Development and evaluation of a mechanistic bioconcentration model for ionogenic organic chemicals in fish

Environmental Toxicology and Chemistry

Volumn 32, Issue 1, 2013, Pages 115-128

  Armitage, James M ^a   Arnot, Jon A ^a,b   Wania, Frank ^a   Mackay, Don ^c  

^a UNIVERSITY OF TORONTO   (Canada)

^b Arnot Research and Consulting   (Canada)

^c TRENT UNIVERSITY   (Canada)

Author keywords

Bioconcentration factor; Ionogenic organic chemicals; Mechanistic model; Perfluoroalkyl acids; Phospholipids

Indexed keywords

BIOCONCENTRATION; BIOCONCENTRATION FACTOR; CHEMICAL ABSORPTION; DEGREE OF IONIZATION; DISTRIBUTION RATIO; EMPIRICAL DATA; GENERIC APPROACH; INPUT PARAMETER; MASS BALANCE; MECHANISTIC MODELS; MODEL APPLICATION; MODEL DEVELOPMENT; MODEL PERFORMANCE; MODEL PREDICTION; PARAMETERIZED; PERFLUOROALKYL ACIDS; PROPERTY ESTIMATION; SORPTION CAPACITIES;

BIOACCUMULATION; ENVIRONMENTAL IMPACT; ESTIMATION; FISH; INDUSTRIAL CHEMICALS; ORGANIC ACIDS; ORGANIC CHEMICALS; PHOSPHOLIPIDS; RATE CONSTANTS; TUNGSTEN; UNCERTAINTY ANALYSIS; WATER SUPPLY SYSTEMS;

SORPTION;

IONOGENIC ORGANIC CHEMICAL; OCTANOL; ORGANIC COMPOUND; PHOSPHOLIPID; UNCLASSIFIED DRUG; WATER;

ABSORPTION; BIOACCUMULATION; BIOTRANSFORMATION; CHEMICAL POLLUTANT; FISH; HYDROPHOBICITY; MASS BALANCE; PH; PHOSPHOLIPID;

ABSORPTION; ACCURACY; ANIMAL EXPERIMENT; ARTICLE; BIOACCUMULATION; BIOLOGICAL MODEL; CONCENTRATION (PARAMETERS); FISH; HYDROPHOBICITY; IONIZATION; NONHUMAN; PH; PRIORITY JOURNAL; RESPIRATORY SYSTEM; TISSUE DISTRIBUTION;

ANIMALS; BIOTRANSFORMATION; ENVIRONMENTAL MONITORING; FISHES; HYDROGEN-ION CONCENTRATION; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MODELS, BIOLOGICAL; MODELS, CHEMICAL; ORGANIC CHEMICALS; REGRESSION ANALYSIS; WATER POLLUTANTS, CHEMICAL;

EID: 84871287019     PISSN: 07307268     EISSN: 15528618     Source Type: Journal    
DOI: 10.1002/etc.2020     Document Type: Article

References (64)

