PREDICTION OF THE METABOLISM AND TOXICOLOGICAL PROFILES OF GASOLINE OXYGENATES

References

• Alarie, Y. 1966. Irritating properties of airborne materials to the upper respiratory tract. Arch. Environ. Health 13:433–449.
   PubMed Web of Science ®Google Scholar
• Alarie, Y. 1973. Sensory irritation by airborne chemicals. Crit. Rev. Toxicol. 2:299–366.
   Google Scholar
• Alarie, Y. 1981. Bioassay for evaluating the potency of airborne sensory irritants and predicting acceptable levels of exposure in man. Food Cosmet. Toxicol. 19:623–626.
   PubMedGoogle Scholar
• Ashby, J., and Morrod, R. S. 1991. Detection of human carcinogens. Nature 352:185–186.
   PubMed Web of Science ®Google Scholar
• Ashby, J., and Tennant, R. W. 1988. Chemical structure, Salmonella mutagenicity and extent of carcinogenicity as indicators of genotoxic carcinogenesis among 222 chemicals tested in rodents by the U.S. NCl/NTP. Mutat. Res. 204:17–115.
   PubMed Web of Science ®Google Scholar
• Ashby, J., and Tennant, R. W. 1991. Definitive relationships among chemical structure, carcino-genicity and mutagenicity for 301 chemicals tested by the U.S. NTP. Mutat. Res. 257:229–306.
   PubMed Web of Science ®Google Scholar
• Ashby, J., Tennant, R. W., Zeiger, E., and Stasiewicz, S. 1989. Classification according to chemi-cal structure, mutagenicity to Salmonella and level of carcinogenicity of a further 42 chemi-cals tested for carcinogenicity by the U.S. National Toxicology Program. Mutat. Res. 223:73–103.
   PubMed Web of Science ®Google Scholar
• Bartsch, H., and Malaveille, C. 1989. Prevalence of genotoxic chemicals among animal and human carcinogens evaluated in the IARC Monograph Series. Cell Biol. Toxic. 5:115–127.
   PubMed Web of Science ®Google Scholar
• Belpoggi, F., Soffritti, M., and Maltoni, M. 1995. Methyl-tertiary-butyl ether (MTBE)-a gasoline additive-causes testicular and lymphohaematopoietic cancers in rats. Toxicol. Ind. Health 11:119–149.
   PubMed Web of Science ®Google Scholar
• Benezra, C., Sigman, C. C., Baghiri, D., Fraginials, R., and Maiback, H. I. 1992. Molecular aspects of allergic contact dermatitis. In Textbook of Contact Dermatitis, eds. R. J. G. Rycroft, J. Menne, P. J. Frosch, C. Benezra, pp. 105–119. Berlin: Springer Verlag.
   Google Scholar
• Briggs, G. G., Freeman, R. K., and Yaffe, S. J. 1990. Drugs in pregnancy and lactation: A refer-ence guide to fetal and neonatal risk, 3rd ed. Baltimore: Williams and Wilkins.
   Google Scholar
• Cinelli, S., Ciliutti, P., Falezza, A., Mele, C., Caserta, L., Marchetti, S., Seebert, A. H., and Vericat, J. A. 1992. Absence of mutagenicity of methyl-tertiary-butyl ether. Toxicol. Lett. Suppl. 1:300.
   Google Scholar
• Costantini, M. G. 1993. Health effects of oxygenated fuels. Environ. Health Perspect. 101:151–160.
   PubMed Web of Science ®Google Scholar
• Cunningham, A., Klopman, G., and Rosenkranz, H. S. 1996. A study of the structural basis of the carcinogenicity of tamoxifen, toremifene and their metabolites. Mutat. Res. 349:85–94.
   PubMed Web of Science ®Google Scholar
• Draize, J. H., Woodward, G., and Calvery, H. 0. 1944. Methods for study of irritation and tox-icity of substances applied topically to the skin and mucous membranes.]. Pharmacol. Exp. Ther. 82:377–381.
