QSBMR - Quantitative structure biomagnification relationships: Physicochemical and structural descriptors important for the biomagniflcation of organochlorines and brominated flame retardants

Journal of Chemometrics

Volumn 20, Issue 8-10, 2006, Pages 392-401

  Lundstedt Enkel, Katrin ^a,b   Lek, Per M ^c   Lundstedt, Torbjörn ^c,d   Örberg, Jan ^a  

^a UPPSALA UNIVERSITY   (Sweden)

^b SWEDISH MUSEUM OF NATURAL HISTORY   (Sweden)

^c AcurePharma AB   (Sweden)

^d UPPSALA UNIVERSITY   (Sweden)

Author keywords

Biomagnification; Persistent organic pollutants; Preditictive models; Risk assessment

Indexed keywords

C (PROGRAMMING LANGUAGE); CHEMICAL PROPERTIES; CONTAMINATION; FLAME RETARDANTS; IMPURITIES; LEAST SQUARES APPROXIMATIONS; POLYCHLORINATED BIPHENYLS; RISK ASSESSMENT; STRUCTURAL PROPERTIES;

BIOMAGNIFICATION; BIOMAGNIFICATION FACTORS; BROMINATED FLAME RETARDANTS; DESCRIPTORS; ORGANOCHLORINES; PERSISTENT ORGANIC POLLUTANT; PREDITICTIVE MODEL; QUANTITATIVE STRUCTURES; RISKS ASSESSMENTS; STRUCTURAL DESCRIPTORS;

ORGANIC POLLUTANTS;

EID: 34249302353     PISSN: 08869383     EISSN: 1099128X     Source Type: Journal    
DOI: 10.1002/cem.1014     Document Type: Article

References (78)

