Insecticide Metabolism in Mammals, Mammalian Enzymes Involved in the Degradation of 2,2-Dichlorovinyl Dimethyl Phosphate

Hodgson, Ernest; Casida, J. E.

doi:10.1021/jf60121a012

Cited by 79 publications

(28 citation statements)

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“…The order of our specific activity for paraoxon differs from that of sarin, which is found in the soluble fraction, microsomes, mithochondria, and nuclei, roughly in the proportions 65:20:10:5, with some variations according to the animal species and the tissues (Adie and Tuba, 1958). Microsomes have no dichlorvos-degrading activity (Hodgson and Casida, 1962). The enzymic degradation of methyl paraoxon, methyl parathion, and methyl sumithion by microsomes and mitochondria observed by Fukami and Shishido (1963) and Shishido and Fukami (1963) may be due to different enzymes from those reported here, since they used EDTA (5mM) to prevent coagulation of the preparations tested.…”

Section: Subcellular Distribution Of the Degrading Systemsmentioning

confidence: 46%

“…The soluble fraction of rat liver has enzymes hydrolyzing sarin (Adie and Tuba, 1958), diazinon (Suwanai and Shishido, 1965), the vinyl phosphate of dichlorvos (Hodgson and Casida, 1962), and also desmethylating enzymes which are capable of catalyzing the desalkylation of dichlorvos (Hodgson and Casida, 1962) and methyl parathion (Fukami and Shishido, 1963).…”

Section: Subcellular Distribution Of the Degrading Systemsmentioning

confidence: 99%

“…b), (3) Aldridge (1951Aldridge ( , 1953b, (4) Erdos and Boggs (1961). ( 5 ) Hodgson and Casida (1962). (6) Suwanai and Shishido (1965), (7) Fukami and Shishido (1963).…”

Section: Activationmentioning

confidence: 99%

“…although usually desalkylation is of minor importance except for cases where a resistance factor of rice stem borer, Cliilo supressalis, to parathion was involved (Iyatomi and Saito, 1965;Kojima et a/., 1963b); and for some dimethyl organophosphates with low mammalian toxicity, particularly Sumithion (Hollingworth et a/.. 1967;Miyamoto, 1964). A desalkylating enzyme for dimethyl organophosphates was found in the soluble fraction of rat liver and other tissues, and insect tissues (Fukami andShishido, 1963, 1966;Hodgson and Casida, 1962;Shishido and Fukami, 1963). There are no reports of the desethylation of paraoxon in vitro.…”

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confidence: 99%

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Para-oxon hydrolyzing enzymes in rat liver

Kojima¹,

O’Brien²

1968

J. Agric. Food Chem.

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H3-Paraoxon was shown to be degraded by at least four distinct enzymes in rat liver with different p H optima, reaction constants, and sensitivities to metallic ions, SH-reagents, and inhibitors. These enzymes were present in a soluble and a particulate state in the liver cell. The specific activity was highest in the crude microsomes and lower in the washed mitochondria and the crude soluble fraction at the respective optimum pH's. The crude soluble fraction contained two different enzymes which were partially purified by ammonium sulfate fractionation. The washed mitochondrial, crude microsomal, crude and partially purified soluble enzymes produced diethyl phosphate as the principal metabolite. A partially purified soluble fraction produced 0-desethyl paraoxon. The enzymes in microsomes and mitochondria were solubilized by treatment with sodium desoxycholate. The above subcellular fractions also degraded H .-parathion. but not necessarily by the enzymes responsible for paraoxon degradation.oxic organophosphates and fluorophosphates are enzymatically hydrolyzed by various organisms.

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Section: Subcellular Distribution Of the Degrading Systemsmentioning

confidence: 46%

Section: Subcellular Distribution Of the Degrading Systemsmentioning

confidence: 99%

“…b), (3) Aldridge (1951Aldridge ( , 1953b, (4) Erdos and Boggs (1961). ( 5 ) Hodgson and Casida (1962). (6) Suwanai and Shishido (1965), (7) Fukami and Shishido (1963).…”

Section: Activationmentioning

confidence: 99%

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confidence: 99%

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Para-oxon hydrolyzing enzymes in rat liver