   Web of Science ®Google Scholar
• Dunkel, V. C., Zeiger, E., Brusick, D., McCoy, E. C., McGregor, D., Mortelmans, K., Rosenkranz, H. S., and Simmon, V. F. 1984. Reproducibility of microbial mutagenicity assays: I. Tests with Salmonella typhimurium and Escherichia coli using standardized protocol. Environ. Mutagen. 6\(suppl. 2):1–254.
   Google Scholar
• Dunkel, V. C., Zeiger, E., Brusick, D., McCoy, E., McGregor, D., Mortelmans, K., Rosenkranz, H. S., and Simmon, V. F. 1985. Reproducibility of microbial mutagenicity assays: II. Testing of carcinogens and noncarcinogens in Salmonella typhimurium and Escherichia coll. Environ. Mutagen. 7\(suppl. 5):1–248.
   Google Scholar
• Ennever, F. K., Noonan, T. J., and Rosenkranz, H. S. 1987. The predictivity of animal bioassays and short-term genotoxicity tests for carcinogenicity and non-carcinogenicity to humans. Mutagenesis 2:73–78.
   PubMed Web of Science ®Google Scholar
• Friedman, J. M., and Polifka, J. E. 1995. Tens and Shepard Catalog. (Available from the Johns Hopkins University Press).
   Google Scholar
• Gold, L. S., Sawyer, C. B., Magaw, R., Backman, G. M., de Veciana, M., Levinson, R., Hooper, N. K., Havender, W. R., Bernstein, L., Peto, R., Pike, M. C., and Ames, B. N. 1984. A carcinogenic potency database of the standardized results of animal bioassays. Environ. Health Perspect. 58:9–319.
   PubMed Web of Science ®Google Scholar
• Gold, L. S., de Veciana, M., Backman, G. M., Magaw, R., Lopipero, P., Smith, M., Blumenthal, M., Levinson, R., Bernstein, L., and Ames, B. N. 1986. Chronological supple-ment to the Carcinogenic Potency Database: Standardized results of animal bioassays pub-lished through December 1982. Environ. Health Perspect. 67:161–200.
   PubMed Web of Science ®Google Scholar
• Gold, L. S., Slone, T. H., Backman, G. M., Magaw, R., Da Costa, M., Lopipero, P., Blumenthal, M., and Ames, B. N. 1987. Second chronological supplement to the Carcinogenic Potency Database: Standardized results of animal bioassays published through December 1984 and by the National Toxicology Program through May 1986. Environ. Health Perspect. 74:237–329.
   PubMed Web of Science ®Google Scholar
• Gold, L. S., Slone, T. H., Backman, G. M., Eisenberg, S., Da Costa, M., Wong, M., Manley, N. B., Rohrbach, L., and Ames, B. N. 1990. Third chronological supplement to the Carcinogenic Potency Database: Standardized results of animal bioassays published through December 1986 and by the National Toxicology Program through June 1987. Environ. Health Perspect. 84:215–286.
   PubMed Web of Science ®Google Scholar
• Gold, L. S., Manley, N. B., Slone, T. H., Garfinkel, G. B., Rohrbach, L., and Ames, B. N. 1993. The fifth plot of the Carcinogenic Potency Database: Results of animal bioassays pub-lished in the general literature through 1988 and by the National Toxicology Program through 1989. Environ. Health Perspect. 100:65–135.
   PubMed Web of Science ®Google Scholar
• Graham, C., Gealy, R., Macina, 0. T., Karol, M. H., and Rosenkranz, H. S. 1996. QSAR for allergic contact dermatitis. Quant. Struct. Activ. Re/at. 15:224-229. Health Effects Institute. 1996. The potential health effects of oxygenates added to gasoline. A review of the current literature. Cambridge, MA: NEI.
