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1
Formation of 2-amino-3-methylimidazo[4,5-f]quinoline- and 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline-sulfamates by cDNA-expressed mammalian phenol sulfotransferases.由cDNA表达的哺乳动物酚磺基转移酶形成2-氨基-3-甲基咪唑并[4,5-f]喹啉和2-氨基-3,8-二甲基咪唑并[4,5-f]喹喔啉-磺酸盐。
Jpn J Cancer Res. 1995 Mar;86(3):264-9. doi: 10.1111/j.1349-7006.1995.tb03049.x.
2
Activation and detoxication of carcinogenic arylamines by sulfation.致癌芳胺的硫酸化激活与解毒作用。
Princess Takamatsu Symp. 1995;23:154-62.
3
Enzymatic phase II activation of the N-hydroxylamines of IQ, MeIQx and PhIP by various organs of monkeys and rats.IQ、MeIQx和PhIP的N-羟基胺在猴子和大鼠各器官中的酶促II相激活作用。
Carcinogenesis. 1993 Oct;14(10):2091-6. doi: 10.1093/carcin/14.10.2091.
4
Characterization of DNA adducts formed in vitro by reaction of N-hydroxy-2-amino-3-methylimidazo[4,5-f]quinoline and N-hydroxy-2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline at the C-8 and N2 atoms of guanine.N-羟基-2-氨基-3-甲基咪唑并[4,5-f]喹啉和N-羟基-2-氨基-3,8-二甲基咪唑并[4,5-f]喹喔啉与鸟嘌呤的C-8和N2原子在体外反应形成的DNA加合物的表征。
Chem Res Toxicol. 1992 Jul-Aug;5(4):479-90. doi: 10.1021/tx00028a005.
5
Metabolic activation of carcinogenic heterocyclic aromatic amines by human liver and colon.人类肝脏和结肠对致癌性杂环芳香胺的代谢活化作用。
Carcinogenesis. 1991 Oct;12(10):1839-45. doi: 10.1093/carcin/12.10.1839.
6
Cytochromes P450 in cynomolgus monkeys mutagenically activate 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) but not 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx).食蟹猴体内的细胞色素P450可通过诱变激活2-氨基-3-甲基咪唑并[4,5-f]喹啉（IQ），但不能激活2-氨基-3,8-二甲基咪唑并[4,5-f]喹喔啉（MeIQx）。
Carcinogenesis. 1995 Jul;16(7):1549-55. doi: 10.1093/carcin/16.7.1549.
7
Metabolism of the food-borne carcinogens 2-amino-3-methylimidazo-[4,5-f]quinoline and 2-amino-3,8- dimethylimidazo[4,5-f]-quinoxaline in the rat as a model for human biomonitoring.以大鼠为人类生物监测模型对食源性致癌物2-氨基-3-甲基咪唑并[4,5-f]喹啉和2-氨基-3,8-二甲基咪唑并[4,5-f]喹喔啉的代谢研究
Environ Health Perspect. 1993 Mar;99:123-8. doi: 10.1289/ehp.9399123.
8
Metabolic processing and disposition of 2-amino-3-methylimidazo[4,5-f] quinoline (IQ), 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx), and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in nonhuman primates.2-氨基-3-甲基咪唑并[4,5-f]喹啉（IQ）、2-氨基-3,8-二甲基咪唑并[4,5-f]喹喔啉（MeIQx）和2-氨基-1-甲基-6-苯基咪唑并[4,5-b]吡啶（PhIP）在非人灵长类动物中的代谢过程及处置情况。
Princess Takamatsu Symp. 1995;23:69-77.
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Cancer Res. 1994 Jul 1;54(13):3422-7.
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Effects of human and rat glutathione S-transferases on the covalent DNA binding of the N-acetoxy derivatives of heterocyclic amine carcinogens in vitro: a possible mechanism of organ specificity in their carcinogenesis.人和大鼠谷胱甘肽S-转移酶对杂环胺致癌物N-乙酰氧基衍生物体外共价DNA结合的影响：其致癌作用中器官特异性的一种可能机制。
Cancer Res. 1994 Sep 15;54(18):4920-6.

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Chem Res Toxicol. 2012 Jul 16;25(7):1316-83. doi: 10.1021/tx300132k. Epub 2012 May 10.
3
Metabolism and biomarkers of heterocyclic aromatic amines in molecular epidemiology studies: lessons learned from aromatic amines.在分子流行病学研究中杂环芳香胺的代谢和生物标志物：从芳香胺中吸取的经验教训。
Chem Res Toxicol. 2011 Aug 15;24(8):1169-214. doi: 10.1021/tx200135s. Epub 2011 Jun 20.
4
A comprehensive approach to the profiling of the cooked meat carcinogens 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine, and their metabolites in human urine.全面分析人尿液中烹饪肉产生的致癌物 2-氨基-3,8-二甲基咪唑[4,5-f]喹喔啉、2-氨基-1-甲基-6-苯基咪唑[4,5-b]吡啶及其代谢物的方法。
Chem Res Toxicol. 2010 Apr 19;23(4):788-801. doi: 10.1021/tx900436m.
5
Phenol sulphotransferase SULT1A1 polymorphism: molecular diagnosis and allele frequencies in Caucasian and African populations.苯酚磺基转移酶SULT1A1基因多态性：白种人和非洲人群中的分子诊断及等位基因频率
Biochem J. 1999 Jan 1;337 ( Pt 1)(Pt 1):45-9.

