Pentachlorocyclohexene, an Intermediate in the Metabolism of Lindane by House Flies1

Sternburg, J. G.; Kearns, C. W.

doi:10.1093/jee/49.4.548

Cited by 50 publications

(23 citation statements)

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“…gen atom. Gamma-PCCH, which can be derived from dehydrochlorination, has been suggested as an intermediate of y-BHC in houseflies (7,15) and as a detoxified product of y-BHC in moist, acidic-to-neutral soils (17). Our experiments, however, showed that it is unlikely that y-PCCH is the unknown metabolite found during y-BHC degradation by the anaerobic bacterium, although this compound was degraded by the bacterium faster than y-BHC.…”

Section: Discussionmentioning

confidence: 99%

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Degradation of benzene hexachloride by a soil bacterium

Sethunathan¹,

Bautista²,

Yoshida³

1969

Can. J. Microbiol.

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Attempts to characterize the breakdown product formed during the anaerobic degradation of the gamma isomer of benzene hexachloride (γ-BHC, C6H6Cl6) by the Clostridium sp. were made. Analysis by gas chromatography and thin-layer chromatography indicated that the degradation product of γ-BHC and α-BHC differed from γ-pentachlorocyclohexene (C6H5Cl5), a direct product of dehydrochlorination of γ-BHC. The ability of the bacterium to convert DDT to DDD by reductive dechlorination suggested that a similar mechanism might degrade γ-BHC to γ-pentachlorocyclohexane (C6H7Cl5). Potassium nitrate inhibited the bacterial degradation of γ-BHC whereas potassium sulfate and potassium chloride enhanced it.

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Section: Discussionmentioning

confidence: 99%

“…This paper presents further results on the degradation of y-BHC by a bacterium isolated from a Philippine rice soil and on the characterization of the unknown compound formed during y-BHC degradation. (7,15); However, Bridges (4), using 14C-labeled Resting CeN Experiments…”

mentioning

confidence: 99%

Degradation of benzene hexachloride by a soil bacterium

Sethunathan¹,

Bautista²,

Yoshida³

1969

Can. J. Microbiol.

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“…Although C1was released during the incubation of this compound with partially purified glutathione S-aryltransferase, these rat-liver preparations are now known to contain an additional enzyme that catalyses glutathione conjugation with some epoxides (Boyland & Williams, 1964). Sternburg, Kearns & Moorefield (1954) have shown the presence of a glutathione-dependent enzyme in strains of houseffies resistant to DDT [1,1,1-trichloro-2,2-di-(p-chlorophenyl)ethane], but this enzyme, DDT dehydrochlorinase, which dehydrochlorinates DDT to the non-toxic DDE [1,1-dichloro-2,2-di-(p-chlorophenyl)ethane], is not involved in Gammexane detoxication by houseflies (Sternburg & Kearns, 1956). No conjugation of glutathione with y-hexachlorocyclohexane was detected in the present work, although experiments showed that soluble supernatant fractions from both Gammexane-resistant and -susceptible strains of houseflies released appreciable amounts of C1from this compound.…”

Section: Discussionmentioning

confidence: 99%

“…Booth, Boyland & Sims (1961) have described an enzyme, termed glutathione S-aryltransferase, in rat liver that catalyses the conjugations of glutathione with aromatic halogen-containing compounds and which is present in a variety of vertebrate species (Grover & Sims, 1964) and in some insects (Boyland, Grover, Sims & Williams, 1963;Cohen, Smith & Turbet, 1964). y-Pentachlorocyclohexene is an intermediate in the metabolism of y-hexachlorocyclohexane (Gammexane) by houseflies (Sternburg & Kearns, 1956), and Bradbury & Standen (1959) showed that water-soluble sulphurcontaining metabolites are formed from Gammexane by this species. Bettini & Boccacci (1958) have reported the conversion of bromoacetic acid into S-(carboxymethyl)glutathione in locusts, and it is possible that the formation of water-soluble glutathione conjugates represents one stage of a common detoxication mechanism in insects.…”

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confidence: 99%

Conjugations With Glutathione. The Enzymic Conjugation of Some Chlorocyclohexenes

Sims¹,

Grover²

1965

Biochemical Journal

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1. alpha-3,4,5,6-Tetrachlorocyclohex-1-ene and gamma-2,3,4,5,6-pentachlorocyclohex-1-ene are conjugated with glutathione in vitro by a rat-liver enzyme that is probably glutathione S-aryltransferase. 2. Chlorocyclohexane and the alpha-, beta-, gamma- and delta-isomers of hexachlorocyclohexane were not substrates for rat-liver glutathione S-aryltransferase. 3. Glutathione-S-aryltransferase activity was present in tissue preparations of houseflies of insecticide-resistant and -susceptible strains. More activity was found in a dieldrin-resistant strain of houseflies fed on dieldrin than in either a dieldrin-resistant strain not fed on dieldrin or a control strain of dieldrin-susceptible houseflies. 4. Housefly soluble supernatant preparations converted S-(2-chloro-4-nitrophenyl)glutathione into the corresponding cysteine and mercapturic acid derivatives.

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“…Dehydrochlorination is involved in the transformation of DDT to DDE (134,135) and of lindane to pentachlorocyclohexene (136). Reductive de chlorination is involved in the formation of DDD from DDT by yeast (137) and rats (134).…”

Section: Biotransformationmentioning

confidence: 99%

Review of the Metabolism of Chlorinated Hydrocarbon Insecticides Especially in Mammals

Wj¹

1965

Annu. Rev. Pharmacol.

119

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This review discusses the absorption, storage, biotransformation, and excretion of chlorinated hydrocarbon insecticides; thus, it emphasizes those aspects of physiology that can be studied by the methods of analytical or ganic chemistry. The broader aspects of toxicity, as they relate to the me tabolism of these materials, were discussed by Winteringham & Barnes (1).This review emphasizes mammalian metabolism of the compounds, but con tains some information on their metaboli sm by other organisms, a subject that has already been reviewed by Perry (2). In relation to mammals, great est interest centers in numerous repeated doses that produce no obvious in jury and that are so small that they might be encountered under practical conditions in the use of insecticides. For this reason, DDT and related re sidual insecticides are emphasized, but some information is given on the chlorinated hydrocarbon fumigants.

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Pentachlorocyclohexene, an Intermediate in the Metabolism of Lindane by House Flies1

Cited by 50 publications

References 0 publications

Degradation of benzene hexachloride by a soil bacterium

Degradation of benzene hexachloride by a soil bacterium

Conjugations With Glutathione. The Enzymic Conjugation of Some Chlorocyclohexenes

Review of the Metabolism of Chlorinated Hydrocarbon Insecticides Especially in Mammals

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