4,4-difluoro-5,7-dimethyl-4-bora-3a,4a-diaza-s-indacene-3-propionic acid succinimidyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4,4-difluoro-5,7-dimethyl-4-bora-3a,4a-diaza-s-indacene-3-propionic acid succinimidyl ester
• 英文别名: BODIPY FL, SE；BODIPY FL SE；(2,5-dioxopyrrolidin-1-yl) 3-[(5Z)-5-[(1-difluoroboranyl-3,5-dimethylpyrrol-2-yl)methylidene]pyrrol-2-yl]propanoate
• 化学式: C₁₈H₁₈BF₂N₃O₄
• 分子量: 389.166
• InChiKey: NTTLXQSRKKYMSD-UVTDQMKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  81
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4,4-difluoro-5,7-dimethyl-4-bora-3a,4a-diaza-s-indacene-3-propionic acid succinimidyl ester 在 甲醇 、 copper(l) iodide 、 四(三苯基膦)钯 、 碳酸氢钠 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 (2S,3S,4S,5R,6S)-6-[4-[(2S,3R)-1-[4-[3-[3-[(5Z)-5-[(1-difluoroboranyl-3,5-dimethylpyrrol-2-yl)methylidene]pyrrol-2-yl]propanoylamino]prop-1-ynyl]phenyl]-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl]phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of fluorescent biochemical tools related to the 2-azetidinone class of cholesterol absorption inhibitors

  摘要：

  Fluorescent analogues of the cholesterol absorption inhibitor (CAI), Sch 58235, have been designed and synthesized as single enantiomers. Biological testing reveals that they are potent CAIs and are suitable tools for the investigation of the azetidinone CAI mechanism of action (MOA). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00752-1

文献信息

• Cellular Uptake of Aminoglycosides, Guanidinoglycosides, and Poly-arginine
  作者：Nathan W. Luedtke、Peter Carmichael、Yitzhak Tor

  DOI：10.1021/ja0360135

  日期：2003.10.1

  Aminoglycosides (including neomycin B and tobramycin) exhibit poor uptake by eukaryotic cell lines. When the amines of these natural products are converted into guanidine groups, their cellular uptake is dramatically enhanced. We have synthesized BODIPY-containing aminoglycosides and guanidinoglycosides to evaluate their cellular uptake properties. Fluorescence activated cell sorting (FACS) and fluorescence microscopy are used to compare the membrane translocation and the cellular localization of these compounds. Upon guanidinylation, the cellular uptake efficiencies of tobramycin and neomycin B are enhanced by 10-fold and 20-fold, respectively. Guanidino-neomycin B exhibits a highly efficient uptake, superior to a fluorescent poly-arginine peptide. Interestingly, the cellular uptake of this common transduction peptide is inhibited by guanidine-neomycin B, suggesting a similar uptake mechanism for both the arginine-rich peptides and the guanidinoglycosides.
• Lanthanide-Binding Tags as Luminescent Probes for Studying Protein Interactions
  作者：Bianca R. Sculimbrene、Barbara Imperiali

  DOI：10.1021/ja061188a

  日期：2006.6.1

  Herein, we report a method for studying protein-peptide interactions which exploits the luminescence properties of Tb(III). Lanthanide-binding tags (LBTs) are short peptide sequences comprising 15-20 naturally occurring amino acids that bind Tb( III) with high affinity. These genetically encodable luminescent tags are smaller in size than the Aequorea victoria fluorescent proteins (AFPs) and benefit from the long-lived luminescence lifetime of lanthanides. In this study, luminescence resonance energy transfer (LRET) was used to monitor the interaction between SH2 domains and different phosphopeptides. For the study, the SH2 domains of Src and Crk kinase were each coexpressed with an LBT, and phosphorylated and nonphosphorylated peptides were chemically synthesized with organic fluorophores. The LRET between the protein-bound Tb(III) and the peptide-based organic fluorophore was shown to be specific for the recognition of the SH2 domain and the peptide binding partner. This method can detect differences in binding affinity and can be used to measure the dissociation constant for the protein-peptide interaction. In addition, decay experiments can be used to calculate the distance between a site in the bound peptide and the protein using Forster theory. In all of these experiments, the millisecond luminescence lifetime of Tb(III) can be exploited using time-resolved detection to eliminate background fluorescence from organic fluorophores.
• Synthesis of fluorescent biochemical tools related to the 2-azetidinone class of cholesterol absorption inhibitors
  作者：Duane A Burnett、Mary Ann Caplen、Margaret E Browne、Hongrong Zhau、Scott W Altmann、Harry R Davis、John W Clader

  DOI：10.1016/s0960-894x(01)00752-1

  日期：2002.2

  Fluorescent analogues of the cholesterol absorption inhibitor (CAI), Sch 58235, have been designed and synthesized as single enantiomers. Biological testing reveals that they are potent CAIs and are suitable tools for the investigation of the azetidinone CAI mechanism of action (MOA). (C) 2002 Elsevier Science Ltd. All rights reserved.