Quantitative structure-property relationships for the chemical reactivity of acrylates and methacrylates

Environmental Toxicology and Chemistry

Volumn 18, Issue 6, 1999, Pages 1133-1139

  Freidig, Andreas P ^a   Verhaar, Henk J M ^a   Hermens, Joop L M ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

Author keywords

Glutathione; Hydrolysis; Linear free energy relationship; Michael addition

Indexed keywords

ACRYLIC ACID DERIVATIVE; METHACRYLIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL WASTE; HYDROLYSIS; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

EID: 0032927173     PISSN: 07307268     EISSN: None     Source Type: Journal    
DOI: 10.1897/1551-5028(1999)018<1133:QSPRFT>2.3.CO;2     Document Type: Article

References (40)

1. Greim H, et al. 1995. Assessment of structurally related chemicals: Toxicity and ecotoxicity of acrylic acid and acrylicacid alkyl esters (acrylates), methacrylic acid and methacrylic acid alkyl esters (methacrylates). Chemosphere 31:2637-2659.
2. Verhaar HJM, VanLeeuwen CJ, Hermens JLM. 1992. Classifying environmental pollutants. 1. Structure-activity relationships for prediction of aquatic toxicity. Chemosphere 25:471-491.
3. Russom CL, Bradbury SP, Broderius SJ, Hammermeister DE, Drummond RA. 1997. Predicting modes of toxic action from chemical structure: Acute toxicity in the fathead minnow (Pimephales promelas). Environ Toxicol Chem 16:948-967.
4. Russom CL, Drummond RA, Hoffman AD. 1988. Acute toxicity and behavioral effects of acrylates and methacrylates to juvenile fathead minnows. Bull Environ Contam Toxicol 41:589-596.
5. Karabunarliev S, Mekenyan OG, Karcher W, Russom CL, Bradbury SP. 1996. Quantum-chemical descriptors for estimating the acute toxicity of electrophiles to the fathead minnow (Pimephales promelas): An analysis based on molecular mechanisms. Quant Struct-Act Relat 15:302-310.
6. Hermens JLM. 1990. Electrophiles and acute toxicity to fish. Environ Health Perspect 87:219-225.
7. Karelson M, Lobanov VS. 1996. Quantum-chemical descriptors in QSAR/QSPR studies. Chem Rev 96:1027-1043.
8. Verhaar HJM, Rorije E, Borkent H, Seinen W, Hermens JLM. 1996. Modelling the nucleophilic reactivity of small organochlorine electrophiles: A mechanistically based quantitative structure-activity relationship. Environ Toxicol Chem 15:1011-1018.
9. Hermens J, DeBruijn J, Pauly J, Seinen W. 1987. QSAR studies for fish toxicity data of organophosphorus compounds and other classes of reactive organic compounds. In Kaiser KLE, ed, QSAR in Environmental Toxicology - II, D. Reidel, Dordrecht, The Netherlands, pp 135-152.
10. Schüürmann G. 1992. Ecotoxicology and structure-activity studies of organophosphorus compounds. In Draber W, Fujita T, eds, Rational Approaches to Structure, Activity and Ecotoxicology of Agrochemicals. CRC, Boca Raton, FL, USA, pp 485-541.
11. Eriksson L, Verhaar HJM, Hermens JLM. 1994. Multivariate characterization and modeling of the chemical reactivity of epoxides. Environ Toxicol Chem 13:683-691.
12. Purdy R. 1991. The utility of computed superdelocalisability for predicting the LC50 values of epoxides to guppy. Sci Total Environ 109/110:553-556.
13. VanWelie RTH, VanDijck RGJM, Vermeulen NPE. 1992. Mercapturic acids, protein adducts and DNA adducts as biomarkers of electrophilic chemicals. Crit Rev Toxicol 22:271-306.
14. Chang LW, Hsia SMT, Chan PC, Hsieh LL. 1994. Macromolecular adducts: Biomarkers for toxicity and carcinogenesis. Annu Rev Pharmacol Toxicol 34:41-67.
15. Bradbury SP. 1994. Predicting modes of toxic action from chemical structure: An overview. SAR & QSAR Environ Res 2:89-104.
