Explanation for main features of structure-genotoxicity relationships of aromatic amines by theoretical studies of their activation pathways in CYP1A2

Journal of the American Chemical Society

Volumn 133, Issue 40, 2011, Pages 16168-16185

  Shamovsky, Igor ^a   Ripa, Lena ^a   Börjesson, Lena ^a   Mee, Christine ^b   Nordén, Bo ^a   Hansen, Peter ^a   Hasselgren, Catrin ^a   O'Donovan, Mike ^b   Sjö, Peter ^a  

^a ASTRAZENECA R AND D   (Sweden)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION PATHWAY; AROMATIC AMINES; BINDING AFFINITIES; BINDING MODES; BIOCONJUGATES; DFT CALCULATION; DRUG DISCOVERY; EXOTHERMICITY; GENOTOXICITIES; H-BONDED; HETEROLYTIC CLEAVAGE; HETEROLYTIC MECHANISMS; HYDROPEROXY RADICAL; KEY FACTORS; MUTAGENICITY; O-H BOND; PROTON ABSTRACTION; RESONANCE STABILIZATION; STRUCTURAL ALTERATIONS; THEORETICAL STUDY;

ABSTRACTING; AROMATIC COMPOUNDS; AROMATIZATION; BINDING ENERGY; HYDROGEN BONDS; HYDROXYLATION; METABOLISM; OXIDANTS; PROTONS; REACTION INTERMEDIATES;

AMINES;

AROMATIC AMINE; CYTOCHROME P450 1A2; IRON; NITROGEN; OXIDIZING AGENT; OXYGEN; PROTON;

ARTICLE; BINDING AFFINITY; CHEMICAL REACTION; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; GENOTOXICITY; HYDROGEN BOND; HYDROXYLATION; METABOLISM; MUTAGENICITY; NONHUMAN; OXIDATIVE STRESS; PROTON TRANSPORT;

AMINES; CYTOCHROME P-450 CYP1A2; HUMANS; HYDROCARBONS, AROMATIC; MODELS, MOLECULAR; MUTAGENS;

EID: 80053521566     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja206427u     Document Type: Article

References (117)

