Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 24, 1994 - Issue 5
68
Views
407
CrossRef citations to date
0
Altmetric
Research Article

Interaction of a series of nitriles with the alcohol-inducible isoform of P450: Computer analysis of structure—activity relationships

, &
Pages 401-408 | Received 31 Jan 1994, Published online: 22 Sep 2008

References

  • Abdul-Ahad P. G., Blair T., Webb G. A. Quantitative structure-activity study of some enzyme-inhibitory quinazolines. International Journal of Quantum Chemistry 1980; 17: 821–831
  • Brown L. P., Lewis D. F. V., Orton T. C., Flint O. P., Gibson G. G. Teratology of phenylhydantoins in an in vitro system: molecular orbital-generated quantitative structure-activity relationships. Xenobiotica 1989; 19: 1471–1481
  • Cammarata A. An apparent correlation between the in vitro activity of chloramphenicol analogues and electronic polarizability. Journal of Medicinal Chemistry 1969; 10: 515–527
  • Gibson G. G. Cytochrome P-450: from biophysics to pharmacology. Development of Drugs and Modern Medicines, J. Gorrod. Chichester, Horwood 1986; 253–266
  • Grogan J., De Vito S. C., Pearlman R. S., Korzekwa K. R. Modelling cyanide release from nitriles: prediction of cytochrome P450 mediated acute nitrile toxicity. Chemical Research in Toxicology 1992; 5: 548–552
  • Hansch C., Coats E. α-Chymotrypsin: a case study of substituent constants and regression analysis in enzyme structure-activity relationships. Journal of Pharmaceutical Science 1970; 59: 731–743
  • Ioannides C., Parke D. V. The cytochromes P-448-A unique family of enzymes involved in chemical toxicity and carcinogenesis. Biochemical Pharmacology 1987; 36: 4197–4207
  • Johannsen F. R., Levinskas G. J. Relationships between toxicity and structure of aliphatic nitriles. Fundamental and Applied Toxicology 1986; 7: 690–697
  • Kopecky J., Gut I., Nerudova J., Zachardora D., Holecek V. Metabolic study of acrylonitrile. Industrial and Environmental Xenobiotics, I. Gut, M. Cikrt, G. L. Plaa. Springer, Berlin, Heidelberg, New York 1981; 221–229
  • Leo A., Hansch C., Church C. Comparison of parameters currently used in the study of structure—activity relationships. Journal of Medicinal Chemistry 1969; 12: 314–317
  • Lewis D. F. V. Molecular orbital calculations on solvents and other small molecules: correlation between electronic and molecular properties. Journal of Computational Chemistry 1987; 8: 1084–1089
  • Lewis D. F. V. The calculation of molar polarizabilities by the CNDO/2 method: correlation with the hydrophobic parameter, log P. Journal of Computational Chemistry 1989; 10: 145–151
  • Lewis D. F. V., Ioannides C., Parke D. V. Structural requirements for substrates of cytochromes P-450 and P-448. Chemico-Biological Interactions 1987; 64: 39–60
  • Lewis D. F. V., Parke D. V. Validation of a novel molecular orbital approach (COMPACT) for the prospective safety evaluation of chemicals, by comparison with rodent carcinogenicity and Salmonella mutagenicity data evaluated by the US NCI/NPT. Mutation Research 1993; 291: 61–77
  • Lewis D. F. V., Tamburini P. P., Gibson G. G. Cytochrome P-450 spin-state equilibria and electronic structural parameters of hydrocarbons. Chemico-Biological Interactions 1986; 58: 289–299
  • Lipnick R. L. Outliers: their origin and use in the classification of molecular mechanisms of toxicity. Science of the Total Environment 1991; 109/110: 131–153
  • Nebert D. W., Gonzalez F. J. P450 genes: structure, evolution and regulation. Annual Reviews of Biochemistry 1987; 56: 945–993
  • Parke D. V., Ioannides C., Lewis D. F. V. Metabolic activation of carcinogens and toxic chemicals. Human Toxicology 1988; 7: 397–404
  • Parke D. V., Ioannides C., Lewis D. F. V. The safety evaluation of drugs and chemicals by the use of computer optimised molecular parametric analysis of chemical toxicity (COMPACT). Alternatives to Laboratory Animals 1990; 18: 91–102
  • Sabbioni G., Wild F. D. Quantitative structure-activity relationships of mutagenic aromatic and heteroaromatic azides and amines. Carcinogenesis 1992; 13: 709–713
  • Silver E. H., Kutlab S. H., Hasan T., Hassau M. Structural consideration in the metabolism of nitriles to cyanide in vivo. Drug Metabolism and Disposition 1982; 10: 495–498
  • Tanii H., Hashimoto K. Studies on the in vitro metabolism acrylamide and related compounds. Archives of Toxicology 1981; 48: 157–166
  • Tanii H., Hashimoto K. Studies on the mechanism of acute toxicity of nitriles in mice. Archives of Toxicology 1984a; 55: 47–54
  • Tanii H., Hashimoto K. Structure toxicity relationship of aliphatic nitriles. Toxicology Letters 1984b; 22: 267–272
  • Tanii H., Hashimoto H. Structure-acute toxicity relationship of dinitriles in mice. Archives of Toxicology 1985; 57: 88–93
  • Tanii H., Hashimoto K. Influence of ethanol on the in vivo and in vitro metabolism of nitriles in mice. Archives of Toxicology 1986; 58: 171–176
  • Wald R. W., Feuer G. Molecular orbital calculations on coumarins and the induction of drug-metabolising enzymes. Journal of Medicinal Chemistry 1971; 14: 1081–1084
  • Willhite C. C., Smith R. P. The role of cyanide liberation in the acute toxicity of aliphatic nitriles. Toxicology and Applied Pharmacology 1981; 59: 589–602

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.