bisjulolidyl ditelluride | 1608131-25-4

• 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: bisjulolidyl ditelluride
• 英文别名: 6-(1-Azatricyclo[7.3.1.05,13]trideca-5,7,9(13)-trien-6-ylditellanyl)-1-azatricyclo[7.3.1.05,13]trideca-5,7,9(13)-triene
• CAS: 1608131-25-4
• 化学式: C₂₄H₂₈N₂Te₂
• 分子量: 599.7
• InChiKey: WFTBAFVMRSNJTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Azatricyclo[7.3.1.05,13]trideca-5,7,9(13)-trien-7-yl(piperidin-1-yl)methanone 、 bisjulolidyl ditelluride 在 四甲基乙二胺 、 仲丁基锂 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 18.0h， 以37.2%的产率得到
  参考文献：
  名称：

  Synthesis and Properties of Heavy Chalcogen Analogues of the Texas Reds and Related Rhodamines

  摘要：

  Analogues of Texas red incorporating the heavy chalcogens S, Se, and Te atoms in the xanthylium core were prepared from the addition of aryl Grignard reagents to appropriate chalcogenoxanthone precursors. The xanthones were prepared via directed metalation of amide precursors, addition of dichalcogenide electrophiles, and electrophilic cyclization of the resulting chalcogenides with phosphorus oxychloride and triethylamine. The Texas red analogues incorporate two fused julolidine rings containing the rhodamine nitrogen atoms. Analogues containing two "half-julolidine" groups (a trimethyltetrahydroquinoline) and one julolidine and one "half-julolidine" were also prepared. The photophysics of the Texas red analogues were examined. The S-analogues were highly fluorescent, the Se-analogues generated single oxygen (O-1(2)) efficiently upon irradiation, and the Te-analogues were easily oxidized to rhodamines with the telluroxide oxidation state. The tellurorhodamine telluroxides absorb at wavelengths >= 690 nm and emit with fluorescence maxima >720 nm. A mesityl-substituted tellurorhodamine derivative localized in the mitochondria of Colo-26 cells (a murine colon carcinoma cell line) and was oxidized in vitro to the fluorescent telluroxide.

  DOI：

  10.1021/om500346j
• 作为产物：
  描述：

  在 碘 、 magnesium 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 54.0h， 生成 bisjulolidyl ditelluride
  参考文献：
  名称：

  Synthesis and Properties of Heavy Chalcogen Analogues of the Texas Reds and Related Rhodamines

  摘要：

  Analogues of Texas red incorporating the heavy chalcogens S, Se, and Te atoms in the xanthylium core were prepared from the addition of aryl Grignard reagents to appropriate chalcogenoxanthone precursors. The xanthones were prepared via directed metalation of amide precursors, addition of dichalcogenide electrophiles, and electrophilic cyclization of the resulting chalcogenides with phosphorus oxychloride and triethylamine. The Texas red analogues incorporate two fused julolidine rings containing the rhodamine nitrogen atoms. Analogues containing two "half-julolidine" groups (a trimethyltetrahydroquinoline) and one julolidine and one "half-julolidine" were also prepared. The photophysics of the Texas red analogues were examined. The S-analogues were highly fluorescent, the Se-analogues generated single oxygen (O-1(2)) efficiently upon irradiation, and the Te-analogues were easily oxidized to rhodamines with the telluroxide oxidation state. The tellurorhodamine telluroxides absorb at wavelengths >= 690 nm and emit with fluorescence maxima >720 nm. A mesityl-substituted tellurorhodamine derivative localized in the mitochondria of Colo-26 cells (a murine colon carcinoma cell line) and was oxidized in vitro to the fluorescent telluroxide.

  DOI：

  10.1021/om500346j

文献信息

• The concept and examples of type-III photosensitizers for cancer photodynamic therapy
  作者：Qichao Yao、Jiangli Fan、Saran Long、Xueze Zhao、Haidong Li、Jianjun Du、Kun Shao、Xiaojun Peng

  DOI：10.1016/j.chempr.2021.10.006

  日期：2022.1

  In conventional photodynamic therapy (PDT), reactive oxygen species are produced to kill cancer cells based on type-I and type-II mechanisms, and the sensitization of photosensitizers is oxygen dependent. However, solid tumors reside in a hypoxic milieu, which hampers the therapeutic efficacy of photosensitive drugs against tumors. Novel photosensitizers NBEX (X = S, Se, Te) were designed to bind to

  在传统的光动力疗法 (PDT) 中，基于 I 型和 II 型机制产生活性氧来杀死癌细胞，并且光敏剂的敏化是氧依赖性的。然而，实体瘤存在于缺氧环境中，这阻碍了光敏药物对肿瘤的治疗效果。新型光敏剂NBEX ( X = S、Se、Te ) 旨在与 RNA 结合而不受其他物种的干扰，并直接转移激发态能量以破坏癌细胞中的 RNA。这种杀死癌细胞的过程完全独立于氧气（III型机制）。值得注意的是，NBEX ( X= S , Se , Te ) 可以自组装成纳米颗粒并在体内数十分钟内积聚在肿瘤区域。NBESe在杀死实体瘤和抑制肿瘤转移方面表现出优异的性能。同时，PDT可以诱导对肿瘤的免疫反应。这种新型光敏剂可能是临床实践中癌症治疗的候选者。