1H,1H,2H,2H-perfluorodecyl-3-(pyridin-3-yl)propanoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1H,1H,2H,2H-perfluorodecyl-3-(pyridin-3-yl)propanoate
• 化学式: C₁₈H₁₂F₁₇NO₂
• 分子量: 597.272
• InChiKey: RLDZRMWWXBJJBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.96
• 重原子数：
  38.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  39.19
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 1H,1H,2H,2H-perfluorodecyl-3-(pyridin-3-yl)propanoate 以 二氯甲烷 为溶剂， 生成 [Ru(η⁶-p-cymene)Cl2(NC5H4(CH2)2COO(CH2)2(CF2)7CF3)]
  参考文献：
  名称：

  用于肿瘤靶向的热敏性有机金属芳烃钌配合物†

  摘要：

  轻度热疗的应用可以增加抗癌药在肿瘤细胞中的细胞毒性。在本报告中，我们描述了具有轻度热疗选择性触发的具有氟链的低分子量基于钌的热活性药物。制备，表征和评价有机金属配合物对一组人类癌细胞系和非癌性永生化细胞的体外细胞毒性。对于具有最长氟链的化合物，这些化合物对癌细胞显示出相当高的化学热选择性（对于健康细胞而言，约为5μM，而对于健康细胞则为> 500μM）。

  DOI：

  10.1039/c3sc53185f
• 作为产物：
  描述：

  3-(3-吡啶基)丙酸 、 1H,1H,2H,2H-全氟-1-癸醇 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 1H,1H,2H,2H-perfluorodecyl-3-(pyridin-3-yl)propanoate
  参考文献：
  名称：

  用于肿瘤靶向的热敏性有机金属芳烃钌配合物†

  摘要：

  轻度热疗的应用可以增加抗癌药在肿瘤细胞中的细胞毒性。在本报告中，我们描述了具有轻度热疗选择性触发的具有氟链的低分子量基于钌的热活性药物。制备，表征和评价有机金属配合物对一组人类癌细胞系和非癌性永生化细胞的体外细胞毒性。对于具有最长氟链的化合物，这些化合物对癌细胞显示出相当高的化学热选择性（对于健康细胞而言，约为5μM，而对于健康细胞则为> 500μM）。

  DOI：

  10.1039/c3sc53185f

文献信息

• Anticancer Organometallic Osmium(II)-<i>p</i>-cymene Complexes
  作者：Emilia Păunescu、Patrycja Nowak-Sliwinska、Catherine M. Clavel、Rosario Scopelliti、Arjan W. Griffioen、Paul J. Dyson

  DOI：10.1002/cmdc.201500221

  日期：2015.9

  Osmium compounds are attracting increasing attention as potential anticancer drugs. In this context, a series of bifunctional organometallic osmium(II)‐p‐cymene complexes functionalized with alkyl or perfluoroalkyl groups were prepared and screened for their antiproliferative activity. Three compounds from the series display selectivity toward cancer cells, with moderate cytotoxicity observed against

  potential化合物作为潜在的抗癌药物正受到越来越多的关注。在这种情况下，一系列的双官能有机金属锇（II） - p制备了被烷基或全氟烷基官能化的苏木精复合物，并筛选了它们的抗增殖活性。该系列中的三种化合物对癌细胞具有选择性，对人卵巢癌（A2780）细胞具有中等细胞毒性，而对非癌性人胚肾（HEK-293）细胞和人内皮（ECRF24）细胞则没有细胞毒性。这三种癌细胞选择性化合物中的两种在很大程度上通过凋亡诱导细胞死亡，并且在鸡胚绒膜尿囊膜（CAM）模型中也发现其破坏血管生成。基于这些有希望的特性，这些化合物具有潜在的临床应用。
• Discovery of a Highly Tumor-Selective Organometallic Ruthenium(II)–Arene Complex
  作者：Catherine M. Clavel、Emilia Păunescu、Patrycja Nowak-Sliwinska、Arjan W. Griffioen、Rosario Scopelliti、Paul J. Dyson

  DOI：10.1021/jm5002748

  日期：2014.4.24

  A ruthenium(II)-arene complex with a perfluoroalkyl-ligand was found to display remarkable selectivity toward cancer cells. IC50 values on several cancer cell lines are in the range of 25-45 mu M, and no cytotoxic effect was observed on nontumorigenic (HEK-293) cells at concentrations up to 500 mu M (the maximum concentration tested). Consequently, this complex was used as the basis for the development of a number of related derivatives, which were screened in cancerous and noncancerous cell lines. The lead compound was then evaluated in vivo for antiangiogenic activity in the CAM model and in a xenografted ovarian carcinoma tumor (A2780) grown on the CAM. A 90% reduction in the tumor growth was observed.
• Modulating the Anticancer Activity of Ruthenium(II)–Arene Complexes
  作者：Catherine M. Clavel、Emilia Păunescu、Patrycja Nowak-Sliwinska、Arjan W. Griffioen、Rosario Scopelliti、Paul J. Dyson

  DOI：10.1021/jm501655t

  日期：2015.4.23

  Following the identification of [Ru(eta(6)-p-cymene)Cl-2(1H,1H,2H,2H-perfluorodecyl-3-(pyridin-3-yl)propanoate)], a ruthenium(II)arene complex with a perfluoroalkyl-modified ligand that displays remarkable in vitro cancer cell selectivity, a series of structurally related compounds were designed. In the new derivatives, the p-cymene ring and/or the chloride ligands are substituted by other ligands to modulate the steric bulk or aquation kinetics. The new compounds were evaluated in both in vitro (cytotoxicity and migration assays) and in vivo (chicken chorioallantoic membrane) models and were found to exhibit potent antivascular effects.
• Thermoresponsive organometallic arene ruthenium complexes for tumour targeting
  作者：Catherine M. Clavel、Emilia Păunescu、Patrycja Nowak-Sliwinska、Paul J. Dyson

  DOI：10.1039/c3sc53185f

  日期：——

  Application of mild hyperthermia can increase the cytotoxicity of anticancer drugs in tumour cells. In this report, we describe low molecular weight thermoactive ruthenium-based drugs with fluorous chains that are selectively triggered by mild hyperthermia. The organometallic complexes were prepared, characterized, and evaluated for their in vitro cytotoxicity against a panel of human cancer cell lines

  轻度热疗的应用可以增加抗癌药在肿瘤细胞中的细胞毒性。在本报告中，我们描述了具有轻度热疗选择性触发的具有氟链的低分子量基于钌的热活性药物。制备，表征和评价有机金属配合物对一组人类癌细胞系和非癌性永生化细胞的体外细胞毒性。对于具有最长氟链的化合物，这些化合物对癌细胞显示出相当高的化学热选择性（对于健康细胞而言，约为5μM，而对于健康细胞则为> 500μM）。