9-N-(2'-hydroxyethyl)berberine chloride | 1060705-11-4

• 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-N-(2'-hydroxyethyl)berberine chloride
• 英文别名: 9-N-2'-hydroxyethylberberine；2-[(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)amino]ethanol;chloride
• CAS: 1060705-11-4
• 化学式: C₂₁H₂₁N₂O₄*Cl
• 分子量: 400.862
• InChiKey: OGLPRQNIABMEQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  63.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  盐酸小檗碱 、 C.I.酸性橙108 以 乙醇 为溶剂， 以47%的产率得到9-N-(2'-hydroxyethyl)berberine chloride
  参考文献：
  名称：

  9-N-Substituted berberine derivatives: Stabilization of G-quadruplex DNA and down-regulation of oncogene c-myc

  摘要：

  A series of 9-N-substituted berberine derivatives (2a-j) were synthesized and evaluated as a new class of G-quadruplex binding ligands. G-quadruplex of DNA had been proven to be the transcription controller of human c-myc gene. The interaction of 9-N-substituted berberine derivatives with G-quadruplex DNA in c-myc was examined via EMSA, CD spectroscopy, FRET-melting method, PCR-stop assay, competitive dialysis, cell proliferation assay and RT-PCR assay. The experiment results indicated that these derivatives could selectively induce and stabilize the formation of intramolecular parallel G-quadruplex in c-myc, which led to down-regulation of transcription of the c-myc in the HL60 lymphomas cell line. The related structure-activity relationships were also discussed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.029

文献信息

• 9-N-Substituted berberine derivatives: Stabilization of G-quadruplex DNA and down-regulation of oncogene c-myc
  作者：Yan Ma、Tian-Miao Ou、Jin-Qiang Hou、Yu-Jing Lu、Jia-Heng Tan、Lian-Quan Gu、Zhi-Shu Huang

  DOI：10.1016/j.bmc.2008.07.029

  日期：2008.8

  A series of 9-N-substituted berberine derivatives (2a-j) were synthesized and evaluated as a new class of G-quadruplex binding ligands. G-quadruplex of DNA had been proven to be the transcription controller of human c-myc gene. The interaction of 9-N-substituted berberine derivatives with G-quadruplex DNA in c-myc was examined via EMSA, CD spectroscopy, FRET-melting method, PCR-stop assay, competitive dialysis, cell proliferation assay and RT-PCR assay. The experiment results indicated that these derivatives could selectively induce and stabilize the formation of intramolecular parallel G-quadruplex in c-myc, which led to down-regulation of transcription of the c-myc in the HL60 lymphomas cell line. The related structure-activity relationships were also discussed. (C) 2008 Elsevier Ltd. All rights reserved.