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反,反-粘康酸,小鼠体内苯的一种开链尿代谢物。通过高压液相色谱法定量。

trans,trans-Muconic acid, an open-chain urinary metabolite of benzene in mice. Quantification by high-pressure liquid chromatography.

作者信息

Gad-El Karim M M, Ramanujam V M, Legator M S

出版信息

Xenobiotica. 1985 Mar;15(3):211-20. doi: 10.3109/00498258509045351.

DOI:10.3109/00498258509045351
PMID:4024657
Abstract

A sensitive h.p.l.c. method is described which separated urinary metabolites from benzene-treated male CD-1 mice. Phenol, trans,trans-muconic acid and quinol in the 48 h urine accounted, respectively, for 12.8-22.8, 1.8-4.7 and 1.5-3.7% of the orally administered single dose of benzene (880, 440 and 220 mg/kg body wt.). Catechol occurred in trace amounts. Ascorbic acid was used to adjust urine pH and increase the extraction efficiency of metabolites, especially muconic acid. It allowed an accurate estimation of quinol by preventing its auto-oxidation. trans,trans-Muconic acid was identified and was unique to benzene as none was detected in urine of mice dosed orally with phenol, catechol or quinol (250, 150 and 200 mg/kg, respectively). The potential existence of a toxic benzene metabolite in the form of an aldehyde precursor of muconic acid in vivo is discussed.

摘要

本文描述了一种灵敏的高效液相色谱法,用于分离经苯处理的雄性CD-1小鼠尿液中的代谢产物。48小时尿液中的苯酚、反,反-粘康酸和对苯二酚分别占口服单剂量苯(880、440和220mg/kg体重)的12.8 - 22.8%、1.8 - 4.7%和1.5 - 3.7%。儿茶酚含量微量。使用抗坏血酸调节尿液pH值并提高代谢产物的提取效率,尤其是粘康酸。通过防止对苯二酚自动氧化,可对其进行准确测定。已鉴定出反,反-粘康酸,它是苯所特有的,因为分别口服苯酚、儿茶酚或对苯二酚(250、150和200mg/kg)的小鼠尿液中未检测到该物质。本文还讨论了体内以粘康酸醛前体形式存在有毒苯代谢产物的可能性。

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1
trans,trans-Muconic acid, an open-chain urinary metabolite of benzene in mice. Quantification by high-pressure liquid chromatography.反,反-粘康酸,小鼠体内苯的一种开链尿代谢物。通过高压液相色谱法定量。
Xenobiotica. 1985 Mar;15(3):211-20. doi: 10.3109/00498258509045351.
2
Determination of benzene metabolites in urine of mice by solid-phase extraction and high-performance liquid chromatography.
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Muconic acid determinations in urine as a biological exposure index for workers occupationally exposed to benzene.尿中粘康酸测定作为职业性接触苯工人的生物接触指标。
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Feasibility of urinary trans, trans-muconic acid determination using high performance liquid chromatography for biological monitoring of benzene exposure.采用高效液相色谱法测定尿中反式、反式粘康酸用于苯暴露生物监测的可行性。
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Comparison of the levels of the urinary benzene metabolite trans,trans-muconic acid in smokers and nonsmokers, and the effects of pregnancy.吸烟者与非吸烟者尿中苯代谢物反式,反式-粘康酸水平的比较及妊娠的影响。
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Urinary excretion of phenol, catechol, hydroquinone, and muconic acid by workers occupationally exposed to benzene.职业接触苯的工人尿中苯酚、儿茶酚、对苯二酚和粘康酸的排泄情况。
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[Urine level of trans, trans-muconic acid used as an index of internal dose of exposure to benzene].[反式、反式粘康酸的尿液水平用作苯暴露内剂量指标]
Zhonghua Yu Fang Yi Xue Za Zhi. 1996 May;30(3):148-50.
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[Technical note: proposal of a routine method of accurate measurement of urinary trans,trans-muconic acid].[技术说明:一种准确测量尿中反,反式粘康酸的常规方法的提议]
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High-pressure liquid chromatographic-mass spectrometric determination of sorbic acid in urine: verification of formation of trans,trans-muconic acid.尿液中山梨酸的高效液相色谱-质谱测定:反,反-粘康酸形成的验证
Chem Biol Interact. 2005 May 30;153-154:243-6. doi: 10.1016/j.cbi.2005.03.029. Epub 2005 Apr 26.

引用本文的文献

1
Deoxyguanosine forms a bis-adduct with E,E-muconaldehyde, an oxidative metabolite of benzene: implications for the carcinogenicity of benzene.脱氧鸟苷与 E,E-反式黏糠醛形成双加合物,E,E-反式黏糠醛是苯的氧化代谢物:对苯致癌性的影响。
Chem Res Toxicol. 2011 Nov 21;24(11):1944-56. doi: 10.1021/tx2002838. Epub 2011 Oct 26.
2
The toxicology of benzene.苯的毒理学
Environ Health Perspect. 1993 Apr;100:293-306. doi: 10.1289/ehp.93100293.
3
Pathways of trans,trans-muconaldehyde metabolism in mouse liver cytosol: reversibility of monoreductive metabolism and formation of end products.
反,反-粘康醛在小鼠肝脏胞质溶胶中的代谢途径:单还原代谢的可逆性及终产物的形成
Arch Toxicol. 1993;67(7):461-7. doi: 10.1007/BF01969916.
4
Evaluation of occupational exposure to benzene by urinalysis.通过尿液分析评估职业性苯暴露。
Int Arch Occup Environ Health. 1995;67(3):195-200. doi: 10.1007/BF00626352.
5
Formation of muconaldehyde, an open-ring metabolite of benzene, in mouse liver microsomes: an additional pathway for toxic metabolites.苯的开环代谢产物粘糠醛在小鼠肝脏微粒体中的形成:有毒代谢产物的另一条途径。
Proc Natl Acad Sci U S A. 1986 Nov;83(21):8356-60. doi: 10.1073/pnas.83.21.8356.
6
Metabolism and toxicity of trans,trans-muconaldehyde, an open-ring microsomal metabolite of benzene.反,反-粘康醛的代谢与毒性,苯的一种开环微粒体代谢产物
Environ Health Perspect. 1989 Jul;82:19-22. doi: 10.1289/ehp.898219.
7
Peroxidase-dependent metabolism of benzene's phenolic metabolites and its potential role in benzene toxicity and carcinogenicity.苯酚类代谢产物的过氧化物酶依赖性代谢及其在苯毒性和致癌性中的潜在作用。
Environ Health Perspect. 1989 Jul;82:23-9. doi: 10.1289/ehp.898223.
8
Improvement in HPLC analysis of urinary trans,trans-muconic acid, a promising substitute for phenol in the assessment of benzene exposure.尿中反式,反式-粘康酸的高效液相色谱分析的改进,反式,反式-粘康酸是评估苯暴露中苯酚的一种有前景的替代物。
Int Arch Occup Environ Health. 1990;62(7):529-34. doi: 10.1007/BF00381185.
9
trans,trans-Muconic acid, a reliable biological indicator for the detection of individual benzene exposure down to the ppm level.反,反-粘康酸,一种可靠的生物指标,用于检测低至百万分之一水平的个体苯暴露。
Int Arch Occup Environ Health. 1992;64(5):309-13. doi: 10.1007/BF00379538.