cis-[Pt(cyclohexylamine)(NH3)I2] | 111716-25-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: cis-[Pt(cyclohexylamine)(NH3)I2]
• 英文别名: cis-Pt(NH3)(cyclohexylamine)I2；cis-[Pt(C6H11NH2)(NH3)I2；azane;cyclohexanamine;diiodoplatinum
• CAS: 111716-25-7
• 化学式: C₆H₁₆I₂N₂Pt
• 分子量: 565.095
• InChiKey: JZIGGHAPVXASFE-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：

  cis-[Pt(cyclohexylamine)(NH3)I2] 在 双氧水 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成
  参考文献：
  名称：

  水溶性双作用和三作用Satraplatin衍生物的合成和细胞毒性：用醋酸盐代替Satraplatin的赤道氯化物。

  摘要：

  Pt（II）配合物，例如顺铂和奥沙利铂，被广泛用作抗癌药物。它们的使用受到毒性副作用和肿瘤对药物产生耐药性的能力的限制。克服这些缺点的一种流行方法是使用它们的动力学惰性八面体Pt（IV）衍生物作为前药。迄今为止，在临床试验中最成功的Pt（IV）复合物是沙铂，cct- [Pt（NH3）（c-己胺）Cl2（OAc）2]，在细胞还原后释放出细胞毒性的顺式[Pt（NH3）（ c-己胺）Cl2]。为了获得水溶性和更有效的细胞毒性Pt（IV）配合物，我们制备了一系列双重和三作用的Satraplatin类似物，其中赤道氯代配体被醋酸盐替代，轴向配体包括无害和生物活性配体。 。用乙酸盐代替氯化物增强了化合物的水溶性，并且，除了一个例外，所有化合物在缓冲液中都非常稳定。通常，具有一个或两个轴向羟基配体的化合物比具有两个轴向羧酸盐的化合物被抗坏血酸还原的速度明显更快。尽管用沙铂中的乙酸盐代替氯化物可降低细胞毒

  DOI：

  10.1021/acs.inorgchem.9b02796
• 作为产物：
  描述：

  ammonium hydroxide 、 [platinum(II)(iodide)(cyclohexylamine)(μ-iodide)platinum(II)(cyclohexylamine)(iodide)] 以 水 为溶剂， 以88%的产率得到cis-[Pt(cyclohexylamine)(NH3)I2]
  参考文献：
  名称：

  Crystal and Molecular Structures of Asymmetric cis- and trans-Platinum(II/IV) Compounds and Their Reactions with DNA Fragments

  摘要：

  The asymmetrically substituted platinum(II) complexes cis-Pt(NH3)(c-C6H11NH2)Cl-2 and trans-Pt(NH3)(c-C6H11NH2)Cl-2 have been synthesized and their crystal structures have been determined. Crystals of cis-Pt(NH3)(c-C6H11NH2)Cl-2 (1) are orthorhombic, space group Pbca (no. 61) with a = 10.1994(12), b = 10.494(2), c = 18.826(2) Angstrom, Z = 8. The structure refinement converged to R1 = 0.0518 and wR2 = 0.1143. Crystals of trans-Pt(NH3)(c-C6H11NH2)Cl-2 (2) are monoclinic, space group P2(1)/c (no. 14) with a = 12.141(3), b = 6.0965(9), c = 19.864(3) Angstrom, beta = 118.71(2)degrees, Z = 4. The structure refinement converged to R1 = 0.0711 and wR2 = 0.1846. In addition, the Pt(IV) analogues with axial hydroxide ligands have been synthesized. Also the corresponding bis(carboxylato)platinum(IV) compound of formula trans,cis,cis-Pt(NH3)(c-C6H11NH2)Cl-2(OOCCH3)(2) has been obtained by conversion of the hydroxide with acetic anhydride. Reactions of these platinum complexes with 9-methylhypoxanthine and guanosine-5'-monophosphate (5'-GMP) have been studied in significant detail. The course of the reactions was followed by NMR spectroscopy, and H-1 and Pt-195 techniques were used to identify the formation of the products. It was found that the Pt(II) compounds easily react with the bases at the N7 position, whereas the Pt(IV) compounds react very slowly (for trans,cis,cis-Pt(NH3)(c-C6H11NH2)Cl-2(OOCCH3)(2)) or not at all (for trans, trans, trans-Pt(NH3)(c-C6H11NH2)Cl-2(OH)(2)), Only in the presence of glutathione does a reaction of the latter with 5'-GMP takes place. In this case a major product was found to be the reduced trans-Pt(II) complex with one molecule of 5'-GMP and one molecule of S-bonded glutathione.