1. Snyder, R. D. Environ. Mol. Mutagen. 2009, 50, 435-450
2. Mizra, A.; Desai, R.; Reynisson, J. Eur. J. Med. Chem. 2009, 44, 5006-5011
3. Hillebrecht, A.; Muster, W.; Brigo, A.; Kansy, M.; Weiser, T.; Singer, T. Chem. Res. Toxicol. 2011, 24, 843-854
4. Rehn, L. Arch. Klin. Chir. 1895, 50, 588-600
5. Case, R. A. M.; Hosker, M.-E.; McDonald, D. B.; Pearson, J. T. Br. J. Ind. Med. 1954, 11, 213-216
6. Turesky, R. J. In The Chemical Biology of DNA Damage; Geacintov, N. E.; Broyde, S., Eds.; Wiley-VCH Verlag: Weinheim, 2010; pp 157-183.
7. Miller, J. A.; Miller, E. C. Environ. Health Perspect. 1983, 49, 3-12
8. Garner, R. C.; Martin, C. N.; Clayson, D. B. In Chemical Carcinogenesis, 2 nd ed.; Searle, C. E., Ed.; American Chemical Society: Washington, DC, 1984; Vol. 1, pp 175-276.
9. Wakabayashi, K.; Nagao, M.; Esumi, H.; Sugimura, T. Cancer Res. 1992, 52, 2092s-2098s
10. Chung, K.-T.; Kirkovsky, L.; Kirkovsky, A.; Purcell, W. P. Mutat. Res. 1997, 387, 1-16
11. Patel, D. J.; Mao, B.; Gu, Z.; Hingerty, B. E.; Gorin, A.; Basu, A. K.; Broyde, S. Chem. Res. Toxicol. 1998, 11, 391-407
12. Felton, J. S.; Knize, M. G.; Bennett, L. M.; Malfatti, M. A.; Colvin, M. E.; Kulp, K. S. Toxicology 2004, 198, 135-145
13. Felton, J. S.; Knize, M. G.; Wu, R. W.; Colvin, M. E.; Hatch, F. T.; Malfatti, M. A. Mutat. Res. 2007, 616, 90-94
14. Beland, F. A.; Kadbular, F. F. Cancinogenesis and Mutagenesis. In Handbook of Experimental Pathology; Cooper, C. S.; Glover, P. L., Eds.; Springer: Heidelberg, 1990; Vol. 94, pp 267-325.
15. Turesky, R. J.; Lang, N. P.; Butler, M. A.; Teitel, C. H.; Kadbular, F. F. Carcinogenesis 1991, 12, 1839-1845
16. Turesky, R. J.; Constable, A.; Richoz, J.; Varga, N.; Markovic, J.; Martin, M. V.; Guengerich, F. P. Chem. Res. Toxicol. 1998, 11, 925-936
17. Kerdar, R. S.; Dehner, D.; Wild, D. Toxicol. Lett. 1993, 67, 73-85
18. Guengerich, F. P.; Hemphreys, W. G.; Yun, C. H.; Hammons, G. J.; Kadlubar, F. F.; Seto, Y.; Okazaki, O.; Martin, M. V. Princess Takamatsu Symp. 1995, 23, 78-84
19. Colvin, M. E.; Hatch, F. T.; Felton, J. S. Mutat. Res. 1998, 400, 479-492
20. Luch, A. Nat. Rev. 2005, 5, 113-125
21. Tsuneoka, Y.; Dalton, T. P.; Miller, M. L.; Clay, C. D.; Shertzer, H. G.; Talaska, G.; Medvedovic, M.; Nebert, D. W. J. Natl. Cancer Inst. 2003, 95, 1227-1237
22. Kim, D.; Guengerich, F. P. Annu. Rev. Pharmacol. Toxicol. 2005, 45, 27-49
23. Butler, M. A.; Guengerich, F. P.; Kadbular, F. F. Cancer Res. 1989, 49, 25-31
24. Eaton, D. L.; Gallagher, E. P.; Bammler, T. K.; Kunze, K. L. Pharmacogenetics 1995, 5, 259-274
25. Weisburger, J. H. Mutat. Res. 2002, 506-507, 9-20
26. Guengerich, F. P. In Cytochrome P450: Structure, Mechanism and Biochemistry, 3 rd ed.; Ortiz de Montellano, P. R., Ed.; Kluwer Academic/Plenum Publishers: New York, 2005; pp 377-530.
27. Hoffmann, G. R.; Fuchs, R. P. P. Chem. Res. Toxicol. 1997, 10, 347-359
