Acute and chronic toxicity toward the bacteria Vibrio fischeri of organic narcotics and epoxides: Structural alerts for epoxide excess toxicity

Chemical Research in Toxicology

Volumn 23, Issue 12, 2010, Pages 1936-1946

  Blaschke, Ulrike ^a,b   Paschke, Albrecht ^a   Rensch, Ines ^a   Schüürmann, Gerrit ^a,b  

^a HELMHOLTZ CENTRE FOR ENVIRONMENTAL RESEARCH UFZ   (Germany)

^b TU BERGAKADEMIE FREIBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 EPOXYBUTANE; 1,2,4 TRICHLOROBENZENE; 2 BUTANONE; 2,3 EPOXYPROPYL ISOPROPYL ETHER; 2,3 EPOXYPROPYL PHENYL ETHER; ACETONE; ALCOHOL; BROMODIPHENHYDRAMINE; BUTANOL; CHALCONE OXIDE; DICHLOROMETHANE; DIPHENYL ETHER; ELECTROPHILE; EPOXIDE; ETHYL 2,3 EPOXY 3 PHENYLPROPIONATE; ETHYLENE GLYCOL; GLYCIDYL METHACRYLATE; HEPTANOL; HEXANOL; ISOBUTANOL; ISOBUTYLENE OXIDE; METHANOL; NARCOTIC AGENT; OCTANOL; PROPANOL; PROPYLENE OXIDE; STYRENE OXIDE; TERT BUTYL METHYL ETHER; UNCLASSIFIED DRUG; UNINDEXED DRUG; XYLENE;

ACUTE TOXICITY; ARTICLE; BIOLUMINESCENCE; CHEMICAL STRESS; CHRONIC TOXICITY; DRUG DOSE; ELECTROPHILICITY; GROWTH INHIBITION; NONHUMAN; NUCLEOPHILICITY; VIBRIO FISCHERI;

ALIIVIBRIO FISCHERI; EPOXY COMPOUNDS; LUMINESCENT MEASUREMENTS; MICROBIAL SENSITIVITY TESTS; MICROBIAL VIABILITY; NARCOTICS; TOXICITY TESTS;

BACTERIA (MICROORGANISMS); VIBRIO FISCHERI;

EID: 78650508726     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx100298w     Document Type: Article

References (31)

