Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 17, 1987 - Issue 8
95
Views
83
CrossRef citations to date
0
Altmetric
Original Article

A QSAR study of the acute toxicity of some industrial organic chemicals to goldfish. Narcosis, electrophile and proelectrophile mechanisms

, &
Pages 1011-1025 | Received 23 Jul 1986, Published online: 30 Sep 2009

References

  • Axelrod J. The enzymic cleavage of aromatic ethers. Biochemical Journal 1956; 63: 634–639
  • Baum F. Zur Theorie der Alkoholnarkose. Zweite Mittheilung. Ein physikalisch-Chemischer Beitrag zur Theorie der Narcotica. Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie 1899; 42: 119–137
  • Bergmann E. D., Ginsburg D., Pappo R. The Michael reaction. Organic Reactions. John Wiley, New York 1959; 179–555, 10
  • Bradbury J. B. Some points connected with sleep, sleeplessness, and hypnotics. British Medical Journal 1899; 2: 4–9
  • Bridie A. L., Wolff C. J. M., Winter M. The acute toxicity of some petrochemicals to goldfish. Water Research 1979; 13: 623–626
  • Brill H. C., Presnell A. K. The physiological activity of certain alcohols and ethers to goldfish. Ohio Journal of Science 1941; 41: 431–440
  • Brown O. H. A pharmacological study of anesthetics and narcotics. American Journal of Physiology 1905–6; 15: 85–97
  • Cairns J., Jr, Scheier A. A comparison of the toxicity of some common industrial waste components tested individually and combined. The Progressive Fish-Culturist 1968; 30: 3–8
  • Cololian P. La toxicité des alcools chez les poissons. Journal de Physiologie et de Pathologie Generate (Paris) 1901; 3: 535–547
  • Dawson G. W., Jennings A. L., Drozdowski D., Rider E. The acute toxicity of 47 industrial chemicals to fresh and saltwater fishes. Journal of Hazardous Materials 1977; 1: 303–318
  • DeMaster E. G., Nagasawa H. T. Inhibition of aldehyde dehydrogenase by propiolaldehyde, a possible metabolite of propargyline. Research Communication in Chemical Pathology and Pharmacology 1978; 21: 497–505
  • Dixon M. Biochemical research on chemical warfare agents. Nature 1946; 158: 432–438
  • Ferguson J. The use of chemical potentials as indices of toxicity. Proceedings of the Royal Society (London), Series B 1939; 127: 387–404
  • Foster A. B., Jarman M., Stevens J. D., Thomas P., Westwood J. H. Isotope effects in O- and N-demethylations mediated by rat liver microsomes: an application of direct insertion electron impact mass spectrometry. Chemico-Biological Interactions 1974; 9: 327–340
  • Fraenkel-Conrat H. The action of 1,2-epoxides on proteins. Journal of Biological Chemistry 1944; 154: 227–238
  • Franke R. Theorctical Drug Design Methods. Elsevier, Amsterdam 1984; 412
  • Hansch C., Dunn W. J., III. Linear relationships between lipophilic character and biological activity of drugs. Journal of Pharmaceutical Sciences 1972; 61: 1–19
  • Hansch C., Leo A. Substituent Constants for Correlation Analysis in Chemistry and Biology. Wiley-Interscience, New York 1979; 339
  • Hansch C., Leo A. Log P and Parameter Database: A Tool for The Quantitative Prediction of Bioactivity. Comtex Scientific Corporation, New York 1983
  • Hermens J., Busser F., Leeuwangh P., Musch A. Quantitative correlation studies between the acute letha! toxicity of 15 organic halides to the guppy (Poecilia reticulata) and chemical reactivity towards 4-nitrobenzylpyridine. Toxicological and Environmental Chemistry 1985; 9: 219–236
  • Hiatt R. W., Naughton J. J., Matthews D. C. Effects of chemicals on a schooling fish. Kuhlia sandvicensis. Biological Bulletin 1953; 104: 28–44
