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四氯化碳的脂质代谢产物

Lipid metabolites of carbon tetrachloride.

作者信息

Gordis E

出版信息

J Clin Invest. 1969 Jan;48(1):203-9. doi: 10.1172/JCI105969.

DOI:10.1172/JCI105969
PMID:5765023
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC322206/
Abstract

5 min after intravenous injection into rats of (14)C- or (36)Cl-carbon tetrachloride, liver lipids were found labeled. Most of the radioactivity was found in the phospholipid fraction. The metabolites were shown to comprise a heterogeneous group of branched long-chain chlorinated fatty acids, probably containing the trichloromethyl side chain. Surviving liver slices also formed these metabolites. In a simple chemical system which generates trichloromethyl free radicals, carbon tetrachloride added to methyl oleate to form esters which behaved like the metabolites during counter-current distribution and urea adduction. The evidence strongly suggests the formation of these metabolites by free radical attack on unsaturated lipids. The relation of these observations to current theories of carbon tetrachloride intoxication is discussed.

摘要

给大鼠静脉注射(14)C或(36)Cl标记的四氯化碳5分钟后,发现肝脏脂质被标记。大部分放射性存在于磷脂部分。这些代谢产物被证明是一组异质的支链长链氯化脂肪酸,可能含有三氯甲基侧链。存活的肝切片也能形成这些代谢产物。在一个能产生三氯甲基自由基的简单化学体系中,将四氯化碳加入油酸甲酯中形成酯,这些酯在逆流分配和尿素加成过程中的行为与代谢产物相似。有力的证据表明,这些代谢产物是自由基对不饱和脂质攻击形成的。本文讨论了这些观察结果与当前四氯化碳中毒理论的关系。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/15ab/322206/0237a79f3a83/jcinvest00207-0223-a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/15ab/322206/0237a79f3a83/jcinvest00207-0223-a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/15ab/322206/0237a79f3a83/jcinvest00207-0223-a.jpg

相似文献

1
Lipid metabolites of carbon tetrachloride.四氯化碳的脂质代谢产物
J Clin Invest. 1969 Jan;48(1):203-9. doi: 10.1172/JCI105969.
2
[Gas-chromatographic analysis of liver fatty acids in normal rats and rats subjected to chronic and acute carbon tetrachloride poisoning].[正常大鼠以及遭受慢性和急性四氯化碳中毒大鼠肝脏脂肪酸的气相色谱分析]
Arch Sci Med (Torino). 1972 Apr-Jun;129(2):69-82.
3
[Changes in the fatty acid composition of lipids from the liver and hepatic microsomes of rats with carbon tetrachloride poisoning].[四氯化碳中毒大鼠肝脏及肝微粒体脂质脂肪酸组成的变化]
Boll Soc Ital Biol Sper. 1969 May 31;45(10):700-3.
4
Carbon tetrachloride hepatotoxicity: an example of lethal cleavage.四氯化碳肝毒性:致死性裂解的一个例子。
CRC Crit Rev Toxicol. 1973 Nov;2(3):263-97. doi: 10.3109/10408447309082019.
5
[Effect of manganese compounds on the fat content in the liver of animals poisoned by carbon tetrachloride].[锰化合物对四氯化碳中毒动物肝脏脂肪含量的影响]
Ukr Biokhim Zh. 1966;38(3):294-6.
6
Early incorporation of carbon-labeled carbon tetrachloride into rat liver particulate lipids and proteins.碳标记的四氯化碳早期掺入大鼠肝脏微粒体脂质和蛋白质中。
Exp Mol Pathol. 1969 Apr;10(2):219-28. doi: 10.1016/0014-4800(69)90041-0.
7
Liver phospholipides after carbon tetrachloride intoxication in rats.四氯化碳中毒大鼠的肝脏磷脂
Experientia. 1965 Apr 15;21(4):215-6. doi: 10.1007/BF02141894.
8
Changes in fatty acid pattern of liver microsomal phospholipids in rats treated with carbon tetrachloride.四氯化碳处理的大鼠肝脏微粒体磷脂脂肪酸模式的变化
Ital J Biochem. 1971 Sep-Dec;20(5):156-65.
9
[Biological aspects of lipid peroxidation].[脂质过氧化的生物学方面]
Minerva Med. 1968 Apr 21;59(32):1873-89.
10
Hepatotoxicity and mechanism of action of haloalkanes: carbon tetrachloride as a toxicological model.卤代烷的肝毒性及作用机制:以四氯化碳作为毒理学模型
Crit Rev Toxicol. 2003;33(2):105-36. doi: 10.1080/713611034.

