Quantitative structure-activity relationship (QSAR) study of toxicity of quaternary ammonium compounds on Chlorella pyrenoidosa and Scenedesmus quadricauda

Chemosphere

Volumn 86, Issue 1, 2012, Pages 76-82

  Jing, Guohua ^a   Zhou, Zuoming ^a   Zhuo, Jing ^a  

^a HUAQIAO UNIVERSITY   (China)

Author keywords

Chlorella Pyrenoidosa; Multiple linear regression; Quantitative structure activity relationship; Quaternary ammonium compounds; Scenedesmus Quadricauda; Toxicity

Indexed keywords

ALGAE; AMMONIUM COMPOUNDS; LINEAR REGRESSION; MOLECULAR GRAPHICS; QUANTUM CHEMISTRY; STRUCTURES (BUILT OBJECTS); TOXICITY;

CHLORELLA PYRENOIDOSA; MULTIPLE LINEAR REGRESSIONS; QUANTITATIVE STRUCTURE ACTIVITY RELATIONSHIP; QUATERNARY AMMONIUM COMPOUND; SCENEDESMUS QUADRICAUDA;

COMPUTATIONAL CHEMISTRY;

QUATERNARY AMMONIUM DERIVATIVE;

AMMONIUM; EMPIRICAL ANALYSIS; GREEN ALGA; PHYSICOCHEMICAL PROPERTY; PHYTOMASS; PHYTOTOXICITY; QUANTITATIVE ANALYSIS; QUANTUM MECHANICS; REGRESSION ANALYSIS;

ACUTE TOXICITY; ARTICLE; CHLORELLA; CONTROLLED STUDY; MICROBIAL BIOMASS; MULTIPLE LINEAR REGRESSION ANALYSIS; PHYSICAL CHEMISTRY; QUANTITATIVE ANALYSIS; QUANTUM CHEMISTRY; SCENEDESMUS; STRUCTURE ACTIVITY RELATION;

ALGAE; CHLORELLA PYRENOIDOSA; SCENEDESMUS QUADRICAUDA;

EID: 82555205239     PISSN: 00456535     EISSN: 18791298     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2011.09.021     Document Type: Article

References (46)

