ROS initiated oxidation of dopamine under oxidative stress conditions in aqueous and lipidic environments

Journal of Physical Chemistry B

Volumn 115, Issue 42, 2011, Pages 12234-12246

  Iuga, Cristina ^a   Alvarez Idaboy, J Raul ^b,c   Vivier Bunge, Annik ^c  

^a UNIVERSIDAD AUTÓNOMA METROPOLITANA AZCAPOTZALCO   (Mexico)

^b UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

^c DEPARTAMENTO DE QUÍMICA   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

COMPUTATIONAL CHEMISTRY; DENSITY FUNCTIONAL THEORY; FREE RADICAL REACTIONS; FREE RADICALS; HYDROGEN; NEURONS; PH; PHENOLS; QUANTUM CHEMISTRY; RATE CONSTANTS; SCAVENGING;

ADDUCT FORMATION; BIOLOGICAL ENVIRONMENTS; BRANCHING RATIO; COMPUTATIONAL KINETICS; ELECTRON-PROTON TRANSFERS; HYDROGEN-ATOM TRANSFER; HYDROPEROXYL RADICAL; HYDROXYL RADICALS; OVERALL RATE; OVERALL REACTIONS; PHYSIOLOGICAL PH; RADICAL SCAVENGERS; STRESS CONDITION;

BRAIN;

EID: 80054898637     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp206347u     Document Type: Article

References (101)