引用本文的文献

1
Inducing Acute Liver Injury in Rats via Carbon Tetrachloride (CCl4) Exposure Through an Orogastric Tube.通过经口胃管给予四氯化碳(CCl₄)诱导大鼠急性肝损伤。
J Vis Exp. 2020 Apr 28(158). doi: 10.3791/60695.
2
Relationship of oxygen and glutathione in protection against carbon tetrachloride-induced hepatic microsomal lipid peroxidation and covalent binding in the rat. Rationale for the use of hyperbaric oxygen to treat carbon tetrachloride ingestion.氧气与谷胱甘肽在保护大鼠免受四氯化碳诱导的肝微粒体脂质过氧化及共价结合中的关系。使用高压氧治疗四氯化碳摄入的理论依据。
J Clin Invest. 1984 Dec;74(6):1996-2001. doi: 10.1172/JCI111621.
3

本文引用的文献

1
Separation of the higher fatty acids.高级脂肪酸的分离
J Biol Chem. 1952 Mar;195(1):299-310.
2
The absorption, distribution and elimination of radioactive carbon tetrachloride by monkeys upon exposure to low vapor concentrations.猴子在暴露于低蒸汽浓度的放射性四氯化碳时,其吸收、分布和消除情况。
J Pharmacol Exp Ther. 1951 Jun;102(2):112-24.
3
A NOTE ON THE RELATIVE TOXIC ACTIVITIES OF TETRACHLOROMETHANE AND TRICHLORO-FLUORO-METHANE ON THE RAT.关于四氯化碳和三氯氟甲烷对大鼠的相对毒性活性的注释
Binding of trichloromethyl radicals to lipids of the hepatic endoplasmic reticulum during tetrachloromethane metabolism.
四氯化碳代谢过程中三氯甲基自由基与肝脏内质网脂质的结合。
Biochem J. 1984 Nov 1;223(3):577-86. doi: 10.1042/bj2230577.
4
Free-radical mechanisms in tissue injury.组织损伤中的自由基机制。
Biochem J. 1984 Aug 15;222(1):1-15. doi: 10.1042/bj2220001.
5
Carbon tetrachloride metabolism in sheep and in Fasciola hepatica.绵羊和肝片吸虫中四氯化碳的代谢
Br J Pharmacol. 1970 Jul;39(3):599-607. doi: 10.1111/j.1476-5381.1970.tb10367.x.
6
Carbon tetrachloride metabolism in the rabbit.家兔体内四氯化碳的代谢
Br J Pharmacol. 1969 Nov;37(3):733-7. doi: 10.1111/j.1476-5381.1969.tb08512.x.
7
[Formation of chloroform from carbon tetrachloride in liver microsomes, lipid peroxidation and destruction of cytochrome P-450].[肝脏微粒体中四氯化碳形成氯仿、脂质过氧化及细胞色素P-450的破坏]
Arch Toxikol. 1972;29(3):219-33.
8
Biochemical studies on the metabolic activation of halogenated alkanes.卤代烷烃代谢活化的生化研究。
Environ Health Perspect. 1985 Dec;64:85-101. doi: 10.1289/ehp.856485.
9
Hyperbaric oxygen treatment for carbon tetrachloride poisoning.高压氧治疗四氯化碳中毒
Drug Saf. 1991 Sep-Oct;6(5):332-8. doi: 10.2165/00002018-199106050-00003.
10
Mechanism of increased hepatic uptake of unesterified fatty acid from serum of ethanol-treated rats.乙醇处理大鼠血清中未酯化脂肪酸肝脏摄取增加的机制。
Biochem J. 1976 Apr 15;156(1):47-54. doi: 10.1042/bj1560047.
Biochem Pharmacol. 1965 Feb;14:178-81. doi: 10.1016/0006-2952(65)90074-2.
4
STUDIES ON CARBON TETRACHLORIDE INTOXICATION. 3. A SUBCELLULAR DEFECT IN PROTEIN SYNTHESIS.四氯化碳中毒研究。3. 蛋白质合成中的亚细胞缺陷。
Biochemistry. 1965 Apr;4:671-9. doi: 10.1021/bi00880a009.
5
A NEW INSIGHT ON CARBON TETRACHLORIDE EFFECT ON TRIGLYCERIDE TRANSPORT.四氯化碳对甘油三酯转运影响的新见解。
Biochem Pharmacol. 1964 Jul;13:949-54. doi: 10.1016/0006-2952(64)90090-5.
6
LIVER PARENCHYMAL CELL INJURY. I. INITIAL ALTERATIONS OF THE CELL FOLLOWING POISONING WITH CARBON TETRACHLORIDE.肝实质细胞损伤。一、四氯化碳中毒后细胞的初始变化。
J Cell Biol. 1963 Oct;19(1):139-57. doi: 10.1083/jcb.19.1.139.
7
An intracellular defect in protein synthesis induced by carbon tetrachloride.四氯化碳诱导的蛋白质合成中的细胞内缺陷。
J Exp Med. 1962 Jul 1;116(1):55-72. doi: 10.1084/jem.116.1.55.
8
Protection by antioxidants against lethal doses of carbon tetrachloride.抗氧化剂对致死剂量四氯化碳的保护作用。
Nature. 1961 Dec 2;192:881-2. doi: 10.1038/192881a0.
9
Reduction of carbon tetrachloride in vivo and reduction of carbon tetrachloride and chloroform in vitro by tissues and tissue constituents.体内四氯化碳的还原以及组织和组织成分在体外对四氯化碳和氯仿的还原作用。
J Pharmacol Exp Ther. 1961 Dec;134:311-9.
10
Relative hepatotoxicity of seven halogenated hydrocarbons.七种卤代烃的相对肝毒性
J Pharmacol Exp Ther. 1958 Jul;123(3):224-9.