1. Franco A, Ferranti A, Davidsen C, Trapp S. 2010. An unexpected challenge: Ionizable compounds in the REACH chemical space. Int J Life Cycle Assess 15: 321-325.
2. Trapp S, Franco A, Mackay D. 2010. Activity-based concept for transport and partitioning of ionizing organics. Environ Sci Technol 44: 6123-6129.
3. Manallack DT. The pKa distribution of drugs: Application to drug discovery. Perspect Med Chem 1: 25-38.
4. Giesy JP, Kannan K. 2001. Global distribution of perfluorooctane sulfonate in wildlife. Environ Sci Technol 35: 1339-1342.
5. Houde M, Martin JW, Letcher RJ, Solomon KR, Muir DCG. 2006. Biological monitoring of polyfluoroalkyl substances: A review. Environ Sci Technol 40: 3463-3473.
6. Houde M, De Silva AO, Muir DCG, Letcher RJ. 2011. Monitoring of perfluorinated compounds in aquatic biota: An updated review. Environ Sci Technol 45: 7962-7973.
7. Brooks BW, Huggett DB, Boxall AB. 2009. Pharmaceuticals and personal care products: Research needs for the next decade. Environ Toxicol Chem 28: 2469-2472.
8. Daughton CG, Brooks BW. 2011. Active pharmaceutical ingredients and fish. In Beyer WN, Meador JP, eds, Environmental Contaminants in Biota: Interpreting Tissue Concentrations, 2nd ed. CRC, Taylor & Francis, Boca Raton, FL, USA.
9. Estimation Program Interface Suite. 2011. U. S. Environmental Protection Agency Exposure Assessment Tools and Models. Office of Pollution Prevention and Toxics, Washington, DC.
10. Huggett DB, Cook JC, Ericson JF, Williams RT. 2003. A theoretical model for utilizing mammalian pharmacology and safety data to prioritize potential impacts of human pharmaceuticals to fish. Hum Ecol Risk Assess 9: 1789-1799.
11. Dimitrov S, Dimitrova N, Parkerton TF, Comber M, Bonnell M, Mekenyan O. 2005. Base-line model for identifying the bioaccumulation potential of chemicals. SAR QSAR Environ Res 16: 531-554.
12. Fu W, Franco A, Trapp S. 2009. Methods for estimating the bioconcentration factor of ionizable organic chemicals. Environ Toxicol Chem 28: 1372-1379.
13. Webster EM, Ellis DA. 2011. Equilibrium modeling: A pathway to understanding observed perfluorocarboxylic and perfluorosulfonic acid behavior. Environ Toxicol Chem 30: 2229-2236.
14. Rodgers T, Leahy D, Rowland M. 2005. Physiologically based pharmacokinetic modeling 1: Predicting the tissue distribution of moderate-to-strong bases. J Pharm Sci 94: 1259-1267.
15. Schmitt W. 2008. General approach for the calculation of tissue to plasma partition coefficients. Toxicol In Vitro 22: 457-467.
16. Arnot JA, Gobas FAPC. 2004. A food web bioaccumulation model for organic chemicals in aquatic ecosystems. Environ Toxicol Chem 23: 2343-2355.
17. Shore PA, Brodie BB, Hogben CAM. 1957. The gastric secretion of drugs: A pH partition hypothesis. J Pharmacol Exp Ther 119: 361-369.
18. Avdeef A, Box KJ, Comer JEA, Hibbert C, Tam KY. 1998. pH-metric logP 10. Determination of liposomal membrane-water partition coefficients of ionizable drugs. Pharmaceut Res 15: 209-215.
19. Escher BI, Schwarzenbach RP, Westall JC. 2000. Evaluation of liposome-water partitioning of organic acids and bases. 1. Development of a sorption model. Environ Sci Technol 34: 3954-3961.
20. Neuwoehner J, Fenner K, Escher BI. 2009. Physiological modes of action of fluoxetine and its human metabolites in algae. Environ Sci Technol 43: 6830-6837.
21. Jabusch TW, Swackhamer DL. 2005. Partitioning of polychlorinated biphenyls in octanol/water, triolein/water, and membrane/water systems. Chemosphere 60: 1270-1278.
22. Endo S, Escher BI, Goss K-U. 2011. Capacities of membrane lipids to accumulate neutral organic chemicals. Environ Sci Technol 45: 5912-5921.
23. Van der Heijden SA, Jonker MTO. 2011. Intra- and interspecies variation in bioconcentration potential of polychlorinated biphenyls: Are all lipids equal? Environ Sci Technol 45: 10408-10414.
