The Role of Structure in the Disposition of Halogenated Aromatic Xenobiotics

Overview

Journal Environ Health Perspect

Date 1985 Sep 1

PMID 2998745

Citations 26

Authors

L S Birnbaum

Affiliations

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Abstract

Halogenated aromatic xenobiotics such as the chlorinated and brominated biphenyls, naphthalenes, dibenzodioxins, and dibenzofurans are widespread environmental contaminants. The number, position, and nature of the halogen atoms as well as the structure of the aromatic rings influence the disposition of these chemicals in living systems. Absorption is governed primarily by the physical properties of lipophilicity and solubility. Distribution through the blood occurs by nonspecific binding to plasma proteins and cellular components. Liver and adipose tissue are the major depots. Metabolism is a prerequisite for excretion. The highly substituted isomers tend to be resistant to metabolism. The route of excretion shifts from urine to feces with increasing size and number of halogen atoms. Although pharmacokinetic modeling has allowed some predictions to be made from one compound to another or across species, more information on metabolism is required in order to improve the ability to predict the disposition in humans of this class of toxic environmental pollutants.

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References

Ioannou Y, Birnbaum L, Matthews H . Toxicity and distribution of 2,3,7,8-tetrachlorodibenzofuran in male guinea pigs. J Toxicol Environ Health. 1983; 12(4-6):541-53. DOI: 10.1080/15287398309530448. View

Birnbaum L, Darcey D, McKinney J . Hexabromonaphthalene contaminants of polybrominated biphenyls: chemical composition and disposition in the rat. J Toxicol Environ Health. 1983; 12(4-6):555-73. DOI: 10.1080/15287398309530449. View

Matthews H, Dedrick R . Pharmacokinetics of PCBs. Annu Rev Pharmacol Toxicol. 1984; 24:85-103. DOI: 10.1146/annurev.pa.24.040184.000505. View

Matthews H, Surles J, Carver J, Anderson M . Halogenated biphenyl transport by blood components. Fundam Appl Toxicol. 1984; 4(3 Pt 1):420-8. DOI: 10.1016/0272-0590(84)90199-4. View

Crummett W, Stehl R . Determination of chlorinated dibenzo-p-dioxins and dibenzofurans in various materials. Environ Health Perspect. 1973; 5:15-25. PMC: 1474977. DOI: 10.1289/ehp.730515. View

Matthews H, Anderson M . The distribution and excretion of 2,4,5,2',5'-pentachlorobiphenyl in the rat. Drug Metab Dispos. 1975; 3(3):211-9. View

Norback D, Engblom J, Allen J . Tissue distribution and excretion of octachlorodibenzo-rho-dioxin in the rat. Toxicol Appl Pharmacol. 1975; 32(2):330-8. DOI: 10.1016/0041-008x(75)90223-9. View

Mathews H, Anderson M . Effect of chlorination on the distribution and excretion of polychlorinated biphenyls. Drug Metab Dispos. 1975; 3(5):371-80. View

Allen J, Van Miller J, Norback D . Tissue distribution, excretion and biological effects of [14C]tetrachlorodibenzo-p-dioxin in rats. Food Cosmet Toxicol. 1975; 13(5):501-5. DOI: 10.1016/0015-6264(75)90002-4. View

10.

Ruzo L, Jones D, Safe S, Hutzinger O . Metabolism of chlorinated naphthalenes. J Agric Food Chem. 1976; 24(3):581-3. DOI: 10.1021/jf60205a007. View

11.

Rose J, Ramsey J, Wentzler T, Hummel R, GEHRING P . The fate of 2,3,7,8-tetrachlorodibenzo-p-dioxin following single and repeated oral doses to the rat. Toxicol Appl Pharmacol. 1976; 36(2):209-26. DOI: 10.1016/0041-008x(76)90001-6. View

12.

Ruzo L, Jones D, Platonow N . Uptake and distribution of chloronaphthalenes and their metabolites in pigs. Bull Environ Contam Toxicol. 1976; 16(2):233-9. DOI: 10.1007/BF01685233. View

13.

Brandt I . Tissue localization of polychlorinated biphenyls. Chemical structure related to pattern of distribution. Acta Pharmacol Toxicol (Copenh). 1977; 40 Suppl 2:1-108. View

14.

Chu I, Secours V, Villeneuve D, Viau A . Metabolism and tissue distribution of (1,4,5,8-14C)--1,2-dichloronaphthalene in rats. Bull Environ Contam Toxicol. 1977; 18(2):177-83. DOI: 10.1007/BF01686064. View

15.

Lutz R, Dedrick R, Matthews H, Eling T, Anderson M . A preliminary pharmacokinetic model for several chlorinated biphenyls in the rat. Drug Metab Dispos. 1977; 5(4):386-96. View

16.

Felt G, Mueller W, Iatropoulos M, COULSTON F, Korte F . Chronic toxicity of 2,5,4'-trichlorobiphenyl in young rhesus monkeys. I. Body distribution, elimination, and metabolism. Toxicol Appl Pharmacol. 1977; 41(3):619-27. DOI: 10.1016/s0041-008x(77)80015-x. View

17.

Matthews H, Kato S, Morales N, Tuey D . Distribution and excretion of 2,4,5,2',4',5'-hexabromobiphenyl, the major component of Firemaster BP-6. J Toxicol Environ Health. 1977; 3(3):599-605. DOI: 10.1080/15287397709529592. View

18.

Hass J, McConnell E, Harvan D . Chemical and toxicologic evaluation of firemaster BP-6. J Agric Food Chem. 1978; 26(1):94-9. DOI: 10.1021/jf60215a006. View

19.

Matthews H, Kato S . The metabolism and disposition of halogenated aromatics. Ann N Y Acad Sci. 1979; 320:131-7. DOI: 10.1111/j.1749-6632.1979.tb56596.x. View

20.

SULLIVAN H, Roffey P, McMahon R . Biotransformation of 4'-ethynl-2-fluorobiphenyl in the rat. In vitro and in vivo studies. Drug Metab Dispos. 1979; 7(2):76-80. View