Enzymatic and nonenzymatic production of free radicals from the carcinogens 4-nitroquinoline N-oxide and 4-hydroxylaminoquinoline N-oxide

Chemical Research in Toxicology

Volumn 12, Issue 5, 1999, Pages 450-458

  Fann, Yang C ^a   Metosh Dickey, Caroline A ^b   Winston, Gary W ^d   Sygula, Andrzej ^c   Ramakrishna Rao, D N ^a   Kadiiska, Maria B ^a   Mason, Ronald P ^a  

^a NATIONAL INSTITUTE OF ENVIRONMENTAL HEALTH SCIENCES   (United States)

^b Advanced BioSystem   (United States)

^c LOUISIANA STATE UNIVERSITY   (United States)

^d NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXYAMINOQUINOLINE 1 OXIDE; 4 NITROQUINOLINE 1 OXIDE; DIMETHYL SULFOXIDE; OXYGEN RADICAL; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE DEHYDROGENASE (UBIQUINONE);

ARTICLE; CHEMICAL CARCINOGENESIS; ELECTRON SPIN RESONANCE; ENZYME ACTIVITY; OXIDATION REDUCTION REACTION; STRUCTURE ANALYSIS;

4-HYDROXYAMINOQUINOLINE-1-OXIDE; 4-NITROQUINOLINE-1-OXIDE; CARCINOGENS; ELECTRON SPIN RESONANCE SPECTROSCOPY; FREE RADICALS; MUTAGENS; NAD(P)H DEHYDROGENASE (QUINONE); NADPH-FERRIHEMOPROTEIN REDUCTASE; SUPEROXIDE DISMUTASE; XANTHINE OXIDASE;

EID: 0032813108     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx980238p     Document Type: Article

References (66)