24. Jones PD, Hu W, de Coen W, Newsted JL, Giesy JP. 2003. Binding of perfluorinated fatty acids to serum proteins. Environ Toxicol Chem 22: 2639-2649.
25. Han X, Kemper RA, Jepson GW. 2005. Subcellular distribution and protein binding of perfluorooctanoic acid in rat liver and kidney. Drug Chem Toxicol 28: 197-209.
26. Lehmler H-J, Bummer PM. 2004. Mixing of perfluorinated carboxylic acids with dipalmitoylphosphatidylchloline. Biochim Biophys Acta 1664: 141-149.
27. Lehmler H-J, Xie W, Bothun GD, Bummer PM, Knutson BL. 2006. Mixing of perfluorooctanesulfonic acid (PFOS) potassium salt with dipalmitoyl phosphatidylcholine (DPPC). Colloid Surface B 51: 25-29.
28. Xie W, Ludewig G, Wang K, Lehmler H-J. 2010. Model and cell membrane partitioning of perfluorooctanesulfonate is independent of lipid chain length. Colloid Surface B 76: 128-136.
29. Xie W, Bothun GD, Lehmler H-J. 2010. Partitioning of perfluorooctanoate into phosphatidylcholine bilayers is chain length-independent. Chem Phys Lipids 163: 300-308.
30. Martin JW, Mabury SA, Solomon KR, Muir DCG. 2003. Bioconcentration and tissue distribution of perfluorinated acids in rainbow trout (Oncorhynchus mykiss). Environ Toxicol Chem 22: 196-204.
31. Inoue Y, Hashizume N, Yakata N, Murakami H, Suzuki Y, Kikushima E, Otsuka M. 2012. Unique physicochemical properties of perfluorinated compounds and their bioconcentration in common carp Cyprinus carpio L. Arch Environ Contam Toxicol 62: 672-680.
32. Schmitt W. 2008. Corrigendum to General approach for the calculation of tissue to plasma partition coefficients. [Toxicol In Vitro 22:457-467]. Toxicol In Vitro 22: 1666.
33. deBruyn AMH, Gobas FAPC. 2007. The sorptive capacity of animal protein. Environ Toxicol Chem 26: 1803-1808.
34. Endo S, Goss K-U. 2011. Serum albumin binding of structurally diverse neutral organic compounds: Data and models. Chem Res Toxicol 24: 2293-2301.
35. Bischel HN, MacManus-Spencer LA, Zhang C, Luthy RG. 2011. Strong associations of short-chain perfluoroalkyl acids with serum albumin and investigation of binding mechanisms. Environ Toxicol Chem 30: 2423-2430.
36. Gobas FAPC, Mackay D. 1987. Dynamics of hydrophobic organic chemical bioconcentration in fish. Environ Toxicol Chem 6: 495-504.
37. Tolls J, Kloepper-Sams P, Sijm DT. 1994. Surfactant bioconcentration-A critical review. Chemosphere 29: 693-717.
38. Erickson RJ, McKim JM, Lien GJ, Hoffman AD, Batterman SL. 2006. Uptake and elimination of ionisable organic chemicals at fish gills: I. Model formulation, parameterization, and behavior. Environ Toxicol Chem 25: 1512-1521.
39. Erickson RJ, McKim JM, Lien GJ, Hoffman AD, Batterman SL. 2006. Uptake and elimination of ionisable organic chemicals at fish gills: II. Observed and predicted effects of pH, alkalinity, and chemical properties. Environ Toxicol Chem 25: 1522-1532.
40. Saarikoski J, Lindström R, Tyynelä M, Viluksela M. 1986. Factors affecting the absorption of phenolics and carboxylic acids in the guppy (Poecilia reticulate). Ecotox Environ Saf 11: 158-173.
41. Missner A, Pohl P. 2009. 110 years of the Meyer-Overton rule: Predicting membrane permeability of gases and other small compounds. Chem Phys Chem 10: 1405-1414.
42. Escher BI, Hunziker R, Schwarzenbach RP. 1999. Kinetic model to describe the intrinsic uncoupling activity of substituted phenols in energy transducing membranes. Environ Sci Technol 33: 560-570.
43. Flewelling RF, Hubbell WL. 1986. Hydrophobic ion interactions with membranes. Thermodynamic analysis of tetraphenylphosphonium binding to vesicles. Biophys J 49: 531-540.
