[PtI2(1(R),2(R)-DACH)]

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: [PtI2(1(R),2(R)-DACH)]
• 英文别名: Pt(dach)I2；[(1R,2R)-2-azanidylcyclohexyl]azanide;diiodoplatinum(2+)
• 化学式: C₆H₁₂I₂N₂Pt
• 分子量: 561.064
• InChiKey: KEZVWGKGXZSYRH-SKSSAGQDSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [PtI2(1(R),2(R)-DACH)] 在 silver nitrate 、 potassium chloride 作用下， 以 水 为溶剂， 反应 30.5h， 以94%的产率得到cis-dichloro-(trans-1R,2R-cyclohexanediamine)platinum(II)
  参考文献：
  名称：

  Revisiting [PtCl₂(cis-1,4-DACH)]: An Underestimated Antitumor Drug with Potential Application to the Treatment of Oxaliplatin-Refractory Colorectal Cancer

  摘要：

  Although the encouraging antitumor activity of [PtCl2(cis-1,4-DACH)] (1; DACH = diaminocyclohexane) was shown in early studies almost 20 years ago, the compound has remained nearly neglected. In contrast, oxaliplatin, containing the isomeric 1(R),2(R)DACH carrier ligand, enjoys worldwide clinic application as a most important therapeutic agent in the treatment of colorectal cancer. By extending the investigation to human chemotherapy-resistant cancer cells, we have demonstrated the real effectiveness of 1 in circumventing cisplatin and oxaliplatin resistance in LoVo colon cancer cells. The uptake of compound 1 by the latter cells was similar to that of sensitive LoVo cells. This is not the case for all other compounds considered in this investigation. Interaction with double-stranded DNA, investigated by a biosensor assay and by quantum mechanical/molecular mechanical geometry optimization of the 1,2-GG intrastrand cross-link, does not show significant differences between 1 and oxaliplatin. However, the DNA adducts of 1 are removed from repair systems with lower efficiency and are more effective in inhibiting DNA and RNA polymerase.

  DOI：

  10.1021/jm3006838
• 作为产物：
  描述：

  potassium tetrachloroplatinate(II) 、 (1R,2R)-1,2-diaminocyclohexane 在 potassium iodide 作用下， 以 水 为溶剂， 反应 3.08h， 以91%的产率得到[PtI2(1(R),2(R)-DACH)]
  参考文献：
  名称：

  Revisiting [PtCl₂(cis-1,4-DACH)]: An Underestimated Antitumor Drug with Potential Application to the Treatment of Oxaliplatin-Refractory Colorectal Cancer

  摘要：

  Although the encouraging antitumor activity of [PtCl2(cis-1,4-DACH)] (1; DACH = diaminocyclohexane) was shown in early studies almost 20 years ago, the compound has remained nearly neglected. In contrast, oxaliplatin, containing the isomeric 1(R),2(R)DACH carrier ligand, enjoys worldwide clinic application as a most important therapeutic agent in the treatment of colorectal cancer. By extending the investigation to human chemotherapy-resistant cancer cells, we have demonstrated the real effectiveness of 1 in circumventing cisplatin and oxaliplatin resistance in LoVo colon cancer cells. The uptake of compound 1 by the latter cells was similar to that of sensitive LoVo cells. This is not the case for all other compounds considered in this investigation. Interaction with double-stranded DNA, investigated by a biosensor assay and by quantum mechanical/molecular mechanical geometry optimization of the 1,2-GG intrastrand cross-link, does not show significant differences between 1 and oxaliplatin. However, the DNA adducts of 1 are removed from repair systems with lower efficiency and are more effective in inhibiting DNA and RNA polymerase.

  DOI：

  10.1021/jm3006838

文献信息

• 抗がん剤
  申请人：国立大学法人金沢大学

  公开号：JP2021088511A

  公开（公告）日：2021-06-10

  【課題】低コストで製造可能であり、且つ高い抗がん活性を有する抗がん剤の提供。【解決手段】式（１）（式中、ｍ及びｎは、それぞれ独立に０、１又は２であり、ｍ＋ｎは２である。）で表される、ｍｙｏ−イノシトール−１，２，３，４，５，６−ヘキサキスホスフェート誘導体であるアニオンと、アルカリ金属イオン、アルカリ土類金属イオン又はプロトンであるカウンターカチオンからなる金属錯体を有効成分として含有する抗がん剤。【選択図】図５

  【问题】提供一种低成本制造且具有高抗癌活性的抗癌药物。 【解决方案】该抗癌药物包含由式（1）表示的m-yo-inositol-1,2,3,4,5,6-hexakisphosphate衍生物的阴离子和碱金属离子、碱土金属离子或质子作为对离子的金属配合物作为有效成分。 【图表】图5
• 金属錯体およびこれを含有する抗癌剤
  申请人：国立大学法人金沢大学

  公开号：JP2016074639A

  公开（公告）日：2016-05-12

  【課題】シスプラチン及びオキサリプラチン等の既存の白金抗癌剤より抗癌活性に優れ、且つ副作用の低減された白金錯体の提供。【解決手段】ｍｙｏ−イノシトール−１，２，３，４，５，６−ヘキサキスホスフェート誘導体である下式（１）で示される白金錯体、及び（１，１０−フェナントロリン）（Ｎ−９−アントラニルメチル−１，４−ブタンジアミン）白金、等の白金錯体。［ｍ及びｎはそれぞれ独立に１又は２、ｍ＋ｎは３］【選択図】なし

  【问题】提供比已有的铂类抗癌药物如顺铂和奥沙利铂更具抗癌活性且副作用更低的铂配合物。 【解决方法】通过下式（1）所示的铂配合物，即myo-肌醇-1,2,3,4,5,6-六磷酸盐衍生物，以及（1,10-菲咯啉）（N-9-蒽甲基-1,4-丁二胺）铂等铂配合物。[m和n分别独立地为1或2，m+n为3] 【选择图】无。
• Revisiting [PtCl₂(<i>cis</i>-1,4-DACH)]: An Underestimated Antitumor Drug with Potential Application to the Treatment of Oxaliplatin-Refractory Colorectal Cancer
  作者：Nicola Margiotta、Cristina Marzano、Valentina Gandin、Domenico Osella、Mauro Ravera、Elisabetta Gabano、James A. Platts、Emanuele Petruzzella、James D. Hoeschele、Giovanni Natile

  DOI：10.1021/jm3006838

  日期：2012.8.23

  Although the encouraging antitumor activity of [PtCl2(cis-1,4-DACH)] (1; DACH = diaminocyclohexane) was shown in early studies almost 20 years ago, the compound has remained nearly neglected. In contrast, oxaliplatin, containing the isomeric 1(R),2(R)DACH carrier ligand, enjoys worldwide clinic application as a most important therapeutic agent in the treatment of colorectal cancer. By extending the investigation to human chemotherapy-resistant cancer cells, we have demonstrated the real effectiveness of 1 in circumventing cisplatin and oxaliplatin resistance in LoVo colon cancer cells. The uptake of compound 1 by the latter cells was similar to that of sensitive LoVo cells. This is not the case for all other compounds considered in this investigation. Interaction with double-stranded DNA, investigated by a biosensor assay and by quantum mechanical/molecular mechanical geometry optimization of the 1,2-GG intrastrand cross-link, does not show significant differences between 1 and oxaliplatin. However, the DNA adducts of 1 are removed from repair systems with lower efficiency and are more effective in inhibiting DNA and RNA polymerase.