1. Rosenkranz, H. S., and Mermelstein, R. (1983) Mutagenicity and genotoxicity of niroarenes, all nitro-containing chemicals were not created equal. Mutat. Res. 114, 217-267.
2. Rickert, D. E. (1987) Metabolism of nitroaromatic compounds. Drug Metab. Rev. 18, 23-53.
3. Nakahara, W., Fukuoka, F., and Sugimura, T. (1957) Carcinogenic action of 4-nitroquinoline-N-oxide. Gann 48, 129-137.
4. Matsushima, T., and Sugimura, T. (1971) Metabolism. In Recent results in cancer research. Chemistry and biological action of 4-nitroquinoline N-oxide (Endo, H., Ono, T., and Sugimura, T., Eds.) pp 53-60, Springer-Verlag, Berlin.
5. Shirasu, Y. (1965) Comparative carcinogenicity of 4-nitroquinoline-1-oxide and 4-hydroxyamino-1-oxide in 3 strains of mice. Proc. Soc. Exp. Biol. Med. 118, 812-814.
6. Kawazoe, Y., Tachibana, M., Aoki, K., and Nakahara, W. (1967) The structure-carcinogenicity relationship among derivatives of 4-nitro and 4-hydroxyaminoquinoline-1-oxides. Biochem. Pharmacol. 16, 631-636.
7. Ishizawa, M., and Endo, H. (1967) On the mode of action of a potent carcinogen 4-hydroxylaminoquinoline 1-oxide on bacteriophase T4. Biochem. Pharmacol. 16, 637-646.
8. Kosuge, T., Zenda, H., and Sawanishi, H. (1969) Formation of pyridazino[3,4-c:5,6,c′]biquinoline compounds. Chem. Pharm. Bull. 17, 2389-2391.
9. Miller, E. C., and Miller, J. A. (1981) Searches for ultimate chemical carcinogens and their reactions with cellular macromoleculaes. Cancer Res. 47, 2327-2345.
10. Kataoka, N., Imamura, A., Kawazoe, Y., Chihara, G., and Nagata, C. (1966) Electron spin resonance study on the photoinduced radicals from related compounds to carcinogenic 4-nitroquinoline 1-oxide. Chem. Pharm. Bull. 14, 1171-1178.
11. Hozumi, M. (1968) Reaction of the carcinogen 4-hydroxyaminoquinoline 1-oxide with sulfhydryl groups of proteins. Biochem. Pharmacol. 17, 769-777.
12. 2 inhibition of nitroredutase. Biochem. Biophys. Res. Commun. 67, 1267-1274.
13. Winston, G. W., and Cederbaum, A. I. (1983) NADPH-dependent production of oxy radicals by purified components of the rat liver mixed function oxidase system. I. Oxidation of hydroxyl radical scavenging agents. J. Biol. Chem. 258, 1508-1513.
14. Winston, G. W., and Cederbaum, A. I. (1983) NADPH-dependent production of oxy radicals by purified components of the rat liver mixed function oxidase system II. Role in microsomal oxidation of ethanol. J. Biol. Chem. 258, 1514-1519.
15. Abramovitch, R. A., and Smith, E. M. (1975) 4-Nitrosoquinoline-1-oxide. J. Heterocycl. Chem. 12, 969-972.
16. Fetizon, M., and Golfier, M. (1968) Oxydation selective des alcools par le carbonate d'argent. C. R. Acad. Sci. Paris, Ser. C 267, 900-903.
17. Dewar, M. J. S., Zoebisch, E. G., Healy, E. F., and Stewart, J. J. P. (1985) AM1: a new general purpose quantum mechanical molecular model. J. Am. Chem. Soc. 107, 3902-3909.
18. Stewart, J. J. P. A general molecular orbital package (MOPAC) version 6.0. QCPE 455.
19. Becke, A. D. (1993) Density-Functional thermochemistry. The role of exact exchange. J. Chem. Phys. 98, 5648-5652.
20. Lee, C., Yang, W., and Parr, R. G. (1988) Development of the ColleSavletti correlation-energy formula into a functional of the electron-density. Phys. Rev. B 37, 785-789.
21. Springborg, M., Ed. (1997) Density-functional methods in chemistry and material science, John Wiley & Sons, New York.
22. Barone, V., Adamo, C., and Russo, N. (1993) Density functional approach to the structures and EPR parameters of open shell systems. The case of fluorovinyl radicals. Chem. Phys. Lett. 212, 5-11.
23. Barone, V. (1994) Inclusion of Hartree-Fock exchange in density functional methods. Hyperfine structure of second row atoms and hydrides. J. Chem. Phys. 101, 6834-6838.
24. Frisch, M. J., Trucks, G. W., Schlegel, H. B., Gill, P. M. W., Johnson, B. G., Wong, M. W., Foresman, J. B., Robb, M. A., HeadGordon, M., Reploge, E. S., Gomperts, R., Andres, J. L., Raghavachari, K., Binkley, J. S., Gonzalez, C., Martin, R. L., Fox, D. J., Defrees, D. J., Baker, J., Stewart, J. J. P., and Pople, J. A. (1993) GAUSSIAN 92/DFT, revision F.4, Gaussian Inc., Pittsburgh, PA.
