2′,7′-dichlorofluorescein dipivalate | 1045836-55-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2′,7′-dichlorofluorescein dipivalate
• 英文别名: [2',7'-Dichloro-6'-(2,2-dimethylpropanoyloxy)-3-oxospiro[2-benzofuran-1,9'-xanthene]-3'-yl] 2,2-dimethylpropanoate
• CAS: 1045836-55-2
• 化学式: C₃₀H₂₆Cl₂O₇
• 分子量: 569.438
• InChiKey: IYVNLUYCLORUHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  39
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-氯间苯二酚 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 甲烷磺酸 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 2′,7′-dichlorofluorescein dipivalate
  参考文献：
  名称：

  Electronic and Steric Optimization of Fluorogenic Probes for Biomolecular Imaging

  摘要：

  Fluorogenic probes are invaluable tools for spatiotemporal investigations within live cells. In common fluorogenic probes, the intrinsic fluorescence of a small-molecule fluorophore is masked by esterification until entry into a cell, where endogenous esterases catalyze the hydrolysis of the masking groups, generating fluorescence: The-susceptibility of masking groups to spontaneous hydrolysis is a major limitation of these probes. Previous attempts to address this problem have incorporated auto-immolativo linkers at the cost of atom economy and synthetic adversity. Here, we report on a linker-free strategy that employs adventitious electronic and steric interactions in easy-to-synthesize probes. We find that X center dot center dot center dot C=O n ->pi* interactions and acyl group size are optimized in 2 ',7 '-dichlorofluorescein diisobutyrate. This probe is relatively stable to spontaneous hydrolysis but is a highly reactive substrate for esterases both in vitro and in cellulo, yielding a bright, photostable fluorophore with utility in biomolecular imaging.

  DOI：

  10.1021/acs.joc.7b00285

文献信息

• Chemodosimetric Hg²⁺-Selective Signaling by Mercuration of Dichlorofluorescein Derivatives
  作者：Myung Gil Choi、De Hun Ryu、Hye Lim Jeon、Sunyoung Cha、Janggeun Cho、Hyun Hye Joo、Kwan Soo Hong、Chulhyun Lee、Sangdoo Ahn、Suk-Kyu Chang

  DOI：10.1021/ol8013446

  日期：2008.9.1

  The chemodosimetric behavior of dichlorofluorescein derivatives toward Hg(2+) ions was investigated. Simple chemodosimetric systems showed selective and efficient signaling behaviors toward micromolar concentrations of Hg(2+) ions over other common interfering metal ions in an aqueous environment. The signaling mechanism is selective mercuration of the 4',5'-position of the xanthene moiety, which results

  研究了二氯荧光素衍生物对Hg（2+）离子的化学计量行为。简单的化学计量学系统显示了相对于水溶液环境中其他常见干扰金属离子的Hg（2+）离子微摩尔浓度的选择性和有效的信号传导行为。信号传导机制是x吨部分4'，5'-位置的选择性汞转移，这导致Hg（2+）离子在水性环境中的有效发色和发荧光信号。
• USRE40572E1
  申请人：——

  公开号：USRE40572E1

  公开（公告）日：2008-11-11
• Electronic and Steric Optimization of Fluorogenic Probes for Biomolecular Imaging
  作者：Wen Chyan、Henry R. Kilgore、Brian Gold、Ronald T. Raines

  DOI：10.1021/acs.joc.7b00285

  日期：2017.4.21

  Fluorogenic probes are invaluable tools for spatiotemporal investigations within live cells. In common fluorogenic probes, the intrinsic fluorescence of a small-molecule fluorophore is masked by esterification until entry into a cell, where endogenous esterases catalyze the hydrolysis of the masking groups, generating fluorescence: The-susceptibility of masking groups to spontaneous hydrolysis is a major limitation of these probes. Previous attempts to address this problem have incorporated auto-immolativo linkers at the cost of atom economy and synthetic adversity. Here, we report on a linker-free strategy that employs adventitious electronic and steric interactions in easy-to-synthesize probes. We find that X center dot center dot center dot C=O n ->pi* interactions and acyl group size are optimized in 2 ',7 '-dichlorofluorescein diisobutyrate. This probe is relatively stable to spontaneous hydrolysis but is a highly reactive substrate for esterases both in vitro and in cellulo, yielding a bright, photostable fluorophore with utility in biomolecular imaging.