Structural alerts for the excess toxicity of acrylates, methacrylates, and propiolates derived from their short-term and long-term bacterial toxicity

Chemical Research in Toxicology

Volumn 25, Issue 1, 2012, Pages 170-180

  Blaschke, Ulrike ^a,b   Eismann, Kathleen ^a   Böhme, Alexander ^a   Paschke, Albrecht ^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

ACRYLIC ACID; ACRYLIC ACID ALLYL ESTER; ACRYLIC ACID BUTYL ESTER; ACRYLIC ACID ETHYL ESTER; ACRYLIC ACID ISOBUTYL ESTER; ACRYLIC ACID METHYL ESTER; ACRYLIC ACID PROPYL ESTER; ACRYLIC ACID TERT BUTYL ESTER; CARBOXYLESTERASE; ELECTROPHILE; ESTER DERIVATIVE; ETHYL METHACRYLATE; GLUTATHIONE; METHACRYLIC ACID; METHACRYLIC ACID METHYL ESTER; METHYL PROPIOLATE; NUCLEOPHILE; PROPARGYL ACRYLATE; PROPARGYL METHACRYLATE; PROPIOLATE; PROPIOLIC ACID ETHYL ESTER; TERT BUTYL PROPIOLATE; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL GROWTH; BIOLUMINESCENCE; CHEMICAL STRUCTURE; GROWTH INHIBITION; HYDROLYSIS; MICHAEL ADDITION; NONHUMAN; PHYSICAL CHEMISTRY; THERMODYNAMICS; TOXICITY TESTING; VIBRIO FISCHERI; VOLATILIZATION;

ACRYLATES; ALIIVIBRIO FISCHERI; ALKYNES; GLUTATHIONE; LUMINESCENT MEASUREMENTS; PROPIONATES;

BACTERIA (MICROORGANISMS); VIBRIO FISCHERI;

EID: 84855834849     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx200395k     Document Type: Article

References (37)

