Biodehalogenation and Metabolism of [125I]-4-iodobiphenyl

Sinsheimerx, J.E.; Shum, Y.Y.

doi:10.1002/jps.2600700521

Cited by 3 publications

(2 citation statements)

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“…The physicochemical properties and electronic parameters of these biphenyls cannot account for the observed differences in hydroxylation. In vivo metabolism studies of 4-iodobiphenyl also showed it to be oxidized primarily to the 4-hydroxy-4'-iodobiphenyl, a situation analogous to the metabolism of 4-chlorobiphenyl (11).…”

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confidence: 94%

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The role of structure in the disposition of halogenated aromatic xenobiotics.

Birnbaum¹

1985

Environ Health Perspect

103

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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.Halogenated aromatic hydrocarbons constitute a broad class of compounds with varying structure, uses, environmental occurrence, and toxicity. The nature of the halogen atoms(s) involved and the structure of the aromatic ring(s) deternines the physical properties of these molecules as well as influencing the response of biological systems to them. The availability of these compounds to their biological target site is governed by a complex interaction of physical and biological factors. In this paper, the structure of halogenated aromatic hydrocarbons will be correlated with their disposition in living systems. Since extensive reviews have been written on the less complex compounds, such as the halogenated benzenes, only the multiring structures such as the halogenated naphthalenes, biphenyls, dibenzodioxins, and dibenzofurans will be considered. Several recent reviews have concerned the pharmacokinetics of polyhalogenated aromatic hydrocarbons (1-4); 2,3,7,8-tetrachlorodibenzofuran (TCDF) (5); 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) (6,7); and a comparison of dioxins and furans (8). I shall attempt to emphasize the similarities and differences in the disposition of these compounds as well as discuss the results of some current investigations both in our laboratory and others.There are 75 possible chlorinated dibenzodioxins and 135 chlorinated dibenzofuran isomers. The total number of chlorinated biphenyl and naphthalene isomers is in the hundreds. Most of these isomers exist in complex indus-

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“…Likewise, brominated dioxins, furans, and naphthalenes are rare, although brominated naphthalenes have been shown to exist as toxic impurities in polybrominated biphenyls (PBBs) (9). Iodinated and fluorinated biphenyls and dioxins have been synthesized for pharmaceutical and research purposes (10,11) but have not been detected as environmental pollutants.…”

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confidence: 99%