[oxoglaucineH][AuCl4]*DMSO | 1357565-67-3

• 英文名称: [oxoglaucineH][AuCl4]*DMSO
• CAS: 1357565-67-3
• 化学式: AuCl₄*C₂H₆OS*C₂₀H₁₈NO₅
• 分子量: 769.28
• InChiKey: OJBGSWUPKJINKO-UHFFFAOYSA-K

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为产物：
  描述：

  chloroauric acid 、 氧海罂粟碱 以 甲醇 、 氯仿 为溶剂， 以65%的产率得到[oxoglaucineH][AuCl4]*DMSO
  参考文献：
  名称：

  TCM Active Ingredient Oxoglaucine Metal Complexes: Crystal Structure, Cytotoxicity, and Interaction with DNA

  摘要：

  The alkaloid oxoglaucine (OG), which is a bioactive component from traditional Chinese medicine (TCM), was synthesized by a two-step reaction and used as the ligand to react with transition metal salts to give four complexes: [OGH][AuCl4]center dot DMSO (1), [Zn(OG)(2)(H2O)(2)](NO3)(2) (2), [Co(OG)(2)(H2O)(2)](ClO4)(2) (3), and [Mn(OG)(2)(H2O)(2)](ClO4)(2) (4). The crystal structures of the metal complexes were confirmed by single crystal X-ray diffraction. Complex 1 is an ionic compound consisting of a charged ligand [OGH](+) and a gold complex [AuCl4](-). Complexes 2-4 all have similar structures (inner-spheres), that is, octahedral geometry with two OG coordinating to one metal center and two aqua ligands occupying the two apical positions of the octahedron, and two NO3- or ClO4- as counteranions in the outer-sphere. The complexation of OG to metal ion was confirmed by ESI-MS, capillary electrophoresis and fluorescence polarization. The in vitro cytotoxicity of these complexes toward a various tumor cell lines was assayed by the MTT method. The results showed that most of these metal-oxoglaucine complexes exhibited enhanced cytotoxicity compared with oxoglaucine and the corresponding metal salts, with IC50 values ranging from 1.4 to 32.7 mu M for sensitive cancer cells, which clearly implied a positive synergistic effect. Moreover, these complexes appeared to be selectively active against certain cell lines. The interactions of oxoglaucine and its metal complexes with DNA and topoisomerase I were investigated by UV-vis, fluorescence, CD spectroscopy, viscosity, and agarose gel electrophoresis, and the results indicated that these OG-metal complexes interact with DNA mainly via intercalation. Complexes 2-4 are metallointercalators, but complex 1 is not. These metal complexes could effectively inhibit topoisomerase I even at low concentration. Cell cycle analysis revealed that 1-3 caused S-phase cell arrest.

  DOI：

  10.1021/ic200443p