cis-PtCl2(3-pyridinecarboxylic acid)2 | 41637-07-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: cis-PtCl2(3-pyridinecarboxylic acid)2
• 英文别名: cis-[PtCl2(3-pycaH)2]；Dichloroplatinum;pyridine-3-carboxylic acid
• CAS: 41637-07-4
• 化学式: C₁₂H₁₀Cl₂N₂O₄Pt
• 分子量: 512.208
• InChiKey: FGCOPWUBNBYDPO-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  100
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  烟酸 、 potassium tetrachloroplatinate(II) 以 甲醇 、 水 为溶剂， 以69%的产率得到cis-PtCl2(3-pyridinecarboxylic acid)2
  参考文献：
  名称：

  Novel platinum pyridinehydroxamic acid complexes: Synthesis, characterisation, X-ray crystallographic study and nitric oxide related properties

  摘要：

  Herein, we describe the synthesis and characterisation of a novel class of Pt-II and Pt-IV pyridinehydroxamic acid (pyhaH) complexes of general formula cis-[(PtCl2)-Cl-II(x-pyhaH)(2)] and cis-[(PtCl4)-Cl-IV(x-pyhaH)(2)], respectively (where x = 3 or 4) in which the pyridinehydroxamic acid is coordinated to the platinum ion via the pyridine nitrogen only leaving the hydroxamic acid free to potentially release cytotoxic nitric oxide (NO). The crystal structure of the Pt-IV derivative, cis-[PtCl4(4-pyhaH)(2)]center dot 2CH(3)OH is reported. To establish the biological effect of the uncoordinated hydroxamic acid moiety in the Pt-II compounds synthesised, the corresponding pyridinecarboxylic acid (pycaH) complexes of general formula cis-[(PtCl2)-Cl-II(x-pycaH)(2)] (where x = 3 or 4) and the Nil pyridine (py) complex, cis-[(PtCl2)-Cl-II(py)(2)] were synthesised and served as reference standards. The NO-releasing properties of each of the Pt-II compounds, the pyhaH and the pycaH ligands were studied. The Pt-II pyridinehydroxamic acid derivatives were found to induce potent in vitro effects attributable to either NO-release from the hydroxamic acid moiety and/or stimulation of inducible nitric oxide synthase of endothelial cells. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2007.03.011

文献信息

• The synthesis, structure-toxicity relationship of cisplatin derivatives for the mechanism research of cisplatin-induced nephrotoxicity
  作者：Jing Hu、Tian-Ming Wu、Hong-Ze Li、Ze-Ping Zuo、Ying-Lan Zhao、Li Yang

  DOI：10.1016/j.bmcl.2017.04.077

  日期：2017.8

  Cisplatin is a widely used antineoplastic drug, while its nephrotoxicity limits the clinical application. Although several mechanisms contributing to nephrotoxicity have been reported, the direct protein targets are unclear. Herein we reported the synthesis of 29 cisplatin derivatives and the structure-toxicity relationship (STR) of these compounds with MTT assay in human renal proximal tubule cells (HK-2) and pig kidney epithelial cells (LLC-PK1). To the best of our knowledge, this study represented the first report regarding the structure-toxicity relationship (STR) of cisplatin derivatives. The potency of biotin-pyridine conjugated derivative 3 met the requirement for target identification, and the preliminary chemical proteomics results suggested that it is a promising tool for further target identification of cisplatin-induced nephrotoxicity. (C) 2017 Published by Elsevier Ltd.
• Novel platinum pyridinehydroxamic acid complexes: Synthesis, characterisation, X-ray crystallographic study and nitric oxide related properties
  作者：Darren Griffith、Alberta Bergamo、Sara Pin、Marta Vadori、Helge Müller-Bunz、Gianni Sava、Celine J. Marmion

  DOI：10.1016/j.poly.2007.03.011

  日期：2007.10

  Herein, we describe the synthesis and characterisation of a novel class of Pt-II and Pt-IV pyridinehydroxamic acid (pyhaH) complexes of general formula cis-[(PtCl2)-Cl-II(x-pyhaH)(2)] and cis-[(PtCl4)-Cl-IV(x-pyhaH)(2)], respectively (where x = 3 or 4) in which the pyridinehydroxamic acid is coordinated to the platinum ion via the pyridine nitrogen only leaving the hydroxamic acid free to potentially release cytotoxic nitric oxide (NO). The crystal structure of the Pt-IV derivative, cis-[PtCl4(4-pyhaH)(2)]center dot 2CH(3)OH is reported. To establish the biological effect of the uncoordinated hydroxamic acid moiety in the Pt-II compounds synthesised, the corresponding pyridinecarboxylic acid (pycaH) complexes of general formula cis-[(PtCl2)-Cl-II(x-pycaH)(2)] (where x = 3 or 4) and the Nil pyridine (py) complex, cis-[(PtCl2)-Cl-II(py)(2)] were synthesised and served as reference standards. The NO-releasing properties of each of the Pt-II compounds, the pyhaH and the pycaH ligands were studied. The Pt-II pyridinehydroxamic acid derivatives were found to induce potent in vitro effects attributable to either NO-release from the hydroxamic acid moiety and/or stimulation of inducible nitric oxide synthase of endothelial cells. (c) 2007 Elsevier Ltd. All rights reserved.