9-(5-(diethylcarbamoyl)thiophen-2-yl)selenorhodamine chloride

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 9-(5-(diethylcarbamoyl)thiophen-2-yl)selenorhodamine chloride
• 英文别名: [6-[5-(Diethylcarbamoyl)thiophen-2-yl]-1,4,4-trimethyl-2,3-dihydroselenochromeno[3,2-g]quinolin-9-ylidene]-dimethylazanium;chloride；[6-[5-(diethylcarbamoyl)thiophen-2-yl]-1,4,4-trimethyl-2,3-dihydroselenochromeno[3,2-g]quinolin-9-ylidene]-dimethylazanium;chloride
• 化学式: C₃₀H₃₆N₃OSSe*Cl
• 分子量: 601.114
• InChiKey: BQDUHMKJWOZTAD-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  37
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  54.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N,N-diethylthiophene-2-carbothioamide 在 正丁基锂 、 N,N-二异丙基乙胺 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 24.53h， 生成 9-(5-(diethylcarbamoyl)thiophen-2-yl)selenorhodamine chloride
  参考文献：
  名称：

  Selenorhodamine Photosensitizers for Photodynamic Therapy of P-Glycoprotein-Expressing Cancer Cells

  摘要：

  We examined a series of selenorhodamines with amide and thioamide functionality at the 5-position of a 9-(2-thienyl) substituent on the selenorhodamine core for their potential as photosensitizers for photodynamic therapy (PDT) in P-glycoprotein (P-gp) expressing cells. These compounds were examined for their photophysical properties (absorption, fluorescence, and ability to generate singlet oxygen), for their uptake into Colo-26 cells in the absence or presence of verapamil, for their dark and phototoxicity toward Colo-26 cells, for their rates of transport in monolayers of multidrug-resistant, P-gp-overexpressing MDCKII-MDR1 cells, and for their colocalization with mitochondrial specific agents in Colo-26 cells. Thioamide derivatives 16b and 18b were more effective photosensitizers than amide derivatives 15b and 17b. Selenorhodamine thioamides 16b and 18b were useful in a combination therapy to treat Colo-26 cells in vitro: a synergistic therapeutic effect was observed when Colo-26 cells were exposed to PDT and treatment with the cancer drug doxorubicin.

  DOI：

  10.1021/jm501259v