Quantitative structure-activity relationship modeling of acute toxicity of quaternary alkylammonium sulfobetaines to Daphnia magna

Environmental Toxicology and Chemistry

Volumn 23, Issue 9, 2004, Pages 2111-2115

  Davies, Joanna ^a   Ward, Robert S ^a   Hodges, Geoffrey ^b   Roberts, David W ^b  

^a SWANSEA UNIVERSITY   (United Kingdom)

^b UNILEVER RESEARCH   (United Kingdom)

Author keywords

Aquatic toxicity; Median effective concentration; Quaternary alkylammonium sulfobetaines; Surfactants; Zwitterions

Indexed keywords

ALCOHOLS; CHROMATOGRAPHIC ANALYSIS; HYDROPHOBICITY; MASS SPECTROMETRY; ORGANIC COMPOUNDS; TOXIC MATERIALS;

QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP (QSAR); STANDARD ACUTE IMMOBILIZATION;

MARINE POLLUTION;

1,4 BUTANESULTONE; AMPHOLYTE; BETAINE DERIVATIVE; CHLOROETHANE; DIMETHYLAMINE; PROPANESULTONE; QUATERNARY AMMONIUM DERIVATIVE; SODIUM 2 CHLOROETHANESULFONATE; SULFONIC ACID DERIVATIVE; SULTONE; UNCLASSIFIED DRUG;

BIOACCUMULATION; ECOTOXICOLOGY; PLANKTON; SURFACTANT; TOXICITY;

ACUTE TOXICITY; AQUATIC ENVIRONMENT; ARTICLE; CHEMICAL REACTION; CONCENTRATION (PARAMETERS); DAPHNIA; ECOTOXICITY; ELECTROSPRAY MASS SPECTROMETRY; HYDROPHOBICITY; INVERTEBRATE; MODEL; NONHUMAN; PARTITION COEFFICIENT; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SYNTHESIS;

ACUTE TOXICITY TESTS; ANIMALS; BETAINE; DAPHNIA; HYDROPHOBICITY; MODELS, BIOLOGICAL; OCTANOLS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; QUATERNARY AMMONIUM COMPOUNDS; SOLUBILITY; SURFACE-ACTIVE AGENTS; WATER;

DAPHNIA; DAPHNIA MAGNA; INVERTEBRATA;

EID: 3943094038     PISSN: 07307268     EISSN: None     Source Type: Journal    
DOI: 10.1897/03-312     Document Type: Article

References (31)