  • House H. O. Modern Synthetic Methods, 2nd edition. W. A. Benjamin, Menlo Park, CA 1972; 335–337
  • James M. O. Overview of in vitro metabolism of drugs by aquatic species. Veterinary and Human Toxicology 1986; 28(Supplement 1)2–8
  • Jocelyn P. C. Biochemistry of the SH Group: The Occurrence, Chemical Properties, Metabolism and Biological Function of Thiols and Disulphides. Academic Press, London 1972; 404
  • Knott G. D. Computer Programs in Biomedicine 1979; 10: 271–280
  • Könemann H. Quantitative structure-activity relationships in fish toxicity studies, Part 1: relationship for 50 industrial pollutants. Toxicology 1981; 19: 223–228
  • Korunova A. E., Kovtun S. N. Relation between the electronic characteristics of allyl monomers and their reactivity. Deposited document, SPSTL 583 Khp-081. Chemical Abstracts 1981; 98(16)7, 127732u
  • Kubinyi H. Quantitative structure—activity relationships. 7. The bilinear model, a new model for nonlinear dependence of biological activity on hydrophobic character. Journal of Medicinal Chemistry 1977; 20: 625–629
  • La Rocca P. T., Carlson G. P., Fuller G. C. Relationship between sulphydryl reactivity and toxicity of vinyl sulfone molluscicidal agents. Toxicology and Applied Pharmacology 1975; 31: 222–232
  • Leo A., Weininger D. Medchem Software Release 3.33, Medicinal Chemistry Project. Pomona College, Claremont, California 1985
  • Lipnick R. L. Editorial: a perspective on quantitative structure—activity relationships in ecotoxicology. Environmental Toxicology and Chemistry 1985a; 4: 255–257
  • Lipnick R. L. Validation and extension of fish toxicity QSARs and interspecies comparisons for certain classes of organic chemicals. QSAR in Toxicology and Xenobiochemistry, M. Tichy. Elsevier, Amsterdam 1985b; 39–52
  • Lipnick R. L. Charles Ernest Overton: narcosis studies and a contribution to general pharmacology. Trends in Pharmacological Sciences 1986; 7: 161–164
  • Lipnick R. L., Dunn W. J., III. A MLAB study of aquatic structure-toxicity relationships. Quantitative Approaches to Drug Design, J. C. Dearden. Elsevier, Amsterdam 1983; 265–266
  • Lipnick R. L., Johnson D. E., Gilford J. H., Bickings C. K., Newsome L. D. Comparison of fish toxicity screening data for 55 alcohols with the quantitative structure-activity relationship predictions of minimum toxicity for nonreactive nonelectrolyte compounds. Environmental Toxicology and Chemistry 1985; 4: 281–296
  • March J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. McGraw-Hill, New York 1977; 1328
  • Meyer H. Zur Theorie der Alcoholnarkose, Erste Mittheilung. Welche Eigenschaft der Anasthetica bedingt ihre narkotische Wirkung. Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie 1899; 42: 109–118
  • Moje W., Martin J. P., Baines R. C. Structural effect of some organic compounds on soil organisms and citrus seedlings grown in an old citrus soil. Agricultural and Food Chemistry 1957; 5: 32–36
  • Nacci D., Jackim E., Walsh R. Comparative evaluation of three rapid marine toxicity tests: sea urchin early embryo growth test, sea urchin sperm cell toxicity test, and microtox. Environmental Toxicology and Chemistry 1986; 5: 521–525
  • Neely W. B. An analysis of aquatic toxicity data: water solubility and acute LC50 fish data. Chemosphere 1984; 13: 813–819
  • Nichols P. L., Jr, Ingham J. D. The inductive effect in ethylene oxide ring openings. Journal of the American Chemical Society 1955; 77: 6547–6551
  • Nicolle P. Etude pharmacodynamique de quelques α-glycols trisubstitutés acycliques doués de propriétés hypnotiques. Bulletin des Sciences Pharmacologiques 1924; 26: 433–442