1. Anastácio P.M., Holten Lützhoft H.C., Halling Sorensen B., Marques J.C. Surfactant (Geanpol OX-80) toxicity to Selenastrum capricornutum. Chemosphere 2000, 40:835-838.
2. Anoune N., Nouiri M., Berrah Y., Gauvrit J.Y., Lanteri P. Critical Micelle concentrations of different classes of surfactants: a quantitative structure property relationship study. J. Surfactants Deterg. 2002, 5:45-53.
3. Boxall A.B.A., Brown C.D., Barrett K.L. Higher-tier laboratory methods for assessing the aquatic toxicity of pesticides. Pest Manag. Sci. 2002, 58:637-648.
4. Bruno E., Eklund B. Two new growth inhibition tests with the filamentous algae Ceramium strictum and C. Tenuicorne (Rhodophyta). Environ. Pollut. 2003, 125:287-293.
5. Campanella L., Cubadda F., Sammartino M.P., Saoncella A. An algal biosensor for the monitoring of water toxicity in estuarine environments. Water Res. 2001, 35:69-76.
6. CESIO, 2004. 6th World Surfactant Congress, Berlin, Germany.
7. Cheng L., Jiang X. Relationship between the concentrations, ionic types and molecular structures of surfactants and their toxicity. Chin. J. Environ. Sci. Manag. 2006, 31:182-185.
8. Dessalew N. QSAR study on aminophenylbenzamides and acrylamides as histone deacetylase inhibitors: an insight into the structural basis of antiproliferative activity. Med. Chem. Res. 2007, 16:449-460.
9. Hrenovic J., Ivankovic T., Sekovanic L., Rozic M. Toxicity of dodecylpyridinium and cetylpyridinium clorides against phosphate-accumulating bacterium. Cent. Eur. J. Biol. 2008, 3:143-148.
10. García M.T., Campos E., Sanchez-Leal J., Ribosa I. Effect of the alkyl chain length on the anaerobic biodegradability and toxicity 340 of quaternary ammonium based surfactants. Chemosphere 1999, 38:3473-3483.
11. García M.T., Ribosa I., Guindulain T., Sánchez-Leal J., Vives-Rego J. Fate and effect of monoalkyl quaternary ammonium surfactants in the aquatic environment. Environ. Pollut. 2001, 111:169-175.
12. George D., Mallery P. SPSS/PC+ step by step, A Simple Guide and Reference 1994, Wadsworth, California.
13. Jalali-Heravi M., Konouz E. Prediction of critical micelle concentration of some anionic surfactants using multiple regression techniques: a quantitative structure-activity relationship study. J. Surfactants Deterg. 2000, 3:47-52.
14. Jing G.H., Li X.L., Zhou Z.M. Quantitative structure-activity relationship (QSAR) study of toxicity of substituted aromatic compounds to Photobacterium phosphoreum. Chin. J. Struct. Chem. 2010, 29:1189-1196.
15. Katagi T. Bioconcentration, bioaccumulation, and metabolism of pesticides in aquatic organisms. Rev. Environ. Contam. Toxicol. 2010, 204:1-132.
16. Kier L.B., Hall H. Molecular Connectivity in Chemistry and Drug Research 1976, Academic Press, New York, pp. 18.
17. Kümmerer K., Eitel A., Braun U., Hubner P., Daschner F., Mascart G., Milandri M., Reinthaler F., Verhoef J. Analysis of benzalkonium chloride in the effluent from European hospitals by solid-phase extraction and high-performance liquid chromatography with post-column ion-pairing and fluorescence detection. J. Chromatogr. A 1997, 774:281-286.
18. Kuz'min V.E., Muratov E.N., Artemenko A.G., Gorb L., Qasim M., Leszczynski J. The effect of nitroaromatics' composition on their toxicity in vivo: novel, efficient non-additive 1D QSAR analysis. Chemosphere 2008, 72:1373-1380.
19. Lee C., Yang W., Parr R.G. Development of the colle-salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B: Condens. Matter. 1988, 37:785-789.
20. Lee P.Y., Chen C.Y. Toxicity and quantitative structure-activity relationships of benzoic acids to Pseudokirchneriella subcapitata. J. Hazard. Mater. 2009, 165:156-161.
21. Lewis M.A. Chronic toxicities of surfactants and detergent builders to algae: a review and risk assessment. Ecotox. Environ. Saf. 1990, 20:123-140.
22. Lukáč M., Lacko I., Bukovský M., Kyselová Z., Karlovská J., Horváth B., Devínsky F. Synthesis and antimicrobial activity of a series of optically active quaternary ammonium salts derived from phenylalanine. Cent. Eur. J. Chem. 2010, 8:194-201.
23. Ma J.Y., Lin F.C., Zhang R.Z., Yu W.W., Lu N.H. Differential sensitivity of two green algae, scenedesmus quadricauda and chlorella vulgaris to 14 Pesticide adjuvants. Ecotox. Environ. Saf. 2004, 58:61-67.
