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在从大鼠肝脏和肾脏新鲜分离的细胞中研究环磷酰胺生物转化过程中丙烯醛的形成、毒性及失活

Formation, toxicity and inactivation of acrolein during biotransformation of cyclophosphamide as studied in freshly isolated cells from rat liver and kidney.

作者信息

Ohno Y, Ormstad K

出版信息

Arch Toxicol. 1985 Jun;57(2):99-103. doi: 10.1007/BF00343118.

DOI:10.1007/BF00343118
PMID:4026579
Abstract

In the present study the formation and the effects of cyclophosphamide-derived acrolein were investigated using isolated cells from rat liver and kidney, with particular regard to the protective action of low molecular weight thiols against cellular toxicity. The results may be summarized as follows: Cyclophosphamide (CTX)-mediated toxicity to isolated cells is dependent on cytochrome P-450 activity; Loss of viability in cells incubated with cyclophosphamide is preceded by a depletion of cellular GSH; Stimulation of cellular GSH synthesis or the presence of low molecular weight thiols in the incubation medium protects against cyclophosphamide-induced toxicity; Acrolein is probably formed extracellularly as well as intracellularly and can be detoxified by thiol compounds, forming a thiochemiacetal or a thioether.

摘要

在本研究中，使用大鼠肝脏和肾脏的分离细胞研究了环磷酰胺衍生的丙烯醛的形成及其作用，特别关注低分子量硫醇对细胞毒性的保护作用。结果可总结如下：环磷酰胺（CTX）介导的对分离细胞的毒性取决于细胞色素P-450活性；用环磷酰胺孵育的细胞活力丧失之前细胞内谷胱甘肽（GSH）会耗尽；刺激细胞内GSH合成或在孵育培养基中存在低分子量硫醇可防止环磷酰胺诱导的毒性；丙烯醛可能在细胞外和细胞内形成，并且可以被硫醇化合物解毒，形成硫代化学缩醛或硫醚。

相似文献

1
Formation, toxicity and inactivation of acrolein during biotransformation of cyclophosphamide as studied in freshly isolated cells from rat liver and kidney.在从大鼠肝脏和肾脏新鲜分离的细胞中研究环磷酰胺生物转化过程中丙烯醛的形成、毒性及失活
Arch Toxicol. 1985 Jun;57(2):99-103. doi: 10.1007/BF00343118.
2
Metabolism and binding of cyclophosphamide and its metabolite acrolein to rat hepatic microsomal cytochrome P-450.环磷酰胺及其代谢产物丙烯醛与大鼠肝微粒体细胞色素P-450的代谢及结合
Cancer Res. 1984 Oct;44(10):4615-21.
3
Effects of propylthiouracil on urinary metabolites of cyclophosphamide in rats.丙硫氧嘧啶对大鼠环磷酰胺尿代谢产物的影响。
Cancer Res. 1983 Nov;43(11):5205-9.
4
Allyl alcohol toxicity in isolated renal epithelial cells: protective effects of low molecular weight thiols.烯丙醇对离体肾上皮细胞的毒性作用：低分子量硫醇的保护作用
Chem Biol Interact. 1985 Jan;52(3):289-99. doi: 10.1016/0009-2797(85)90024-9.
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Cellular target of cyclophosphamide toxicity in the murine liver: role of glutathione and site of metabolic activation.环磷酰胺对小鼠肝脏毒性的细胞靶点：谷胱甘肽的作用及代谢活化位点
Hepatology. 1996 Oct;24(4):830-7. doi: 10.1002/hep.510240414.
6
Effect of sulfhydryl compounds and glutathione depletion on rat heart myocyte toxicity induced by 4-hydroperoxycyclophosphamide and acrolein in vitro.巯基化合物和谷胱甘肽耗竭对4-氢过氧环磷酰胺和丙烯醛体外诱导的大鼠心肌细胞毒性的影响。
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Cancer Res. 1981 Sep;41(9 Pt 1):3584-91.
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Mechanism of allyl alcohol toxicity and protective effects of low-molecular-weight thiols studied with isolated rat hepatocytes.用分离的大鼠肝细胞研究烯丙醇毒性机制及低分子量硫醇的保护作用。
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Effect of thiols on toxicity and carcinostatic activity of cyclophosphamide.硫醇对环磷酰胺毒性及抑癌活性的影响。
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10
Studies on the in vivo formation of acrolein: 3-hydroxy-propylmercapturic acid as an index of cyclophosphamide (NSC-26271) activation.体内丙烯醛形成的研究：以3-羟基丙基巯基尿酸作为环磷酰胺（NSC-26271）活化指标的研究。
Cancer Treat Rep. 1976 Apr;60(4):327-35.

