Search tips
Search criteria 


Logo of envhperEnvironmental Health PerspectivesBrowse ArticlesAbout EHPGeneral InformationAuthorsMediaProgramsPartnerships
Environ Health Perspect. 1994 May; 102(5): 464–469.
PMCID: PMC1567124
Research Article

Selective retention of hydroxylated PCB metabolites in blood.


Polychlorinated biphenyls (PCBs) are important environmental contaminants, and their toxicity to wildlife and humans are of major concern. PCBs form persistent and abundant metabolites, PCB methyl sulfones, that accumulate in biota. We now report that certain hydroxylated PCB metabolites show a strong and selective accumulation in mammalian blood. Plasma from experimentally PCB-dosed rats and blood from environmentally exposed grey seals (Halichoerus grypus) and humans were analyzed. Among all possible hydroxylated metabolites of PCB that may be formed, only a few, dominated by 4-OH-2,3,5,3',4'-pentachlorobiphenyl and 4-OH-2,3,5,6,2',4',5'-heptachlorobiphenyl, were found in the blood samples. All identified compounds have a structure with the hydroxy group in a para or meta position, with chlorine atoms on vicinal carbon atoms. The concentrations of hydroxylated PCB in the blood were almost in the same range as the most persistent PCB congeners both for seals and humans.

Full text

Full text is available as a scanned copy of the original print version. Get a printable copy (PDF file) of the complete article (1.6M), or click on a page image below to browse page by page. Links to PubMed are also available for Selected References.