  DOI：

  10.1021/ic960983u

文献信息

• 一种含三氟甲基的铂类抗肿瘤化合物及其制备方法和应用
  申请人：浙江工业大学

  公开号：CN115181134A

  公开（公告）日：2022-10-14

  本发明公开了一种含三氟甲基的铂类抗肿瘤化合物及其制备方法和应用，该化合物的结构式如式(Ⅰ)所示，其中式(Ⅰ)中的Am为氨基载体配体，取代基R1取代或不取代，R1为羟基、氨基、三氟甲基、糖基、连接有生物活性化合物的酯键、连接有生物活性化合物的酰胺键或连接有生物活性化合物的醚键。本发明的化合物体外对肺癌细胞A549、肝癌细胞HepG2、乳腺癌细胞MCF‑7和人结肠癌细胞HCT‑116的生长均有明显的抑制作用，抗癌活性大于卡铂，其中个别化合物的抗肿瘤活性优于奥沙利铂，与顺铂相近，并且对于正常肺上皮细胞BEAS‑2B的细胞毒活性较小，具有良好的临床应用前景。
• Synthesis, Cytotoxicity, and DNA‐Binding Levels of Ammine/Cyclohexylamine Platinum(II) Complexes with Dicarboxylates
  作者：Jinchao Zhang、Shen Yong

  DOI：10.1080/15533170600651462

  日期：2006.5.1

  Four new ammine/cyclohexylamine platinum(II) complexes with dicarboxylates (a-d) have been synthesized and characterized by elemental analysis, conductivity, IR, UV, and (HNMR)-H-1 spectra techniques. The cytotoxicity of the complexes was tested by MTT assay. The cell cycle analysis and the levels of total platinum bound to DNA were measured by flow cytometry and ICP-MS. The results show that the cytotoxicity of complexes (a-d) against EJ, HCT-8, BGC-823, HL-60, and MCF-7 cell lines decreases in the sequence: b>a>c>d. Complexes (a-d) have better cytotoxicity against EJ and HL-60 and complex (b) demonstrates cytotoxicity superior to that of the clinically established cisplatin. The complexes (a-d) induced a concentration-dependent accumulation of HL-60 cells in the G(2)/M phase of the cell cycle as cisplatin. The levels of total platinum bound to DNA in HL-60 and EJ cells decrease in the sequence: b>cisplatin>a>c>d under the same experimental conditions.
• Synthesis and biological evaluation of mixed ammine/amine platinum(II) complexes with dicarboxylate containing organic nitrate as ligand
  作者：Jian Zhao、Shaohua Gou、Gang Xu

  DOI：10.1016/j.ica.2013.09.034

  日期：2014.1

  Two novel platinum(II) complexes cis-[Pt(L')(NH3)X] (where L' = cyclopentylamine or cyclohexylamine, X = 3-(nitrooxy)cyclobutane-1,1-dicarboxylate) were synthesized and spectrally characterized in this study. The purity of complexes 1 and 2 were studied by HPLC-MS spectra, and the contents of complexes 1 and 2 were more than 98%. It was demonstrated that the newly synthesized compounds with dicarboxylate containing organic nitrate as ligand possessed DNA unwinding capability similar to cisplatin by the means of agarose gel electrophoresis. In addition, the antiproliferative study by WST-8 assay revealed that these platinum(II) complexes exhibited considerable cytotoxicity against tested cancer cell lines in vitro compared with positive agents (cisplatin, oxaliplatin and carboplatin), especially complex 1, showing higher in vitro antitumoractivity than oxaliplatin and carboplatin in SGC7901 and A549 cell lines. (C) 2013 Elsevier B.V. All rights reserved.