Unique Physicochemical Properties of Perfluorinated Compounds and Their Bioconcentration in Common Carp Cyprinus carpio L.

Carp (Cyprinus carpio L.) was exposed to perfluorinated compounds (PFCs)—perfluoroalkyl carboxylic acids (number of carbon atoms, C = 8, 11, 12, 14, 16, and 18) and perfluorooctane sulfonate (PFOS)—in bioconcentration tests to compare the bioconcentration factors (BCFs) and physicochemical properties of each specific compound. Despite having the same number of carbon atoms (C = 8), the BCFs of perfulorooctanoic acid (PFOA) and PFOS differed by more than two orders of magnitude (PFOA BCF = < 5.1 to 9.4; PFOS BCF = 720 to 1300). The highest BCFs were obtained from perfluorododecanoic acid (BCF = 10,000 to 16,000) and perfluorotetradecanoic acid (BCF = 16,000 to 17,000). The longest observed depuration half-lives were for perfluorohexadecanoic acid (48 to 54 days) and PFOS (45 to 52 days). The concentrations of PFCs were highest in the viscera, followed by the head, integument, and remaining parts of the test fish. PFCs concentrations in the integument, which was in direct contact with the test substances, were relatively greater than that of other lipophilic substance (hexachlorobenzene). It is likely that Clog P would be a better parameter than log Kow for the prediction of BCFs for PFCs. Threshold values for PFCs bioaccumulation potential (molecular weight = 700, maximum diameter = 2 nm) seemed to deviate from those generally reported because of the specific steric bulk effect of molecule size.

[1]  Jeffrey H Mandel,et al.  Perfluorooctanesulfonate and other fluorochemicals in the serum of American Red Cross adult blood donors. , 2003, Environmental health perspectives.

[2]  Gilman D. Veith,et al.  Predicting bioconcentration factors of highly hydrophobic chemicals. Effects of molecular size , 2002 .

[3]  Nobuyoshi Yamashita,et al.  Occurrence of Perfluoroalkyl Surfactants in Water, Fish, and Birds from New York State , 2006, Archives of environmental contamination and toxicology.

[4]  Caroline Vanparys,et al.  Estrogen-Like Properties of Fluorotelomer Alcohols as Revealed by MCF-7 Breast Cancer Cell Proliferation , 2005, Environmental health perspectives.

[5]  Uta Berger,et al.  Perfluoroalkyl and polyfluoralkyl substances (PFASs) in the environment: terminology, classification, and origins , 2011 .

[6]  D. Hoekman Exploring QSAR Fundamentals and Applications in Chemistry and Biology, Volume 1. Hydrophobic, Electronic and Steric Constants, Volume 2 J. Am. Chem. Soc. 1995, 117, 9782 , 1996 .

[7]  Frank A. P. C. Gobas,et al.  A review of bioconcentration factor (BCF) and bioaccumulation factor (BAF) assessments for organic chemicals in aquatic organisms , 2006 .

[8]  D. Waxman,et al.  trans-activation of PPARalpha and induction of PPARalpha target genes by perfluorooctane-based chemicals. , 2004, Toxicological sciences : an official journal of the Society of Toxicology.

[9]  C. Lau,et al.  Perfluoroalkyl acids: a review of monitoring and toxicological findings. , 2007, Toxicological sciences : an official journal of the Society of Toxicology.

[10]  A. Langley,et al.  Thyroid, bradycardic and hypothermic effects of perfluoro-n-decanoic acid in rats. , 1985, Journal of toxicology and environmental health.

[11]  Wei Liu,et al.  PFOS and PFOA in environmental and tap water in China. , 2009, Chemosphere.

[12]  J. Holson,et al.  An oral two-generation reproductive toxicity study of S-111-S-WB in rats. , 2008, Reproductive toxicology.

[13]  J. Tietge,et al.  Reproductive toxicity and disposition of 2,3,7,8‐tetrachlorodibenzo‐p‐dioxin in adult brook trout (Salvelinus fontinalis) following a dietary exposure , 1998 .

[14]  Nobuyoshi Yamashita,et al.  A survey of perfluorooctane sulfonate and related perfluorinated organic compounds in water, fish, birds, and humans from Japan. , 2003, Environmental science & technology.

[15]  J. Depierre,et al.  Effects of peroxisome proliferators on the thymus and spleen of mice , 2000, Clinical and experimental immunology.

[16]  J. Gulliver,et al.  Partitioning Characteristics of Perfluorooctane Sulfonate Between Water and Foods , 2011, Archives of Environmental Contamination and Toxicology.

[17]  J. Tolls,et al.  Surfactant bioconcentration--a critical review. , 1994, Chemosphere.

[18]  J. Nichols,et al.  Evaluation of log KOW and tissue lipid content as predictors of chemical partitioning to fish tissues , 1998 .

[19]  Kurunthachalam Kannan,et al.  Perfluoroalkyl and polyfluoroalkyl substances: current and future perspectives , 2011 .

