Metabolic hydroxylation of the aromatic rings of 1,1-dichloro-2,2-bis(4-chlorophenyl)ethylene (p,p'-DDE) by the rat

Sundström, Gerdt

doi:10.1021/jf60209a003

Cited by 18 publications

(2 citation statements)

References 28 publications

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“…Therefore, it seems less likely that an arene oxide intermediate is involved in the lung binding of the four isomers. An arene oxide intermediate is implied in the metabolism of the structurally related p,p'-DDE, leading to formation of either hydroxylated DDE or methylsulphonyl-DDE (Sundstrom 1977;Jensen & Jansson 1976). However, all four DDD-isomers are characterized by an identical chlorinated ethane side-chain.…”

Section: Discussionmentioning

confidence: 99%

Covalent Binding of Four DDD Isomers in the Mouse Lung: Lack of Structure Specificity

Lund

Ghantous

Bergman

et al. 1989

Pharmacology & Toxicology

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Previous studies have shown that o,p'-DDD is activated and covalently bound in the mouse lung. In order to examine the structure dependency of the selective lung binding, the 14C-labelled DDD isomers p,p'-DDD, m,p'-DDD and o,m'-DDD were injected intravenously into female C57B1 mice and covalent binding was measured. Autoradiography of solvent-extracted tape-sections showed that all isomers were selectively and covalently bound in the lung alveolar region. As determined by exhaustive extraction of homogenized tissue, maximal binding was observed 4 hr after injection, although the lung/liver concentration ratio increased for 12 days. Covalent protein binding was also observed in vitro, implying that the activation of DDD to a reactive metabolite takes place in the target organ. Since the aryl-chlorine substitution pattern did not change the selective lung binding, bioactivation of DDD may take place at the ethane side-chain.

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Section: Discussionmentioning

confidence: 99%

Covalent Binding of Four DDD Isomers in the Mouse Lung: Lack of Structure Specificity

Lund

Ghantous

Bergman

et al. 1989

Pharmacology & Toxicology

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“…These routes are: reductive dechlorination to DDD, dehydrodechlorination to DDE and oxidation to DDA.14 However, unlike their degradation profiles in microorganisms, DDE, o,p'-DDT, o,p'-DDE and o,p'-DDD are, in addition, ring-hydroxylated at the C-2, C-3 and/or C-4 positions in several mammal species.' [5][6][7][8][9][10][11][12][13][14][15][16][17][18] To our knowledge, the occurrence of DDT ring-hydroxylated metabolites has never been reported previously in microbial systems. These data are in accmdance with the generalization that the resistance of DDT and some of its breakdown products to biotransformation may be attributed to their common parachlorine substitution pattern.…”

Section: Introductionmentioning

confidence: 99%

Characterization of new bacterial transformation products of 1,1,1-trichloro-2,2-bis-(4-chlorophenyl) ethane (DDT) by gas chromatography/mass spectrometry

Massé

Lalanne

Messier

et al. 1989

Biol. Mass Spectrom.

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The microbial transformation of DDT, DDD and DDE was studied in Gram-negative strain B-206 and a number of phenolic metabolites were identified as the trimethylsilyl derivatives in the bacterial extracts by gas chromatography/mass spectrometry. The major metabolites of DDT were DDD, DDE, DDMU, 1,1,1-trichloro-2-(2-hydroxy-4-chlorophenyl)-2-(4'-chlorophenyl) ethane, 1,1,1-trichloro-2-(2-hydroxy-4-chlorophenyl)-2-(4'-hydroxyphenyl) ethane, and 1,1,1-trichloro-2,2-bis-(2-hydroxy-4-chlorophenyl) ethane. Conversely, DDD was mainly degraded into DDE, 1,1-dichloro-2-(2-hydroxy-4-chlorophenyl)-2-(4'-chlorophenyl) ethane and 1,1-dichloro-2-(2-hydroxy-4-chlorophenyl)-2-(4'-hydroxyphenyl) ethane. Finally, DDE was transformed into DDMU, 1,1-dichloro-2-(2-hydroxy-4-chlorophenyl)-2-(4'-chlorophenyl) ethylene, 1,1-dichloro-2-(2-hydroxy-4-chlorophenyl)-2-(4'hydroxyphenyl) ethylene and 1-chloro-2-(2-hydroxy-4-chlorophenyl)-2-(4'-chlorophenyl) ethylene. The phenolic metabolites exhibited [M - TMSCl]+., [M - HCl - TMSCl]+. and/or [M - HCl - TMSCl - Me]+ fragment ions which reflect the presence of an ortho hydroxyl group in these molecules. Other mass spectral features used to determine their structure are presented and a metabolic scheme accounting for their formation is proposed.

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Insecticides, Organochlorines

Plimmer¹,

Gammon²

2002

Encyclopedia of Agrochemicals

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Few chlorinated organic insecticides remain in use in North America and Europe. Several have been classified as Persistent Organic Pollutants and proscribed globally. However, their considerable benefits to humanity in the past should not be overlooked nor should the lessons that were learned during the period when they were applied to control disease vectors and agricultural pests throughout the world. Organochlorine compounds were not only used as pesticides, but they also had many industrial uses. Chlorinated organic compounds were also byproducts of a number of chemical manufacturing processes, and as a result of the careless disposal and handling of wastes, quantities were applied into the environment.

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Metabolic hydroxylation of the aromatic rings of 1,1-dichloro-2,2-bis(4-chlorophenyl)ethylene (p,p'-DDE) by the rat

Cited by 18 publications

References 28 publications

Covalent Binding of Four DDD Isomers in the Mouse Lung: Lack of Structure Specificity

Covalent Binding of Four DDD Isomers in the Mouse Lung: Lack of Structure Specificity

Characterization of new bacterial transformation products of 1,1,1-trichloro-2,2-bis-(4-chlorophenyl) ethane (DDT) by gas chromatography/mass spectrometry

Insecticides, Organochlorines

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