   Google Scholar
• IARC. 1987. Overall evaluation of carcinogenicity: An updating of IARC Monographs Volume 1 to 42. Monogr. EvaL Carcinogen. Risks Hum. Genetic and Related Effects, Suppl. 7. Lyon: IARC. IARC. 1994. Some industrial chemicals. IARC Monogr. Eva'. Carcinogen. Risks Hum. 60:139. Lyon: ARC.
   Google Scholar
• Jelovsek, F. R., Mattison, D. R., and Chen, J. J. 1989. Prediction of risk for human developmen-tal toxicity: how important are animal studies for hazard identification. Obstet. Gynecol. 74:624–636.
   PubMed Web of Science ®Google Scholar
• Jelovsek, F. R., Mattison, D. R., and Young, J. F. 1990. Eliciting principles of hazard identifica-tion from experts. Teratology 42:521–533.
   Google Scholar
• Klopman, G. 1984. Computer automated structure evaluation of organic molecules.]. Am. Chem. Soc. 106:7315–7324.
   Web of Science ®Google Scholar
• Klopman, G. 1992. MULTICASE 1. A hierarchical computer automated structure evaluation pro-gram. Quant. Struct. Active Re/at. 11:176–184.
   Google Scholar
• Klopman, G., Pichelintsev, D., Frierson, M., Pennisi, S., Renskers, K., and Dickens, M. 1993. Multiple computer automated structure evaluation methodology as an alternative to in vivo eye irritation testing. Alternatives to LaboratoryAnimals 21:14–27.
   Web of Science ®Google Scholar
• Klopman, G., Dimayuga, M., and Talafons, J. 1994. META. 1. A program for the evaluation of metabolic transformation of chemicals./ Chem. Inf. Comput. ScL 34:1320–1325.
   Google Scholar
• Klopman, G., Zhang, Z., Balthasar, D. M., and Rosenkranz, H. S. 1995. Computer-automated prediction of aerobic biodegradation transformation in the environment. Environ. Toxicol. Chem. 14:395–403.
   Web of Science ®Google Scholar
• Macina, 0. T., Klopman, G., and Rosenkrantz, H. S. 1997. Structural basis of sensory irritation. Inhal. Tox., in press.
   Google Scholar
• Macina, 0. T., Zhang, Y. P., and Rosenkranz, H. S. 1997. Improved predictivity of carcinogens: The use of a battery of SAR models. In Testing, predictingand interpretingcarcinogenicity, ed. K. T. Kitchin. New York: Marcel Dekker.
   Google Scholar
• Mattison, D. R., Ghanooni, M., Zhang, Y. P., Macina, 0. T., and Rosenkranz, H. S. 1997. Structural determinants associated with risk of developmental toxicity in humans. J. Am. CynecoL Obstet. Soc., in press.
   Google Scholar
• Mersch-Sundermann, V., Klopman, G., and Rosenkranz, H. S. 1992. Structural requirements for the induction of the SOS repair in bacteria by nitrated polycyclic aromatic hydrocarbons & related chemicals. Mutat. Res. 265:61–73.
   Google Scholar
• Mortelmans, K., Haworth, S., Lawlor, T., Speck, W. T., Tainer, B., and Zeiger, E. 1986. Salmonella mutagenicity tests. II. Results from the testing of 270 chemicals. Environ. Mutagen. 8:1–119.
   PubMedGoogle Scholar
• National Toxicology Program. 1994. NTP Technical Report on the Toxicology and Carcinogenesis Studies of t-Butyl Alcohol. NTP TR 436. NIH Publication No. 94–3167. NTP. Research Triangle Park, NC.
   Google Scholar
• Rosenkranz, H. S., and Klopman, G. 1990a. The structural basis of the mutagenicity of chemi-cals in Salmonella typhimurium: The National Toxicology Program data base. Mutat. Res. 228:51–80.
   PubMed Web of Science ®Google Scholar
• Rosenkranz, H. S., and Klopman, G. 1990b. Structural basis of carcinogenicity in rodents of genotoxicants and non-genotoxicants. Mutat. Res. 228:105–124.
