3-[2-[2-[3-[2-[3,3-dimethyl-1-(3-sulfonatopropyl)indol-1-ium-2-yl]ethenyl]-4-hydroxyphenyl]ethenyl]-3,3-dimethylindol-1-ium-1-yl]propane-1-sulfonate | 1400743-62-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-[2-[2-[3-[2-[3,3-dimethyl-1-(3-sulfonatopropyl)indol-1-ium-2-yl]ethenyl]-4-hydroxyphenyl]ethenyl]-3,3-dimethylindol-1-ium-1-yl]propane-1-sulfonate
• CAS: 1400743-62-5
• 化学式: C₃₆H₄₀N₂O₇S₂
• 分子量: 676.855
• InChiKey: ZNKBZMTYRQJLQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  47
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  157
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-[2-[2-[3-[2-[3,3-dimethyl-1-(3-sulfonatopropyl)indol-1-ium-2-yl]ethenyl]-4-hydroxyphenyl]ethenyl]-3,3-dimethylindol-1-ium-1-yl]propane-1-sulfonate 在 sodium acetate 、 sodium hydroxide 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 1.0h， 生成 2-(4-hydroxystyryl)-3,3-dimethyl-1-(3-sulfopropyl)-3H-indolium
  参考文献：
  名称：

  Water-soluble 4-hydroxystyryl and 4-hydroxyphenyl-butadienyls dyes with switchable fluorescence

  摘要：

  Fluorescent 4-hydroxystyryl dyes are useful for many biomedical and pharmaceutical assays, and other analyte sensing applications. However, these dyes often suffer from limited applicability in analytical and bioanalytical utilization due to insufficient water-solubility, high acid-Ionization constants (pK(a)) and short-wavelength absorption and emission. To solve these issues, a series of new, water-soluble 4-hydroxystyryl and longer-wavelength 4-hydroxyphenyl-butadienyl dyes were synthesized and the spectral and protolytic properties were studied. These new dyes contain electron-withdrawing substituents ortho to the triggering 4-hydroxyl group. The introduction of the cyano and formyl groups was found to decrease the pK(a) and extend the pH-sensing region of these fluorophores. In respect of the molecular structure, these dyes exhibit either a "turn-on" activatable fluorescence, or a dual-fluorescence that enables ratiometric measurements. The 4-hydroxyphenyl-butadienyl dye was evaluated for fluorescence monitoring of drug delivery. These new dyes are promising fluorophores for acidity measurements and other sensing applications.

  DOI：

  10.1016/j.dyepig.2019.107801
• 作为产物：
  描述：

  2,3,3-三甲基-3H-吲哚 在 potassium carbonate 作用下， 以 甲醇 、 乙酸酐 、 甲苯 为溶剂， 反应 2.0h， 生成 3-[2-[2-[3-[2-[3,3-dimethyl-1-(3-sulfonatopropyl)indol-1-ium-2-yl]ethenyl]-4-hydroxyphenyl]ethenyl]-3,3-dimethylindol-1-ium-1-yl]propane-1-sulfonate
  参考文献：
  名称：

  瞬时荧光探针，用于H 2 S的特异性检测

  摘要：

  开发了用于检测H 2 S的新型基于花青的荧光探针。所开发的探针在生理条件下是稳定的。水溶性荧光探针2对H 2 S表现出超快的特异性响应，在不使用有机溶剂或表面活性剂的辅助下，其NIR荧光的开启限为115倍，检出限为11 nM。细胞成像实验表明，探头2是细胞渗透性的，并能检测ħ 2在溶酶体灵敏S上。此外，我们的探针能够检测ħ 2 s本质产生ħ 2通过从半胱氨酸/ GSH的酶/非酶促生物合成途径S上。此外，我们应用了探针2检测ħ 2 S IN活小鼠并证实H的快速代谢2 S.因此，探针2示出了很有希望作为对H A记者2 S.

  DOI：

  10.1016/j.saa.2019.01.085

文献信息

• Water solubility is essential for fluorescent probes to image hypochlorous acid in live cells
  作者：Panfei Xing、Zhe Zhang、Yiming Niu、Yaning Qi、Lei Dong、Chunming Wang

  DOI：10.1039/c8cc04631j

  日期：——

  We synthesised four probes and compared their HClO-detecting ability in different solvents. The data showed that only hydrophilic probes could sensitively and accurately detect HClO in live cells. Meanwhile, the addition of organic solvents, as is commonly practised, weakens the oxidising capacity of HClO and thus generates inaccurate outcomes.