25. Chipman, D. M. (1989) Gaussian basis set for calculations of spin densities in first-row atoms. Theor. Chim. Acta 76, 73-84.
26. Chipman, D. M. (1989) Calculations of spin densities in diatomic first-row hydrides. J. Chem. Phys. 91, 5455-5465.
27. Fritsch, J. M., Layloff, T. P., and Adams, R. N. (1965) Electrontransfer reactions of aromatic radical ions. J. Am. Chem. Soc. 87, 1724-1726.
28. Gamba, A., Malatesta, V., Morosi, G., Oliva, C., and Simonetta, M. (1973) Ultraviolet and electron spin resonance spectra of nitropyridines and nitropyridines N-oxide. J. Chem. Phys. 77, 2744-2752.
29. Ayscough, P. B., Sargent, F. P., and Wilson, R. (1966) Electron spin resonance studies of radicals and radical-ions in solution. Part IV. Further intermediates in the reduction of aromatic nitro- and nitroso-compounds. J. Chem. Soc. B, 903-906.
30. Shein, S. M., Starichenko, V. F., Bil'kis, I. I., Rogvik, V. M., and Belous, L. P. (1976) Formation of free radicals during the catalytic hydrogenation of aromatic nitro compounds. Zh. Org. Khim. 12, 2478-2479.
31. Kodama, M., Nagata, C., Mochizuki, M., and Masashi, O. (1978) Binding of polynucleotides with 4-nitrosoquinoline 1-oxide producing the same free radical as that produced from 4-hydroxyaminoquinoline 1-oxide. Gann 69, 285-286.
32. Kataoka, N., Imamura, A., Kawazoe, Y., Chihara, G., and Nagata, C. (1967) The structure of the free radical produced from carcingenic 4-hydroxyaminoquinoline 1-oxide. Bull. Chem. Soc. Jpn. 40, 62-68.
33. Duling, D. R. (1994) Simulation of multiple isotropic spin-trap EPR spectra. J. Magn. Reson. 104, 105-110.
34. Motten, A. G., Duling, D. R., and Schreiber, J. (1987) Proton coupling constant extraction. A fast method for analyzing ESR spectra by computer. J. Magn. Reson. 71, 34-44.
35. Duling, D. R., Motten, A. G., and Mason, R. P. (1988) Generation and evaluation of isotropic ESR spectrum simulations. J. Magn. Reson. 77, 504-511.
36. Kano, K., Uno, B., Kaida, N., Zhang, Z., Kubota, T., Takahashi, K., and Kawazoe, Y. (1987) Voltammetric and spectroscopic studies on the carcinogen 4-(hydroxyamino)quinoline N-oxide and its analogues. Chem. Pharm. Bull. 38, 1702-1714.
37. Djuric, Z., Potter, D. W., Heflich, R. H., and Beland, F. A. (1986) Aerobic and anaerobic reduction of nitrated pyrenes in vitro. Chem.-Biol. Interact. 59, 309-324.
38. Metosh-Dickey, C. A., Mason, R. P., and Winston, G. W. (1998) Single electron reduction of xenobiotic compounds by glucose oxidase from Aspergillus niger. Free Radical Biol. Med. 24, 155-160.
39. Li, A. S. W., Cummings, K. B., Roethling, H. P., Buettner, G. R., and Chignell, C. F. (1988) A spin-trapping database implemented on the IBM PC/AT. J. Magn. Reson. 79, 140-142 (the spintrapping database is available through our Internet server, http://epr.niehs.nih.gov/).
40. Buettner, G. R., and Mason, R. P. (1990) Spin-trapping methods for detecing superoxide and hydroxyl free radicals in vitro and in vivo. Methods Enzymol. 186, 127-133.
41. Buettner, G. R. (1985) Spin trapping of hydroxyl radicals. In Handbook of Methods for Oxygen Radical Research (Greenwald, R. A., Ed.) pp 151-155, CRC Press, Boca Raton, FL.
42. Kataoka, N., Shibata, S., Imamura, A., Kawazoe, Y., Chihara, G., and Nagata, C. (1967) Oxidation reaction of carcinogenic 4-hydroxyaminoquinoline 1-oxide. Chem. Pharm. Bull. 15, 220-225.
43. Cohen, M. J., and Chong, D. P. (1995) Density functional calculations of Fermi contact hyperfine coupling parameters. Chem. Phys. Lett. 234, 405-412.
44. Shepard, M. J., and Paddon-Row, M. N. (1995) Gas-phase structure of the bicyclo[2.2.1]heptane (norbornane) cation radical: a combined ab initio MO and density functional study. J. Phys. Chem. 99, 3101-3108.
