rhodamine 6G tetraphenyl borate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: rhodamine 6G tetraphenyl borate
• 英文别名: [9-(2-Ethoxycarbonylphenyl)-6-(ethylamino)-2,7-dimethylxanthen-3-ylidene]-ethylazanium;tetraphenylboranuide；[9-(2-ethoxycarbonylphenyl)-6-(ethylamino)-2,7-dimethylxanthen-3-ylidene]-ethylazanium;tetraphenylboranuide
• 化学式: C₂₄H₂₀B*C₂₈H₃₀N₂O₃*H
• 分子量: 762.8
• InChiKey: IJTGQOJUQOVCBP-UHFFFAOYSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  58
• 可旋转键数：
  11
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  61.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  四苯硼钠 、 rhodamine 6G 以 二氯甲烷 、 水 为溶剂， 反应 24.0h， 以96.4%的产率得到rhodamine 6G tetraphenyl borate
  参考文献：
  名称：

  Tunable Cytotoxicity of Rhodamine 6G via Anion Variations

  摘要：

  Chemotherapeutic agents with low toxicity to normal tissues are a major goal in cancer research. In this regard, the therapeutic activities of cationic dyes, such as rhodamine 6G, toward cancer cells have been studied for decades with observed toxicities toward normal and cancer cells. Herein, we report rhodamine 6G-based organic salts with varying counteranions that are stable under physiological conditions, display excellent fluorescence photostability, and more importantly have tunable chemotherapeutic properties. Our in vitro studies indicate that the hydrophobic compounds of this series allow production of nanoparticles which are nontoxic to normal cells and toxic to cancer cells. Furthermore, the anions, in combination with cations such as sodium, were observed to be nontoxic to both normal and cancer cells. To the best of our knowledge, this is the first demonstration that both the cation and anion play an extremely important and cooperative role in the antitumor properties of these compounds.

  DOI：

  10.1021/ja407164w

文献信息

• Tunable Cytotoxicity of Rhodamine 6G via Anion Variations
  作者：Paul K. S. Magut、Susmita Das、Vivian E. Fernand、Jack Losso、Karen McDonough、Brittni M. Naylor、Sita Aggarwal、Isiah M. Warner

  DOI：10.1021/ja407164w

  日期：2013.10.23

  Chemotherapeutic agents with low toxicity to normal tissues are a major goal in cancer research. In this regard, the therapeutic activities of cationic dyes, such as rhodamine 6G, toward cancer cells have been studied for decades with observed toxicities toward normal and cancer cells. Herein, we report rhodamine 6G-based organic salts with varying counteranions that are stable under physiological conditions, display excellent fluorescence photostability, and more importantly have tunable chemotherapeutic properties. Our in vitro studies indicate that the hydrophobic compounds of this series allow production of nanoparticles which are nontoxic to normal cells and toxic to cancer cells. Furthermore, the anions, in combination with cations such as sodium, were observed to be nontoxic to both normal and cancer cells. To the best of our knowledge, this is the first demonstration that both the cation and anion play an extremely important and cooperative role in the antitumor properties of these compounds.