaboy, J. R. Phys. Chem. Chem. Phys. 2011, 13, 11199-11205
98. Martínez, A.; Galano, A.; Vargas, R. J. Phys. Chem. B 2011, 115, 12591-12598
99. Galano, A. Phys. Chem. Chem. Phys. 2011, 13, 7147-7157
100. Galano, A.; Francisco-Márquez, M. J. Phys. Chem. B 2009, 113, 16077-16081
101. Galano, A.; Alvarez-Idaboy, J. R. RSC Adv. 2011, 1, 1763-1771