[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[9-(2,4-dimethoxyphenyl)-6-oxoxanthen-3-yl]oxyoxan-2-yl]methyl acetate | 942424-80-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[9-(2,4-dimethoxyphenyl)-6-oxoxanthen-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 942424-80-8
• 化学式: C₃₅H₃₄O₁₄
• 分子量: 678.647
• InChiKey: DFIFVVPLNKTTMF-CYNLXDPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  49
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  168
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[9-(2,4-dimethoxyphenyl)-6-oxoxanthen-3-yl]oxyoxan-2-yl]methyl acetate 在 碘 、 碘酸 作用下， 以 乙醇 、 水 为溶剂， 反应 0.58h， 以72%的产率得到
  参考文献：
  名称：

  Development of enzyme-activated photosensitizer based on intramolecular electron transfer

  摘要：

  Photosensitizers produce cytotoxic reactive oxygen species (ROS) upon light illumination, but it is difficult to ablate cells of a specific type (e. g., tumor cells) in the presence of other cell populations, because of the limited precision with which light illumination can be directed to small areas. Here, we report a strategy to achieve cell type-specific ablation by using an enzyme-activated off/on switch for oxidative stress induction. In the unactivated photosensitizer, induction of oxidative stress is quenched by intramolecular electron transfer. However, the target cells express an enzyme that hydrolyzes a substrate moiety of the photosensitizer and the activated photosensitizer induces oxidative stress. As proof of concept, we designed and synthesized a xanthene-based photosensitizer, TGI-beta Gal, whose oxidative stress induction ability is switched on following hydrolysis reaction with beta-galactosidase, a widely used gene marker. TGI-beta Gal could selectively ablate lacZ-positive cells, whereas it showed no toxicity to lacZ-negative cells, upon light illumination. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.091
• 作为产物：
  描述：

  9-(2,4-dimethoxyphenyl)-6-hydroxy-3H-xanthen-3-one 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃糖溴化物 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以88%的产率得到[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[9-(2,4-dimethoxyphenyl)-6-oxoxanthen-3-yl]oxyoxan-2-yl]methyl acetate
  参考文献：
  名称：

  Development of enzyme-activated photosensitizer based on intramolecular electron transfer

  摘要：

  Photosensitizers produce cytotoxic reactive oxygen species (ROS) upon light illumination, but it is difficult to ablate cells of a specific type (e. g., tumor cells) in the presence of other cell populations, because of the limited precision with which light illumination can be directed to small areas. Here, we report a strategy to achieve cell type-specific ablation by using an enzyme-activated off/on switch for oxidative stress induction. In the unactivated photosensitizer, induction of oxidative stress is quenched by intramolecular electron transfer. However, the target cells express an enzyme that hydrolyzes a substrate moiety of the photosensitizer and the activated photosensitizer induces oxidative stress. As proof of concept, we designed and synthesized a xanthene-based photosensitizer, TGI-beta Gal, whose oxidative stress induction ability is switched on following hydrolysis reaction with beta-galactosidase, a widely used gene marker. TGI-beta Gal could selectively ablate lacZ-positive cells, whereas it showed no toxicity to lacZ-negative cells, upon light illumination. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.091