1. Pavlou SP, Dexter RN. Distribution of polychlorinated biphenyls (PCB) in estuarine ecosystems. Testing the concept of equilibrium partitioning in the marine environment. Environ. Sci. Technol. 1979; 13: 65-71.
2. Gray JS. Biomagnification in marine systems: the perspective of an ecologist. Mar. Pollut. Bull. 2002; 45: 46-52.
3. Drouillard KG, Fernie KJ, Smits JE, Bortolotti GR, Bird DM, Norstrom RJ. Bioaccumulation and toxicokinetics of 42 polychlorinated biphenyl congeners in American kestrels (Falco sparverius). Environ. Toxicol. Chem. 2001; 20: 2514-2522.
4. Hendriks AJ, van der Linde A, Cornelissen G, Sijm DT. The power of size. 1. Rate constants and equilibrium ratios for accumulation of organic substances related to octanol-water partition ratio and species weight. Environ. Toxicol. Chem. 2001; 20: 1399-1420.
5. Lin HI, Berzins DW, Myers L, George WT, Abdelghani A, Watanabe KH. A Bayesian approach to parameter estimation for a crayfish (Procambarus spp.) bioaccumulation model. Environ. Toxicol. Chem. 2004; 23: 2259-2266.
6. Wang X, Harada S, Watanabe M, Koshikawa H, Geyer HJ. Modelling the bioconcentration of hydrophobic organic chemicals in aquatic organisms. Chemosphere 1996; 32: 1783-1793.
7. Wintermyer M, Skaidas A, Roy A, Yang Y-C, Georgapoulos P, Burger J, Cooper K. The development of a physiologically-based pharmacokinetic model using the distribution of 2,3,7,8-tetrachlorodibenzo-p-dioxin in the tissues of the eastern oyster (Crassostrea virginica). Mar. Environ. Res. 2005; 60: 133-152.
8. Mackay D, Fraser A. Bioaccumulation of persistent organic chemicals: mechanisms and models. Environ. Pollut. 2000; 110: 375-391.
9. Fraser AJ, Burkow IC, Wolkers H, Mackay D. Modeling biomagnification and metabolism of contaminants in harp seals of the Barents Sea. Environ. Toxicol. Chem. 2002; 21: 55-61.
10. Gorree M, Tamis WLM, Traas TP, Elbers MA. BIOMAG: a model for biomagnification in terrestrial food chains. The case of cadmium in the Kempen, The Netherlands. Sci. Total Environ. 1995; 168: 215-223.
11. Linkov I, Burmistrov D. Model uncertainty and choices made by modelers: lessons learned from the International Atomic Energy Agency model inter-comparisons. Risk Anal. 2003; 23: 1297-1308.
12. Devillers J, Bintein S, Domine D. Comparison of BCF models based on log P. Chemosphere 1996; 33: 1047-1065.
13. Hill AJ, Teraoka H, Heideman W, Peterson RE. Zebrafish as a model vertebrate for investigating chemical toxicity. Toxicol. Sci. 2005; 86: 6-19.
14. Eriksson L, Johansson E, Lindgren F, Wold S. GIFI-PLS: Modeling of non-linearities and discontinuities in QSAR. Quant. Struct.-Act. Rel. 2000; 19: 345-355.
15. Hansch C. QSAR and the role of luck in research. Il Farmaco 2003; 58: 621-623.
16. Patel H, ten Berge W, Cronin MTD. Quantitative structure-activity relationships (QSARs) for the prediction of skin permeation of exogenous chemicals. Chemosphere 2002; 48: 603-613.
17. Geyer HJ, Scheunert I, Bruggemann R, Steinberg C, Korte F, Kettrup A. QSAR for organic chemical bioconcentration in Daphnia, algae, and mussels. Sci. Total Environ. 1991; 109-110: 387-394.
18. Dimitrov SD, Dimitrova NC, Walker JD, Veith GD, Mekenyan OG. Bioconcentration potential predictions based on molecular attributes - an early warning approach for chemicals found in humans, birds, fish and wildlife. QSAR Comb. Sci. 2003; 22: 58-68.
19. Cronin MTD, Aptula AO, Duffy JC, Netzeva TI, Rowe PH, Valkova IV, Wayne Schultz T. Comparative assessment of methods to develop QSARs for the prediction of the toxicity of phenols to Tetrahymena pyriformis. Chemosphere 2002; 49: 1201-1221.
20. Gramatica P, Vighi M, Consolaro F, Todeschini R, Finizio A, Faust M. QSAR approach for the selection of congeneric compounds with a similar toxicological mode of action. Chemosphere 2001; 42: 873-883.
21. Walker JD. Applications of QSARs in toxicology: a US Government perspective. J. Mol. Struc.-Theochem 622: 167-184.
22. Hansch C, Bonavida B, Jazirehi AR, Cohen JJ, Milliron C, Kurup A. Quantitative structure-activity relationships of phenolic compounds causing apoptosis. Bioorgan. Med. Chem. 2003; 11: 617-620.
23. Schultz TW, Cronin MTD, Walker JD, Aptula AO. Quantitative structure-activity relationships (QSARs) in toxicology: a historical perspective. J. Mol. Struc.-Theochem 2003; 622: 1-22.
24. Schultz TW, Cronin MTD, Netzeva TI. The present status of QSAR in toxicology. J. Mol. Struc.-Theochem 2003; 622: 23-38.
25. Bradbury SP. Quantitative structure-activity relationships and ecological risk assessment: an overview of predictive aquatic toxicology research. Toxicol. Lett. 1995; 79: 229-237.