1. Roberts DW, Marshall SJ. 1995. Application of hydrophobicity parameters to prediction of the acute aquatic toxicity of commercial surfactant mixtures. SAR QSAR Environ Res 4:167-176.
2. Bradbury SP. 1995. Quantitative structure-activity relationships and ecological risk assessment: An overview of predictive aquatic toxicology research. Toxicol Lett 79:229-237.
3. Schultz TW, Cronin MTD, Walker JD, Aptula AO. 2003. Quantitative structure-activity relationships (QSARs) in toxicology: A historical perspective. J Mol Struct (Theochem) 622:1-22.
4. Hawker DW, Connell DW. 1986. Bioconcentration of lipophilic compounds by some aquatic organisms. Ecotoxicol Environ Saf 11:184-197.
5. Donkin P. 1994. Quantitative structure-activity relationships. In Calow P, ed, Handbook of Ecotoxicology, Vol 2. Blackwell Science, London, UK, pp 321-347.
6. Lipnick RL. 1990. Narcosis: Fundamental and baseline toxicity mechanism for nonelectrolyte organic chemicals. In Karcher W, Devillers J, eds, Practical Applications of Quantitative-Structure Activity Relationships (QSAR) in Environmental Chemistry and Toxicology. Kluwer, Dordrecht, The Netherlands, p 281.
7. Roberts DW. 1991. QSAR issues in aquatic toxicity of surfactants. Sci Total Environ 109/110:557-568.
8. Könemann H. 1981. Quantitative structure-activity relationships in fish toxicity studies. Toxicology 19:209-221.
9. Saarikoski J, Viluksela M. 1982. Relationship between physicochemical properties of phenols and their toxicity and accumulation in fish. Ecotoxol Environ Saf 6:501-512.
10. Hall L, Kier LB. 1984. Molecular connectivity of phenols and their toxicity to fish. Bull Environ Contam Toxicol 32:354-362.
11. Moulton MP. 1988. Regression analysis in QSAR-Potential pitfalls in modeling polar narcotic phenols. Proceedings, Third International Workshop of QSAR in Environmental Toxicology, Knoxville, TN, USA, May 22-26, pp 1-9.
12. Pratic M, Sabljic A. 1989. QSAR of acute toxicity of commercial chemicals on fathead minnows: Effect of molecular size. Aquatic Toxicol 14:47-64.
13. Cronin MTD, Schultz TW. 1996. Structure-toxicity relationships for phenols to Tetrahymena pyriformis. Chemosphere 32:1453-1468.
14. Hansch C, Leo A. 1979. Substituent Constants for Correlation Analysis in Chemistry and Biology. John Wiley, New York, NY, USA.
15. Roberts DW, Costello JF. 2003. QSAR and mechanism of action for aquatic toxicity of cationic surfactants. QSAR Comb Sci 22:220-225.
16. Vaes WHJ, Ramos EU, Verhaar HJM, Hermens JLM. 1998. Acute toxicity of nonpolar versus polar narcosis: Is there a difference? Environ Toxicol Chem 17:1380-1384.
17. Roberts DW, Costello JF. 2003. Mechanisms of action for polar and general narcosis: A difference in dimension. QSAR Comb Sci 22:226-233.
18. Domingo X. 1996. Betaines. In Lomax, EG, ed, Surfactant Science Series, 2nd ed, Vol 59 - Amphoteric Surfactants. Marcel Dekker, New York, NY, USA, pp 75-190.
19. Ernst R, Miller EJ. 1982. Surface-active betaines. In Bluestein BR, Hilton CL, eds, Surfactant Science Series, Vol 12-Amphoteric Surfactants. Marcel Dekker, New York, NY, USA, pp 71-173.
20. Ward RS, Davies J, Hodges G, Roberts DW. 2002. Synthesis of quaternary alkylammonium sulfobetaines. Synthesis 2431-2439.
21. Dearden JC, Bresnen G. 1988. Measurement of partition coefficients. Quant Struct-Act Relat 7:133-144.
22. Organisation for Economic Cooperation and Development. 1981. Guideline for the Testing of Chemicals. 107. May 12, Paris, France.
23. Organisation for Economic Cooperation and Development. 2000. Guideline for the Testing of Chemicals. Revised proposal for updating Guideline 202, Daphnia sp., Acute Immobilisation Test. Revised Draft Document, Paris, France.
24. Ward RS, Davies J, Hodges G, Roberts DW. 2003. Applications of immobilized artificial membrane chromatography to quaternary alkylammonium sulfobetaines and comparison of chromatographic methods for estimating the octanol-water partition coefficient. J Chromatogr A 1007:67-75.
25. European Community. 1979. Directive 79/831 EC of the European Economic Community. Official Journal of the European Communities. L259 22 Brussels, Belgium.
26. Turner L, Choplin F, Dugard P, Hermens J, Jaeckh R, Marsmann M, Roberts D. 1997. Structure-activity relationships in toxicology and ecotoxicology: An assessment. Toxicol In Vitro 1:143-171.
27. Schultz TW, Cronin MTD, Netzeva TI. 2003. The present status in QSAR toxicology. J Mol Struct (Theochem) 622:23-38.
28. Walker JD, Jaworska J, Comber MHI, Schultz TW, Dearden JC. 2003. Guidelines for using and developing quantitative structure-activity relationships. Environ Toxicol Chem 22:1653-1665.
29. Schultz TW, Cronin MTD. 2003. Essential and desirable characteristics of ecotoxicity quantitative structure-activity relationships. Environ Toxicol Chem 22:599-607.
30. European Community. 2003. Proposal for a Regulation of the European Parliament and of the Council Concerning the Registration, Authorisation and Restrictions of Chemicals, Establishing a European Chemicals Agency and Amending Directive 199/45/ EC and Regulation EC on Persistent Organic Pollutants. Brussels, Belgium.
31. Davies J. 2003. Synthesis of zwitterionic compounds for aquatic toxicity testing for QSAR correlation studies. PhD thesis. University of Wales Swansea, Swansea, UK.