Guanine N<sup>7</sup>‐Alkylation in Mice <i>in Vivo</i> by Metrifonate – Discussion of Possible Genotoxic Risk in Mammals

Dedek, W.

doi:10.1111/j.1600-0773.1981.tb03251.x

Cited by 14 publications

(2 citation statements)

References 38 publications

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“…This proposed pathway may demonstrate the growth of PA F-2 in the solid plate supplemented with TCF as sole phosphorus and sole carbon–phosphorus sources (Figure S1). Chloral hydrate is spontaneously converted to trichloroethanal, and these two chlorides are then utilized in glucuronide synthesis by organisms. , The synthesized glucuronide could be used as a carbon source by PA F-2. However, trimethyl orthophosphate and dichloromethane in the DDCV biodegradation pathways were proposed as primary metabolites.…”

Section: Results and Discussionmentioning

confidence: 99%

“…Chloral hydrate is spontaneously converted to trichloroethanal, and these two chlorides are then utilized in glucuronide synthesis by organisms. 10,33 The synthesized glucuronide could be used as a carbon source by PA F-2. However, trimethyl orthophosphate and dichloromethane in the DDCV biodegradation pathways were proposed as primary metabolites.…”

Section: Journal Of Agricultural and Food Chemistrymentioning

confidence: 99%

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Biodegradation of the Organophosphate Trichlorfon and Its Major Degradation Products by a Novel Aspergillus sydowii PA F-2

Tian

Dong

Zhao

et al. 2016

J. Agric. Food Chem.

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Trichlorfon (TCF) is an important organophosphate pesticide in agriculture. However, limited information is known about the biodegradation behaviors and kinetics of this pesticide. In this study, a newly isolated fungus (PA F-2) from pesticide-polluted soils was identified as Aspergillus sydowii on the basis of the sequencing of internal transcribed spacer rDNA. This fungus degraded TCF as sole carbon, sole phosphorus, and sole carbon-phosphorus sources in a mineral salt medium (MSM). Optimal TCF degradation conditions were determined through response surface methodology, and results also revealed that 75.31% of 100 mg/L TCF was metabolized within 7 days. The degradation of TCF was accelerated, and the mycelial dry weight of PA F-2 was remarkably increased in MSM supplemented with exogenous sucrose and yeast extract. Five TCF metabolic products were identified through gas chromatography-mass spectrometry. TCF could be initially hydrolyzed to dichlorvos and then be degraded through the cleavage of the P-C bond to produce dimethyl hydrogen phosphate and chloral hydrate. These two compounds were subsequently deoxidized to produce dimethyl phosphite and trichloroethanal. These results demonstrate the biodegradation pathways of TCF and promote the potential use of PA F-2 to bioremediate TCF-contaminated environments.

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Section: Results and Discussionmentioning

confidence: 99%

Section: Journal Of Agricultural and Food Chemistrymentioning

confidence: 99%

Biodegradation of the Organophosphate Trichlorfon and Its Major Degradation Products by a Novel Aspergillus sydowii PA F-2

