Radical model of arsenic(III) toxicity: Theoretical and EPR spin trapping studies

Chemical Research in Toxicology

Volumn 27, Issue 5, 2014, Pages 765-774

  Zamora, Pedro L ^a   Rockenbauer, Antal ^b   Villamena, Frederick A ^a  

^a THE OHIO STATE UNIVERSITY COLLEGE OF MEDICINE   (United States)

^b BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

5,5 DIMETHYL 1 PYRROLINE 1 OXIDE; ARSENIC ACID DERIVATIVE; ARSENIC TRIOXIDE; DIMETHYLARSINOUS ACID; HYDROXIDE; MONOMETHYLARSONOUS ACID; OXYGEN; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG; ARSENOUS ACID DERIVATIVE; CACODYLIC ACID; ORGANOMETALLIC COMPOUND;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; DRUG TOXICITY; ELECTRON SPIN RESONANCE; ENTHALPY; METHYLATION; OXIDATION REDUCTION STATE; RADICAL REACTION; SPIN TRAPPING; THEORETICAL STUDY; TOXICITY TESTING; ANALOGS AND DERIVATIVES; CHEMISTRY; HUMAN; METABOLISM; PROCEDURES; TOXICITY;

ARSENITES; CACODYLIC ACID; ELECTRON SPIN RESONANCE SPECTROSCOPY; HUMANS; MODELS, MOLECULAR; ORGANOMETALLIC COMPOUNDS; REACTIVE OXYGEN SPECIES; SPIN TRAPPING;

EID: 84901019264     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx4004227     Document Type: Article

References (65)