[20]  James E Klaunig,et al.  PPARalpha agonist-induced rodent tumors: modes of action and human relevance. , 2003, Critical reviews in toxicology.

[21]  M. Saha,et al.  Levels, Temporal Trends, and Tissue Distribution of Perfluorinated Surfactants in Freshwater Fish from Asian Countries , 2011, Archives of environmental contamination and toxicology.

[22]  D. Poppinger,et al.  Bioaccumulation of dyestuffs and organic pigments in fish. Relationships to hydrophobicity and steric factors , 1988 .

[23]  K. Failing,et al.  Carryover of Perfluorooctanoic Acid (PFOA) and Perfluorooctane Sulfonate (PFOS) from Soil to Plants , 2009, Archives of environmental contamination and toxicology.

[24]  G. Olsen,et al.  Perfluoroalkyl chemicals and human fetal development: an epidemiologic review with clinical and toxicological perspectives. , 2009, Reproductive toxicology.

[25]  Scott A Mabury,et al.  Bioconcentration and tissue distribution of perfluorinated acids in rainbow trout (Oncorhynchus mykiss) , 2003, Environmental toxicology and chemistry.

[26]  Jon A Arnot,et al.  Molecular size cutoff criteria for screening bioaccumulation potential: Fact or fiction? , 2010, Integrated environmental assessment and management.

[27]  T. Tsuda,et al.  Seasonal Changes of PFOS and PFOA Concentrations in Lake Biwa Water , 2010, Bulletin of environmental contamination and toxicology.

[28]  Aaron T. Fisk,et al.  Dietary accumulation and depuration of hydrophobic organochlorines: Bioaccumulation parameters and their relationship with the octanol/water partition coefficient , 1998 .

[29]  W. J. Dyer,et al.  A rapid method of total lipid extraction and purification. , 1959, Canadian journal of biochemistry and physiology.

[30]  J. Giesy,et al.  Global distribution of perfluorooctane sulfonate in wildlife. , 2001, Environmental science & technology.

[31]  Robert A Hoke,et al.  Are PFCAs bioaccumulative? A critical review and comparison with regulatory criteria and persistent lipophilic compounds. , 2008, Environmental science & technology.

[32]  Hans-Joachim Lehmler,et al.  Synthesis of environmentally relevant fluorinated surfactants--a review. , 2005, Chemosphere.

[33]  Frank A. P. C. Gobas,et al.  Relationship between bioconcentration in fish and steric factors of hydrophobic chemicals , 1985 .

[34]  Yu-Jui Yvonne Wan,et al.  Inhibition of Carrageenan-Induced Cutaneous Inflammation by PPAR Agonists Is Dependent on Hepatocyte-Specific Retinoid X ReceptorAlpha , 2006, PPAR research.

[35]  Jianying Hu,et al.  Tissue distribution and maternal transfer of poly- and perfluorinated compounds in Chinese sturgeon (Acipenser sinensis): implications for reproductive risk. , 2010, Environmental science & technology.

[36]  Y. Yakabe,et al.  Unique bioconcentration characteristics of new aryl fluoroalkyl ethers in common carp (Cyprinus carpio). , 2003, Chemosphere.

[37]  A. Calafat,et al.  Serum concentrations of 11 polyfluoroalkyl compounds in the u.s. population: data from the national health and nutrition examination survey (NHANES). , 2007, Environmental science & technology.

[38]  Nobuyoshi Yamashita,et al.  Perfluoroalkyl Acids in Marine Organisms from Lake Shihwa, Korea , 2009, Archives of environmental contamination and toxicology.

[39]  N. Yamashita,et al.  Alkaline Digestion and Solid Phase Extraction Method for Perfluorinated Compounds in Mussels and Oysters from South China and Japan , 2006, Archives of environmental contamination and toxicology.

[40]  M. A. Mohd,et al.  Perfluorooctanesulfonate and related fluorochemicals in human blood from several countries. , 2004, Environmental science & technology.

[41]  Gilman D. Veith,et al.  Bioconcentration potential predictions based on molecular attributes – an early warning approach for chemicals found in humans, birds, fish and wildlife , 2003 .

[42]  James Franklin,et al.  Perfluoroalkyl and Polyfluoroalkyl Substances in the Environment: Terminology, Classification, and Origins , 2011, Integrated environmental assessment and management.

[43]  Katsumi Kobayashi,et al.  Molecular size as a limiting characteristic for bioconcentration in fish. , 2008, Journal of environmental biology.

[44]  Masanori Otsuka,et al.  Comparison of Nitrofen Uptake via Water and Food and its Distribution in Tissue of Common Carp, Cyprinus carpio L. , 2011, Bulletin of environmental contamination and toxicology.

[45]  F. Gobas,et al.  Mechanism of Biomagnification in Fish under Laboratory and Field Conditions , 1999 .