From mutagenic to non-mutagenic nitroarenes: Effect of bulky alkyl substituents on the mutagenic activity of 4-nitrobiphenyl in Salmonella typhimurium. Part I. Substituents ortho to the nitro group and in 2'-position

Mutation Research - Genetic Toxicology and Environmental Mutagenesis

Volumn 467, Issue 1, 2000, Pages 55-68

  Klein, Markus ^a   Voigtmann, Ulrike ^a   Haack, Torsten ^a   Erdinger, Lothar ^b   Boche, Gernot ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

^b Hygieneinstitut Heidelberg   (Germany)

Author keywords

4 Nitrobiphenyl; Alkyl substituents; Mutagenicity; Nitroaromatics; Nitroso; Ortho; QSAR; Salmonella

Indexed keywords

ALKYL GROUP; AROMATIC NITRO COMPOUND; BIPHENYL DERIVATIVE;

ARTICLE; MUTAGEN TESTING; MUTAGENICITY; NONHUMAN; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; SALMONELLA TYPHIMURIUM;

BIPHENYL COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; MUTAGENICITY TESTS; MUTAGENS; NITRO COMPOUNDS; SALMONELLA TYPHIMURIUM;

SALMONELLA; SALMONELLA TYPHIMURIUM; TYPHIMURIUM;

EID: 0034643448     PISSN: 13835718     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1383-5718(00)00012-7     Document Type: Article

References (36)