Selected References

These references are in PubMed. This may not be the complete list of references from this article.
  • Perry CB. Review of the Literature on Acute Rheumatism During the Years 1939-1945. Ann Rheum Dis. 1947;6(3):162–183. [PMC free article] [PubMed]
  • Poland A, Glover E, Kende AS. Stereospecific, high affinity binding of 2,3,7,8-tetrachlorodibenzo-p-dioxin by hepatic cytosol. Evidence that the binding species is receptor for induction of aryl hydrocarbon hydroxylase. J Biol Chem. 1976 Aug 25;251(16):4936–4946. [PubMed]
  • Poland A, Knutson JC. 2,3,7,8-tetrachlorodibenzo-p-dioxin and related halogenated aromatic hydrocarbons: examination of the mechanism of toxicity. Annu Rev Pharmacol Toxicol. 1982;22:517–554. [PubMed]
  • Safe S, Bandiera S, Sawyer T, Zmudzka B, Mason G, Romkes M, Denomme MA, Sparling J, Okey AB, Fujita T. Effects of structure on binding to the 2,3,7,8-TCDD receptor protein and AHH induction--halogenated biphenyls. Environ Health Perspect. 1985 Sep;61:21–33. [PMC free article] [PubMed]
  • Gillner M, Bergman J, Cambillau C, Fernström B, Gustafsson JA. Interactions of indoles with specific binding sites for 2,3,7,8-tetrachlorodibenzo-p-dioxin in rat liver. Mol Pharmacol. 1985 Oct;28(4):357–363. [PubMed]
  • Preston BD, Miller JA, Miller EC. Reactions of 2,2',5,5'-tetrachlorobiphenyl 3,4-oxide with methionine, cysteine and glutathione in relation to the formation of methylthio-metabolites of 2,2',5,5'-tetrachlorobiphenyl in the rat and mouse. Chem Biol Interact. 1984 Aug;50(3):289–312. [PubMed]
  • Van den Berg KJ, van Raaij JA, Bragt PC, Notten WR. Interactions of halogenated industrial chemicals with transthyretin and effects on thyroid hormone levels in vivo. Arch Toxicol. 1991;65(1):15–19. [PubMed]
  • Brandt I, Darnerud PO, Bergman A, Larsson Y. Metabolism of 2,4'5-trichlorobiphenyl: enrichment of hydroxylated and methyl sulphone metabolites in the uterine luminal fluid of pregnant mice. Chem Biol Interact. 1982 May;40(1):45–56. [PubMed]
  • Bakke JE, Feil VJ, Bergman A. Metabolites of 2,4',5-trichlorobiphenyl in rats. Xenobiotica. 1983 Sep;13(9):555–564. [PubMed]
  • Wehler EK, Bergman A, Brandt I, Darnerud PO, Wachtmeister CA. 3,3',4,4'-Tetrachlorobiphenyl. Excretion and tissue retention of hydroxylated metabolites in the mouse. Drug Metab Dispos. 1989 Jul-Aug;17(4):441–448. [PubMed]
  • Yoshimura H, Yonemoto Y, Yamada H, Koga N, Oguri K, Saeki S. Metabolism in vivo of 3,4,3',4'-tetrachlorobiphenyl and toxicological assessment of the metabolites in rats. Xenobiotica. 1987 Aug;17(8):897–910. [PubMed]
  • Koga N, Beppu M, Ishida C, Yoshimura H. Further studies on metabolism in vivo of 3,4,3',4'-tetrachlorobiphenyl in rats: identification of minor metabolites in rat faeces. Xenobiotica. 1989 Nov;19(11):1307–1318. [PubMed]
  • Jensen S, Sundström G. Metabolic hydroxylation of a chlorobiphenyl containing only isolated unsubstituted positions--2,2',4,4' ,5,5'-hexachlorobiphenyl. Nature. 1974 Sep 20;251(5472):219–220. [PubMed]
  • Brouwer A, van den Berg KJ. Binding of a metabolite of 3,4,3',4'-tetrachlorobiphenyl to transthyretin reduces serum vitamin A transport by inhibiting the formation of the protein complex carrying both retinol and thyroxin. Toxicol Appl Pharmacol. 1986 Sep 30;85(3):301–312. [PubMed]
  • Brouwer A, Blaner WS, Kukler A, Van den Berg KJ. Study on the mechanism of interference of 3,4,3',4'-tetrachlorobiphenyl with the plasma retinol-binding proteins in rodents. Chem Biol Interact. 1988;68(3-4):203–217. [PubMed]
  • Lans MC, Klasson-Wehler E, Willemsen M, Meussen E, Safe S, Brouwer A. Structure-dependent, competitive interaction of hydroxy-polychlorobiphenyls, -dibenzo-p-dioxins and -dibenzofurans with human transthyretin. Chem Biol Interact. 1993 Jul;88(1):7–21. [PubMed]
  • Rickenbacher U, McKinney JD, Oatley SJ, Blake CC. Structurally specific binding of halogenated biphenyls to thyroxine transport protein. J Med Chem. 1986 May;29(5):641–648. [PubMed]
  • Brouwer A. Inhibition of thyroid hormone transport in plasma of rats by polychlorinated biphenyls. Arch Toxicol Suppl. 1989;13:440–445. [PubMed]
  • Gray LE, Jr, Ostby J, Marshall R, Andrews J. Reproductive and thyroid effects of low-level polychlorinated biphenyl (Aroclor 1254) exposure. Fundam Appl Toxicol. 1993 Apr;20(3):288–294. [PubMed]
  • Morse DC, Groen D, Veerman M, van Amerongen CJ, Koëter HB, Smits van Prooije AE, Visser TJ, Koeman JH, Brouwer A. Interference of polychlorinated biphenyls in hepatic and brain thyroid hormone metabolism in fetal and neonatal rats. Toxicol Appl Pharmacol. 1993 Sep;122(1):27–33. [PubMed]
  • Ness DK, Schantz SL, Moshtaghian J, Hansen LG. Effects of perinatal exposure to specific PCB congeners on thyroid hormone concentrations and thyroid histology in the rat. Toxicol Lett. 1993 Jun;68(3):311–323. [PubMed]
  • Krishnan V, Safe S. Polychlorinated biphenyls (PCBs), dibenzo-p-dioxins (PCDDs), and dibenzofurans (PCDFs) as antiestrogens in MCF-7 human breast cancer cells: quantitative structure-activity relationships. Toxicol Appl Pharmacol. 1993 May;120(1):55–61. [PubMed]
  • Jansen HT, Cooke PS, Porcelli J, Liu TC, Hansen LG. Estrogenic and antiestrogenic actions of PCBs in the female rat: in vitro and in vivo studies. Reprod Toxicol. 1993 May-Jun;7(3):237–248. [PubMed]
  • Korach KS, Sarver P, Chae K, McLachlan JA, McKinney JD. Estrogen receptor-binding activity of polychlorinated hydroxybiphenyls: conformationally restricted structural probes. Mol Pharmacol. 1988 Jan;33(1):120–126. [PubMed]

Articles from Environmental Health Perspectives are provided here courtesy of National Institute of Environmental Health Science