   PubMed Web of Science ®Google Scholar
• Rosenkranz, H. S., and Klopman, G. 1995. The application of structural concepts to the predic-tion of the carcinogenicity of therapeutic agents. In Burger's medicinal chemistry and drug dis-covery, 5th ed., vol. 1, Principles and practice, ed. M. E. Wolff, pp. 223–249. New York: John Wiley & Sons.
   Google Scholar
• Rosenkranz, H. S., Ennever, F. K., Dimayuga, M., and Klopman, G. 1990. Significant differences in the structural basis of the induction of sister chromatid exchanges and chromosomal aberrations in Chinese hamster ovary cells. Environ. MoL Mutagen. 16:149–177.
   PubMed Web of Science ®Google Scholar
• Rosenkranz, H. S., Takihi, N., and Klopman, G. 1991. Structure activity-based predictive toxicol-ogy: An efficient and economical methods for generating non-congeneric data bases. Mutagenesis 6:391–394.
   Google Scholar
• Schaper, M. 1993. Development of a data base for sensory irritants and its use in establishing occupational exposure limits. Am. Ind. Hyg. Assoc. J. 54:488–544.
   PubMed Web of Science ®Google Scholar
• Scheper, R. J., and von Blomberg, M. E. 1996. Mechanisms of allergic contact dermatitis to chemicals. In Allergic hypersensitivities induced by chemicals, eds. J. G. Vos, M. Younes, and E. Smith, pp. 185–201. Boca Raton, FL: CRC Press.
   Google Scholar
• Shelby, M. D. 1988. The genetic toxicity of human carcinogens and its implications. Mutat. Res. 204:3–15.
   PubMed Web of Science ®Google Scholar
• Takihi, N., Rosenkranz, H. S., Klopman, G., and Mattison, D. R. 1994. Structural determinants of developmental toxicity. Risk Anal. 14:649–657.
   PubMed Web of Science ®Google Scholar
• Talafous, J., Sayre, L. M., Mieyal, J. J., and Klopman, G. 1994. Meta. 2. A dictionary model of mammalian xenobiotic metabolism.]. Chem. Info. Comput. ScL 34:1326–1333.
   Google Scholar
• Tennant, R. W., and Ashby, J. 1991. Classification according to chemical structure, mutagenicity to Salmonella and level of carcinogenicity of a further 39 chemicals tested for carcinogenicity by the U.S. National Toxicology Program. Mutat. Res. 257:209–227.
   PubMed Web of Science ®Google Scholar
• Tepper, J. S., Jackson, M. C., McGee, J. K., Costa, D. L., and Graham, J. A. 1994. Estimation of respiratory irritancy from inhaled methyl tertiary butyl ether in mice. InhaL ToxicoL 6:563–569.
   Web of Science ®Google Scholar
• Zeiger, E. 1987. Carcinogenicity of mutagens: Predictive capability of the Salmonella mutagenesis assay for rodent carcinogenicity. Cancer Res. 47:1287–1296.
   PubMed Web of Science ®Google Scholar
• Zeiger, E., Anderson, B., Haworth, S., Lawlor, T., Mortel mans, K., and Speck, W. 1987. Salmonella mutagenicity tests: III. Results from 255 chemicals. Environ. Mutagen. 9\(suppl. 9): 1–109.
   Google Scholar
• Zeiger, E., Anderson, B., Haworth, S., Lawlor, T., and Mortelmans, K. 1 988. Salmonella muta-genicity tests: IV. Results from the testing of 300 chemicals. Environ. MoL Mutagen. 11\(suppl. 12)1–157.
   Google Scholar
• Zhang, Y. P., Sussman, N., Macina, 0. T., Rosenkranz, H. S., and Klopman, G. 1 996. Prediction of the carcinogenicity of a second group of chemicals undergoing carcinogenicity testing. Environ. Health Perspect. 104:1045-1050.
   Google Scholar