本文引用的文献

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Expression and functional characterization of a rat sulfotransferase (ST1A1) cDNA for sulfations of phenolic substrates in COS-1 cells.
Jpn J Pharmacol. 1993 Feb;61(2):153-6. doi: 10.1254/jjp.61.153.
2
Metabolic activation and deactivation of arylamine carcinogens by recombinant human NAT1 and polymorphic NAT2 acetyltransferases.重组人NAT1和多态性NAT2乙酰基转移酶对芳胺致癌物的代谢激活与失活作用。
Carcinogenesis. 1993 Aug;14(8):1633-8. doi: 10.1093/carcin/14.8.1633.
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Isolation and expression of a cDNA encoding a male-specific rat sulfotransferase that catalyzes activation of N-hydroxy-2-acetylaminofluorene.一种编码雄性特异性大鼠磺基转移酶的cDNA的分离与表达，该酶催化N-羟基-2-乙酰氨基芴的活化。
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4
Enzymatic phase II activation of the N-hydroxylamines of IQ, MeIQx and PhIP by various organs of monkeys and rats.IQ、MeIQx和PhIP的N-羟基胺在猴子和大鼠各器官中的酶促II相激活作用。
Carcinogenesis. 1993 Oct;14(10):2091-6. doi: 10.1093/carcin/14.10.2091.
5
Cytochrome P450 mediated metabolism of diazepam in human and rat: involvement of human CYP2C in N-demethylation in the substrate concentration-dependent manner.细胞色素P450介导的地西泮在人和大鼠体内的代谢：人CYP2C以底物浓度依赖性方式参与N-去甲基化作用。
Pharmacogenetics. 1993 Dec;3(6):291-301. doi: 10.1097/00008571-199312000-00003.
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Structural similarity and diversity of sulfotransferases.
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Activation of 2-hydroxyamino-1-methyl-6-phenylimidazo[4,5-b] pyridine by cDNA-expressed human and rat arylsulfotransferases.由cDNA表达的人和大鼠芳基磺基转移酶对2-羟基氨基-1-甲基-6-苯基咪唑并[4,5-b]吡啶的激活作用。
Jpn J Cancer Res. 1994 Dec;85(12):1220-8. doi: 10.1111/j.1349-7006.1994.tb02933.x.
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Primary structures and properties of two related forms of aryl sulfotransferases in human liver.
Pharmacogenetics. 1995;5 Spec No:S135-40. doi: 10.1097/00008571-199512001-00015.
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Species differences in the N-acetylation by liver cytosol of mutagenic heterocyclic aromatic amines in protein pyrolysates.
Carcinogenesis. 1984 May;5(5):683-6. doi: 10.1093/carcin/5.5.683.
10
Sulfamate formation is a major route for detoxification of 2-amino-3-methylimidazo[4,5-f]quinoline in the rat.氨基磺酸酯的形成是大鼠体内2-氨基-3-甲基咪唑[4,5-f]喹啉解毒的主要途径。
Carcinogenesis. 1986 Sep;7(9):1483-5. doi: 10.1093/carcin/7.9.1483.

由cDNA表达的哺乳动物酚磺基转移酶形成2-氨基-3-甲基咪唑并[4,5-f]喹啉和2-氨基-3,8-二甲基咪唑并[4,5-f]喹喔啉-磺酸盐。

Formation of 2-amino-3-methylimidazo[4,5-f]quinoline- and 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline-sulfamates by cDNA-expressed mammalian phenol sulfotransferases.

作者信息

Ozawa S, Nagata K, Yamazoe Y, Kato R

机构信息

Department of Pharmacology, School of Medicine, Keio University, Tokyo.

出版信息

Jpn J Cancer Res. 1995 Mar;86(3):264-9. doi: 10.1111/j.1349-7006.1995.tb03049.x.

DOI:10.1111/j.1349-7006.1995.tb03049.x
PMID:7744696
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5920814/
Abstract

In rat liver cytosol systems, 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) and 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) were converted into their sulfamates in the presence of 3'-phosphoadenosine 5'-phosphosulfate at rates of 51.2 and 50.7 pmol/min/mg cytosol in the male, and 23.7 and 22.5 pmol/min/mg cytosol in the female, respectively. IQ-sulfamate formation was low (0.24 pmol/min/mg cytosol) in human liver cytosols, and MeIQx-sulfamate was not detected (< 0.1 pmol/min/mg cytosol). These results suggest only a minor contribution of IQ- and MeIQx-sulfamate formation to the detoxification of both heterocyclic amines in humans. Using sulfotransferase cDNA-expression systems, a rat ST1A1 arylsulfotransferase has been shown to catalyze the formation of the sulfamates, suggesting a role of the ST1A type of sulfotransferase in the N-sulfation of heterocyclic amines.

摘要

在大鼠肝脏胞质溶胶系统中，在3'-磷酸腺苷5'-磷酸硫酸酯存在的情况下，2-氨基-3-甲基咪唑并[4,5-f]喹啉（IQ）和2-氨基-3,8-二甲基咪唑并[4,5-f]喹喔啉（MeIQx）分别以雄性51.2和50.7皮摩尔/分钟/毫克胞质溶胶、雌性23.7和22.5皮摩尔/分钟/毫克胞质溶胶的速率转化为它们的氨基磺酸酯。在人肝脏胞质溶胶中，IQ-氨基磺酸酯的形成较低（0.24皮摩尔/分钟/毫克胞质溶胶），且未检测到MeIQx-氨基磺酸酯（<0.1皮摩尔/分钟/毫克胞质溶胶）。这些结果表明，IQ-和MeIQx-氨基磺酸酯的形成对人体中这两种杂环胺解毒的贡献较小。利用磺基转移酶cDNA表达系统，已证明大鼠ST1A1芳基磺基转移酶可催化氨基磺酸酯的形成，这表明ST1A类型的磺基转移酶在杂环胺的N-硫酸化中发挥作用。