  • Overton E. Ueber die allgemeinen osmotischen Eigenschaften der Zelle, ihre Vermutlichen Ursachen und ihre Bedeutung für die Physiologie. Vierteljahrsschrift der Naturforschenden Gesellschaft in Zuerich 1899; 44: 88–135
  • Overton E. Studies uber die Narkose zugleich ein Beitrag zur allgemeinen Pharmakologie. Gustav Fischer, JenaGermany 1901; 195
  • Parke D. V. The Biochemistry of Foreign Compounds. Pergamon Press, Oxford 1968; 37, 50–51
  • Rabuteau. De quelques propriétés nouvelles ou peu connues de l'alcool du vin ou alcool ethylique; déductions thérapeutiques de ces propriétés. Des effets toxiques des alcools butylique et amylique. Application a l'alcoolisatron du vin improprement appelée vinage. L'Union Medicale, Third Series 1870; 10: 165–173
  • Renson J., Weissbach H., Udenfriend S. On the mechanism of oxidative cleavage of aryl-alkyl ethers by liver microsomes. Molecular Pharmacology 1965; 1: 145–148
  • Riesser G. H. Chlorohydrins. Kirk-Othmer Encyclopedia of Chemical Technology, Vol 5, 3rd edition. Wiley, New York 1979; 848–864
  • Roberts D. W., Williams D. L. The derivation of quantitative correlations between skin sensitization and physico-chemical parameters for alkylating agents, and their application to experimental data for sultones. Journal of Theoretical Biology 1982; 99: 807–825
  • Roberts D. W., Goodwin B. F. J., Williams D. L., Jones K., Johnson A. W., Alderson J. C. E. Correlations between skin sensitization potential and chemical reactivity for p-nitrobenzyl compounds. Food and Chemical Toxicology 1983; 21: 811–813
  • Ross W. C. J. The reactions of certain epoxides in aqueous solutions. Journal of the Chemical Society (London) 1950; 2257–2272
  • Ross W. C. J. Biological Alkylating Agents: Fundamental Chemistry and the Design of Compounds for Selective Toxicity. Butterworths, London 1962; 232
  • Salistyi S. M., Krasnobaeva V. S., Sukhov V. D., Mosilevich M. M. Oxidation of polyfunctional allyl esters and ethers. Izvestiya Vysshikh Uchebnykh Zavedenii Khimiya i Khimicheskaya Tekhnologiya 1979; 22: 1100–1103, Chemical Abstracts, 92, (4), 22887w
  • Shelford V. E. An experimental study of the effects of gas waste upon fishes, with especial reference to stream pollution. Bulletin of the Illinois State Laboratory of Natural History 1917; 11: 381–412
  • Comprehensive Organic Chemistry: The Synthesis and Reactions of Organic Compounds, J. F. Stoddart. Pergamon Press, Oxford 1979; Vol. 1: 832–835
  • Turnbull H., DeMann J. G., Reston R. F. Toxicity of various refinery materials to fresh water fish. Industrial and Engineering Chemistry 1954; 46: 324–333
  • Veith G. D., Call D. J., Brooke L. T. Structure-toxicity relationships for the fathead minnow, Pimephales promelas: narcotic industrial chemicals. Canadian Journal of Fisheries and Aquatic Sciences 1983; 40: 743–748
  • Wallen I. E., Greer W. C., Lasater R. Toxicity to Gambusia affinis of certain pure chemicals in turbid waters. Sewage and Industrial Wastes 1957; 29: 695–711
  • Walles S. A. S. Determination of reaction rate constants for alkylation of 4-(p-nitrobenzyl)pyridine by different alkylating agents. Toxicology Letters 1980; 5: 161–167
  • Weigelt C., Saare O., Schwab L. Die Schädigung von Fischerei und Fischzucht durch Industrie und Haus-Abwässer. Eine experimentelle Studie. Archiv für Hygiene (Munich) 1885; 3: 39–117
  • Wolf C. R. Oxidation of foreign compounds at carbon atoms. Metabolic Basis of Detoxication: Metabolism of Functional Groups, W. B. Jakoby, J. R. Bend, J. Caldwell. Academic Press, New York 1982; 13, 18, 19

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.