[ring-U-(14)C]-p,p'-methoxychlor

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [ring-U-(14)C]-p,p'-methoxychlor
• 英文别名: Methoxychlor,[ring-14c(u)]；1-methoxy-4-[2,2,2-trichloro-1-(4-methoxy(1,2,3,4,5,6-14C6)cyclohexa-1,3,5-trien-1-yl)ethyl](1,2,3,4,5,6-14C6)cyclohexa-1,3,5-triene
• 化学式: C₁₆H₁₅Cl₃O₂
• 分子量: 369.521
• InChiKey: IAKOZHOLGAGEJT-BVVISOKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [ring-U-(14)C]-p,p'-methoxychlor 在 aeromonas hydrophila 、 air 、 R₂A broth 作用下， 以 丙酮 为溶剂， 生成
  参考文献：
  名称：

  Reductive Dechlorination of Methoxychlor by Bacterial Species of Environmental Origin: Evidence for Primary Biodegradation of Methoxychlor in Submerged Environments

  摘要：

  Methoxychlor [1,1,1-trichloro-2,2-bis(4-methoxyphenyl)ethane] is an organochlorine insecticide that undergoes dechlorination in natural submerged environments. We investigated the ability to dechlorinate this compound in seven environmental bacterial species (Aeromonas hydrophila, Enterobacter amnigenus, Klebsiella terrigena, Bacillus subtilis, Achromobacter xylosoxidans, Acinetobacter calcoaceticus, and Mycobacterium obuense) and the enteric bacterium Escherichia coli as a positive control. In R2A broth at 25 degrees C under aerobic, static culture, all species except Ach. xylosoxidans were observed to convert methoxychlor to dechlorinated methoxychlor [1,1-dichloro-2,2-bis(4-methoxyphenyl)ethane]. The medium was aerobic at first, but bacterial growth resulted in the consumption of oxygen and generated microaerobic and weakly reductive conditions. Replacement of the headspace of the culture tubes with nitrogen gas was found to decrease the dechlorination rate. Our findings suggest that extensive bacterial species ubiquitously inhabiting the subsurface water environment play an important role in the primary dechlorination of methoxychlor.

  DOI：

  10.1021/jf2048614

文献信息

• Metabolism of Methoxychlor by the P450-Monooxygenase CYP6G1 Involved in Insecticide Resistance of<i>Drosophila melanogaster</i>after Expression in Cell Cultures of<i>Nicotiana tabacum</i>
  作者：Nicole Joußen、Ingolf Schuphan、Burkhard Schmidt

  DOI：10.1002/cbdv.200900020

  日期：2010.3

  metabolize the insecticide methoxychlor (=1,1,1‐trichloro‐2,2‐bis(4‐methoxyphenyl)ethane, 1) against the background of endogenous enzymes of the corresponding non‐transgenic culture. The Cyp6g1‐transgenic cell culture metabolized 96% of applied methoxychlor (45.8 μg per assay) within 24 h by demethylation and hydroxylation mainly to trishydroxy and catechol methoxychlor (16 and 17%, resp.). About 34%

  黑腹果蝇的细胞色素 P450 单加氧酶 CYP6G1 在烟草的细胞悬浮培养物中异源表达。该体外系统用于研究 CYP6G1 在相应的内源酶背景下代谢杀虫剂甲氧氯（=1,1,1-三氯-2,2-双（4-甲氧基苯基）乙烷，1）的能力。非转基因培养。Cyp6g1 转基因细胞培养物在 24 小时内通过去甲基化和羟基化作用代谢了 96% 的甲氧基氯（每次测定 45.8 μg），主要代谢为三羟基和邻苯二酚甲氧基氯（分别为 16% 和 17%）。大约 34% 的代谢和三羟基和儿茶酚甲氧氯的独特形成是由于外来酶 CYP6G1。此外，在同时加入胡椒基丁醚（458 μg）后，甲氧氯的代谢被抑制了 43%，而在非转基因培养物中的抑制率为 92%。此外，两种培养物中的糖基化速率均降低。在胡椒基丁醚（200 μg）存在下，Cyp6g1 转基因培养物中杀虫剂吡虫啉（6；20 μg，24 小时）的代谢抑制了 82%，支持这些结果。由于