9-O-(4-carboxybenzyl)berberine | 1412500-91-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 原小檗碱生物碱及其衍生物
• 英文名称: 9-O-(4-carboxybenzyl)berberine
• 英文别名: 4-[(17-Methoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-16-yl)oxymethyl]benzoate；4-[(17-methoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-16-yl)oxymethyl]benzoate
• CAS: 1412500-91-4
• 化学式: C₂₇H₂₁NO₆
• 分子量: 455.467
• InChiKey: YYPICZZQTHSNNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  80.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  copper(II) nitrate trihydrate 、 9-O-(4-carboxybenzyl)berberine 以 甲醇 为溶剂， 反应 0.5h， 以30%的产率得到[Cu(CBB)2](NO3)2*2H2O
  参考文献：
  名称：

  Synthesis, characterization and potent DNA-cleaving activity of copper(II)-complexed berberine carboxylate

  摘要：

  9-O-(4-carboxybenzyl)berberine (CBB) 1 was synthesized from the reaction of berberrubine with methyl 4-(bromomethyl)benzoate and subsequent hydrolysis. Its Cu(II) complex 2 was prepared from the reaction with Cu(NO3)(2)center dot 3H(2)O, and established as [Cu(CBB)(2)](NO3)(2)center dot 2H(2)O by means of H-1 NMR, UV, IR, elemental analysis and TGA measurements. Agarose gel electrophoresis study on the cleavage of plasmid pBR322 DNA indicated that complex 2 was capable of efficiently cleaving DNA under physiological conditions, most probably via an oxidative mechanistic pathway involving the formation of singlet oxygen as the reactive species. Kinetic assay afforded the maximal first-order rate constant k(max) of 2.41 h (1) and Michaelis constant K-M of 2.64 mM, respectively, representing ca. 10(8)-fold acceleration in the cleavage. This catalytic efficacy is attributed to the Cu(II)-assisted formation of dimeric species, in which the two berberine subunits cooperatively bind to DNA, whereas the carboxylate-coordinated Cu(II) moiety functions as the cleavage-active center. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.087
• 作为产物：
  描述：

  小檗红碱 在 potassium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 21.5h， 生成 9-O-(4-carboxybenzyl)berberine
  参考文献：
  名称：

  Synthesis, characterization and potent DNA-cleaving activity of copper(II)-complexed berberine carboxylate

  摘要：

  9-O-(4-carboxybenzyl)berberine (CBB) 1 was synthesized from the reaction of berberrubine with methyl 4-(bromomethyl)benzoate and subsequent hydrolysis. Its Cu(II) complex 2 was prepared from the reaction with Cu(NO3)(2)center dot 3H(2)O, and established as [Cu(CBB)(2)](NO3)(2)center dot 2H(2)O by means of H-1 NMR, UV, IR, elemental analysis and TGA measurements. Agarose gel electrophoresis study on the cleavage of plasmid pBR322 DNA indicated that complex 2 was capable of efficiently cleaving DNA under physiological conditions, most probably via an oxidative mechanistic pathway involving the formation of singlet oxygen as the reactive species. Kinetic assay afforded the maximal first-order rate constant k(max) of 2.41 h (1) and Michaelis constant K-M of 2.64 mM, respectively, representing ca. 10(8)-fold acceleration in the cleavage. This catalytic efficacy is attributed to the Cu(II)-assisted formation of dimeric species, in which the two berberine subunits cooperatively bind to DNA, whereas the carboxylate-coordinated Cu(II) moiety functions as the cleavage-active center. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.087