[(η6-C6H6)ruthenium(II)(p-2-(4-bromophenyl)imidazole[4,5-f ][1,10]-phenanthroline)Cl]Cl | 1442692-03-6

• 英文名称: [(η6-C6H6)ruthenium(II)(p-2-(4-bromophenyl)imidazole[4,5-f ][1,10]-phenanthroline)Cl]Cl
• 英文别名: [(η⁶-C₆H₆)ruthenium(II)(p-2-(4-bromophenyl)imidazole[4,5-f ][1,10]-phenanthroline)Cl]Cl；[(η⁶-C₆H₆)Ru(p-BrPIP)Cl]Cl
• CAS: 1442692-03-6
• 化学式: C₂₅H₁₇BrClN₄Ru*Cl
• 分子量: 625.317
• InChiKey: VFBCMCABUUEVGT-UHFFFAOYSA-L

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：

  [RuCl2(benzene)]2 、 2-(4-bromophenyl)-1H-imidazo[4,5-f][1,10]phenanthroline 以 二氯甲烷 为溶剂， 反应 0.5h， 以89.8%的产率得到[(η6-C6H6)ruthenium(II)(p-2-(4-bromophenyl)imidazole[4,5-f ][1,10]-phenanthroline)Cl]Cl
  参考文献：
  名称：

  Microwave-assisted synthesis of arene ruthenium(II) complexes that induce S-phase arrest in cancer cells by DNA damage-mediated p53 phosphorylation

  摘要：

  A series of arene ruthenium(II) complexes coordinated by phenanthroimidazole derivates, [(C6H6)Ru(L) Cl]Cl center dot 2H(2)O (1b L = IP, 2b L = p-NMe2PIP, 3b L = p-MeOPIP, 4b L = p-HOPIP, 5b L = p-COOHPIP, 6b L = p-CF3PIP, 7b L = p-BrPIP) have been synthesized in yields of 89-92% under microwave irradiation in 30 min, and the crystal structure of 1b by XRD gives a typical "piano stool" conformation. The antitumor activity of these complexes against various tumor cells have been evaluated by MTT assay, and the results show that this type of arene Ru(II) complexes exhibit acceptable inhibitory effect against all of these tumor cells, especially osteosarcoma MG-63 cells, but with low toxicity toward HK-2 human normal cells. Studies on the mechanism revealed that cell cycle arrest at S-phase in MG-63 cells induced by the arene Ru(II) complex 2b, which was confirmed by the increase in the percentage of cells at S-phase and down-regulator of cyclin A. The further studies by Comet assay at single cell level indicated that DNA damage in MG-63 cells was triggered by 2b, following with the up-regulation of phosphorylated p53 and histone. The studies by spectroscopy in vitro also indicate that 2b bind to DNA molecule by intercalative mode to disturb the bio-function of tumor cells. In conclusion, the synthetic arene Ru(II) complexes could serve as novel p53 activator with potential application in cancer chemotherapy. (c) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.037

文献信息

• Arene Ruthenium(II) Complexes as Low-Toxicity Inhibitor against the Proliferation, Migration, and Invasion of MDA-MB-231 Cells through Binding and Stabilizing <i>c-myc</i> G-Quadruplex DNA
  作者：Qiong Wu、Kangdi Zheng、Siyan Liao、Yang Ding、Yangqiu Li、Wenjie Mei

  DOI：10.1021/acs.organomet.5b00820

  日期：2016.2.8

  Arene Ru(II) complexes have long been extensively studied as potential inhibitors against the proliferation of tumor cells, but their behavior against the migration and invasion of tumor cells needs further research. In this work, a series of arene Ru(II) complexes, (n(6-)C(6)H(6))Ru(p-XPIP)Cl]Cl (X = H, 1; F, 2; Cl, 3; Br, 4; and I, 5), have been synthesized, and their inhibitory activity against the migration and invasion of MDA-MB-231 breast cancer cells have been investigated. It is found that all of these complexes exhibit excellent inhibitory activity (IC50) against the growth of MDA-MB-231 breast cancer cells, and the value of IC50 for 1, 2, 3, 4, and 5 is about >300, 52.6, 11.4, 45.5, and 59.1 mu M, respectively. Further studies by wound-healing assay, FITC-geltain assay, and flow cytometry assay showed that 3 can apparently suppress the migration and invasion of MDA-MB-231 cells via the joint action of S-phase arrest and apoptosis. Moreover, the binding behavior of these arene Ru(II) complexes with c-myc G-quadruplex DNA has also been studied, and the results showed that these complexes can bind and stabilize c-myc Gquadruplex DNA in groove binding mode. Also, the low toxicity of 3 was confirmed by its low inhibitory activity against the growth of normal MCF-10A breast cells in vitro and the development of zebrafish embryos in vivo. In other words, these results indicated that synthetic arene Ru(II) complexes can be developed as low-toxicity agents against the proliferation, migration, and invasion of breast cancer cells.