1. Morales, K. H., Ryan, L., Kuo, T. L., Wu, M. M., and Chen, C. J. (2000) Risk of internal cancers from arsenic in drinking water Environ. Health Perspect. 108, 655-661 (Pubitemid 30657871)
2. States, J. C., Srivastava, S., Chen, Y., and Barchowsky, A. (2009) Arsenic and cardiovascular disease Toxicol. Sci. 107, 312-323
3. Vahidnia, A., van der Voet, G. B., and de Wolff, F. A. (2007) Arsenic neurotoxicity - a review Hum. Exp. Toxicol. 26, 823-832 (Pubitemid 350221398)
4. Argos, M., Kalra, T., Rathouz, P. J., Chen, Y., Pierce, B., Parvez, F., Islam, T., Ahmed, A., Rakibuz-Zaman, M., Hasan, R., Sarwar, G., Slavkovich, V., van Geen, A., Graziano, J., and Ahsan, H. (2010) Arsenic exposure from drinking water, and all-cause and chronic-disease mortalities in Bangladesh (HEALS): a prospective cohort study Lancet 376, 252-258
5. Mandal, B. K. and Suzuki, K. T. (2002) Arsenic round the world: a review Talanta 58, 201-235 (Pubitemid 34857394)
6. Hughes, M. F. (2002) Arsenic toxicity and potential mechanisms of action Toxicol. Lett. 133, 1-16 (Pubitemid 34655541)
7. Zakharyan, R. A., Sampayo-Reyes, A., Healy, S. M., Tsaprailis, G., Board, P. G., Liebler, D. C., and Aposhian, H. V. (2001) Human monomethylarsonic acid (MMA(V)) reductase is a member of the glutathione-S-transferase superfamily Chem. Res. Toxicol. 14, 1051-1057 (Pubitemid 32800161)
8. Vahter, M. and Concha, G. (2001) Role of metabolism in arsenic toxicity Pharmacol. Toxicol. 89, 1-5 (Pubitemid 32664563)
9. Hernandez, A., Xamena, N., Surralles, J., Sekaran, C., Tokunaga, H., Quinteros, D., Creus, A., and Marcos, R. (2008) Role of the Met(287) Thr polymorphism in the AS3MT gene on the metabolic arsenic profile Mutat. Res. 637, 80-92 (Pubitemid 350256765)
10. Aposhian, H. V., Gurzau, E. S., Le, X. C., Gurzau, A., Healy, S. M., Lu, X., Ma, M., Yip, L., Zakharyan, R. A., Maiorino, R. M., Dart, R. C., Tircus, M. G., Gonzalez-Ramirez, D., Morgan, D. L., Avram, D., and Aposhian, M. M. (2000) Occurrence of monomethylarsonous acid in urine of humans exposed to inorganic arsenic Chem. Res. Toxicol. 13, 693-697 (Pubitemid 30663445)
11. 3 combination yields a high quality remission and survival in newly diagnosed acute promyelocytic leukemia Proc. Natl. Acad. Sci. U.S.A. 101, 5328-5335 (Pubitemid 38481160)
12. Soignet, S. L., Maslak, P., Wang, Z. G., Jhanwar, S., Calleja, E., Dardashti, L. J., Corso, D., DeBlasio, A., Gabrilove, J., Schienberg, D. A., and Pandolfi, P. P. (1998) Complete remission after treatment of acute promyelocytic leukemia with arsenic trioxide N. Engl. J. Med. 339, 1341-1348 (Pubitemid 28509343)
13. Liu, S. X., Athar, M., Lippai, I., Waldren, C., and Hei, T. K. (2001) Induction of oxyradicals by arsenic: implication for mechanism of genotoxicity Proc. Natl. Acad. Sci. U.S.A. 98, 1643-1648 (Pubitemid 32165551)
14. Naranmandura, H., Carew, M. W., Xu, S., Lee, J., Leslie, E. M., Weinfeld, M., and Le, X. C. (2011) Comparative toxicity of arsenic metabolites in human bladder cancer EJ-1 cells Chem. Res. Toxicol. 24, 1586-1596
15. Shi, H., Shi, X., and Liu, K. J. (2004) Oxidative mechanism of arsenic toxicity and carcinogenesis Mol. Cell. Biochem. 255, 67-68
16. Nesnow, S., Roop, B. C., Lambert, G., Kadiiska, M., Mason, R. P., Cullen, W. R., and Mass, M. J. (2002) DNA damage induced by methylated trivalent arsenicals is mediated by reactive oxygen species Chem. Res. Toxicol. 15, 1627-1634 (Pubitemid 36008211)
17. Kojima, C., Ramirez, D. C., Tokar, E. J., Himeno, S., Drobna, Z., Styblo, M., Mason, R. P., and Waalkes, M. P. (2009) Requirement of arsenic biomethylation for oxidative DNA damage J. Natl. Cancer Inst. 101, 1670-1681
18. Frisch, M. J., (2010) Gaussian 09, revision C.01, Gaussian, Inc., Wallingford, CT.
19. Labanowski, J. W. and Andzelm, J. (1991) Density Functional Methods in Chemistry, Springer, New York.
20. Parr, R. G. and Yang, W. (1989) Density Functional Theory in Atoms and Molecules, Oxford University Press, New York.
