对硫磷（4-硝基苯基硫代磷酸二乙酯）的体外代谢研究
Studies on the metabolism of diethyl 4-nitrophenyl phosphorothionate (parathion) in vitro.
作者信息
Neal R A
出版信息
Biochem J. 1967 Apr;103(1):183-91. doi: 10.1042/bj1030183.
Abstract
- The metabolism of the phosphorothionate parathion in vitro was examined by using [(32)P]parathion and microsomes isolated from the livers of various animal species. 2. The major metabolic products of parathion in this system in vitro were identified as diethyl 4-nitrophenyl phosphate (paraoxon), diethyl hydrogen phosphate, diethyl hydrogen phosphorothionate and p-nitrophenol. 3. The reaction leading to the formation of diethyl hydrogen phosphorothionate and p-nitrophenol requires the same cofactors (NADPH and oxygen) required for metabolism of parathion to its active anti-acetylcholinesterase paraoxon. 4. The enzyme activity towards parathion per unit weight of liver is increased some 65-130% by pretreatment of male rats with phenobarbital and 3,4-benzopyrene. 5. The metabolism of parathion is inhibited by incubation in a nitrogen atmosphere and in an atmosphere containing carbon monoxide. Pure oxygen is also inhibitory. These results are discussed in terms of a deficiency of oxygen for maximal activity as well as the lability of some component of the system to oxidation.
摘要
- 利用[³²P]对硫磷和从各种动物肝脏中分离出的微粒体，对硫代磷酸酯对硫磷的体外代谢进行了研究。2. 该体外系统中对硫磷的主要代谢产物被鉴定为4-硝基苯基磷酸二乙酯（对氧磷）、磷酸二乙酯、硫代磷酸二乙酯和对硝基苯酚。3. 导致硫代磷酸二乙酯和对硝基苯酚形成的反应所需的辅因子（NADPH和氧气）与对硫磷代谢为其活性抗乙酰胆碱酯酶对氧磷所需的相同。4. 用苯巴比妥和3,4-苯并芘预处理雄性大鼠后，每单位肝脏重量对对硫磷的酶活性提高了约65%-130%。5. 在氮气气氛和含一氧化碳的气氛中孵育会抑制对硫磷的代谢。纯氧也有抑制作用。就最大活性所需的氧气缺乏以及系统某些成分对氧化的不稳定性而言，对这些结果进行了讨论。
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本文引用的文献
1
Separation of the phosphoric esters on the filter paper chromatogram.磷酸酯在滤纸色谱上的分离
Nature. 1949 Dec 31;164(4183):1107-12, illust. doi: 10.1038/1641107a0.
2
Cholinesterase inhibition by parathion in vivo.对硫磷在体内对胆碱酯酶的抑制作用。
Nature. 1951 Dec 8;168(4284):998. doi: 10.1038/168998a0.
3
Cholinesterase inhibition in vitro by OO-diethyl O-p-nitrophenyl thiophosphate (parathion, E 605).对硫磷（E 605）对体外胆碱酯酶的抑制作用
Biochem J. 1951 Sep;49(4):491-4. doi: 10.1042/bj0490491.
4
The purification of the enzyme hydrolysing diethyl p-nitrophenyl phosphate (paraoxon) in sheep serum.绵羊血清中对氧磷酶（水解对硝基苯基磷酸二乙酯的酶）的纯化
Biochem J. 1960 Jan;74(1):10-20. doi: 10.1042/bj0740010.
5
STUDIES ON THE MECHANISM OF DETOXIFICATION OF CHOLINERGIC PHOSPHOROTHIOATES.胆碱能硫代磷酸酯解毒机制的研究
J Pharmacol Exp Ther. 1965 May;148:185-92.
6
PARATHION ACTIVATION ENZYMES IN THE FAT BODY MICROSOMES OF THE AMERICAN COCKROACH.美国蟑螂脂肪体微粒体中的对硫磷激活酶。
J Econ Entomol. 1965 Jun;58:500-9. doi: 10.1093/jee/58.3.500.
7
PHOTOCHEMICAL ACTION SPECTRUM OF THE TERMINAL OXIDASE OF MIXED FUNCTION OXIDASE SYSTEMS.混合功能氧化酶系统末端氧化酶的光化学作用光谱
Science. 1965 Jan 22;147(3656):400-2. doi: 10.1126/science.147.3656.400.
8
PARATHION ACTIVATION BY LIVERS OF AQUATIC AND TERRESTRIAL VERTEBRATES.水生和陆生脊椎动物肝脏对对硫磷的激活作用
Science. 1964 Apr 3;144(3614):55-7. doi: 10.1126/science.144.3614.55.
9
Parathion metabolism in female rat.雌性大鼠体内对硫磷的代谢
Arch Int Pharmacodyn Ther. 1959 Feb 1;118(3-4):308-16.
10
Activation of thionophosphates by liver microsomes.硫代磷酸酯被肝微粒体激活。
Nature. 1959 Jan 10;183(4654):121-2. doi: 10.1038/183121a0.
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