Partitioning of polychlorinated biphenyls into human cells and adipose tissues: Evaluation of octanol, triolein, and liposomes as surrogates

Environmental Science and Technology

Volumn 48, Issue 10, 2014, Pages 5920-5928

  Quinn, Cristina L ^a,b   Van Der Heijden, Stephan A ^a   Wania, Frank ^b   Jonker, Michiel T O ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

^b UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL RESINS; ALCOHOLS; BIOCHEMISTRY; HISTOLOGY; HYDROPHOBICITY; ORGANIC POLLUTANTS; PHOSPHOLIPIDS; POLYCHLORINATED BIPHENYLS; TISSUE;

COMPARATIVE EVALUATIONS; DEGREE OF SATURATIONS; EXPERIMENTAL DETERMINATION; HYDROPHOBIC ORGANIC CONTAMINANT; PARTITION COEFFICIENT; POLYCHLORINATED BIPHENYL (PCBS); POLYPARAMETER LINEAR FREE ENERGY RELATIONSHIPS; ROOT-MEAN SQUARE ERRORS;

LIPOSOMES;

LIPOSOME; MEMBRANE LIPID; OCTANOL; POLYCHLORINATED BIPHENYL; SATURATED FATTY ACID; TRIOLEIN;

BIOACCUMULATION; LIPID; ORGANIC POLLUTANT; PARTITION COEFFICIENT; PCB; PUBLIC HEALTH; SORPTION;

ABDOMINAL FAT; ADIPOSE TISSUE; ARTICLE; BIOACCUMULATION; BIOMASS PARTITIONING; CHLORINATION; CONTROLLED STUDY; FEMALE; HUMAN; HUMAN CELL; HUMAN TISSUE; HYDROPHOBICITY; IN VITRO STUDY; MCF 7 CELL LINE; MOLECULAR WEIGHT;

ADIPOSE TISSUE; ADULT; AGED; CHLORINE; FEMALE; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; LIPIDS; LIPOSOMES; MCF-7 CELLS; MIDDLE AGED; OCTANOLS; POLYCHLORINATED BIPHENYLS; THERMODYNAMICS; TRIOLEIN; WATER;

EID: 84900993113     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es500090x     Document Type: Article

References (37)