28. Guengerich, F. P.; Rarikh, A.; Yun, C.-H.; Kim, D.; Nakamura, K.; Notley, L. M.; Gillam, E. M. J. Drug Metab. Rev. 2000, 32, 267-281
29. Kulkarni, S. A.; Moir, D.; Zhu, J. SAR QSAR Environ. Res. 2007, 18, 459-514
30. Grant, D. M.; Josephy, P. D.; Lord, H. L.; Morrison, L. D. Cancer Res. 1992, 52, 3961-3964
31. Novak, M.; Rajagopal, S.; Xu, L.; Kazerani, S.; Toth, K.; Brooks, M.; Nguyen, T.-M. J. Phys. Org. Chem. 2004, 17, 615-624
32. Cho, B. In The Chemical Biology of DNA Damage; Geacintov, N. E.; Broyde, S., Eds.; Wiley-VCH Verlag: Weinheim, 2010; pp 217-238.
33. Hatch, F. T.; Knize, M. G.; Felton, J. S. Environ. Mol. Mutagen. 1991, 17, 4-19
34. Mao, B.; Hingerty, B. E.; Broyde, S.; Patel, D. J. Biochemistry 1998, 37, 81-94
35. Chiapperino, D.; McIlroy, S.; Falvey, D. E. J. Am. Chem. Soc. 2002, 124, 3567-3577
36. Dutta, S.; Li, Y.; Johnson, D.; Dzantiev, L.; Richardson, C. C.; Romano, L. J.; Ellenberger, T. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 16186-16191
37. Loeb, L.; Harris, C. C. Cancer Res. 2008, 68, 6863-6872
38. Beland, F. A.; Melchior, W. B., Jr.; Mourato, L. L. G.; Santos, M. A.; Marques, M. M. Mutat. Res. 1997, 376, 13-19
39. Hatch, F. T.; Knize, M. G.; Colvin, M. E. Environ. Mol. Mutagen. 2001, 38, 268-291
40. Kriek, E. Cancer Res. 1972, 32, 2042-2048
41. Parks, J. M.; Ford, G. P.; Cramer, C. J. J. Org. Chem. 2001, 66, 8997-9004
42. Hirano, T.; Higashi, K.; Sakai, A.; Tsurudome, Y.; Ootsuyama, Y.; Kido, R.; Kasai, H. Jpn. J. Cancer Res. 2000, 91, 681-685
43. Siraki, A. G.; Chan, T. S.; Galati, G.; Teng, S.; O'Brien, P. J. Drug Metab. Rev. 2002, 34, 549-564
44. Makena, P. S.; Chung, K.-T. Environ. Mol. Mutagen. 2007, 48, 404-413
45. Blair, I. A. J. Biol. Chem. 2008, 283, 15545-15549
46. Shafirovich, V.; Geacintov, N. E. In The Chemical Biology of DNA Damage; Geacintov, N. E.; Broyde, S., Eds.; Wiley-VCH Verlag: Weinheim, 2010; pp 82-104.
47. Knutson, C. G.; Marnett, L. J. In The Chemical Biology of DNA Damage; Geacintov, N. E.; Broyde, S., Eds.; Wiley-VCH Verlag: Weinheim, 2010; pp 105-129.
48. Shahin, M. M. Mutat. Res. 1987, 181, 243-256
49. Sabbioni, G.; Wild, D. Carcinogenesis 1992, 13, 709-713
50. Ford, G. P.; Griffin, G. R. Chem.-Biol. Interact. 1992, 81, 19-33
51. Ford, G. P.; Herman, P. S. Chem.-Biol. Interact. 1992, 81, 1-18
52. Debnath, A. K.; Debnath, G.; Shusterman, A. J.; Hansch, C. Environ. Mol. Mutagen. 1992, 19, 37-52
53. Benigni, R.; Andreoli, C.; Giuliani, A. Environ. Mol. Mutagen. 1994, 24, 208-219
54. Benigni, R.; Giuliani, A.; Franke, R.; Gruska, A. Chem. Rev. 2000, 100, 3697-3714
55. Leach, A. G.; Cann, R.; Tomasi, S. Chem. Commun 2009, 1094-1096
56. Bentzien, J.; Hickey, E. R.; Kemper, R. A.; Brewer, M. L.; Dyekjar, J. D.; East, S. P.; Whittaker, M. J. Chem. Inf. Model. 2010, 50, 274-297