24. McBain A.J., Ruth Ledder R.G., Moore L.E., Catrenich C.E., Gilbert P. Effects of quaternary-ammonium-based formulations on bacterial community dynamics and antimicrobial susceptibility. Appl. Environ. Microbiol. 2004, 70:3449-3456.
25. Nalecz-Jawecki G., Grabińska-Sota E., Narkiewicz P. The toxicity of cationic surfactants in four bioassays. Ecotox. Environ. Saf. 2003, 54:87-91.
26. Nyberg H. Growth of Sclanastrum capricornutum in the presence of synthetic surfactants. Water Res. 1988, 22:217-223.
27. OECD (Organization for Economic Cooperation and Development), 2006. OECD Guidelines for the Testing of Chemicals. Paris, France.
28. OECD, 2007. Guidance Document on the Validation of (Quantitative) Structure-Activity Relationships [(Q)SAR] Models. Paris, France.
29. Osten D.W. Selection of optimal regression models via cross-validation. J. Chemometr. 1988, 2:39-48.
30. Pantani C., Spreti N., Maggitti M.C., Germani R. Acute toxicity of some synthetic cationic and zwitterionic surfactants to freshwater amphipod Echinogammarus tibaldii. Bull. Environ. Contam. Toxicol. 1995, 55:179-186.
31. Patrauchan M.A., Oriel P.J. Degradation of benzyldimethylalkylammonium chloride by Aeromonas hydrophila sp K. J. Appl. Microbiol. 2003, 94:266-272.
32. Qian H.F., Chen W., Sheng G.D., Xu X.Y., Liu W.P., Fu Z.W. Effects of glufosinate on antioxidant enzymes, subcellular structure, and gene expression in the unicellular green alga Chlorella vulgaris. Aquat. Toxicol. 2008, 88:301-307.
33. Randic M. Characterization of molecular branching. J. Am. Chem. Soc. 1975, 23:3309-6615.
34. Roberts D.W. Aquatic toxicity - are surfactant properties relevant?. J. Surfactants Deterg. 2000, 3:309-315.
35. Rosen M.J., Li F., Morrall S.W., Versteeg D.J. The relationship between the interfacial properties of surfactants and their toxicity to aquatic organisms. Crit. Rev. Environ. Sci. Technol. 2001, 35:954-959.
36. Selck H., Riemann B., Christoffersen K., Forbes V.E., Gustavson K., Hansen B.W., Jacobsen J.A., Kusk O.K., Petersen S. Comparing sensitivity of ecotoxicological effect endpoints between laboratory and field. Ecotox. Environ. Saf. 2002, 52:97-112.
37. Sun X.X., Han K.N., Choi J.K., Kim E.K. Screening of surfactants for harmful algal blooms mitigation. Mar. Pollut. Bull. 2004, 48:937-945.
38. Tang Q.Y., Feng M.G. DPS Data Processing System: Experimental Design, Statistical Analysis, and Data Mining 2007, Science Press, Beijing.
39. Uppgård L.L., Lindgren å., Sjöström M., Wold S. Multivariate quantitative structure- activity relationships for the aquatic toxicity of technical nonionic surfactants. J. Surfactants Deterg. 2000, 3:33-41.
40. Wijk D.V., Gyimesi-van den Bos M., Garttener-Arends I., Geurts M., Kamstra J., Thomas P. Bioavailability and detoxification of cationics: I. Algal toxicity of alkyltrimethyl ammonium salts in the presence of suspended sediment and humic acid. Chemosphere 2009, 75:303-309.
41. Wilson B.A., Smith V.H., Denoyelles F.J., Larive C.K. Effects of three pharmaceutical and personal care products on natural freshwater algal assemblages. Environ. Sci. Technol. 2003, 37:1713-1719.
42. Xu H.Y., Yu Q.S., Zou J.W., Wang Y.H., Wang H.Q., Chen X.S. A QSRR study on the relative retention time of halogenated methyl-phenyl ethers. Chin. J. Struct. Chem. 2006, 25:811-817.
43. Yuan X., Lu G.H., Su L.M. Correlation study of toxicity of substituted phenois to river bacteria and their biodegradability in river water. Biomed. Environ. Sci. 2005, 18:281-285.
44. Zhu M.J., Ge F., Zhu R.L., Wang X.Y., Zheng X.Y. A DFT-based QSAR study of the toxicity of quaternary ammonium compounds on Chlorella vulgaris. Chemosphere 2010, 80:46-52.
45. Zvinavashe E., Berg H., vanden Soffers A.E.M.F., Vervoort J., Freidig A., Murk A.J., Rietjens I.M.C.M. QSAR models for predicting in vivo aquatic toxicity of chlorinated alkanes to fish. Chem. Res. Toxicol. 2008, 21:739-745.
46. Zvinavashe E., Du T.T., Griff T., Van den Berg H.H.J., Soffers A.E.M.F., Vervoort J., Murk A.J., Rietjens I.M.C.M. Quantitative structure-activity relationship modeling of the toxicity of organothiophosphate pesticides to Daphnia magna and Cyprinus carpio. Chemosphere 2009, 75:1531-1538.