26. Tosato ML, Piazza R, Chiorboli C, Passerini L, Pino A, Cruciani G, Clementi S. Application of chemometrics to the screening of hazardous chemicals. A case study. Chemometr. Intell. Lab. Syst. 1992; 16: 155-167.
27. Jonsson J, Eriksson L, Sjöström M, Wold S, Tosato ML. A strategy for ranking environmentally occurring chemicals. Chemometr. Intell. Lab. Syst. 1989; 5: 169-186.
28. Dunn WJ. III. QSAR approaches to predicting toxicity. Toxicol. Lett. 1988; 43: 277-283.
29. Carlson R, Gautun H. Combinatorial libraries and the development of organic synthetic methods. PLS modelling to discriminate between successful and failed reaction systems. Chemometr. Intell. Lab. Syst. 2005; 78: 113-124.
30. Wold S, Sjöström M. Chemometrics, present and future success. Chemometr. Intell. Lab. Syst. 1998; 44: 3-14.
31. Turner JV, Glass BD, Agatonovic-Kustrin S. Prediction of drug bioavailability based on molecular structure. Anal. Chim. Acta 2003; 485: 89-102.
32. Lundstedt T. A QSAR strategy for screening of drugs, and predicting their clinical activity. Drug. News Perspect. 1991; 4: 468-475.
33. Dunn WJ III. Quantitative structure-activity relationships (QSAR). Chemometr. Intell. Lab. Syst. 1989; 6: 181-190.
34. Calamari D. Assessment of persistent and bioaccumulating chemicals in the aquatic environment. Toxicology 2002; 181-182: 183-186.
35. Trapp S, Schwartz S. Proposals to overcome limitations in the EU chemical risk assessment scheme. Chemosphere 2000; 41: 965-971.
36. Jacobs MN. In silico tools to aid risk assessment of endocrine disrupting chemicals. Toxicology 2004; 205: 43-53.
37. Leonards PE, Broekhuizen S, de Voogt P, Van Straalen NM, Brinkman UA, Cofino WP, van Hattum B. Studies of bioaccumulation and biotransformation of PCBs in mustelids based on concentration and congener patterns in predators and preys. Arch. Environ. Contam. Toxicol. 1998; 35: 654-665.
38. Boon JP, Reijnders PJH, Dols J, Wensvoort P, Hillebrand MTJ. The kinetics of individual polychlorinated biphenyl congeners in female harbour seals (Phoca vitulina), with evidence for structure-related metabolism. Aquatic Toxicol. 1987; 10: 307-324.
39. Looser R, Ballschmiter K. Biomagnification of polychlorinated biphenyls (PCBs) in freshwater fish. Anal. Bioanal. Chem. 1998; 360: 816-819.
40. Russell RW, Gobas FAPC, Haffner DG. Role of chemical and ecological factors in trophic transfer of organic chemicals in aquatic food webs. Environ. Toxicol. Chem. 1999; 18: 1250-1257.
41. Kannan N, Reusch TBH, Schulzbull DE, Petrick G, Duinker JC. Chlorobiphenyls - model compounds for metabolism in food-chain organisms and their potential use as ecotoxicological stress indicators by application of the metabolic slope concept. Environ. Sci. Technol. 1995; 29: 1851-1859.
42. Lundstedt-Enkel K, Tysklind M, Trygg J, Schüller P, Asplund L, Eriksson U, Häggberg L, Odsjö T, Hjelmberg M, Olsson M, Örberg J. A statistical resampling method to calculate biomagnification factors exemplified with organochlorine data from herring (Clupea harengus) muscle and guillemot (Una aalge) egg from the Baltic Sea. Environ. Sci. Technol. 2005; 39: 8395-8402.
43. Lundstedt-Enkel K, Asplund L. Biomagnification factors calculated with the randomly sampled ratios method for Brominated flame retardants in Baltic Sea herring (Clupea harengus) and guillemot (Uria aalge) Manuscript.
44. Bignert A, Asplund L, Wilander A. Comments concerning the national Swedish contaminant monitoring programme in marine biota, 2005; http://www2.nrm.se/ mg/mcom05.pdf/ [accessed 15 August 2006].
45. Lundstedt-Enkel K, Asplund L, Nylund K, Bignert A, Tysklind M, Olsson M, Örberg J. Multivariate data analysis of organochlorines and brominated flame retardants in Baltic Sea guillemot (Uria aalge) egg and muscle. Chemosphere 2006; In Press.
46. Wold S, Albano C, Dunn WJ III, Edlund U, Esbensen K, Geladi P, Hellberg S, Johansson E, Lindberg W, Sjöström
47. M. Chemometrics: Mathematics and Statistics in Chemistry; NATO ASI Series C: Mathematical and Physical Sciences 138; Kowalski BR; Reidel Publishing: Dordrecht, The Netherlands, 1984.
48. Kvalheim OM. Model building in chemistry, a unified approach. Anal. Chim. Acta 1989; 223: 53-73.
49. Carlson R, Lundstedt T, Albano C. Screening of suitable solvents for organic Synthesis. Strategies for solvent Selection. Acta Chem. Scand. B 1984; 39: 79-91.
50. Lundstedt T, Andersson PM, Linusson A, Sjöström M, Wold S, Norden B, Clementi S, Cruciani G, Pastor M. Intelligent combinatorial libraries; Computer-assisted lead finding and optimization; van de Waterbeemd H, Testa B, Folkes G; Wiley-VCH: Basel, 1997.
51. Eriksson L, Johansson E. Multivariate design and modeling in QSAR. Chemometr. Intell. Lab. Syst. 1996; 34: 1-19.