57. McCarren, P.; Bebernitz, G. R.; Gedeck, P.; Glowienke, S.; Grondine, M. S.; Kirman, L. C.; Klickstein, J.; Schuster, H. F.; Whitehead, L. Bioorg. Med. Chem. 2011, 19, 3173-3182
58. Kadbular, F. F.; Beland, F. A. In Polycyclic Hydrocarbons and Carcinogenesis; ACS Symposium Series 283; Harvey, R. G., Ed.; American Chemical Society: Washington, DC, 1985; pp 341-370.
59. Wild, D.; Dirr, A. Mutagenesis 1989, 4, 446-452
60. Borosky, G. L. Chem. Res. Toxicol. 2007, 20, 171-180
61. Hatch, F. T.; Colvin, M. E.; Seidl, E. T. Environ. Mol. Mutagen. 1996, 27, 314-330
62. Sabbioni, G. Environ. Health Perspect. 1994, 102, 61-67
63. Purohit, V.; Basu, A. K. Chem. Res. Toxicol. 2000, 13, 673-692
64. Sasaki, J. C.; Fellers, R. S.; Colvin, M. E. Mutat. Res. 2002, 506-507, 79-89
65. Guengerich, F. P. Chem. Res. Toxicol. 2001, 14, 611-650
66. Filatov, M.; Harris, N.; Shaik, S. Angew. Chem., Int. Ed. 1999, 38, 3510-3512
67. Shaik, S.; Cohen, S.; Wang, Y.; Chen, H.; Kumar, D.; Thiel, W. Chem. Rev. 2010, 110, 949-1017
68. Rittle, J.; Green, M. T. Science 2010, 330, 933-937
69. Franke, R.; Gruska, A.; Giuliani, A.; Benigni, R. Carcinogenesis 2001, 22, 1561-1571
70. Sushko, I. J. Chem. Inf. Model. 2010, 50, 2094-2111
71. Muratov, E.; et al. The 241st ACS National Meeting, Anaheim, CA, 2011; CINF-58.
72. Becke, A. J. Chem. Phys. 1993, 98, 5648-5652
73. Meunier, B.; de Visser, S. P.; Shaik, S. Chem. Rev. 2004, 104, 3947-3980
74. Cundari, T. R.; Stevens, W. J. J. Chem. Phys. 1993, 98, 5555-5565
75. Siegbahn, E. M. J. Biol. Inorg. Chem. 2006, 11, 695-701
76. Clark, T.; Chandrasekhar, J.; Spitznagel, G. W.; Schleyer, P. v. R. J. Comput. Chem. 1983, 4, 294-301
77. Zhao, Y.; Truhlar, D. G. J. Phys. Chem. 2006, 110, 5121-5129
78. Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618-622
79. Sansen, S.; Yano, J. K.; Reynald, R. L.; Schoch, G. A.; Griffin, K. J.; Stout, C. D.; Johnson, E. F. J. Biol. Chem. 2007, 282, 14348-14355
80. Frisch, M. J.; et al. Gaussian 09, revision B.01; Gaussian, Inc.: Wallingford, CT, 2010.
81. Maron, D. M.; Ames, B. N. Mutat. Res. 1983, 113, 173-215
82. Mortelmans, K.; Zeiger, E. Mutat. Res. 2000, 455, 29-60
83. Sugimura, T. Environ. Health Perspect. 1998, 106, A522-A523
84. Ohnishi, S.; Murata, M.; Oikawa, S.; Totsuka, Y.; Takamura, T.; Wakabayashi, K.; Kawanishi, S. Mutat. Res. 2001, 494, 63-72
85. Denisov, I. G.; Makris, T. M.; Sligar, S. G.; Schlichting, I. Chem. Rev. 2005, 105, 2253-2277
86. Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841-2887
87. Toy, P. H.; Newcomb, M.; Coon, M. J.; Vaz, A. D. N. J. Am. Chem. Soc. 1998, 120, 9718-9719
88. Newcomb, M.; Shen, R.; Choi, S.-Y.; Toy, P. H.; Hollenberg, P. F.; Vaz, A. D. N.; Coon, M. J. J. Am. Chem. Soc. 2000, 122, 2677-2686
89. Newcomb, M.; Toy, P. H. Acc. Chem. Res. 2000, 33, 449-455
90. Volz, T. J.; Rock, D. A.; Jones, J. P. J. Am. Chem. Soc. 2002, 124, 9724-9725