21. Becke, A. D. (1988) Density-functional exchange-energy approximation with correct asymptotic behavior Phys. Rev. A 38, 3098-3100
22. Becke, A. D. (1993) A new mixing of Hartree-Fock and local density-functional theories J. Chem. Phys. 98, 1372-1377
23. Hehre, W. J., Radom, L., Schleyer, P. V., and Pople, J. A. (1986) Ab Initio Molecular Orbital Theory, John Wiley & Sons, New York.
24. Lee, C., Yang, W., and Parr, R. G. (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Phys. Rev. B: Condens. Matter 37, 785-789
25. Reed, A. E., Curtiss, L. A., and Weinhold, F. (1988) Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint Chem. Rev. 88, 899-926
26. Barone, V., Cossi, M., and Tomasi, J. (1997) A new definition of cavities for the computation of solvation free energies by the polarizable continuum model J. Chem. Phys. 107, 3210-3221 (Pubitemid 127568937)
27. Barone, V., Cossi, M., and Tomasi, J. (1998) Geometry optimization of molecular structures in solution by the polarizable continuum model J. Comput. Chem. 19, 404-417 (Pubitemid 128573764)
28. Cossi, M., Barone, V., Cammi, R., and Tomasi, J. (1996) Ab initio study of solvated molecules: a new implementation of the polarizable continuum model Chem. Phys. Lett. 255, 327-335 (Pubitemid 126163033)
29. Tomasi, J., Mennucci, B., and Cammi, R. (2005) Quantum mechanical continuum solvation models Chem. Rev. 105, 2999-3094
30. Tomasi, J. and Persico, M. (1994) Molecular interactions in solution: an overview of methods based on continuous distributions of the solvent Chem. Rev. 94, 2027-2094 (Pubitemid 124000195)
31. Bauza, A., Alkorta, I., Frontera, A., and Elguero, J. (2011) On the reliability of pure and hybrid DFT methods for the evaluation of halogen, chalcogen, and pnicogen bonds involving anionic and neutral electron donors J. Chem. Theory Comput. 9, 5201-5210
32. 2As=O free radical J. Chem. Phys. 131, 114310
33. Rassolov, V. A., Ratner, M. A., Pople, J. A., Redfern, P. C., and Curtiss, L. A. (2001) 6-31G* basis set for third-row atoms J. Comput. Chem. 22, 976-984 (Pubitemid 32455735)
34. Scott, A. P. and Radom, L. (1996) Harmonic vibrational frequencies: An evaluation of Hartree-Fock, Møller-Plesset, quadratic configuration interaction, density functional theory, and semiempirical scale factors J. Phys. Chem. 100, 16502-16513 (Pubitemid 126787989)
35. Cullen, W. R., McBride, B. C., Manji, H., Pickett, A. W., and Reglinski, J. (1989) The metabolism of methylarsine oxide and sulfide Appl. Organomet. Chem. 3, 71-78
36. Scott, N., Hatlelid, K. M., MacKenzie, N. E., and Carter, D. E. (1993) Reactions of arsenic(III) and arsenic(V) species with glutathione Chem. Res. Toxicol. 6, 102-106 (Pubitemid 23040380)
37. Burrows, G. J. and Turner, E. E. (1920) A new type of compound containing arsenic J. Chem. Soc., Trans. 117, 1373-1383
38. Rockenbauer, A. and Korecz, L. (1996) Automatic computer simulations of ESR spectra Appl. Magn. Reson. 10, 29-43 (Pubitemid 126675693)
39. Xie, R., Johnson, W., Spayd, S., Hall, G. S., and Buckley, B. (2006) Arsenic speciation analysis of human urine using ion exchange chromatography coupled to inductively coupled plasma mass spectrometry Anal. Chim. Acta 578, 186-194 (Pubitemid 44396928)
40. Kao, W. H. and Kuwana, T. (1984) Electrochemical oxidation of arsenious acid at a platinum electrode J. Electroanal. Chem. Interfacial Electrochem. 169, 167-179 (Pubitemid 14632025)
41. 4] Organometallics 10, 3764-3766
42. 2 suspension: kinetics and mechanisms Environ. Sci. Technol. 36, 3872-3878 (Pubitemid 35006344)
43. 2As=O, the prototypical arsenyl free radical J. Chem. Phys. 131, 114311
44. Cullen, W. R., McBride, B. C., and Reglinski, J. (1984) The reaction of methylarsenicals with thiols: some biological implications J. Inorg. Biochem. 21, 179-194