16. Soffers AEF, Ploemen JHTM, Moonen MJH, Wobbes T, Van Ommen B, Vervoort J, Van Bladeren PJ, Ritjens IMCM. 1996. Regioselectivity and quantitative structure-activity relationships for the conjugation of a series of fluoronitrobenzenes by purified glutathione S-transferase enzymes from rat and man. Chem Res Toxicol 9:638-646.
17. VanderAar EM, De Groot MJ, Bijloo GJ, Van Der Groot H, Vermeulen NPE. 1996. Structure-activity relationships for the glutathione conjugation of 2-substituted 1-chloro-4-nitrobenzenes by rat glutathione s-transferase 4-4. Chem Res Toxicol 9:527-534.
18. Frederick CB, Reynolds CH. 1989. Modeling the reactivity of acrylic acid and acrylate anion with biological nucleophiles. Toxicol Lett 47:241-247.
19. Hashimoto K, Aldridge WN. 1970. Biochemical studies on acrylamide, a neurotoxic agent. Biochem Pharmacol 19:2591-2604.
20. McCarthy TJ, Hayes EP, Schwartz CS, Witz G. 1994. The reactivity of selected acrylate esters toward glutathione and deoxyribonucleosides in vitro: Structure-activity relationships. Fundam Appl Toxicol 22:543-548.
21. Fleming I. 1978. Frontier Orbitals and Organic Chemical Reactions. John Wiley & Sons, New York, NY, USA.
22. Cohn VH, Lyle J. 1966. A fluorometric assay for glutathione. Anal Biochem 14:434-440.
23. Fujita M, Sano M, Tekeda K, Tomita I. 1993. Fluorescence detection of glutathione S conjugate with aldehyde by high-performance liquid chromatography with post-column derivatisation. Analyst 118:1289-1292.
24. Schwarzenbach RP, Gschwend PM, Imboden DM. 1993. Environmental Organic Chemistry. John Wiley & Sons, New York, NY, USA.
25. Mabey W, Mill T. 1978. Critical review of hydrolysis of organic compounds in water under environmental conditions. J Phys Chem Ref Data 7:383-415.
26. Hehre W. 1995. SPARTAN 4.0.4. Wavefunction, Irvine, CA, USA.
27. Giesen DJ, et al. 1996. AMSOL 6.0. Oxford Molecular, Oxford, UK.
28. Taft RW. 1956. Steric Effects in Organic Chemistry. John Wiley & Sons, New York, NY, USA.
29. Hansch C, Leo A. 1979. Substituent Constants far Correlation Analysis in Chemistry and Biology. John Wiley & Sons, New York, NY, USA.
30. Martin YC. 1978. Quantitative Drug Design. Marcel Dekker, New York, NY, USA.
31. Perrin DD, Dempsey B, Sergeant EP. 1981. pKa Prediction for Organic Acids and Bases. Chapman & Hall, London, UK.
32. Klopman G. 1968. Chemical reactivity and the concept of charge-and frontier-controlled reactions. J Am Chem Soc 90:223-234.
33. Eriksson L, Johansson E. 1996. Multivariate design and modeling in QSAR. Chemom Intell Lab Syst 34:1-20.
34. Geladi P, Kowalski BR. 1986. Partial least-squares regression: A tutorial. Anal Chim Acta 185:1-17.
35. Satho K. 1995. The high non-enzymatic conjugation rates of some glutathione S-transferase (GST) substrates at high glutathione concentrations. Carcinogenesis 16:869-874.
36. Osman R, Namboodiri K, Weinstein H, Rabinowitz JR. 1988. Reactivities of acrylic and methacrylic acids in a nucleophilic addition model to their biological activity. J Am Chem Soc 110: 1701-1707.
37. Badr MZ, Belinsky SA, Kauffman FC, Thurman RG. 1986. Mechanism of hepatotoxicity to periportal regions of liver lobule due to allyl alcohol: Role of oxygen and lipid peroxidation. J Pharmacol Exp Ther 238:1138-1142.
38. Droy BF, Davis ME, Hinton DE. 1998. Mechanism of allyl formate-induced hepatoxicity in rainbow trout. Toxicol Appl Pharmacol 98:313-324.
39. Frederick CB, Potter DW, Midey IC, Andersen ME. 1992. A physiologically based pharmacokinetic and pharmacodynamic model to describe the oral dosing of rats with ethyl acrylate and its implications for risk assessment. Toxicol Appl Pharmacol 114: 246-260.
40. Ghanayem BI, Maronpot RR, Matthews HB. 1985. Ethyl acrylate-induced gastric toxicity. II. Structure-toxicity relationships and mechanism. Toxicol Appl Pharmacol 80:336-344.