91. Wang, A.; Savas, U.; Stout, C. D.; Johnson, E. F. J. Biol. Chem. 2011, 286, 5736-5743
92. White, R. E. Pharmacol. Ther. 1991, 49, 21-42
93. Darbyshire, J. F.; Iyer, K. R.; Grogan, J.; Korzekwa, K. R.; Trager, W. F. Drug Metab. Dispos. 1996, 24, 1038-1045
94. Sarabia, S. F.; Zhu, B. T.; Kurosawa, T.; Tohma, M.; Liehr, J. G. Chem. Res. Toxicol. 1997, 10, 767-771
95. Rydberg, P.; Ryde, U.; Olsen, L. J. Phys. Chem. A 2008, 112, 13058-13065
96. Shvedova, A. A.; Kommineni, C.; Jeffries, B. A.; Castranova, V.; Tyurina, Y. Y.; Tyurin, V. A.; Serbinova, E. A.; Fabisiak, J. P.; Kagan, V. E. J. Invest. Dermatol. 2000, 114, 354-364
97. Ingold, K. U.; Wright, J. S. J. Chem. Educ. 2000, 77, 1062-1064
98. Bach, R. D.; Ayala, P. Y.; Schlegel, H. B. J. Am. Chem. Soc. 1996, 118, 12758-12765
99. Meunier, B.; Bernadou, J. Struct. Bonding 2000, 97, 1-35
100. Groenhof, A. R.; Ehlers, A. W.; Lammertsma, K. J. Am. Chem. Soc. 2007, 129, 6204-6209
101. Kaila, V. R. I.; Verkhovsky, M. I.; Wikström, M. Chem. Rev. 2010, 110, 7062-7081
102. Guengerich, F. P.; Miller, G. P.; Hanna, I. H.; Sato, H.; Martin, M. V. J. Biol. Chem. 2002, 277, 33711-33719
103. Krishtal, A.; Vanommeslaeghe, K.; Olatz, A.; Veszprémi, T.; van Alsenoy, C.; Geerlings, P. J. Chem. Phys. 2009, 130, 174101-174108
104. Zimmer, D.; Mazurek, J.; Petzold, G.; Bhuyan, B. K. Mutat. Res. 1980, 77, 317-326
105. Klopman, G.; Frierson, M. R.; Rosenkranz, H. S. Environ. Mutagen. 1985, 7, 625-644
106. Thompson, D. C.; Josephy, P. D.; Chu, J. W. K.; Eling, T. E. Mutat. Res. 1992, 279, 83-89
107. Trieff, N. M.; Biagi, G. L.; Ramanujam, V. M. S.; Connor, T. H.; Cantelli-Forti, G.; Guerra, M. C.; Bunce, H., III; Legator, M. S. J. Mol. Toxicol. 1989, 2, 53-65
108. Campbell, J. J.; Glover, S. A.; Hammond, G. P.; Rowbottom, C. A. J. Chem. Soc., Perkin Trans. 2 1991, 2067-2079
109. Lau, E. Y.; Felton, J. S.; Lightstone, F. C. Chem. Res. Toxicol. 2006, 19, 1182-1190
110. Wu, H.; Dombrovsky, L.; Tempel, W.; Martin, F.; Loppnau, P.; Goodfellow, G. H.; Grant, D. M.; Plotnikov, A. N. J. Biol. Chem. 2007, 282, 30189-30197
111. Qiao, Q.-A.; Yang, C.; Qu, R.; Jin, Y.; Wang, M.; Zhang, Z.; Xu, Q.; Yu, Z. Biophys. Chem. 2006, 122, 215-220
112. Grant, D. M. Curr. Drug Metab. 2008, 9, 465-470
113. Oglesby, L. A.; Hix, C.; Snow, L.; MacNair, P.; Seig, M.; Langenbach, R. Cancer Res. 1983, 43, 5194-5199
114. Ashby, J.; Paton, D.; Lefevre, P. A.; Styles, J. A.; Rose, F. L. Carcinogenesis 1982, 3, 1277-1282
115. Chung, K.-T.; Chen, S.-C.; Claxton, L. D. Mutat. Res. 2006, 612, 58-76
116. Dimethyl-4-phenylenediamine (DMPD) was shown to generate free radicals: Ben Mansour, H.; Barillier, D.; Corroler, D.; Ghedira, K.; Chekir-Ghedira, L.; Mosrati, R. Environ. Toxicol. Chem. 2009, 28, 489-495
117. Brennan, R. J.; Schiestl, R. H. Mutat. Res. 1999, 430, 37-45