4,4-difluoro-2,6-di-iodo-8-(4-(methoxycarbonyl)phenyl)-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,4-difluoro-2,6-di-iodo-8-(4-(methoxycarbonyl)phenyl)-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene
• 英文别名: Methyl 4-(2,2-difluoro-5,11-diiodo-4,6,10,12-tetramethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaen-8-yl)benzoate；methyl 4-(2,2-difluoro-5,11-diiodo-4,6,10,12-tetramethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaen-8-yl)benzoate
• 化学式: C₂₁H₁₉BF₂I₂N₂O₂
• 分子量: 634.011
• InChiKey: MAECHYIBYYFITK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.69
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  34.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(1-methyl-o-carborane)methylphenylboronic acid 、 4,4-difluoro-2,6-di-iodo-8-(4-(methoxycarbonyl)phenyl)-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以89%的产率得到
  参考文献：
  名称：

  Synthesis and properties of a series of carboranyl-BODIPYs

  摘要：

  A series of four BODIPYs containing one or two ortho- or para-carborane clusters were synthesized using palladium(0)-catalyzed Suzuki cross-coupling or nucleophilic substitution reactions, at the 2,6- or the 8-positions of halogenated boron dipyrromethenes (BODIPYs). The spectroscopic, structural (including one X-ray) and in vitro BBB permeability of the BODIPYs using hCMEC/D3 brain endothelial cells were investigated. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2015.05.009
• 作为产物：
  描述：

  8-(4-(甲氧羰基)苯基)-1,3,5,7-四甲基BODIPY 在 碘 、 碘酸 作用下， 以 乙醇 、 水 为溶剂， 以88%的产率得到4,4-difluoro-2,6-di-iodo-8-(4-(methoxycarbonyl)phenyl)-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  具有动态感应能力的选择性溶剂化变色传感器的自由基氧化反应

  摘要：

  摘要设计并表征了一种新型的BODIPY（boradiazaindacene）染料，该染料被称为BODIPY-DT，其中含有三联吡啶单元。发现该染料是测试有机溶剂中对DMF的选择性和可视溶剂变色传感器。传感过程以发射颜色显示时间可控的动态信号输出，包括红色，紫色，黄色甚至白色发射颜色。提出了选择性自由基氧化反应发生在识别过程中。

  DOI：

  10.1016/j.cclet.2019.12.025

文献信息

• The tumor phototherapeutic application of nanoparticles constructed by the relationship between PTT/PDT efficiency and 2,6- and 3,5-substituted BODIPY derivatives
  作者：Juanjuan Yin、Xu Jiang、Guomin Sui、Yingying Du、Enyun Xing、Ruijie Shi、Chengzhi Gu、Xiaona Wen、Yaqing Feng、Zhongqiang Shan、Shuxian Meng

  DOI：10.1039/d1tb01155c

  日期：——

  water solubility and biological stability, but also could act as superior agents for photothermal and photodynamic synergistic therapy of tumors. Finally, we obtained BODIPY NPs that exhibited excellent photothermal and photodynamic effects at the same time under single irradiation with an 808 nm laser (photothermal conversion efficiency: 42.76%, A/A0: ∼0.05). In conclusion, this work provides a direction

  BODIPY 染料最近已用于肿瘤的光热和光动力疗法。然而，复杂的多材料系统、多个激发波长以及 BODIPY 结构与其 PTT/PDT 效率之间的关系不明确仍然是主要问题。在我们的研究中，设计并成功合成了九种新型 BODIPY 近红外染料，然后详细研究了 BODIPY 结构与其 PTT/PDT 效率之间的关系。结果表明，在 BODIPY 核的 3,5 位上进行共轭结构的修饰比在 2,6 位上用卤素原子修饰对光热和光动力效率的影响更好。密度泛函理论（DFT）计算表明，这主要是由于共轭链的延伸和光致电子转移（PET）效应。通过用两亲性 DSPE-PEG 封装 BDPX-M2000 -RGD和卵磷脂，得到的NPs不仅具有良好的水溶性和生物稳定性，而且可以作为光热和光动力协同治疗肿瘤的优良药剂。最后，我们获得了在808 nm激光单次照射下同时表现出优异光热和光动力效应的BODIPY NPs（光热转换效率：42
• 新型光治疗BODIPY脂质体纳米粒子
  申请人：天津大学

  公开号：CN111789947A

  公开（公告）日：2020-10-20

  本发明属于光治疗领域，具体涉及一种新型光治疗BODIPY脂质体纳米粒子；包含BODIPY分子，其中BODIPY分子具有下述结构； 其中，R’为CH2＝ R；X为H、Cl、Br、或者I； 。本发明提供了一种新型的具有光热或者光动作用的纳米粒子，经过测试显示，本发明设计的纳米粒子具有良好的光热或者光动治疗作用。
• Spectroscopic, computational modeling and cytotoxicity of a series of meso-phenyl and meso-thienyl-BODIPYs
  作者：Jaime H. Gibbs、Larry T. Robins、Zehua Zhou、Petia Bobadova-Parvanova、Michael Cottam、Gregory T. McCandless、Frank R. Fronczek、M. Graça H. Vicente

  DOI：10.1016/j.bmc.2013.07.017

  日期：2013.9

  A series of twenty-two BODIPY compounds were synthesized, containing various meso-phenyl and meso-thienyl groups, and their spectroscopic and structural properties were investigated using both experimental and computational methods. Further functionalization of the BODIPY framework via iodination at the 2,6-pyrrolic positions was explored in order to determine the effect of these heavy atoms on the photophysical and cytotoxicity of the meso-aryl-BODIPYs. BODIPYs bearing meso-thienyl substituents showed the largest red-shifted absorptions and emissions and reduced fluorescence quantum yields. The phototoxicity of the BODIPYs in human carcinoma HEp2 cells depends on both the presence of iodines and the nature of the meso-aryl groups. Six of the eleven 2,6-diiodo-BODIPYs investigated showed at least a sevenfold enhancement in phototoxicity (IC50 = 3.5-28 mu M at 1.5 J/cm(2)) compared with the non-iodinated BODIPYs, while the others showed no cytotoxicity, while their singlet oxygen quantum yields ranged from 0.02 to 0.76. Among the series investigated, BODIPYs 2a and 4a bearing electron-donating meso-dimethoxyphenyl substituents showed the highest phototoxicity and dark/phototoxicity ratio, and are therefore the most promising for application in PDT. (C) 2013 Elsevier Ltd. All rights reserved.