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本文引用的文献

1
High-performance liquid chromatography analysis of nanomole levels of glutathione, glutathione disulfide, and related thiols and disulfides.谷胱甘肽、二硫化谷胱甘肽及相关硫醇和二硫化物纳摩尔水平的高效液相色谱分析。
Anal Biochem. 1980 Jul 15;106(1):55-62. doi: 10.1016/0003-2697(80)90118-9.
2
Role of glutathione in the metabolism-dependent toxicity and chemotherapy of cyclophosphamide.谷胱甘肽在环磷酰胺代谢依赖性毒性和化疗中的作用。
Cancer Res. 1981 Sep;41(9 Pt 1):3584-91.
3
Decrease of reduced glutathione in isolated rat hepatocytes caused by acrolein, acrylonitrile, and the thermal degradation products of styrene copolymers.
基于纳米结构化脂质载体的口服谷胱甘肽制剂通过反相高效液相色谱胶束液相色谱法证实介导了对环磷酰胺诱导的肾毒性的肾保护作用，并提高了谷胱甘肽的口服生物利用度。
Molecules. 2021 Dec 10;26(24):7491. doi: 10.3390/molecules26247491.
4
Effect of diethyldithiocarbamate in cyclophosphamide-induced nephrotoxicity: Immunohistochemical study of superoxide dismutase 1 in rat.二乙基二硫代氨基甲酸盐对环磷酰胺诱导的肾毒性的影响：大鼠超氧化物歧化酶1的免疫组织化学研究
Indian J Pharmacol. 2018 Jan-Feb;50(1):4-11. doi: 10.4103/ijp.IJP_850_16.
5
Oral glutamine attenuates cyclophosphamide-induced oxidative stress in the bladder but does not prevent hemorrhagic cystitis in rats.口服谷氨酰胺可减轻环磷酰胺诱导的膀胱氧化应激，但不能预防大鼠出血性膀胱炎。
J Med Toxicol. 2011 Jun;7(2):118-24. doi: 10.1007/s13181-010-0103-9.
6
Acrolein inhibits NADH-linked mitochondrial enzyme activity: implications for Alzheimer's disease.丙烯醛抑制与NADH相关的线粒体酶活性：对阿尔茨海默病的影响。
Neurotox Res. 2003;5(7):515-20. doi: 10.1007/BF03033161.
7
L-cysteine prodrug protects against cyclophosphamide urotoxicity without compromising therapeutic activity.L-半胱氨酸前药可预防环磷酰胺所致的尿路毒性，且不影响其治疗活性。
Cancer Chemother Pharmacol. 1991;28(3):166-70. doi: 10.1007/BF00685504.
丙烯醛、丙烯腈及苯乙烯共聚物热降解产物导致离体大鼠肝细胞中还原型谷胱甘肽含量降低。
Toxicology. 1980;17(3):333-41. doi: 10.1016/0300-483x(80)90014-1.
4
Interaction of cyclophosphamide metabolites with membrane proteins: an in vitro study with rabbit liver microsomes and human red blood cells. Effect of thiols.环磷酰胺代谢产物与膜蛋白的相互作用：兔肝微粒体和人红细胞的体外研究。硫醇的影响。
Biochem Pharmacol. 1982 Nov 15;31(22):3535-41. doi: 10.1016/0006-2952(82)90572-x.
5
Protective role of thiols in cyclophosphamide-induced urotoxicity and depression of hepatic drug metabolism.硫醇在环磷酰胺诱导的尿路毒性及肝脏药物代谢抑制中的保护作用。
Cancer Res. 1982 Sep;42(9):3688-95.
6
The development of mesna for the inhibition of urotoxic side effects of cyclophosphamide, ifosfamide, and other oxazaphosphorine cytostatics.美司钠用于抑制环磷酰胺、异环磷酰胺及其他氮杂磷环类细胞抑制剂的尿路毒性副作用的研发。
Recent Results Cancer Res. 1980;74:270-8. doi: 10.1007/978-3-642-81488-4_32.
7
Pharmacokinetics and metabolism of sodium 2-mercaptoethanesulfonate in the rat.大鼠体内2-巯基乙烷磺酸钠的药代动力学与代谢
Cancer Res. 1983 Jan;43(1):333-8.
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[Studies on the spontaneous decomposition of 4-hydroxyphosphamide and 4-hydroperoxyphosphamide by means of thin-layer chromatography].[利用薄层色谱法对4-羟基磷酰胺和4-氢过氧磷酰胺自发分解的研究]
Arzneimittelforschung. 1974 Aug;24(8):1172-6.
9
Metabolism of cyclophosphamide by rat hepatic microsomes.大鼠肝微粒体对环磷酰胺的代谢
Cancer Res. 1971 Jun;31(6):901-8.
10
Mechanism of allyl alcohol toxicity and protective effects of low-molecular-weight thiols studied with isolated rat hepatocytes.用分离的大鼠肝细胞研究烯丙醇毒性机制及低分子量硫醇的保护作用。
Toxicol Appl Pharmacol. 1985 Apr;78(2):169-79. doi: 10.1016/0041-008x(85)90281-9.