44. Peterson U, Mannock DA, Lewis RNAH, Pohl P, McElhaney RN, Pohl EE. 2002. Origin of membrane dipole potential: Contribution of the phospholipid fatty acid chains. Chem Phys Lipids 117: 19-27.
45. Haynes DH, Simkowitz P. 1977. 1-Anilino-8-napthalenesulfonate: A fluorescent probe of ion and ionophore transport kinetics and trans-membrane asymmetry. J Membr Biol 33: 63-108.
46. Neubert R. 1989. Ion pair transport across membranes. Pharmaceut Res 6: 743-747.
47. Obata K, Sugano K, Saitoh R, Higashida A, Nabuchi Y, Machida M, Aso Y. 2005. Prediction of oral drug absorption in humans by theoretical passive absorption model. Int J Pharmacol 293: 183-192.
48. Knezovich JP, Lawton MP, Inouye LS. 1989. Bioaccumulation and tissue distribution of a quaternary ammonium surfactant in three aquatic species. Bull Environ Contam Toxicol 42: 87-93.
49. Jafvert CT, Westall JC, Grieder E, Schwarzenbach RP. 1990. Distribution of hydrophobic ionogenic organic compounds between octanol and water: Organic acids. Environ Sci Technol 24: 1795-1803.
50. McKim J, Schmieder P, Veith G. 1985. Absorption dynamics of organic chemical transport across trout gills as related to octanol-water partition coefficient. Toxicol Appl Pharmacol 77: 1-10.
51. Ward PD, Tippin TK, Thakker DR. 2000. Enhancing paracellular permeability by modulating epithelial tight junctions. Pharm Sci Technol Today 3: 346-358.
52. Hendriks AJ, Traas TP, Huijbregts MAJ. 2005. Critical body residues linked to octanol-water partitioning, organism composition, and LC50 QSARs: Meta-analysis and model. Environ Sci Technol 39: 3226-3236.
53. Spycher S, Smejtek P, Netzeva TI, Escher BI. 2008. Toward a class-independent quantitative structure-activity relationship for uncouplers of oxidative phosphorylation. Chem Res Toxicol 21: 911-927.
54. Abraham MH, Zhao YH, Le J, Hersey A, Luscombe CN, Reynolds DP, Beck G, Sherborn B, Cooper I. 2002. On the mechanism of human intestinal absorption. Eur J Med Chem 37: 595-605.
55. Arnot JA, Mackay D, Parkerton TF, Bonnell M. 2008. A database of fish biotransformation rates for organic chemicals. Environ Toxicol Chem 27: 2263-2270.
56. Arnot JA, Meylan W, Tunkel J, Howard PH, Mackay D, Bonnell M, Boethling RS. 2009. A quantitative structure-activity relationship for predicting metabolic biotransformation rates for organic chemicals in fish. Environ Toxicol Chem 28: 1168-1177.
57. Arnot JA, Gobas FAPC. 2006. A review of bioconcentration factor (BCF) and bioaccumulation factor (BAF) assessments for organic chemicals in fish. Environ Rev 14: 257-297.
58. Versonnen B. 2006. ECO7: Development of a Reference Database (Bioconcentration Factors, BCF). Cefic LRI-ECO7-EURAS-0608. Long-Range Research Initiative, Cefic, Brussels, Belgium.
59. Manchester J, Walkup G, Rivin O, You Z. 2010. Evaluation of pKa estimation methods on 211 druglike compounds. J Chem Inf Model 50: 565-571.
60. Liao C, Nicklaus MC. 2009. Comparison of nine programs predicting pKa values of pharmaceutical substances. J Chem Inf Model 49: 2801-2812.
61. Liu C, Gin KYH, Chang VWC, Goh BPL, Reinhard M. 2011. Novel perspectives on the bioaccumulation of PFCs-the concentration dependency. Environ Sci Technol 45: 9758-9764.
62. European Chemical Agency. 2008. ECHA Guidance on Information Requirements and Chemical Safety Assessment. Chapter R.11: PBT assessment. Guidance for the Implementation of REACH. European Chemicals Agency, Helsinki, Finland.
63. Endo S, Bauerfeind J, Goss K-U. 2012. Partitioning of neutral organic chemicals to structural proteins. Platform presentation ET04C-4, 6th SETAC World Congress/SETAC Europe, 22nd Annual Meeting, Berlin, Germany, May 20-24.
64. Droge STJ, Goss K-U. 2012. Effect of sodium and calcium cations on the ion-exchange affinity of organic cations for soil organic matter. Environ Sci Technol 46: 5894-5901.