1. Serra, P. A.; Esposito, G.; Enrico, P.; Mura, M. A.; Migheli, R.; Delogu, M. R.; Miele, M.; Desole, M. S.; Grella, G.; Miele, E. Br. J. Pharmacol. 2000, 130, 937
2. Liu, X.; Yamada, N.; Maruyama, W.; Osawa, T. J. Biol. Chem. 2008, 283, 34887
3. Floyd, R. A. Proc. Soc. Exp. Biol. Med. 1999, 222, 236
4. Gilgun-Sherki, Y.; Melamed, E.; Offen, D. Neuropharmacology 2001, 40, 959
5. Cao, G.; Sofic, E.; Prior, L. R. Free Radicals Biol. Med. 1997, 22, 749
6. Kerry, N.; Rice-Evans, C. J. Neurochem. 1999, 73, 247
7. Kienzl, E.; Jellinger, K.; Stachelberger, H.; Linert, W. Life Sci. 1999, 65, 1973
8. Linert, W.; Jameson, G. N. L. J. Inorg. Biochem. 2000, 79, 319
9. Terland, O.; Almas, B.; Flatmark, T.; Andersson, K. K.; Srlie, M. Free Radic. Biol. Med. 2006, 41, 1266
10. Hattoria, N.; Wanga, M.; Taka, H.; Fujimura, T.; Yoritaka, A.; Kubo, S.; Mochizuki, H. Parkinsonism Relat. Disord. 2009, 15, S35
11. Stokes, A. H.; Hastings, T. G.; Vrana, K. E. J. Neurosci. Res. 1999, 15, 659
12. Andén, N. E.; Fuxe, K.; Hamberger, B.; Hokfelt, T. Acta Physiol. Scand. 1996, 67, 306
13. Cooper, J. R.; Bloom, F. E.; Roth, R. H. The Biochemical Basis of Neuropharmacology; Oxford University Press: New York, 1986.
14. Birkmayer, W.; Riederer, P. Understanding the Neurotransmitters: Key to the Workings of the Brain; Springer-Verlag: New York, 1989.
15. Mathews, C. K.; Van Holde, K. E. Biochemistry; The Benjamin/Cummings Publishing Company, Inc.: Menlo Park, CA, 1996.
16. Anbar, N.; Neta, P. Int. J. Appl. Radiat. Isot. 1967, 18, 493-523
17. Dorfman, L. M.; Adams, G. E. National Standard Reference Data System; National Bureau of Standards: Washington, DC, 1973.
18. Bielski, B. H.; Gebieki, J. M. Application of radiation chemistry to biology. In Free Radicals in Biology; Pryor, W. A., Ed.; Academic Press: New York, 1977; Vol. 3, pp 2-48.
19. Cohen, G. Photochem. Photobiol. 1978, 28, 669-675
20. Brawn, K.; Fridovich, I. Arch. Biochem. Biophys. 1981, 206, 414-419
21. Richmond, R.; Halliwell, B.; Chauhan, J.; Darbre, A. Anal. Biochem. 1981, 118, 328-335
22. Ingelman-Sundberg, M.; Ekstrom, G. Biochem. Biophys. Res. Commun. 1982, 106, 625-631
23. Balasubramanian, B.; Pogozelski, W. K.; Tullius, T. D. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 9738
24. Candeias, L. P.; Steenken, S. Chem.-Eur. J. 2000, 6, 475
25. Chatgilialoglu, C.; D'Angelantonio, M.; Guerra, M.; Kaloudis, P.; Mulazzani, Q. G. Angew. Chem., Int. Ed. 2009, 48, 2214
26. de Grey, A. D. N. J. DNA Cell Biol. 2002, 21, 251
27. Zareba, M.; Bober, A.; Korytowski, W.; Zecca, L.; Sarna, T. Biochim. Biophys. Acta 1995, 1271, 343-348
28. Korytowski, W.; Sarna, T.; Zarba, M. Arch. Biochem. Biophys. 1995, 319, 142-148
29. Solmajer, P.; Kocjan, D.; Solmajer, T. Z. Naturforsch. 1983, 38c, 758
30. Urban, J. J.; Cramer, C. J.; Famini, G. R. J. Am. Chem. Soc. 1992, 114, 8226
31. Cramer, C. J.; Truhlar, D. G. J. Am. Chem. Soc. 1991, 113, 8305
32. Urban, J. J.; Cronin, C. W.; Roberts, R. R.; Famini, G. R. J. Am. Chem. Soc. 1997, 119, 12292
33. Alagona, G.; Ghio, C. Chem. Phys. 1996, 204, 239
34. Richter, H. W.; Waddell, W. H. J. Am. Chem. Soc. 1983, 105, 5434-5440
35. Valgimigli, L.; Ingold, K. U.; Lusztyk, J. J. Am. Chem. Soc. 1996, 118, 3545
36. Barclay, L. R. C.; Edwards, C. E.; Vinqvist, M. R. J. J. Am. Chem. Soc. 1999, 121, 6226
37. Burton, G. W.; Ingold, K. U. Acc. Chem. Res. 1986, 19, 194
38. Pryor, W. A. Free Radical Biol. Med. 1988, 4, 219
39. Draganic, I. G.; Draganic, Z. D. The Radiation Chemistry of Water; Academic Press: New York, 1971.
40. Marnett, L. J. Carcinogenesis 1987, 8, 1365
41. Pryor, W. A. Annu. Rev. Physiol. 1986, 48, 657
42. 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, Jr., J. A.; 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, Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R. E.; Stratmann, O.; Yazyev, A. J.; Austin, R.; Cammi, C.; Pomelli, J. W.; Ochterski, R.; 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.08; Gaussian, Inc.: Wallingford CT, 2009.
43. Zhao, Y.; Schultz, N. E.; Truhlar, D. G. J. Chem. Theory Comput. 2006, 2, 364
44. Zavala-Oseguera, C.; Alvarez-Idaboy, J. R.; Merino, G.; Galano, A. J. Phys. Chem. A 2009, 113, 13913
45. Velez, E.; Quijano, J.; Notario, R.; Pabón, E.; Murillo, J.; Leal, J.; Zapata, E.; Alarcón, G. J. Phys. Org. Chem. 2009, 22, 971
46. Galano, A.; Francisco-Marquez, M.; Alvarez-Idaboy, J. R. Phys. Chem. Chem. Phys. 2011, 13, 11199