1. Mackay, D.; Fraser, A. Bioaccumulation of persistent organic chemicals: Mechanisms and models Environ. Pollut. 2000, 110, 375-391
2. Escher, B. I.; Schwarzenbach, R. P.; Westall, J. C. Evaluation of liposome-water partitioning of organic acids and bases. 1. Development of a sorption model Environ. Sci. Technol. 2000, 34, 3954-3961
3. Endo, S.; Escher, B. I.; Goss, K.-U. Capacities of membrane lipids to accumulate neutral organic chemicals Environ. Sci. Technol. 2011, 45, 5912-5921
4. Chiou, C. T. Partition coefficients of organic compounds in lipid water-systems and correlation of the fish bioconcentration factors Environ. Sci. Technol. 1985, 19, 57-62
5. Gobas, F.; Lahittete, J. M.; Garofalo, G.; Shiu, W. Y.; Mackay, D. A novel method for measuring membrane-water partition coefficients of hydrophobic organic chemicals: Comparison with 1-octanol-water partitioning J. Pharm. Sci. 1988, 77, 265-272
6. Van der Heijden, S. A.; Jonker, M. T. O. Intra- and interspecies variation in bioconcentration potential of polychlorinated biphenyls: Are all lipids equal? Environ. Sci. Technol. 2011, 45, 10408-10414
7. Jabusch, T. W.; Swackhamer, D. L. Partitioning of polychlorinated biphenyls in octanol/water, triolein/water, and membrane/water systems Chemosphere 2005, 60, 1270-1278
8. Van der Heijden, S. A.; Jonker, M. T. O. Evaluation of liposome-water partitioning for predicting bioaccumulation potential of hydrophobic organic chemicals Environ. Sci. Technol. 2009, 43, 8854-8859
9. Dulfer, W. J.; Govers, H. A. J. Membrane water partitioning of polychlorinated biphenyls in small unilamellar vesicles of 4 saturated phosphatidylcholines Environ. Sci. Technol. 1995, 29, 2548-2554
10. Escher, B. I.; Schwarzenbach, R. P. Partitioning of substituted phenols in liposome-water, biomembrane-water, and octanol-water systems Environ. Sci. Technol. 1996, 30, 260-270
11. Gennis, R. B. Biomembranes: Molecular Structure and Function; Springer-Verlag: New York, 1989.
12. Khemtémourian, L.; Doménech, E.; Doux, J. P. F.; Koorengevel, M. C.; Killian, J. A. Low pH acts as inhibitor of membrane damage induced by human islet amyloid polypeptide J. Am. Chem. Soc. 2011, 133 (39) 15598-15604
13. Amaru, D. L.; Field, C. J. Conjugated linoleic acid decreases MCF-7 human breast cancer cell growth and insulin-like growth factor-1 receptor levels Lipids 2009, 44, 449-458
14. Janes, N.; Hsu, J. W.; Rubin, E.; Taraschi, T. F. Nature of alcohol and anesthetic action on cooperative membrane equilibria Biochemistry 1992, 31, 9467-9472
15. Koynova, R.; Caffrey, M. Phases and phase transitions of the hydrated phosphatidylethanolamines Chem. Phys. Lip. 1994, 69, 1-34
16. Cullis, P. R.; Dekruijff, B. Lipid polymorphism and the functional roles of lipids in biological membranes Biochim. Biophys. Acta 1979, 559, 399-420
17. Bligh, E. G.; Dyer, W. J. A rapid method of total lipid extraction and purification Can. J. Biochem. Phys. 1959, 37, 911-917
18. Jonker, M. T. O.; Koelmans, A. A. Polyoxymethylene solid phase extraction as a partitioning method for hydrophobic organic chemicals in sediment and soot Environ. Sci. Technol. 2001, 35, 3742-3748
19. Hawthorne, S. B.; Jonker, M. T. O.; van der Heijden, S. A.; Grabanski, C. B.; Azzolina, N. A.; Miller, D. J. Measuring picogram per liter concentrations of freely dissolved parent and alkyl PAHs (PAH-34), using passive sampling with polyoxymethylene Anal. Chem. 2011, 83, 6754-6761
20. Li, N. Q.; Wania, F.; Lei, Y. D.; Daly, G. L. A comprehensive and critical compilation, evaluation, and selection of physical-chemical property data for selected polychlorinated biphenyls J. Phys. Chem. Ref. Data 2003, 32, 1545-1590
21. Sabljic, A.; Gusten, H.; Hermens, J.; Opperhuizen, A. Modeling octanol/water partition coefficients by molecular topology: Chlorinated benzenes and biphenyls Environ. Sci. Technol. 1993, 27, 1394-1402
22. Schenker, U.; MacLeod, M.; Scheringer, M.; Hungerbühler, K. Improving data quality for environmental fate models: A least-squares adjustment procedure for harmonizing physicochemical properties of organic compounds Environ. Sci. Technol. 2005, 39, 8434-8441
23. Hawker, D. W.; Connell, D. W. Octanol water partition-coefficients of polychlorinated biphenyl congeners Environ. Sci. Technol. 1988, 22, 382-387
24. Geisler, A.; Endo, S.; Goss, K.-U. Partitioning of organic chemicals to storage lipids: Elucidating the dependence on fatty acid composition and temperature Environ. Sci. Technol. 2012, 46, 9519-24
25. Abraham, M. H.; Andonian-Haftvan, J.; Whiting, G. S.; Leo, A.; Taft, R. S. Hydrogen-bonding 34. The factors that influence the solubility of gases and vapors in water at 298 K, and a new method for its determination J. Chem. Soc.-Perkin Trans. 2 1994, 1777-1791
26. Goss, K. U. Predicting the equilibrium partitioning of organic compounds using just one linear solvation energy relationship (LSER) Fluid Phase Equilib. 2005, 233, 19-22
27. Abraham, M. H.; Al-Hussaini, A. J. M. Solvation parameters for the 209 PCBs: Calculation of physicochemical properties J. Environ. Monit. 2005, 7, 295-301
28. Van Noort, P. C. M.; Haftka, J. J. H.; Parsons, J. R. Updated Abraham solvation parameters for polychlorinated biphenyls Environ. Sci. Technol. 2010, 44, 7037-7042
29. Endo, S.; Brown, T. N.; Goss, K.-U. General model for estimating partition coefficients to organisms and their tissues using the biological compositions and polyparameter linear free energy relationships Environ. Sci. Technol. 2013, 47, 6630-6639
30. Endo, S.; Bauerfeind, J.; Goss, K.-U. Partitioning of neutral organic compounds to structural proteins Environ. Sci. Technol. 2012, 46, 12697-12703
31. Quinn, C. L.; Wania, F.; Czub, G.; Breivik, K. Investigating intergenerational differences in human PCB exposure due to variable emissions and reproductive behaviors Environ. Health Perspect. 2011, 119, 641-646
32. ow) Data for Hydrophobic Organic Compounds: DDT and DDE as a Case Study; Water-Resources Investigations Report 01-4201; U.S. Geological Survey: Reston, VA, 2001; 51 pp.
33. Chiou, C. T.; Schmedding, D. W.; Manes, M. Partitioning of organic compounds in octanol-water systems Environ. Sci. Technol. 1982, 16, 4-10
34. Leo, A.; Hansch, C.; Elkins, D. Partition coefficients and their uses Chem. Rev. 1971, 71, 525-616
35. Jonker, M. T. O.; Van der Heijden, S. A. Bioconcentration factor hydrophobicity cutoff: An artificial phenomenon reconstructed Environ. Sci. Technol. 2007, 41, 7363-7369
36. Bahadur, N. P.; Shiu, W. Y.; Boocock, D. G. B.; Mackay, D. Tricaprylin-water partition coefficients and their temperature dependence for selected chlorobenzenes J. Chem. Eng. Data 1999, 44, 40-43
37. Jonker, M. T. O.; Koelmans, A. A. Sorption of polycyclic aromatic hydrocarbons and polychlorinated biphenyls to soot and soot-like materials in the aqueous environment: Mechanistic considerations Environ. Sci. Technol. 2002, 36, 3725-3734