Tian

Dong

Zhao

et al. 2016

J. Agric. Food Chem.

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Organophosphorus Compounds

Storm¹

2001

Patty's Toxicology

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Organophosphate pesticides are a highly diverse group of chemicals to which workers may be exposed during manufacture and formulation and during or after application for their intended uses. They are all characterized by their ability to inhibit the enzyme acetylcholinesterase (AChE) that deactivates the neurotransmitter acetylcholine (ACh). Compounds in this class are numerous and have been categorized in many ways according to the nature of the substituents. Gallo and Lawryk, for example, categorized them into four main categories (Groups I‐IV) based on the characteristics of the leaving group (X). Group I compounds, phosphorylcholines, have a leaving group that contains a quaternary nitrogen and are among the most potent organophosphates (e.g., Shradan). Group II compounds, fluorophosphates, have a fluoride leaving group and are also generally highly toxic (e.g., diisopropyl fluorophosphate). Group III compounds have leaving groups that contain cyanide or a halogen other than fluoride and are generally less potent than Groups I or II (e.g., Parathion). Group IV contains most of the organophosphates used as insecticides today. These compounds have alkoxy, alkylthio, aryloxy, arylthio or heterocyclic leaving groups and a wide variety of other substituents. Another classification scheme is based on the nature of the atoms that immediately surround the central phosphorus atom and results in 14 different categories. According to this scheme, phosphates are the prototype for the entire class and are those compounds where all four atoms that surround the phosphorus atom are oxygen (e.g., dichlorvos, mevinphos). Sulfur‐containing organophosphate compounds (phosphorothioates; phosphorothiolates; phosphorodithioates; phosphorodithiolates) are far more numerous than phosphates and include well recognized organophosphate insecticides such as parathion, diazinon, chlorpyrifos, etc. Other groups contain nitrogen (phosphoramides and phosphorodiamides), nitrogen and sulfur (phosphoramidothionates and phosphoramidothiolates), carbon (phosphonates and phosphinates), or carbon and sulfur (phosphonothionates, phosphonothionothiolates and phosphinothionates). All aspects of organophosphate chemistry, toxicity, analysis, and exposure potential have been previously reviewed. Additionally information regarding the toxicity of this class of compounds has expanded greatly in recent years as a result of toxicity data supplied by registrants to the U.S. EPA's Office of Pesticides to support reregistration. These data are being made publically available by the U.S. EPA on their internet web site. The following discussion draws heavily from recent reviews but also includes summaries of relevant toxicity data submitted to the U.S. EPA available when this chapter was completed. Due to space limitations detailed data reviews are included here for only 30 organophosphate pesticides. Information on other pesticides registered or undergoing reregistration in the United States can be readily obtained from the previously mentioned website.

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The effect of trichlorfon and other organophosphates on prenatal brain development in the guinea pig

et al. 1994

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The organophosphates trichlorfon, dichlorvos, dimethoate, soman, triortho-cresyl phosphate (TOCP), and the diethoxy-analogue of trichlorfon (O,O-diethyl 2,2,2-trichloro-1-hydroxyethylphosphonate, ethyl-trichlorfon), were administered to guinea pigs between day 42 and 46 of gestation. When the offsprings were examined at birth, there was a severe reduction in brain weight in the case of trichlorfon and dichlorvos, but not after treatment with the other organophosphates. The reduction in weight was most pronounced for cerebellum, medulla oblongata, thalamus/hypothalamus and quadrigemina. The effect was less marked for cerebral cortex and hippocampus. Since soman, a potent anticholinesterase, and TOCP, an inhibitor of neuropathy target esterase, did not show any effects, this excludes that the brain hypoplasia can be caused by inhibition of these two enzymes. Further, the lack of effect with ethyl-trichlorfon has shed some light on the part of the trichlorfon molecule which could be involved in the formation of the hypoplasia. It is suggested that alkylation of DNA may be involved in the development of the lesion. The possible consequences for a teratogenic effect of trichlorfon and dichlorvos on humans are discussed.

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Guanine N⁷‐Alkylation in Mice in Vivo by Metrifonate – Discussion of Possible Genotoxic Risk in Mammals

Cited by 14 publications

References 38 publications

Biodegradation of the Organophosphate Trichlorfon and Its Major Degradation Products by a Novel Aspergillus sydowii PA F-2

Biodegradation of the Organophosphate Trichlorfon and Its Major Degradation Products by a Novel Aspergillus sydowii PA F-2

Organophosphorus Compounds

The effect of trichlorfon and other organophosphates on prenatal brain development in the guinea pig

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Guanine N7‐Alkylation in Mice in Vivo by Metrifonate – Discussion of Possible Genotoxic Risk in Mammals

Cited by 14 publications

References 38 publications

Biodegradation of the Organophosphate Trichlorfon and Its Major Degradation Products by a Novel Aspergillus sydowii PA F-2

Biodegradation of the Organophosphate Trichlorfon and Its Major Degradation Products by a Novel Aspergillus sydowii PA F-2

Organophosphorus Compounds

The effect of trichlorfon and other organophosphates on prenatal brain development in the guinea pig

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Guanine N⁷‐Alkylation in Mice in Vivo by Metrifonate – Discussion of Possible Genotoxic Risk in Mammals