Effects of the nitro-group on the mutagenicity and toxicity of some benzamines

Environmental and Molecular Mutagenesis

Volumn 27, Issue 1, 1996, Pages 67-74

  Chung, King Thom ^a   Murdock, Chris A ^a   Zhou, Yonggui ^a   Stevens Jr , S Edward ^a   Li, Ying Sing ^a   Wei, Cheng I ^b   Fernando, S Y ^b   Chou, Ming W ^c  

^a UNIVERSITY OF MEMPHIS   (United States)

^b UNIVERSITY OF FLORIDA   (United States)

^c NATIONAL CENTER FOR TOXICOLOGICAL RESEARCH   (United States)

Author keywords

Benzamines; Chromosomal aberrations; Cytotoxicity; Mutagenicity; Oxidative potential

Indexed keywords

1,2 PHENYLENEDIAMINE; ANILINE; ANILINE DERIVATIVE; AROMATIC NITRO COMPOUND; NITROREDUCTASE; PHENYLENEDIAMINE; PHENYLENEDIAMINE DERIVATIVE;

AMES TEST; ANIMAL CELL; ARTICLE; CHO CELL; CHROMOSOME ABERRATION; CONTROLLED STUDY; CYTOTOXICITY; FEMALE; MUTAGENICITY; NONHUMAN;

ANILINE COMPOUNDS; ANIMALS; BIOTRANSFORMATION; CELL SURVIVAL; CHEMISTRY, PHYSICAL; CHO CELLS; CHROMOSOME ABERRATIONS; CRICETINAE; DOSE-RESPONSE RELATIONSHIP, DRUG; MALE; MOLECULAR STRUCTURE; MUTAGENICITY TESTS; NITRO COMPOUNDS; NITROREDUCTASES; OXIDATION-REDUCTION; PHENYLENEDIAMINES; RATS; RATS, SPRAGUE-DAWLEY; SALMONELLA TYPHIMURIUM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0029930126     PISSN: 08936692     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1098-2280(1996)27:1<67::AID-EM9>3.0.CO;2-B     Document Type: Article

References (39)