Kojima¹,

O’Brien²

1968

J. Agric. Food Chem.

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“…However, 0-(3-chloro-4-methyluInbelliferone) ddiethyl, phosphate was metabolized into the* O-desethyl phosphate in rats (K;qeger, Calida &;Niedermeier, 1959). The dimethyl vinyl pliosphate, methyl 3-(dimethoxyphosphinyloxy)crotonate, was not O-demethylated in cows (%#ida, Gatterdam, Knaak Lance & Niedermeier, 1958), whereas 2,2-dichlorovinyl dimethyl phosphate yielded the O-demethyl phosphate in mammals (Hodgson & Casida, 1962;Casida, McBride & Niedermeier, 1962). Thus when the present work was undertaken there was insufficient information available for the course of hydrolysis an vivo of a dialkyl vinyl phosphate, such as Chlorfenvinphos, to be predicted.…”

Section: Discussionmentioning

confidence: 99%

The metabolism of 2-chloro-1-(2′,4′-dichlorophenyl)vinyl diethyl phosphate (Chlorfenvinphos) in the dog and rat

Hutson¹,

Akintonwa²,

Hathway³

1967

Biochemical Journal

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1. A single oral dose of [(14)C]Chlorfenvinphos to rats is quantitatively eliminated in 4 days. Rats do not show a sex difference in the elimination pattern and show only a small degree of biological variation in the total excretion data. Of the label 87.2% is excreted in the urine (67.5% in the first day after dosage), 11.2% in the faeces and 1.4% in the expired gases; less than 0.9% of (14)C is present in the gut and contents after 4 days. 2. After oral administration of [(14)C]Chlorfenvinphos to dogs, 94.0% (91.8-97.6%) of the (14)C is excreted in the urine and faeces during 4 days. Dogs do not show a sex difference in the pattern of elimination, and excretion of radioactivity in the urine is very rapid: 86.0% of (14)C during 0-24hr. 3. Chlorfenvinphos is completely metabolized in rats and dogs: unchanged Chlorfenvinphos is absent from the urine and from the carcass, when elimination is complete. In rats, 2-chloro-1-(2',4'-dichlorophenyl)vinyl ethyl hydrogen phosphate accounts for 32.3% of a dose of Chlorfenvinphos, [1-(2',4'-dichlorophenyl)ethyl beta-d-glucopyranosid]uronic acid for 41.0%, 2,4-dichloromandelic acid for 7.0%, 2,4-dichlorophenylethanediol glucuronide for 2.6% and 2,4-dichlorohippuric acid for 4.3%; in dogs, 2-chloro-1-(2',4'-dichlorophenyl)vinyl ethyl hydrogen phosphate accounts for 69.6%, [1-(2',4'-dichlorophenyl)ethyl beta-d-glucopyranosid] uronic acid for 3.6%, 2,4-dichloromandelic acid for 13.4% and 2,4-dichlorophenylethanediol glucuronide for 2.7%. 4. Dogs and rats show a species difference in the rate of excretion of (14)C in the urine, and in the proportions of the metabolites, with the exception of 2,4-dichlorophenylethanediol glucuronide, that are excreted in the urine. Alternative explanations for the latter species difference are suggested. 5. 2-Chloro-1-(2',4'-dichlorophenyl)vinyl ethyl hydrogen phosphate and 2,4-dichlorophenacyl chloride probably lie on the main metabolic pathway of Chlorfenvinphos, since, in common with that insecticide, they give rise to [1-(2',4'-dichlorophenyl)ethyl beta-d-glucopyranosid]uronic acid and 2,4-dichloromandelic acid as major metabolites in the urine. 6. The proposed scheme for the metabolism of Chlorfenvinphos represents a detoxication mechanism.

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Hydrolytic Transformation of Environmental Pollutants

Ecobichon

1977

Comprehensive Physiology

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The sections in this article are: Ester Hydrolysis Organophosphorus Triesters Phosphorylphosphatases (Fluorophosphatases) Arylesterases Carboxylesterases Carboxyamidase Other Hydrolytic Mechanisms Carbamic Acid Esters Pyrethyroid Ester Insecticides Herbicide Esters Phthalic Acid Esters

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Insecticide Metabolism in Mammals, Mammalian Enzymes Involved in the Degradation of 2,2-Dichlorovinyl Dimethyl Phosphate

Cited by 79 publications

References 15 publications

Para-oxon hydrolyzing enzymes in rat liver

Para-oxon hydrolyzing enzymes in rat liver

The metabolism of 2-chloro-1-(2′,4′-dichlorophenyl)vinyl diethyl phosphate (Chlorfenvinphos) in the dog and rat

Hydrolytic Transformation of Environmental Pollutants

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