| 124620-12-8

• 分子结构分类: 有机化合物
• CAS: 124620-12-8
• 化学式: C₂₉H₄₃SeTe*F₆P
• 分子量: 743.185
• InChiKey: RZLCKUBFCDEPDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.52
• 重原子数：
  38.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  在 双氧水 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以75%的产率得到
  参考文献：
  名称：

  Detty, Michael R.; Merkel, Paul B., Journal of the American Chemical Society, 1990, vol. 112, # 10, p. 3845 - 3855

  摘要：

  DOI：
• 作为产物：
  描述：

  在 sodium hydrogensulfite 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 0.08h， 以96%的产率得到
  参考文献：
  名称：

  Chalcogenapyrylium dyes as photochemotherapeutic agents. 2. Tumor uptake, mitochondrial targeting, and singlet-oxygen-induced inhibition of cytochrome c oxidase

  摘要：

  Cationic selena- and tellurapyrylium dyes 1d-g and 1i were found to inhibit cytochrome c oxidase upon irradiation of isolated mitochondrial suspensions treated with 10 microM solutions of dye. The amount of inhibition by these dyes was found to be related to oxygen concentration and inversely related to the concentration of added imidazole, a singlet-oxygen trap, suggesting that singlet oxygen is responsible, at least in part, for the inhibition of the enzyme. Dyes 1d-g and 1i, containing either selenium or tellurium, produce singlet oxygen with a quantum efficiency, phi (1O2), between 0.005 and 0.09 in methanol. Dyes 1a-c, containing the lighter chalcogens oxygen and sulfur, have values of phi (1O2) that are less than 0.0008 in methanol and do not inhibit cytochrome c oxidase in irradiated mitochondrial suspensions. Dyes 1c and 1d have nearly identical spectral and redox properties. Only the selenapyrylium dye 1d inhibits the enzyme, suggesting that neither ground-state nor excited-state electron transfer is important in inhibition of the enzyme. Electron micrographs of human U251 glioma cells, treated in vitro with 1i and light, showed pronounced morphology changes in the mitochondrial membranes relative to electron micrographs of untreated cells. Epifluorescence microscopy of the treated cells showed granular yellow-green fluorescence presumably from photooxidized dye in the mitochondria.

  DOI：

  10.1021/jm00166a005

文献信息

• Shining Light on the Solution- and Excited-State Dynamics of Chalcogenopyrylium Polymethine Dyes
  作者：Lauren E. Rosch、Matthew R. Crawley、Ryan M. O’Donnell、Thomas N. Rohrabaugh、Trenton R. Ensley、Thomas A. Sobiech、Timothy R. Cook

  DOI：10.1021/acs.organomet.2c00263

  日期：2022.8.22

  singlet oxygen yields as high as 12% for certain dyes, we observe no evidence for 1O2 from direct phosphorescence measurements. We now fill in many of these gaps through steady-state and pulsed-laser kinetic experiments on a family of 14 dyes, including six novel dyes, selected to vary physical and electronic structure. These structural changes encompass the selenium and tellurium heteroatoms, phenyl,

  尽管 40 年来人们对硫属吡喃多甲炔染料感兴趣，但我们对其光物理特性的理解仍存在重大差距。这些差距阻碍了将这些染料应用为光动力疗法和/或生物医学传感剂的努力，其中完全了解它们的激发态动力学和化学是很重要的。例如，尽管先前的报道确定某些染料的单线态氧产量高达 12%，但我们没有观察到1 O 2的证据来自直接磷光测量。我们现在通过对 14 种染料家族（包括六种新型染料）进行稳态和脉冲激光动力学实验来填补这些空白，这些染料被选为改变物理和电子结构。这些结构变化包括硒和碲杂原子、苯基、噻吩、叔-丁基取代基和次甲基接头长度。通过飞秒瞬态吸收光谱获得激发态寿命。寿命都低于 300 ps，这表明它们的激发态会快速弛豫。值得注意的是，我们没有观察到任何三重态瞬态过程的证据。磷光仅在 77 K 的样品中观察到。变温 NMR 实验表明，吡喃环围绕次甲基骨架的旋转是这些染料动力学的关键决定因素，从而将它们的光物