1. Hartter D.R. The use and importance of nitroaromatic chemicals in the chemical industry. Rickert D.E. Toxicity of Nitroaromatic Compounds. 1985;1-13 Hemisphere, New York.
2. Tokiwa H., Ohnishi Y. Mutagenicity and carcinogenicity of nitroarenes and their sources in the environment. CRC Crit. Rev. Toxicol. 17:1986;23-60.
3. Tokiwa H., Sera N., Kai M., Horikawa K., Ohnishi Y. The role of nitroarenes in the mutagenicity of airborne particles indoors and outdoors. Waters M.D.et al. Genetic Toxicology of Complex Mixtures. 1990;165-172 Plenum, New York.
4. Morris H.P., Dubnik C.S., Johnson J.M. Studies of the carcinogenic action in the rat of 2-nitro, 2-amino-, 2-acetylamino-, and 2-diacetylaminofluorene after ingestion and after painting. J. Natl. Cancer Inst. 10:1950;1201-1212.
5. F.A. Beland, F.F. Kadlubar, Metabolic activation and DNA adducts of aromatic amines and nitroaromatic hydrocarbons, in C.S. Cooper, P.L. Grover (Eds.), Chemical Carcinogenesis and Mutagenesis, Handbook exp. Pharmacol. I/8, 267-325.
6. Heflich R.H., Howard P.C., Beland F.A. 1-Nitrosopyrene: an intermediate in the metabolic activation of 1-nitropyrene in Salmonella typhimurium TA1538. Mutat. Res. 149:1985;25-32.
7. Ning S., Xiaobai X. Reductive metabolism of 4-nitrobiphenyl by rat liver fraction. Carcinogenesis. 18(6):1997;1233-1240.
8. Saito K., Yamazoe Y., Kamataki T., Kato R. Mechanism of activation of proximate mutagens in ames tester strains: the acetyl-CoA dependent enzyme in Salmonella typhimurium TA98 deficient in TA98/1,8-DNP6 catalyses DNA-binding as the cause of mutagenicity. Biochem. Biophys. Res. Commun. 116:1983;141-147.
9. Sera N., Kukuhara K., Miyata N., Tokiwa H. Mutagenicity of nitrophenanthrene derivatives for Salmonella typhimurium: effects of nitroreductase and acetyltransferase. Mutat. Res. 349:1996;137-144.
10. Zhou L., Rajabzadeh M., Traficante D., Cho B.P. Conformational heterogeneity of arylamine-modified DNA: 19F evidence. J. Am. Chem. Soc. 119:1997;5384-5389.
11. Hecht S.S., El-Bayoumy K., Tulley L., LaVoie E. Structure-mutagenicity relationships of N-oxidised derivatives of aniline, o-toluidine, 2′-methyl-4-aminobiphenyl, and 3,2′-dimethyl-4-aminobiphenyl. J. Med. Chem. 22:1979;981-987.
12. Nohara M., Hirayama T., Fujioka Y., Ozasa S., Ibucki E., Fukui S. Relationship between mutagenic potency in Salmonella typhimurium and chemical structure of amino- and nitro-substituted biphenyls. Mutat. Res. 149:1985;9-15.
13. Vance W.A., Levin D.E. Structural features of nitroaromatics that determine mutagenic activity in Salmonella typhimurium. Environ. Mutagen. 6:1984;797-811.
14. Fu P.P., Chou M.W., Miller D.W., White G.L., Heflich R.H., Beland F.A. The orientation of the nitro-substituent predicts the direct-acting bacterial mutagenicity of nitrated polycyclic aromatic hydrocarbons. Mutat. Res. 143:1985;173-181.
15. Fu P.P., Chou M.W., Beland F.A. Effects of nitro substitution on the in vitro metabolic activation of polycyclic aromatic hydrocarbons. Yang S.K., Silverman B.D. Polycyclic Aromatic Hydrocarbon Carcinogenesis: Structure-Activity Relationships. 1988;37-65 CRC Press, Boca Raton, FL.
16. Jung H., Shaikh A.U., Heflich R.H., Fu P.P. Nitro group orientation, reduction potential and direct-acting mutagenicity of nitro-polycyclic aromatic hydrocarbons. Environ. Mol. Mutagen. 17:1991;169-180.
17. El-Bayoumy K., LaVoie E.J., Tulley-Freiler L., Hecht S.S. Effects of ortho-methyl substituents on the mutagenicity of aminobiphenyls and aminonaphthalenes. Mutat. Res. 90:1981;345-354.
18. El-Bayoumy K., Vavoie E.J., Hecht S.S., Fow E.A., Hoffmann D. The influence of methyl substitution on the mutagenicity of nitronaphthalenes and nitrobiphenyls. Mutat. Res. 81:1981;143-153.
19. Ashby J., Paton D., Lefevre P.A., Styles J.A., Rose F.L. Evaluation of two suggested methods of deactivating organic carcinogens by molecular modification. Carcinogenesis. 3:1982;1283-1287.
20. Debnath A.K., Lopez de Compadre R.L., Debnath G., Shusterman A.J., Hansch C. Structure-activity relationship of mutagenic aromatic and hetreoaromatic nitro compounds. Correlation with molecular orbital energies and hydrophobicity. J. Med. Chem. 34:1991;786-797.
21. Debnath A.K., Lopez de Compadre R.L., Shusterman A.J., Hansch C. Quantitative structure-activity relationship investigation of the role of hydrophobicity in regulating mutagenicity in the ames test: 2. Mutagenicity of aromatic and heteroaromatic nitro compounds in Salmonella typhimurium TA100. Environ. Mol. Mutagen. 19:1992;53-70.
22. Jendrella H., Granzer E., Kerekjarto B.v. Synthesis and biological activity of new HMG-CoA reductase inhibitors: 3. Lactones of phenoxy-3,5-dihydroxyhexanoic acids. J. Med. Chem. 34:1991;2962-2983.
23. Voigtmann U. Mutagenitätsuntersuchungen an ortho-alkylierten 4-nitrobiphenylen. Diplomarbeit. 1996;Philipps-Universität Marburg.
24. Suzuki A., Watanabe T., Miyaura N. Synthesis of sterically hindered biaryls via the palladium-catalysed cross-coupling reaction of arylboronic acids or their esters with haloarenes. Synlett. 1992;207-210.
25. Klein M. Mutagenitätsuntersuchungen an substituierten 4-nitrobiphenylen. Diplomarbeit. 1997;Philipps-Universität Marburg.
26. Calo V., Lopez L. A selective bromination of aromatic amines. J. Chem. Soc. C. 1971;3652-3653.
27. Krohn K., Küpke J., Rieger H. Zirkonium katalysierte oxidation von primären aromatischen Aminen zu nitroverbindungen mit tert-butylhydroperoxid. J. Prakt. Chem. 339:1997;335-339.
28. 2O)(HMPA). Chem. Commun. 1993;1510-1511.
29. Hesse M., Meier H., Zeeh B. Spektrokopische Methoden in der Organischen Chemie. 1991;248 Georg. Thieme Verlag, Stuttgart.
30. France H., Heilborn I.M., Hey D.H. Studies in the Terphenyl Series: Part II. Hydroxy- and Methyl-p-terphenyls. J. Chem. Soc. 1939;1283-1287.
31. Dewar M.J.S., Zoebisch E.G., Healy E.F., Stewart J.J.P. AM1: a new general purpose quantum mechanical molecular model. J. Am. Chem. Soc. 107:1985;3902-3909.
32. Maron D.M., Ames B.N. Revised methods for the Salmonella mutagenicity test. Mutat. Res. 113:1983;173-215.
33. Numann M., Schenk H., Döpp D. Structure of 1,3,5-triisopropyl-2-nitrobenzene. Acta Crystallogr., Sect. C. 51:1995;260-266.
34. DeRidder J.A., Schenk H., Döpp D. 1,5-Di-tert-butyl-2,4-dinitrobenzene. Acta Crystallogr., Sect. C. 49:1993;1970-1974.
35. Chiu C.W., Lee L.H., Wang C.Y., Bryan G.T. Mutagenicity of some commercially available nitro compounds for Salmonella typhimurium. Mutat. Res. 58:1978;11-22.
36. Klein M, Erdinger L., Boche G. From mutagenic to non-mutagenic nitroarenes: effect of bulky alkyl substituents on the mutagenic activity of nitroaromatics in Salmonella typhimurium. Part II. Substituents far away from the nitro group. Mutat. Res. 467:2000;69-82. this issue.