9-(5-(piperidylcarbamothioyl)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-(piperidylcarbamothioyl)thiophen-2-yl)selenorhodamine chloride
• 英文别名: Dimethyl-[1,4,4-trimethyl-6-[5-(piperidine-1-carbothioyl)thiophen-2-yl]-2,3-dihydroselenochromeno[3,2-g]quinolin-9-ylidene]azanium;chloride；dimethyl-[1,4,4-trimethyl-6-[5-(piperidine-1-carbothioyl)thiophen-2-yl]-2,3-dihydroselenochromeno[3,2-g]quinolin-9-ylidene]azanium;chloride
• 化学式: C₃₁H₃₆N₃S₂Se*Cl
• 分子量: 629.192
• InChiKey: BNNKWSKTBZHAEN-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  38
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  69.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  piperidin-1-yl(thiophen-2-yl)methanethione 在 正丁基锂 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 16.42h， 生成 9-(5-(piperidylcarbamothioyl)thiophen-2-yl)selenorhodamine chloride
  参考文献：
  名称：

  [EN] METHODS AND COMPOUNDS FOR PHOTOTHERAPY WITH CHALCOGENORHODAMINE PHOTOSENSITIZERS
  [FR] PROCÉDÉS ET COMPOSÉS DE PHOTOTHÉRAPIE FAISANT APPEL À DES PHOTOSENSIBILISANTS DE TYPE CHALCOGÉNORHODAMINE

  摘要：

  一种从血细胞组合物中选择性消耗致病性T淋巴细胞的方法是通过(a)在体外将细胞组合物与有效量的活性化合物结合，然后(b)在体外用光辐照细胞，时间和强度足以选择性地杀死该细胞组合物中的致病性T淋巴细胞。还描述了作为这种活性化合物有用的硫属罗丹明光敏剂。

  公开号：

  WO2015187940A1

文献信息

• Selenorhodamine Photosensitizers for Photodynamic Therapy of P-Glycoprotein-Expressing Cancer Cells
  作者：Jacqueline E. Hill、Michelle K. Linder、Kellie S. Davies、Geri A. Sawada、Janet Morgan、Tymish Y. Ohulchanskyy、Michael R. Detty

  DOI：10.1021/jm501259v

  日期：2014.10.23

  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.