45. Feller, D., and Davidson, E. R. (1988) A multireference CI determination of the Isotropic hyperfine constants for the first row atoms B-F. J. Chem. Phys. 88, 7580-7587.
46. Bauschlicher, C. W., Langhoff, S. R., Patridge, H., and Chong, D. P. (1988) Theoretical study of the nitrogen atom hyperfine coupling constant. J. Chem. Phys. 89, 2985-2992.
47. Bauschlicher, C. W. (1990) Theoretical study of the nitrogen-atom hyperfine coupling constant. II. J. Chem. Phys. 92, 518-521.
48. Mason, R. P. (1982) Free radical intermediates in the metabolism of toxic chemicals. In Free Radicals in Biology (Pryor, W. A., Ed.) Vol. V, pp 161-222, Academic Press, New York.
49. Mason, R. P., and Josephy, P. D. (1985) Free radical mechanism of nitroreductase. In Toxicity of Nitroaromatic Compounds (Rickert, D. E., Ed.) pp 121-140, Hemisphere, New York.
50. DeFlora, S., Bennicelli, C., Camoirano, A., Serra, D., and Hochstein, P. (1988) Influence of DT diaphorase on the mutagenicity of organic and inorganic compounds. Carcinogenesis 9, 611-617.
51. Okey, A. B. (1990) Enzyme induction in the cytochrome P-450 system. Pharmacol. Ther. 45, 241-298.
52. Hajos, A. K. D., and Winston, G. W. (1991) Dinitropyrene nitroreductase activity of purified NAD(P)H quinone oxidoreductase: Role in rat liver cytosol and induction by Aroclor-1254 pretreatment. Carcinogenesis 12, 697-702.
53. Hajos, A. K. D., and Winston, G. W. (1991) Purified NAD(P)H-quinone oxidoreductase enhances the mutagenicity of dinotropyrenes in vitro. J. Biochem. Toxicol. 6, 277-282.
54. Rota, C., Barr, D. P., Martin, M. V., Guengerich, F. P., Tomasi, A., and Mason, R. P. (1997) Detection of free radicals produced from the reaction of cytochrome P-450 with lineolic acid hydroperoxide. Biochem. J. 328, 565-571.
55. Abbondanza, A., Batelli, M. G., Soffritti, M., and Cessi, C. (1989) Xanthine oxidase status in ethanol-intoxicated rat liver. Alcohol: Clin. Exp. Res. 13, 841-844.
56. Howard, P. C., and Beland, F. A. (1982) Xanthine oxidase catalyzed binding of 1-nitropyrene to DNA. Biochem. Biophys. Res. Commun. 104, 727-732.
57. Djuric, Z., and McGunagle, D. L. (1989) Differences in reduction of 1,6-dinitropyrene and 1-nitro-6-nitrosopyrene by rat liver cytosolic enzymes and formation of oxygen-reactive metabolites by nitrosoreduction. Cancer Lett. 48, 13-18.
58. Ernster, L. (1969) DT-diaphorase. Methods Enzymol. 10, 309-317.
59. Brunmark, A., and Cadenas, E. (1989) Redox and addition chemistry of quinoid compounds and its biological implications. Free Radical Biol. Med. 7, 435-477.
60. Hajos, A. K. D., and Winston, G. W. (1991) Dintropyrene-nitroreduction by rat liver cytosolic DT-diaphorase: Stereoselectivity and induction by Aroclor 1254. Carcinogenesis 12, 697-702.
61. Prochaska, H. J., and Talalay, P. (1986) Purification and characterization of two isofunctional forms of NAD(P)H:quinone reductase from mouse liver. J. Biol. Chem. 261, 1372-1378.
62. Traynor, C. A., Shane, B. S., and Winston, G. W. (1988) Role of the microsomal and cytosolic fractions on the mutagenicity of dinitropyrenes (DNP) following chronic ethanol (EtOH)-ingestion. Alcohol.: Clin. Exp. Res. 12, 320.
63. Shah, A. B., Combes, R. D., and Rowland, I. R. (1990) Activation and detoxification of 1,8-dinitropyrene by mammalian hepatic fractions in the Salmonella mutagenicity assay. Mutagenesis 6, 45-49.
64. Maskos, Z., and Winston, G. W. (1993) Alcohol dehydrogense-dependent reduction of 2-nitrosofluorene and rearrangement of N-hydroxy-2-aminofluorene. Biochemistry 32, 12768-12773.
65. Maskos, Z., and Winston, G. W. (1994) Mechanism of p-nitrosophenol reduction catalyzed by horse liver and human π-alcohol dehydrogenase (ADH). Human π-ADH as a quinone reductase. J. Biol. Chem. 269, 31579-31584.
66. Garcia-Martinez, P., Hajos, A. K. D., Livingstone, D. R., and Winston, G. W. (1992) Metabolism and mutagenicity of 4-nitroquinoline N-oxide by microsomes and cytosol of digestive gland of the mussel Mytilus edulis L. Mar. Environ. Res. 34, 303-307.