8-{4-[1-(2-tert-butoxy-2-oxoethyl)-1H-1,2,3-triazol-4-yl]phenyl}-4,4-di-fluoro-2,6-diiodo-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene | 1430657-59-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 8-{4-[1-(2-tert-butoxy-2-oxoethyl)-1H-1,2,3-triazol-4-yl]phenyl}-4,4-di-fluoro-2,6-diiodo-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene
• 英文别名: Tert-butyl 2-[4-[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)phenyl]triazol-1-yl]acetate；tert-butyl 2-[4-[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)phenyl]triazol-1-yl]acetate
• CAS: 1430657-59-2
• 化学式: C₂₇H₂₈BF₂I₂N₅O₂
• 分子量: 757.168
• InChiKey: NTGLBXZUOKSEOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  39
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  65
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  叠氮基乙酸叔丁酯 、 在 tetrakis(actonitrile)copper(I) hexafluorophosphate 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以51 mg的产率得到8-{4-[1-(2-tert-butoxy-2-oxoethyl)-1H-1,2,3-triazol-4-yl]phenyl}-4,4-di-fluoro-2,6-diiodo-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  Synthesis and in vitro evaluation of a PDT active BODIPY–NLS conjugate

  摘要：

  Two new photosensitizers based on the BODIPY scaffold have been synthesized, of which one bears an NLS peptide, which is linked to the BODIPY's core using the copper catalysed azide-alkyne click reaction. The phototoxicities of these BODIPY based photosensitizers have been determined, as well as their dark toxicities. Although the conjugation of a single NLS peptide to the BODIPY did not lead to any observable nuclear localization, the photosensitizer did exhibit a superior photoxicity. Cellular co-localization experiments revealed a localization of both dyes in the lysosomes, as well as a partial localization within the ER (for the peptide-bearing BODIPY). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.128

文献信息

• Synthesis and in vitro evaluation of a PDT active BODIPY–NLS conjugate
  作者：Peter Verwilst、Charlotte C. David、Volker Leen、Johan Hofkens、Peter A.M. de Witte、Wim M. De Borggraeve

  DOI：10.1016/j.bmcl.2013.03.128

  日期：2013.6

  Two new photosensitizers based on the BODIPY scaffold have been synthesized, of which one bears an NLS peptide, which is linked to the BODIPY's core using the copper catalysed azide-alkyne click reaction. The phototoxicities of these BODIPY based photosensitizers have been determined, as well as their dark toxicities. Although the conjugation of a single NLS peptide to the BODIPY did not lead to any observable nuclear localization, the photosensitizer did exhibit a superior photoxicity. Cellular co-localization experiments revealed a localization of both dyes in the lysosomes, as well as a partial localization within the ER (for the peptide-bearing BODIPY). (C) 2013 Elsevier Ltd. All rights reserved.