Uptake and distribution of chloronaphthalenes and their metabolites in pigs

Ruzo, Luis O.; Safe, S.; Jones, Daniel; Platonow, N

doi:10.1007/bf01685233

Cited by 20 publications

(8 citation statements)

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“…Takeshita and Yoshida (57) could detect no relationship between the degree of chlorination and the extent of tissue retention using a polychlorinated naphthalene mixture. Both 1-and 2-chloronaphthalene were readily metabolized to their corresponding hy-droxylated metabolites (58). Two dichloronaphthalenes, 1,2-and 1,4-, were hydroxylated via arene oxides to monohydroxy derivatives, as was the more highly chlorinated isomer, 1,2,3,4-tetrachloronaphthalene (59).…”

Section: However a Clear Species Difference Was Found Between The mentioning

confidence: 99%

The Role of Structure in the Disposition of Halogenated Aromatic Xenobiotics

Birnbaum¹

1985

Environmental Health Perspectives

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Section: However a Clear Species Difference Was Found Between The mentioning

confidence: 99%

The Role of Structure in the Disposition of Halogenated Aromatic Xenobiotics

Birnbaum¹

1985

Environmental Health Perspectives

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“…Takeshita and Yoshida (57) could detect no relationship between the degree of chlorination and the extent of tissue retention using a polychlorinated naphthalene mixture. Both 1-and 2-chloronaphthalene were readily metabolized to their corresponding hydroxylated metabolites (58). Two dichloronaphthalenes, 1,2-and 1,4-, were hydroxylated via arene oxides to monohydroxy derivatives, as was the more highly chlorinated isomer, 1,2,3,4-tetrachloronaphthalene (59).…”

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confidence: 99%

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

Birnbaum¹

1985

Environ Health Perspect

101

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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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“…rats and rabbits (Chu et al ., 1976(Chu et al ., , 1977a(Chu et al ., , 1977b and pigs (Ruzo et al ., 1975(Ruzo et al ., , 1976a(Ruzo et al ., , 1976b, followed by urine analysis. The most common metabolites found were chlorinated naphthols which were either partially dechlorinated or which had undergone rearrangement of the substituted chlorines.…”

Section: Metabolism and Half-livesmentioning

confidence: 96%

Polychlorinated naphthalenes (PCNs) in foods: sources, analytical methodology, occurrence and human exposure

Fernandes

2013

Persistent Organic Pollutants and Toxic Metals in Foods

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Uptake and distribution of chloronaphthalenes and their metabolites in pigs

Cited by 20 publications

References 9 publications

The Role of Structure in the Disposition of Halogenated Aromatic Xenobiotics

The Role of Structure in the Disposition of Halogenated Aromatic Xenobiotics

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

Polychlorinated naphthalenes (PCNs) in foods: sources, analytical methodology, occurrence and human exposure

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