47. Galano, A.; Alvarez-Idaboy, J. R. Org. Lett. 2009, 11, 5114
48. Perez-Gonzalez, A.; Galano, A. J. Phys. Chem. B 2011, 115, 1306
49. Leon-Carmona, J. R.; Galano, A. J. Phys. Chem. B 2011, 115, 4538
50. Galano, A. Phys. Chem. Chem. Phys. 2011, 13, 7147
51. Black, G.; Simmie, J. M. J. Comput. Chem. 2010, 31, 1236
52. Furuncuoglu, T.; Ugur, I.; Degirmenci, I.; Aviyente, V. Macromolecules 2010, 43, 1823
53. Gao, T.; Andino, J. M.; Alvarez-Idaboy, J. R. Phys. Chem. Chem. Phys. 2010, 12, 9830
54. Iuga, C.; Sainz-Díaz, C. I.; Vivier-Bunge, A. Geochim. Cosmochim. Acta 2010, 74, 3587
55. Iuga, C.; Alvarez-Idaboy, J. R.; Vivier-Bunge, A. J. Phys. Chem. A 2011, 115, 5138
56. Alvarez-Idaboy, J. R.; Mora-Diez, N.; Vivier-Bunge, A. J. Am. Chem. Soc. 2000, 122, 3715
57. Alvarez-Idaboy, J. R.; Mora-Diez, N.; Boyd, R. J.; Vivier-Bunge, A. J. Am. Chem. Soc. 2001, 123, 2018
58. Galano, A. J. Phys. Chem. A 2006, 110, 9153
59. Iuga, C.; Alvarez-Idaboy, J. R.; Vivier-Bunge, A. Theor. Chem. Acc. 2011, 129, 209
60. Iuga, C.; Alvarez-Idaboy, J. R.; Reyes, L.; Vivier-Bunge, A. J. Phys. Chem. Lett. 2010, 1, 3112
61. Marenich, A. V.; Cramer, J.; Truhlar, D. G. J. Phys. Chem. B 2009, 113, 6378
62. Okuno, Y. Chem.-Eur. J. 1997, 3, 212
63. Benson, S. W. The Foundations of Chemical Kinetics; Krieger: FL, 1982.
64. Ardura, D.; Lopez, R.; Sordo, T. L. J. Phys. Chem. B 2005, 109, 23618
65. Alvarez-Idaboy, J. R.; Reyes, L.; Cruz, J. Org. Lett. 2006, 8, 1763
66. Alvarez-Idaboy, J. R.; Reyes, L.; Mora-Diez, N. Org. Biomol. Chem. 2007, 5, 3682
67. Galano, A. J. Phys. Chem. A 2007, 111, 1677
68. Galano, A. J. Phys. Chem. C 2008, 112, 8922
69. Galano, A.; Cruz-Torres, A. Org. Biomol. Chem. 2008, 6, 732
70. Galano, A.; Francisco-Márquez, M. Chem. Phys. 2008, 345, 87
71. Mora-Diez, N.; Keller, S.; Alvarez-Idaboy, J. R. Org. Biomol. Chem 2009, 7, 3682
72. Eyring, H. J. Chem. Phys. 1935, 3, 107
73. Evans, M. G.; Polanyi, M. Trans. Faraday Soc. 1935, 31, 875
74. Truhlar, D. G.; Hase, W. L.; Hynes, J. T. J. Phys. Chem. 1983, 87, 2264
75. Duncan, W. T.; Bell, R. L.; Truong, T. N. J. Comput. Chem. 1998, 19, 1039
76. Zhang, S.; Truong, T. N. VKLab version 1.0, University of Utah, 2001.
77. Truhlar, D. G.; Kuppermann, A. J. Am. Chem. Soc. 1971, 1840
78. Eckart, C. Phys. Rev. 1930, 35, 1303
79. Marcus, R. A. Rev. Mod. Phys. 1993, 65, 599
80. Marcus, R. A. Pure Appl. Chem. 1997, 69, 13
81. Nelsen, S. F.; Weaver, M. N.; Luo, Y.; Pladziewicz, J. R.; Ausman, L. K.; Jentzsch, T. L.; O'Konek, J. J. J. Phys. Chem. A 2006, 110, 11665
82. Collins, F. C.; Kimball, G. E. J. Colloid Sci. 1949, 4, 425
83. Smoluchowski, M. Z. Phys. Chem. 1917, 92, 129
84. Truhlar, D. G. J. Chem. Educ. 1985, 62, 104
85. Einstein, A. Ann. Phys. (Leipzig) 1905, 17, 549
86. Stokes, G. G. Mathematical and Physical Papers; Cambridge University Press: Cambridge, 1903; Vol. 3, esp. Sect. IV, p 55.
87. Cooper, J. R.; Bloom, F. E.; Roth, R. H. The Biochemical Basis of Neuropharmacology; Oxford University Press: New York, 1986.
88. Corona-Avendao, S.; Alarcón-Angeles, G.; Rosquete-Pina, G. A.; Rojas-Hernandez, A.; Gutierrez, A.; Ramírez-Silva, M. T.; Romero-Romo, M.; Palomar-Pardavé, M. J. Phys. Chem. B 2007, 111, 1640-1647
89. Sanchez-Rivera, A. E.; Corona-Avendao, S.; Alarcon-Angeles, G.; Rojas-Henandez, A.; Ramrez-Silva, M. T.; Romero-Romo, M. A. Spectrochim. Acta, Part A 2003, 59, 3193
90. Solmajer, P.; Kocjan, D.; Solmajer, T. Z. Naturforsch. 1983, 38c, 758
91. Cooper, J. R.; Bloom, F. E.; Roth, R. H. The Biochemical Basis of Neuropharmacology; Oxford University Press: New York, 1986.
92. Grierson, L.; Hildenbrand, K.; Bothe, E. Int. J. Radiat. Biol. 1992, 62, 265
93. Zhao, R.; Lind, J.; Merbnyi, G.; Eriksen, T. E. J. Am. Chem. Soc. 1994, 116, 12010
94. Friedman, M. J. Agric. Food Chem. 1997, 45, 1523
95. Galano, A.; Alvarez-Idaboy, J. R.; Ruiz-Santoyo, M. E.; Vivier-Bunge, A. J. Phys. Chem. A 2002, 106, 9520
96. Porter, W.; Black, E. D.; Drolet, A. M. J. Agric. Food Chem. 1989, 37, 615
97. Frankel, E.; Huang, S. W.; Kanner, J.; German, J. B. J. Agric. Food Chem. 1994, 42, 1054
98. Cuvelier, M. E.; Bondet, V.; Berset, C. J. Am. Oil Chem. Soc. 2000, 77, 819
99. Galano, A.; Alvarez-Idaboy, J. R. J. Chem. Theory Comput. 2008, 4, 322
100. Galano, A.; Alvarez-Diduk, R.; Ramírez-Silva, M. T.; Alarcón-Angeles, G.; Rojas-Hernández, A. Chem. Phys. 2009, 363, 13
101. Galano, A.; Alvarez-Idaboy, J. R. RSC Adv. 2011, DOI: 10.1039/C1RA00474C.