| 1394898-48-6

• CAS: 1394898-48-6
• 化学式: C₂₁H₂₄Cl₂N₂O₂Ru
• 分子量: 508.41
• InChiKey: JGCOYYFRXYKJSQ-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  ammonium hexafluorophosphate 、 、 三苯基膦 以 甲醇 为溶剂， 反应 1.0h， 以90%的产率得到
  参考文献：
  名称：

  Somatostatin Subtype-2 Receptor-Targeted Metal-Based Anticancer Complexes

  摘要：

  Conjugates of a dicarba analogue of octreotide, a potent somatostatin agonist whose receptors are overexpressed on tumor cells, with [PtCl2(dap)] (dap = 1-(carboxylic acid)-1,2-diaminoethane) (3), [(eta(6)-bip)Os(4-CO2-pico)Cl] (bip = biphenyl, pico = picolinate) (4), [(eta(6)-p-cym)RuCl](dap)(+) (p-cym = p-cymene) (5), and [(eta(6)-p-cym)RuCl(imidazole-CO2H)(PPh3)](+) (6), were synthesized by using a solid-phase approach. Conjugates 3-5 readily underwent hydrolysis and DNA binding, whereas conjugate 6 was inert to ligand substitution. NMR spectroscopy and molecular dynamics calculations showed that conjugate formation does not perturb the overall peptide structure. Only 6 exhibited antiproliferative activity in human tumor cells (IC50 = 63 +/- 2 mu M in MCF-7 cells and IC50 = 26 +/- 3 mu M in DU-145 cells) with active participation of somatostatin receptors in cellular uptake. Similar cytotoxic activity was found in a normal cell line (IC50 = 45 +/- 2.6 mu M in CHO cells), which can be attributed to a similar level of expression of somatostatin subtype-2 receptor. These studies provide new insights into the effect of receptor-binding peptide conjugation on the activity of metal-based anticancer drugs, and demonstrate the potential of such hybrid compounds to target tumor cells specifically.

  DOI：

  10.1021/bc300173h
• 作为产物：
  描述：

  [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 4-(1H-咪唑-1-基)苯甲酸甲酯 以 二氯甲烷 为溶剂， 反应 4.0h， 以50%的产率得到
  参考文献：
  名称：

  Somatostatin Subtype-2 Receptor-Targeted Metal-Based Anticancer Complexes

  摘要：

  Conjugates of a dicarba analogue of octreotide, a potent somatostatin agonist whose receptors are overexpressed on tumor cells, with [PtCl2(dap)] (dap = 1-(carboxylic acid)-1,2-diaminoethane) (3), [(eta(6)-bip)Os(4-CO2-pico)Cl] (bip = biphenyl, pico = picolinate) (4), [(eta(6)-p-cym)RuCl](dap)(+) (p-cym = p-cymene) (5), and [(eta(6)-p-cym)RuCl(imidazole-CO2H)(PPh3)](+) (6), were synthesized by using a solid-phase approach. Conjugates 3-5 readily underwent hydrolysis and DNA binding, whereas conjugate 6 was inert to ligand substitution. NMR spectroscopy and molecular dynamics calculations showed that conjugate formation does not perturb the overall peptide structure. Only 6 exhibited antiproliferative activity in human tumor cells (IC50 = 63 +/- 2 mu M in MCF-7 cells and IC50 = 26 +/- 3 mu M in DU-145 cells) with active participation of somatostatin receptors in cellular uptake. Similar cytotoxic activity was found in a normal cell line (IC50 = 45 +/- 2.6 mu M in CHO cells), which can be attributed to a similar level of expression of somatostatin subtype-2 receptor. These studies provide new insights into the effect of receptor-binding peptide conjugation on the activity of metal-based anticancer drugs, and demonstrate the potential of such hybrid compounds to target tumor cells specifically.

  DOI：

  10.1021/bc300173h