45. Leyssens, T. and Peeters, D. (2004) Theoretical study of the influence of phosphorus containing substituents on organic molecules J. Mol. Struct. 686, 71-82
46. Egorochkin, A. N., Kuznetsova, O. V., Khamaletdinova, N. M., and Domratcheva-Lvova, L. G. (2013) Toxicity of organometallic compounds: Correlation analysis via substituent constants J. Organomet. Chem. 735, 88-92
47. - in aqueous solution J. Phys. Chem. Ref. Data 17, 513
48. Klaening, U. K., Bielski, B. H. J., and Sehested, K. (1989) Arsenic(IV). A pulse-radiolysis study Inorg. Chem. 28, 2717-2724
49. 2: Is superoxide the main oxidant in normal air-saturated aqueous solutions? Environ. Sci. Technol. 45, 4532-4539
50. 17O-enriched oxygen Can. J. Chem. 56, 2163-2166 (Pubitemid 9013858)
51. Yamanaka, K., Hoshino, M., Okamoto, M., Sawamura, R., Hasegawa, A., and Okada, S. (1990) Induction of DNA damage by dimethylarsine, a metabolite of inorganic arsenics, is for the major part likely due to its peroxyl radical Biochem. Biophys. Res. Commun. 168, 58-64 (Pubitemid 20142585)
52. Hug, S. J. and Leupin, O. (2003) Iron-catalyzed oxidation of arsenic(III) by oxygen and by hydrogen peroxide: pH-Dependent formation of oxidants in the Fenton reaction Environ. Sci. Technol. 37, 2734-2742 (Pubitemid 36706016)
53. Mass, M. J., Tennant, A. H., Roop, B. C., Cullen, W. R., Styblo, M., Thomas, D. J., and Kligerman, A. D. (2001) Methylated trivalent arsenic species are genotoxic Chem. Res. Toxicol. 14, 355-361 (Pubitemid 32367468)
54. Petrick, J. S., Ayala-Fierro, F., Cullen, W. R., Carter, D. E., and Vasken Aposhian, H. (2000) Monomethylarsonous acid (MMA(III) is more toxic than arsenite in Chang human hepatocytes Toxicol. Appl. Pharmacol. 163, 203-207 (Pubitemid 30152096)
55. 50 in hamsters and in vitro inhibition of pyruvate dehydrogenase Chem. Res. Toxicol. 14, 651-656 (Pubitemid 32565713)
56. Muniz Ortiz, J. G., Wallace, K. A., Leinisch, F., Kadiiska, M. B., Mason, R. P., and Kligerman, A. D. (2013) Catalase has a key role in protecting cells from the genotoxic effects of monomethylarsonous acid: a highly active metabolite of arsenic Environ. Mol. Mutagen. 54, 317-326
57. Zhang, W., Xue, J., Ge, M., Yu, M., Liu, L., and Zhang, Z. (2013) Resveratrol attenuates hepatotoxicity of rats exposed to arsenic trioxide Food. Chem. Toxicol. 51, 87-92
58. Kumazaki, M., Ando, H., Kakei, M., Ushijima, K., Taniguchi, Y., Yoshida, M., Yamato, S., Washino, S., Koshimizu, T. A., and Fujimura, A. (2013) a-Lipoic acid protects against arsenic trioxide-induced acute QT prolongation in anesthetized guinea pigs Eur. J. Pharmacol. 705, 1-10
59. 3 oxidation by vitamin C: cell culture studies Biometals 25, 103-113
60. Ramanathan, K., Anusuyadevi, M., Shila, S., and Panneerselvam, C. (2005) Ascorbic acid and alpha-tocopherol as potent modulators of apoptosis on arsenic induced toxicity in rats Toxicol. Lett. 156, 297-306 (Pubitemid 40292803)
61. Aposhian, H. V., Zakharyan, R. A., Avram, M. D., Kopplin, M. J., and Wollenberg, M. L. (2003) Oxidation and detoxification of trivalent arsenic species Toxicol. Appl. Pharmacol. 193, 1-8 (Pubitemid 37373761)
62. Bailey, K. A., Hester, S. D., Knapp, G. W., Owen, R. D., and Thai, S.-F. (2010) Gene expression of normal human epidermal keratinocytes modulated by trivalent arsenicals Mol. Carcinog. 49, 981-998
63. Chen, Y. C., Lin-Shiau, S. Y., and Lin, L. K. (1998) Involvement of reactive oxygen species and caspase 3 activation in arsenite-induced apoptosis J. Cell. Physiol. 177, 324-333
64. Wang, T. S., Kuo, C. L., Jan, K. Y., and Huang, H. (1996) Arsenite induces apoptosis in Chinese hamster ovary cells by generation of reactive oxygen species J. Cell. Physiol. 169, 256-268 (Pubitemid 26389031)
65. Thomas, D. J., Li, J., Waters, S. B., Xing, W., Adair, B. M., Drobna, Z., Devesa, V., and Styblo, M. (2007) Arsenic (+3 oxidation state) methyltransferase and the methylation of arsenicals Exp. Biol. Med. 232, 3-13 (Pubitemid 46089936)