52. Olsson O, Nilsson T, Fransson T. Long-term study of mortality in the common guillemot in the Baltic Sea; Report from Swedish Environmental Protection Agency: 2000. Report No. 5057. http://www.naturvardsverket.se/bokhandeln/pdf/ 620-6121-6.pdf/ [accessed 15 August 2006].
53. Lundstedt-Enkel K, Johansson AK, Tysklind M, Asplund L, Nylund K, Olsson M, Örberg J. Multivariate data analyses of chlorinated and brominated contaminants and biological characteristics in adult guillemot (Uria aalge) from the Baltic Sea. Environ. Sci. Technol. 2005; 39: 8630-8637.
54. Lundstedt-Enkel K, Asplund L, Nylund K, Bignert A, Tysklind M, Olsson M, Orberg J. Multivariate data analysis of organochlorines and brominated flame retardants in Baltic Sea guillemot (Uria aalge) egg and muscle. Chemosphere 2006; 65: 1591-1599.
55. Jensen S, Reutergårdh L, Jansson B. Manual of methods in aquatic environment research. Part 9 - Analyses of metals and organochlorines in fish. Analytical methods for measuring organochlorines and methyl mercury by gas chromatography. FAO Fish. Tech. Pap. 1983: 21-33.
56. Eriksson U, Häggberg L, Kärsrud A-S, Litzén K, Asplund L. Analytical method for determination of chlorinated organic contaminants in biological matrices; ITM, Institute of Applied Environmental Research, Stockholm University, Sweden: 1997. 59.
57. Taylor JK. Quality assurance of chemical measurements. Lewis Publishers, Inc.: Chelsea, MI, USA, 1987.
58. Lundstedt-Enkel K, Schüller P. Randomly Sampled Ratios, version 1.3, Infidyne: Uppsala, Sweden. http:// www.Infidyne.com/ [accessed 15 August 2006].
59. TSAR. http://www.accelrys.com/ [assessed 15 August 2006].
60. Hawker DW, Connell DW. Octanol water partition-coefficients of polychlorinated biphenyl congeners. Environ. Sci. Technol. 1988; 22: 382-387.
61. SRC. Syracuse Research Corporation. The Physical Properties Database (PHYSPROP); http://www.syrres.com/ esc/physdemo.htm/ [accessed 15 August 2006].
62. Hansch C, Leo A, Hoekman D. Exploring QSAR. Hydrophobic, electronic, and steric constants; American Chemical Society, Professional Reference Book; Washington, DC, 1995.
63. Braekevelt E, Tittlemier SA, Tomy GT. Direct measurement of octanol-water partition coefficients of some environmentally relevant brominated diphenyl ether congeners. Chemosphere 2002; 51: 563-567.
64. Great Lakes Chemical Corporation. Material safety data sheet, Hexabromocyclododecane; http://www.el.greatlakes. com/common/msdspdf/00177.pdf/ [assessed 15 August 2006].
65. SIMCA-P+. version 11.0.0, Umetrics: Umeå, Sweden 2004. http://www.umetrics.com/ [accessed 15 August 2006].
66. Wold S. Personal memories of the early PLS development. Chemometr. Intell. Lab. Syst. 2001; 58: 83-84.
67. Höskuldsson A. PLS regression methods. J. Chemom. 1988; 2: 211-228.
68. Martens H. Reliable and relevant modelling of real world data: A personal account of the development of PLS Regression. Chemometr. Intell. Lab. Syst. 2001; 58: 85-95.
69. Wold S, Esbensen K, Geladi P. Principal component analysis. Chemometr. Intell. Lab. Syst. 1987; 2: 37-52.
70. Lundstedt T, Seifert E, Abramo L, Thelin B, Nyström Å, Pettersen J, Bergman R. Experimental design and optimization. Chemometr. Intell. Lab. Syst. 1998; 42: 3-40.
71. Eriksson L, Johansson E, Kettaneh Wold N, Wold S. Introduction to Multi- and Megavariate Data Analysis using projection methods (PCA and PLS). Umetrics: Umeå, 1999.
72. Wold S, Sjöström M, Carlson R, Lundstedt T, Hellberg S, Skagerberg B, Wikström C, Öhman J. Multivariate design. Anal. Chim. Acta 1986; 191: 17.
73. Borlakoglu JT, Wilkins JPG. Metabolism of di-, tri- and tetrabromobiphenyls by hepatic microsomes isolated from control animals and animals treated with Aroclor 1254, a commercial mixture of polychlorinated biphenyls (PCBs). Comp. Biochem. Physiol. 1993; 105C: 107-112.
74. Andersson PM, Linusson A, Wold S, Sjöström M, Lundstedt T, Nordén B. Design of small libraries for lead exploration; Molecular Diversity in Drug Design; Dean PM, Lewis RA; KluwerAcademic Publishers: Dordrecht, The Netherlands, 1999.
75. Lundstedt T. The Willgerodt-Kindler reaction. A multivariate approach; PhD thesis, Umeå University. 1986.
76. Linusson A, Gottfries J, Lindgren F, Wold S. Statistical molecular design of building blocks for combinatorial chemistry. J. Med. Chem. 2000; 43: 1320-1328.
77. Tysklind M, Andersson P, Haglund P, van Bavel B, Rappe C. Selection of polychlorinated biphenyls for use in quantitative structure-activity modelling. SAR QSAR Environ. Res. 1995; 4: 11-19.
78. Olsson I-M, Gottfries J, Wold S. D-optimal onion designs in statistical molecular design. Chemometr. Intell. Lab. Syst. 2004; 73: 37-46.