[14C]-IQ | 161406-40-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: [14C]-IQ
• 英文别名: 2-Amino-3-methyl-3H-imidazo[4,5-f]quinoline-2-14C；3-methyl(214C)imidazolo[4,5-f]quinolin-2-amine
• CAS: 161406-40-2
• 化学式: C₁₁H₁₀N₄
• 分子量: 200.216
• InChiKey: ARZWATDYIYAUTA-OZUIXNLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  56.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [14C]-IQ 在 potassium phosphate buffer 、 sodium N,N-(diethylamino)diazen-1-ium-1,2-diolate 作用下， 反应 0.5h， 生成
  参考文献：
  名称：

  通过反应性氮氧对2-氨基-3-甲基咪唑并[4,5-f]喹啉进行亚硝化和硝化。

  摘要：

  人们认为煮熟的红肉摄入量和慢性炎症/感染都在结肠癌的病因中起作用。杂环胺2-氨基-3-甲基咪唑并[4,5-f]喹啉（IQ）是在烹饪红肉时形成的，可能与结肠癌的发生有关。炎性反应的组成部分反应性氮氧（RNOS）有助于归因于正常组织炎症的有害影响。这项研究评估了RNOS可能对智商进行化学转化。在各种条件下生成与（14）C-IQ反应的RNOS，并通过HPLC评估样品。髓过氧化物酶（MPO）催化的反应取决于H（2）O（2）和NO（2）（-）。该反应产生了偶氮-IQ二聚体和IQ二聚体，以及通过ESI / MS鉴定的两种硝化的IQ产物。未检测到2-Nitro-IQ。2 mM氰化物抑制产物形成。用0.5 mM牛磺酸不会改变用100 mM氯化物观察到的硝化产物的减少。硝酸盐化产物还可以通过其他条件产生，即ONOO（-）和NO（2）（-）+ HOCl，它们会生成二氧化氮自由基。相反，产生N（2）O（3）的条

  DOI：

  10.1021/tx020008h

文献信息

• Prostaglandin-H synthase mediated metabolism and mutagenic activation of 2-amino-3-methylimidazo [4,5-f] quinoline (IQ)
  作者：E. Wolz、D. Wild、G. H. Degen

  DOI：10.1007/s002040050154

  日期：1995.1

  Prostaglandin-H synthase (PHS), a mammalian peroxidase of interest for the extrahepatic formation of reactive intermediates of carcinogens, catalyzes in vitro the metabolic activation of the mutagen and carcinogen 2-amino-3-methylimidazo[4,5-f]quinoline (IQ). Incubation of C-14-labeled IQ with ram seminal vesicle microsomes (RSVM), a rich source of PHS, resulted in protein binding and generated products mutagenic in S. typhimurium YG1024. The mutagenic activity produced in IQ/PHS incubations was stable and extractable with ethyl acetate. Upon fractionation of such extracts by HPLC and subsequent analysis, two metabolites were identified as 2,2'-azo-bis-3-methylimidazo[4,5-f]quinoline (azo-IQ) and 3-methyl-2-nitro-imidazo[4,5-f]quinoline (nitro-IQ) confirmed by comparison of HPLC retention times, UV/VIS-, H-1-NMR-spectroscopy, and mass spectrometry of synthesized standards. Azo-IQ was obtained by chemical oxidation of IQ with metasodium periodate. It was the major metabolite in PHS incubations, but has not been detected in monooxygenase incubations. Azo-IQ, without metabolic activation, was much less mutagenic in S. typhimurium YG1024 (308 rev/nmol) than nitro-IQ and 3-methyl-2-nitroso-imidazo[4,5-f]quinoline (nitroso-IQ), two other S9-independent mutagens which have been synthesized by chemical oxidation of IQ with sodium nitrite. Nitro-IQ was formed only in trace amounts but due to its potent mutagenicity in S. typhimurium YG1024 (2 x 10(6) rev/nmol) it accounted for most of the mutagenic activity of the incubations. These data show that PHS-mediated in vitro metabolism of IQ results in its metabolic activation; thus PHS may contribute to the genotoxicity of IQ in extrahepatic tissues.