1. Greim, H., Ahlers, J., Blas, R., Broecker, B., Hollander, H., Gelbke, H. P., Jacobi, S., Klimisch, H. J., Mangelsdorf, I., Mayr, W., Schon, N., Stropp, G., Stahnecker, P., Vogel, R., Weber, C., Zieglerskylakakis, K., and Bayer, E. (1995) Assessment of structurally related chemicals - toxicity and ecotoxicity of acrylic-acid and acrylic-acid alkyl esters (acrylates), methacrylic-acid and methacrylic-acid alkyl esters (methacrylates) Chemosphere 31, 2637-2659
2. Freidig, A. P., Verhaar, H. J. M., and Hermens, J. L. M. (1999) Quantitative structure-property relationships for the chemical reactivity of acrylates and methacrylates Environ. Toxicol. Chem. 18, 1133-1139 (Pubitemid 29233296)
3. 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
4. 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. 23, 1905-1912
5. 50 Regul. Toxicol. Pharmacol. 7, 384-389 (Pubitemid 18020399)
6. Russom, C. L., Drummond, R. A., and Hoffman, A. D. (1988) Acute toxicity and behavioral effects of acrylates and methacrylates to juvenile fathead minnows Bull. Environ. Contam. Toxicol. 41, 589-596
7. Freidig, A. P., Verhaar, H. J. M., and Hermens, J. L. M. (1999) Comparing the potency of chemicals with multiple modes of action in aquatic toxicology: Acute toxicity due to narcosis versus reactive toxicity of acrylic compounds Environ. Sci. Technol. 33, 3038-3043 (Pubitemid 29422460)
8. Harder, A., Escher, B., Landini, P., Tobler, N., and Schwarzenbach, R. (2003) Evaluation of bioanalytical assays for toxicity assessment and mode of toxic action classification of reactive chemicals Environ. Sci. Technol. 37, 4962-4970 (Pubitemid 37369887)
9. Ohno, Y., Ormstad, K., Ross, D., and Orrenius, S. (1985) Mechanism of ally1 alcohol toxicity and protective effects of low-molecular-weight thiols studied with isolated rat hepatocytes Toxicol. Appl. Pharmacol. 78, 169-179 (Pubitemid 15081077)
10. Potter, D. W. and Tran, T.-B. (1992) Rates of ethyl acrylate binding to glutathione and protein Toxicol. Lett. 62, 275-285
11. McCarthy, T. J., Hayes, E. P., Schwartz, C. S., and Witz, G. (1994) The reactivity of selected acrylate esters toward glutathione and deoxyribonucleosides in vitro: structure-activity relationships Fundam. Appl. Toxicol. 22, 543-548 (Pubitemid 24194717)
12. Johannsen, F. R., Vogt, B., Waite, M., and Deskin, R. (2008) Mutagenicity assessment of acrylate and methacrylate compounds and implications for regulatory toxicology requirements Regul. Toxicol. Pharmacol. 50, 322-335
13. Roberts, D. W. and Natsch, A. (2009) High throughput kinetic profiling approach for covalent binding to peptides: application to skin sensitization potency of michael acceptor electrophiles Chem. Res. Toxicol. 22, 592-603
14. Wondrousch, D., Böhme, A., Thaens, D., Ost, N., and Schüürmann, G. (2010) Local electrophilicity predicts toxicity-relevant reactivity of Michael acceptors J. Phys. Chem. Lett. 1, 1605-1610
15. Schwöbel, J. A. H., Wondrousch, D., Koleva, Y. K., Madden, J. C., Cronin, M. T. D., and Schüürmann, G. (2010) Prediction of Michael-type acceptor reactivity toward glutathione Chem. Res. Toxicol. 23, 1576-1585
16. Paasche, A., Schiller, M., Schirmeister, T., and Engels, B. (2010) Mechanistic study of the reaction of thiol-containing enzymes with α,β-unsaturated carbonyl substrates by computation and chemoassays ChemMedChem 5, 869-880
17. Krenske, E. H., Petter, R. C., Zhu, Z., and Houk, K. N. (2011) Transition states and energetics of nucleophilic additions of thiols to substituted α,β-unsaturated ketones: substituent effects involve enone stabilization, product branching, and solvation J. Org. Chem. 76, 5074-5081
18. Mulliner, D., Wondrousch, D., and Schüürmann, G. (2011) Predicting Michael-acceptor reactivity and toxicity through quantum-chemical transition-state calculations Org. Biomol. Chem. 9, 8400-8412
19. Schwöbel, J. A. H., Madden, J. C., and Cronin, M. T. D. (2011) Application of a computational model for Michael addition reactivity in the prediction of toxicity to Tetrahymena pyriformis Chemosphere 85, 1066-1074
20. Lipnick, R. L., Watson, K. R., and Strausz, A. K. (1987) A QSAR study of the acute toxicity of some industrial organic-chemicals to goldfish: Narcosis, electrophile and proelectrophile mechanism Xenobiotica 17, 1011-1025 (Pubitemid 17142889)
21. Lipnick, R. L. (1991) Outliers: their origin and use in the classification of molecular mechanisms of toxicity Sci. Total Environ. 109/110, 131-153
22. 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 (Pubitemid 40393175)
23. Blaschke, U., Paschke, A., Rensch, I., and Schüürmann, G. (2010) Acute and chronic toxicity toward the bacteria Vibrio fischeri of organic narcotics and epoxides: structural alerts for epoxide excess toxicity Chem. Res. Toxicol. 23, 1936-1946
24. Schramm, F., Müller, A., Hammer, H., Paschke, A., and Schüürmann, G. (2011) Epoxide and thiirane toxicity in vitro with the ciliates Tetrahymena pyriformis: structural alerts indicating excess toxicity Environ. Sci. Technol. 45, 5812-5819
25. REACH 2007 (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. Official Journal of the European Union, L 136/3, 29.05.2007.
26. 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
27. US EPA (2009) Estimation Programs Interface Suite for Microsoft (EPISuite), version 3.20, United States Environmental Protection Agency, Washington, DC.
28. Schüürmann, G., Kühne, R., Kleint, F., Ebert, R. U., Rothenbacher, C., and Herth, P. (1997) A Software System for Automatic Chemical Property Estimation from Molecular Structure, in QSAR in Environmental Sciences VII (Chen, F. and Schüürmann, G., Eds.) pp 93-114, SETAC Press, Pensacola, FL.
29. ChemIDplus Advanced Database 2010, National Library of Medicine of the National Institutes of Health (NIH), http://chem.sis.nlm.nih.gov/chemidplus/ chemidheavy.jsp, 06.05.2010.
30. McCarthy, T. J. and Witz, G. (1997) Structure-activity relationships in the hydrolysis of acrylate and methacrylate esters by carboxylesterase in vitro Toxicology 116, 153-158 (Pubitemid 27051281)
31. Droy, B. F., Davis, M. E., and Hinton, D. E. (1989) Mechanism of ally1 formate-induced hepatotoxicity in rainbow trout Toxicol. Appl. Pharmacol. 98, 313-324 (Pubitemid 19122378)
32. Sang, Y., Xiong, G., and Maser, E. (2011) Steroid degradation and two steroid-inducible enzymes in the marine bacterium H5 Chem.-Biol. Interact. 191, 89-94
33. Toyama, H., Mathews, F. S., Adachi, O., and Matsushita, K. (2004) Quinohemoprotein alcohol dehydrogenases: structure, function, and physiology Arch. Biochem. Biophys. 428, 10-21 (Pubitemid 38844905)
34. Van Bogaert, I. N. A., Groeneboer, S., Saerens, K., and Soetaert, W. (2011) The role of cytochrome P450 monooxygenases in microbial fatty acid metabolism FEBS J. 278, 206-221
35. 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
36. Schüürmann, G., Ebert, R. U., Chen, J., Wang, B., and Kühne, R. (2008) External validation and prediction employing the predictive squared correlation coefficient: test set activity mean vs training set activity mean J. Chem. Inf. Model. 48, 2140-2145
37. Van Leeuwen, C. J., van der Zandt, P. T. J., Aldenberg, T., Verhaar, H. J. M., and Hermens, J. L. M. (1992) Application of QSARs, extrapolation and equilibrium partitioning in aquatic effects assessment. I. Narcotic industrial pollutants Environ. Toxicol. Chem. 11, 267-282