The Metabolism of Biphenyl by Isolated Viable Rat Hepatocytes

Wiebkin, Philip; Fry, Jeffrey R.; Jones, Carol; Lowing, Ray K.; Bridges, James W.

doi:10.3109/00498257609151390

Cited by 50 publications

(16 citation statements)

References 35 publications

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“…Table IV also shows, that the conjugates were formed only with NH z and 3-or 5-hydroxyl groups, indicating that the B ring does not undergo any significant metabolism. This can be explained in terms of stereochemistry which may be expected to block the 2-positions, however, these positions have been shown to be available for oxidation in biphenyl (20), 4-aminobiphenyl (16), and 3-aminobiphenyl (10, 20). This suggests that the amino group blocks the 2-position but does not explain the lack of hydroxylation at position 6-which must be due to electronic effects.…”

Section: Discussionmentioning

confidence: 95%

Metabolism of [14C]2-aminobiphenylin vivo by different species

Kajbaf

Gorrod

1987

European Journal of Drug Metabolism and Pharmacokinetics

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[14C] 2-Aminobiphenyl is predominantly metabolised in vivo to 3- and 5-hydroxy conjugated derivatives in all species. In some species, 2-aminobiphenyl is also excreted to a small extent as N-conjugated derivatives. Renal excretion accounts for about 30-40% of the administered dose during the first 24 hours. The 5-O-sulphate and 5-O-glucuronide of 2-amino-5-hydroxybiphenyl have been found as major metabolites with all species; 2-amino-3-hydroxybiphenyl-O-sulphate is also a significant metabolite. There were metabolic differences observed between species in this study. HPLC and TLC analytical techniques were used for separation and detection of [14C] 2-aminobiphenyl and its metabolites. Formation of different isomeric metabolites may be explained by electronic Hückel molecular orbital calculations and stereochemical factors.

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Section: Discussionmentioning

confidence: 95%

Metabolism of [14C]2-aminobiphenylin vivo by different species

Kajbaf

Gorrod

1987

European Journal of Drug Metabolism and Pharmacokinetics

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“…The filamentous fungus Cunninghamella elegans produces glucuronide conjugates during biphenyl metabolism (6) and glucoside conjugates during the transformation of PAHs (22), as does Phanerochaete chrysosporium (32). Mammals and fungi also produce glucuronide and sulfate conjugates (3,12,37). Rhizoctonia solani was even able to produce xylose conjugates with anthracene (33).…”

Section: Discussionmentioning

confidence: 99%

“…Filamentous fungi and mammals favor initial hydroxylation at the 2 and 4 positions, respectively, followed by further hydroxylation on the second ring (6,12,25,31). Conjugates of these hydroxylated derivatives of biphenyl have also been reported (6,12,37). In contrast, some yeasts prefer the same aromatic ring for the second hydroxylation (19).…”

mentioning

confidence: 99%

Novel Ring Cleavage Products in the Biotransformation of Biphenyl by the Yeast Trichosporon mucoides

Sietmann

Hammer

Specht

et al. 2001

Appl Environ Microbiol

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The yeast Trichosporon mucoides, grown on either glucose or phenol, was able to transform biphenyl into a variety of mono-, di-, and trihydroxylated derivatives hydroxylated on one or both aromatic rings. While some of these products accumulated in the supernatant as dead end products, the ortho-substituted dihydroxylated biphenyls were substrates for further oxidation and ring fission. These ring fission products were identified by high-performance liquid chromatography, gas chromatography-mass spectrometry, and nuclear magnetic resonance analyses as phenyl derivatives of hydroxymuconic acids and the corresponding pyrones. Seven novel products out of eight resulted from the oxidation and ring fission of 3,4-dihydroxybiphenyl. Using this compound as a substrate, 2-hydroxy-4-phenylmuconic acid, (5-oxo-3-phenyl-2,5-dihydrofuran-2-yl)acetic acid, and 3-phenyl-2-pyrone-6-carboxylic acid were identified. Ring cleavage of 3,4,4-trihydroxybiphenyl resulted in the formation of [5-oxo-3-(4-hydroxyphenyl)-2,5-dihydrofuran-2-yl]acetic acid, 4-(4-hydroxyphenyl)-2-pyrone-6-carboxylic acid, and 3-(4-hydroxyphenyl)-2-pyrone-6-carboxylic acid. 2,3,4-Trihydroxybiphenyl was oxidized to 2-hydroxy-5-phenylmuconic acid, and 4-phenyl-2-pyrone-6-carboxylic acid was the transformation product of 3,4,5-trihydroxybiphenyl. All these ring fission products were considerably less toxic than the hydroxylated derivatives.

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“…From the metabolic aspects, these fungicides are xenobiotics for the body and detoxified by the microsomal mixed-functionoxidase system in the liver. 10.11) However, it has never been proven that this system would work normally in the simultaneous presence of these three fungicides.…”

Section: Lemonsmentioning

confidence: 99%