[Pt(3-[(butylamino)(pyridin-2-yl)methyl]-2-hydroxy-1,4-naphthoquinone)Cl2] | 1258440-39-9

• 英文名称: [Pt(3-[(butylamino)(pyridin-2-yl)methyl]-2-hydroxy-1,4-naphthoquinone)Cl2]
• CAS: 1258440-39-9
• 化学式: C₂₀H₂₀Cl₂N₂O₃Pt
• 分子量: 602.376
• InChiKey: LBUFEIMQLBLELR-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

• 作为反应物：
  描述：

  [Pt(3-[(butylamino)(pyridin-2-yl)methyl]-2-hydroxy-1,4-naphthoquinone)Cl2] 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Exploring the DNA binding/cleavage, cellular accumulation and topoisomerase inhibition of 2-hydroxy-3-(aminomethyl)-1,4-naphthoquinone Mannich bases and their platinum(II) complexes

  摘要：

  Several chlorido and amino Pt2+ complexes of 2-hydroxy-3-(aminomethyl)-1,4-naphthoquinone Mannich bases HL exhibiting moderate to high cytotoxicity against cancer cell lines were studied in order to investigate their modes of DNA binding, in vitro DNA strand breaks, mechanism of topoisomerase (Topo I) inhibition and cellular accumulation. DNA model base studies have shown that complex la [Pt(HL1)Cl-2] was capable of binding covalently to 9-ethylguanine (9-EtG) and 5'-GMP. H-1 NMR and mass spectrometry studies have shown that both chlorides were substituted by 9-EtG ligands, whereas 5'-GMP was able to replace only one chlorido ligand, due to steric hindrance. The chlorido Pt2+ complexes [Pt(HL)Cl-2] highly accumulate in prostate (PC-3) and melanoma (MDA-MB-435) cell lines, being able to induce DNA strand breaks in vitro and inhibit Topo I by a catalytic mode. On the other hand, the free 2-hydroxy-3-(aminomethyl)-1,4-naphthoquinones HL and the amino Pt2+ complexes [Pt(L-)(NH3)(2)]NO3 neither cause DNA strand breakage nor exhibit strong DNA interaction, nevertheless the latter were also found to be catalytic inhibitors of Topo I at 100 mu M. Thus, coordination of the Mannich bases HL to the "PtCl2" fragment substantially affects the chemical and biophysical properties of the pro-ligands, leading to an improvement of their DNA binding properties and generating compounds that cleave DNA and catalytically inhibit Topo I. Finally, the high cytotoxicity exhibited by the free (uncomplexed) 2-hydroxy-3-(aminomethyl)-1,4-naphthoquinones might be associated with their decomposition in solution, which is not observed for the Pt2+ complexes. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2012.10.007
• 作为产物：
  描述：

  dichlorobis(dimethyl sulfoxide)platinum(II) 、 2-hydroxy-3-[(n-butylamino)(pyridin-2-yl)methyl]-1,4-naphthoquinone 以 N,N-二甲基甲酰胺 为溶剂， 以60%的产率得到[Pt(3-[(butylamino)(pyridin-2-yl)methyl]-2-hydroxy-1,4-naphthoquinone)Cl2]
  参考文献：
  名称：

  3-（氨基甲基）萘醌曼尼希碱的 新型铂（ii）配合物：合成，晶体结构和细胞毒性活性†

  摘要：

  第一个例子 铂金（II） 的复合体 3-（氨基甲基）萘醌已经合成了曼尼希碱，并描述了其晶体结构。已获得中性和带电复合物，对其进行了充分表征，还研究了它们的细胞毒性活性。3-[（R 1-氨基）（吡啶-2-基）甲基] -2-羟基-1,4-萘醌（R 1 =正丁基，HL1 ;n，HL2 ; 糠基，HL3 ;正庚基，HL4和正癸基，HL5）协调到铂金（II）通过两个氮原子。中性复合物顺式-[Pt（HL）Cl 2 ] 1a-5a与顺铂与双齿配体HL和两个氯原子占据顺式位置。在电荷的复合物的顺式- [铂（大号- ）（NH 3）2 ] NO 3 1B-5B的去质子化的配体的形式大号-也坐标经由氮原子，和周围的其它两个位置铂金（II）离子用NH 3配体完成。已测试了所有化合物对六种不同癌细胞系的细胞毒活性：MDA-MB-435（黑色素瘤），HL-60（早幼粒细胞白血病），HCT-8 （冒号）， SF-295

  DOI：

  10.1039/c0dt00572j