1. Ames BN, Kammen HO, Yamasaki E (1975): Hair dyes are mutagenic: Identification of a variety of mutagenic ingredients. Proc Natl Acad Sci USA 72:2427-2433.
2. Calapietro M, Domenicano A, Potalone G, Schultz G, Hargittai I (1987): Molecular structure of p-diaminobenzene in the gaseous phase and in the crystal. J Physical Chem 91:1728-1737.
3. Campadre RLL, Debnat AK, Shusterman AJ, Hansch C (1990): LUMO energies and hydrophobicity as determinants of mutagenicity by nitroaromatic compounds in Salmonella typhimurium. Environ Mol Mutagen 15:44-55.
4. Cerniglia CE (1985): Metabolism of 1-nitropyrene and 6-nitrobenzo(a)-pyrene by intestinal microflora. Westmann B, Pleasents JR, Pollard M, Teah BA, Wagner M (eds): "Germfree Research: Microflora Control and Its Application to the Biomedical Sciences." New York: Alan R. Liss, pp 133-137.
5. Cerniglia CE, Howard PC, Fu P, Franklin W (1984): Metabolism of nitropolycyclic aromatic hydrocarbon by human intestinal microflora Biochem Biophy Res Commun 123:262-270.
6. Chung K-T, Cerniglia CE (1992). Mutagenicity of azo dyes: Structure-activity relationships. Mutat Res 277:201-220.
7. Chung K-T, Stevens SE Jr (1993): Degradation of azo dyes by environmental microorganisms and helminths. Environ Toxicol Chem 12:2121-2132.
8. Chung K-T, Stevens SE Jr, Cerniglia CE (1992): A review of reduction of azo dyes by intestinal microflora. Crit Rev Microbiol 18.175-390.
9. Chung K-T, Murdock CA, Stevens SE Jr, Li Y-S, Wei CI, Huang T-S, Chou MW (1995): Mutagenicity and toxicity studies of p-phenylenediamine and its derivatives. Toxicol Lett (in press).
10. Delclos KB, Cerniglia CE, Dooley KL, Campbell WL, Franklin W, Walker RP (1990). The role of intestinal microflora in the metabolic activation of 6-nitrochrysene to DNA-binding derivatives in mice. Toxicology 60:137-150.
11. Delclos KB, Herreno-Saenz D, Lai CC, Fu PP, Evans FE (1991): Formation of DNA adducts from the in vitro reaction of metabolites of 3-amino-chrysene with calf thymus DNA. Proc Am Assoc Cancer Res 32:89.
12. Dewar MJS, Thiel W (1977): Ground states of molecules. 38. The MNDO method approximations and parameters. J Am Chem Soc 99:4899-4907.
13. Fu PP (1990): Metabolism of nitropolycyclic aromatic hydrocarbons. Drug Metab Rev 22:209-268.
14. Fu PP, Chou MW, Miller MW, White GL, Heflich RH, Beland FA (1985): The orientation of the nitro-substitution predicts the direct-acting bacterial mutagenicity of nitrated polycyclic aromatic hydrocarbons. Mutat Res 143:173-182.
15. Fu PP, Heflich RH, Von Tungeln LS, Yang DTC, Fifer EK, Beland FA (1986): Effect of the nitro group conformation on the rat liver microsomal metabolism and bacterial mutagenicity of 2- and 9-nitroanthracene. Carcinogenesis 7:1819-1927.
16. Fu PP, Chou MW, Beland FA (1988): Effects of nitrosubstitution on the in vitro metabolic activation of polycyclic aromatic hydrocarbons. In Yang SK, Silverman BD (eds): "Polycyclic Aromatic Hydrocarbon Carcinogenesis: Structure-Activity Relationships," Vol II. Boca Raton: CRC Press, pp 37-65.
17. Galloway SM, Bloom AD, Resnick M, Margolin BH, Nakamura F, Archer P, Zeiger E (1985): Development of a standard protocol for in vitro cytogenetic testing with Chinese hamster ovary cells: Comparison of results of 22 compounds in two laboratories. Environ Mutagen 7:1-51.
18. Herreno-Saenz D, Evans PE, Heinze T, Lewtas J, Kadlubar FF, Fu PP (1991): In vitro metabolism and DNA adduct formation from 2-nitro-fluoranthene. Proc Am Assoc Cancer Res 32:88.
19. Howard PC, Beland FA, Cerniglia CE (1983): Reduction of the carcinogen 1-nitropyrene and 1-aminopyrene by rat intestinal bacteria. Carcinogenesis 4:985-990.
20. Jung J, Shaikh AU, Heflich RH, Fu PP (1991): Nitro group orientation, reduction potential, and direct-acting mutagenicity of nitro-polycyclic aromatic hydrocarbons. Environ Mol Mutagen 17:169-180.
21. Kadlubar FF, Fu PP, Jung H, Shaikh AU, Beland FA (1990): The metabolic N-oxidation of carcinogenic arylamines in relation to nitrogen charges density and oxidation potential. Environ Health Perspect 87:233-236
22. Lai DY, Woo Y-T, Argus MF, Arco JC (1994): Structural element consideration for assessing the carcinogens hazard/risk of new and untested aromatic amines. Toxicologist 14:134.
23. Lister DG, Tyler JK, Hog JH, Larsen NW (1974): The microwave spectrum, structure, and dipole moment of aniline. J Mol Struct 23.253-264.
24. Lowry OH, Rosebrough WJ, Farr AL, Randall RJ (1951): Protein measurement with the Folin phenol reagent. J Biol Chem 193:265-275.
25. Manning BW, Cerniglia CE, Federle TW (1986): Biotransformation of 1-nitropyrene to 1-aminopyrene and N-formyl-1-aminopyrene by the human intestinal microbiota. J Toxicol Environ Health 18:339-346.
26. Maron DM, Ames BN (1983): Revised methods for the Salmonella mutagenicity test. Mutat Res 113:173-215.
27. McCoy EC, Anders M, Rosenkranz HS (1983): The basis of the insensitivity of Salmonella typhimurium strain TA98/1,8-DNP6 to the mutagenic action of nitroarenes. Mutat Res 121:17-23.
28. Miller EC, Lotliker PD, Pitot HC, Fletcher TL, Miller JA (1966): N-hydroxy metabolites of 2-acetylaminophenanthrene and 7-fluoro-2-acetylaminofluorene as proximate carcinogens in the rat Cancer Res 26:2239-2247.
29. Oshiro Y, Piper CE, Garriott ML, Balwierz PS, Soelter SG, Rohrbacher E (1993). Genetic toxicology studies with a tumor promoter. J Appl Toxicol 13:91-101.
30. Rafii F, Franklin W, Heflich RH, Cerniglia CE (1991): Reduction of nitroaromatic compounds by anaerobic bacteria isolated from human gastrointestinal tract. Appl Environ Microbiol 57:962-968.
31. Rosenkranz HS, Poirier LA (1979): An evaluation of the mutagenicity and DNA modifying activity in microbial systems of carcinogens and non-carcinogens. JNCI 62:873-892.
32. Rosenkranz HS, Speck WT (1975): Mutagenicity of metronidazole: Activation by mammalian liver microsomes. Biochem Biophys Res Commun 66.520-525.
33. Rosenkranz HS, Speck WT (1976). Activation of nitrofurantoin to a mutagen by rat liver nitroreductase. Biochem Pharmacol 25:1555-1556.
34. Sadova NI, Penionzhkevich NP, Vilkov LV (1976): Study of molecular structure of p-nitroaniline using electron-diffraction method. Eh Struct Khim 17:1122-1123.
35. Shahin MM (1994): Structure-activity relationships within various series of p-phenylenediamine derivatives. Mutat Res 307:83-93.
36. Terasima T, Tolmach LJ (1961): Change in X-ray sensitivity of HeLa cells during the division cycle Nature 190:1210-1211.
37. Tokiwa H, Ohnishi Y (1986): Mutagenicity and carcinogenicity of nitroarenes and their sources in the environment. CRC Crit Rev Toxicol 17:23-60.
38. Wei CI, Huang TS, Fernando SY, Chung K-T (1991): Mutagenicity studies of kojic acid Toxicol Lett 59:213-220.
39. Woo Y-T, Arcos JC, Lai DY (1988): Metabolic and chemical activation of carcinogens: an overview. In Politzer P, Matin FJ Jr (eds): "Bioactive Molecules, Volume 5. Chemical Carcinogens." Amsterdam: Elsevier, pp 1-31.