bisjulolidyl disulfide | 1608130-85-3

• 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 disulfide
• 英文别名: thiojulolidine；6-(1-Azatricyclo[7.3.1.05,13]trideca-5,7,9(13)-trien-6-yldisulfanyl)-1-azatricyclo[7.3.1.05,13]trideca-5,7,9(13)-triene
• CAS: 1608130-85-3
• 化学式: C₂₄H₂₈N₂S₂
• 分子量: 408.632
• InChiKey: LGVTWFDAMQRJBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.88
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  6.48
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  bisjulolidyl disulfide 在 四甲基乙二胺 、 仲丁基锂 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 环己烷 、 乙腈 为溶剂， 反应 18.0h， 生成 3-Thia-9,23-diazaheptacyclo[17.7.1.15,9.02,17.04,15.023,27.013,28]octacosa-1(27),2(17),4(15),5(28),13,18-hexaen-16-one
  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 disulfide
  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

• 噁嗪类化合物及其用途
  申请人：大连理工大学

  公开号：CN109678888B

  公开（公告）日：2021-06-18

  噁嗪类化合物及其用途，所述的噁嗪类化合物具有通式F的结构。上述本发明的具有通式F的噁嗪类化合物对线粒体具有特异性响应，能够快速进入细胞，与线粒体迅速结合并发出较强信号的荧光。无论在固定细胞还是在活细胞实验中，均对线粒体体现较好的专一性识别标记。再者，本发明的化合物是一类具有近红外吸收发射的同时具备光敏及声敏特性的光/声动力活性有机分子。该类化合物最大吸收和发射波长均大于690nm，三线态转化率高，在光照或超声条件下，可较高效率产生活性氧物种，对于癌细胞和癌组织具有较好的杀伤作用，在对肿瘤达到光/声动力治疗的同时几乎不对正常组织增加毒副作用。
• 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。
• OXAZINE COMPOUND AND APPLICATION THEREOF
  申请人：Dalian University of Technology

  公开号：EP3792265A1

  公开（公告）日：2021-03-17

  Disclosed are an oxazine compound and an application thereof. The oxazine compound has a structure of a general formula F. The oxazine compound described in the disclosure is a photo/acoustic dynamic active organic molecule with near-infrared absorption-emission function as well as photosensitivity and acoustic sensitivity. Maximum absorption and emission wavelengths of the compound are both greater than 660 nanometers, and a triplet-state conversion rate of the compound is high; and under illumination or ultrasound, the compound can produce reactive oxygen species with high efficiency, which has a good killing effect on cancer cells and cancer tissues, and almost has no toxic or side effects on normal tissues while achieving photo/acoustic dynamic therapy on tumors.

  本发明公开了一种噁嗪化合物及其应用。本公开所述的噁嗪化合物是一种光/声动态活性有机分子，具有近红外吸收-发射功能以及光敏性和声敏性。该化合物的最大吸收波长和发射波长均大于660纳米，三态转换率高，在光照或超声作用下，能高效产生活性氧，对癌细胞和癌组织有很好的杀伤作用，对正常组织几乎无毒副作用，同时实现对肿瘤的光/声动态治疗。