1. Ehrenberg, L. and Hussain, S. (1981) Genetic toxicity of some important epoxides Mutat. Res. 86, 1-113
2. Morisseau, C. and Hammock, B. D. (2005) Epoxide hydrolases: Mechanisms, inhibitor designs, and biological roles Annu. Rev. Pharmacol. 45, 311-333
3. Guengerich, F. P. (2008) Cytochrome P450 and chemical toxicology Chem. Res. Toxicol. 21, 70-83
4. Niklasson, I. B., Broo, K., Jonsson, C., Luthman, K., and Karlberg, A. T. (2009) Reduced sensitizing capacity of epoxy resin systems: A structure-activity relationship study Chem. Res. Toxicol. 22, 1787-1794
5. Nilsson, A. M., Bergstrom, M. A., Luthman, K., Nilsson, J. L. G., and Karlberg, A. T. (2005) A conjugated diene identified as a prohapten: Contact allergenic activity and chemical reactivity of proposed epoxide metabolites Chem. Res. Toxicol. 18, 308-316
6. Deneer, J. W., Sinnige, T. L., Seinen, W., and Hermens, J. L. M. (1988) A quantitative structure activity relationship for the acute toxicity of some epoxy compounds to the guppy Aquat. Toxicol. 13, 195-204
7. Lipnick, R. L. (1991) Outliers: their origin and use in the classification of molecular mechanisms of toxicity Sci. Total Environ. 109/110, 131-153
8. Niederer, C., Behra, R., Harder, A., Schwarzenbach, R. P., and Eschert, B. I. (2004) Mechanistic approaches for evaluating the toxicity of reactive organochlorines and epoxides in green algae Environ. Toxicol. Chem. 23, 697-704
9. Böhme, A., Thaens, D., Schramm, F., Paschke, A., and Schüürmann, G. (2010) Thiol reactivity and its impact on the ciliate toxicity of α,β -unsaturated aldehydes, ketones and esters. Chem. Res. Toxicol., DOI: 10.1021/tx100226n.
10. Böhme, A., Thaens, D., Paschke, A., and Schüürmann, G. (2009) Kinetic glutathione chemoassay to quantify thiol reactivity of organic electrophiles: application to α,β-unsaturated ketones, acrylates, and propiolates Chem. Res. Toxicol. 22, 742-750
11. Kaiser, K. L. E. (1998) Correlations of Vibrio fischeri bacteria test data with bioassay data for other organisms Environ. Health Perspect. 106, 583-591
12. REACH 2007. Regulation (EC) No 1907/2006 the European Parliament and of the Council of 18 December 2006 concerning the Registration, Evaluation, Authorisation and Restriction of Chemicals (REACH), establishing a European Chemicals Agency, amending Directive 1999/45/EC and repealing Council Regulation (EEC) No 793/93 and Commission Regulation (EC) No 1488/94 as well as Council Directive 76/769/EEC and Commission Derectives 91/155/EEC, 93/67/EEC, 93/105/EC and 2000/21/EC. Off. J. Eur. Union, L 136/3, 29.05.2007.
13. Kahru, A. (2006) Ecotoxicological tests in non-ecotoxicological research: Contribution to 3Rs. Use of luminescent photobacteria for evaluating the toxicity of 47 MEIC Chemicals ALTEX 23, 1069-1083
14. Mortimer, M., Kasemets, K., Heinlaan, M., Kurvet, I., and Kahru, A. (2008) High throughput kinetic Vibrio fischeri bioluminescence inhibition assay for study of toxic effects of nanoparticles Toxicol. in Vitro 22, 1412-1417
15. Von der Ohe, P. C., Kühne, R., Ebert, R. U., Altenburger, R., Liess, M., and Schüürmann, G. (2005) Structural alerts: a new classification model to discriminate excess toxicity from narcotic effect levels of organic compounds in the acute daphnid assay Chem. Res. Toxicol. 18, 536-555
16. US E. P. A. (2009) Estimation Programs Interface Suite for Microsoft (EPISuite), v3.20, United States Environmental Protection Agency, Washington, DC.
17. Urbanczyk, H., Ast, J. C., Higgins, M. J., Carson, J., and Dunlap, P. V. (2007) Reclassification of Vibrio fischeri, Vibrio logei, Vibrio salmonicida and Vibrio wodanis as Aliivibrio fischeri gen. nov., comb. nov., Aliivibrio logei comb. nov., Aliivibrio salmonicida comb. nov and Aliivibrio wodanis comb. nov Int. J. Syst. Evol. Microbiol. 57, 2823-2829
18. Schüürmann, G., Somashekar, R. K., and Kristen, U. (1996) Structure-activity relationships for chloro- and nitrophenol toxicity in the pollen tube growth test Environ. Toxicol. Chem. 15, 1702-1708
19. McCarty, L. S., Mackay, D., Smith, A. D., Ozburn, G. W., and Dixon, D. G. (1993) Residue-based interpretation of toxicity and bioconcentration QSARs from aquatic bioassays: polar narcotic organics Ecotox. Environ. Saf. 25, 253-270
20. Sijm, D., Schipper, M., and Opperhuizen, A. (1993) Toxicokinetics of halogenated benzenes in fish: lethal body burden as a toxicological end-point Environ. Toxicol. Chem. 12, 1117-1127
21. Vighi, M., Migliorati, S., and Monti, G. S. (2009) Toxicity on the luminescent bacterium Vibrio fischeri (Beijerinck). I: QSAR equation for narcotics and polar narcotics Ecotox. Environ. Saf. 72, 154-161
22. Sawatari, K., Nakanishi, Y., and Matsushima, T. (2001) Relationships between chemical structures and mutagenicity: A preliminary survey for a database of mutagenicity test results of new work place chemicals Ind. Health 39, 341-345
23. Wade, D. R., Airy, S. C., and Sinsheimer, J. E. (1978) Mutagenicity of aliphatic epoxides Mutat. Res. 58, 217-223
24. Voogd, C. E., Vanderstel, J. J., and Jacobs, J. (1981) The mutagenic action of aliphatic epoxides Mutat. Res. 89, 269-282
25. Vonderhude, W., Carstensen, S., and Obe, G. (1991) Structure-activity- relationships of epoxides: induction of sister-chromatid exchanges in chinese-hamster V79 cells Mutat. Res. 249, 55-70
26. Canter, D. A., Zeiger, E., Haworth, S., Lawlor, T., Mortelmans, K., and Speck, W. (1986) Comparative mutagenicity of aliphatic epoxides in Salmonella Mutat. Res. 172, 105-138
27. National Toxicology Program (NTP) database 2010, National Institute of Environmental Health Sciences of the National Institutes of Health (NIEHS/NIH), USA, http://ntp-apps.niehs.nih.gov/ntp-tox/, 06.05.2010.
28. Gellert, G. (2000) Sensitivity and significance of luminescent bacteria in chronic toxicity testing based on growth and bioluminescence Ecotox. Environ. Saf. 45, 87-91
29. Fröhner, K., Backhaus, T., and Grimme, L. H. (2000) Bioassays with Vibrio fischeri for the assessment of delayed toxicity Chemosphere 40, 821-821
30. El-Alawi, Y. S., McConkey, B. J., Dixon, D. G., and Greenberg, B. M. (2002) Measurement of short- and long-term toxicity of polycyclic aromatic hydrocarbons using luminescent bacteria Ecotox. Environ. Saf. 51, 12-21
31. Wondrousch, D., Böhme, A., Thaens, D., Ost, N., and Schüürmann, G. (2010) Local electrophilicity predicts the toxicity-relevant reactivity of Michael Acceptors J. Phys. Chem. Lett. 1, 1605-1610