  我们合成了四种探针，并比较了它们在不同溶剂中对HClO的检测能力。数据表明，只有亲水性探针才能灵敏，准确地检测活细胞中的HClO。同时，通常采用的添加有机溶剂会削弱HClO的氧化能力，从而产生不准确的结果。
• A Unique Paradigm for a Turn-ON Near-Infrared Cyanine-Based Probe: Noninvasive Intravital Optical Imaging of Hydrogen Peroxide
  作者：Naama Karton-Lifshin、Ehud Segal、Liora Omer、Moshe Portnoy、Ronit Satchi-Fainaro、Doron Shabat

  DOI：10.1021/ja203145v

  日期：2011.7.20

  The development of highly sensitive fluorescent probes in combination with innovative optical techniques is a promising strategy for intravital noninvasive quantitative imaging. Cyanine fluorochromes belong to a superfamily of dyes that have attracted substantial attention in probe design for molecular imaging. We have developed a novel paradigm to introduce a Turn-ON mechanism in cyanine molecules, based on a distinctive change in their pi-electrons system. Our new cyanine fluorochrome is synthesized through a simple two-step procedure and has an unprecedented high fluorescence quantum yield of 16% and large extinction coefficient of 52 000 M(-1) cm(-1). The synthetic strategy allows one to prepare probes for various analytes by introducing a specific triggering group on the probe molecule. The probe was equipped with a corresponding trigger and demonstrated efficient imaging of endogenous hydrogen peroxide, produced in an acute lipopolysaccharide-induced inflammation model in mice. This approach provides, for the first time, an available methodology to prepare modular molecular Turn-ON probes that can release an active cyanine fluorophore upon reaction with specific analyte.
• Switchable phenolo-cyanine reporters containing reactive alkylcarboxylic groups for fluorescence-based targeted drug delivery monitoring
  作者：Maksym Bokan、Kateryna Bondar、Vered Marks、Gary Gellerman、Leonid D. Patsenker

  DOI：10.1016/j.dyepig.2018.05.046

  日期：2018.12
• Water-soluble 4-hydroxystyryl and 4-hydroxyphenyl-butadienyls dyes with switchable fluorescence
  作者：Kateryna Bondar、Maksym Bokan、Gary Gellerman、Leonid D. Patsenker

  DOI：10.1016/j.dyepig.2019.107801

  日期：2020.1

  Fluorescent 4-hydroxystyryl dyes are useful for many biomedical and pharmaceutical assays, and other analyte sensing applications. However, these dyes often suffer from limited applicability in analytical and bioanalytical utilization due to insufficient water-solubility, high acid-Ionization constants (pK(a)) and short-wavelength absorption and emission. To solve these issues, a series of new, water-soluble 4-hydroxystyryl and longer-wavelength 4-hydroxyphenyl-butadienyl dyes were synthesized and the spectral and protolytic properties were studied. These new dyes contain electron-withdrawing substituents ortho to the triggering 4-hydroxyl group. The introduction of the cyano and formyl groups was found to decrease the pK(a) and extend the pH-sensing region of these fluorophores. In respect of the molecular structure, these dyes exhibit either a "turn-on" activatable fluorescence, or a dual-fluorescence that enables ratiometric measurements. The 4-hydroxyphenyl-butadienyl dye was evaluated for fluorescence monitoring of drug delivery. These new dyes are promising fluorophores for acidity measurements and other sensing applications.
• Instantaneous fluorescent probe for the specific detection of H2S
  作者：Xianfeng Lin、Xiuhong Lu、Junliang Zhou、Hang Ren、Xiaochun Dong、Weili Zhao、Zhongjian Chen

  DOI：10.1016/j.saa.2019.01.085

  日期：2019.4

  cyanine-based fluorescent probes for the detection of H2S were developed. The probes developed are stable under physiological conditions. The water soluble fluorescent probe 2 displayed ultrafast and specific response to H2S displaying NIR fluorescence of 115-fold turn-on with the detection limit of 11 nM without assistance of organic solvent or surfactant. Cell imaging experiments indicated that probe 2 was

  开发了用于检测H 2 S的新型基于花青的荧光探针。所开发的探针在生理条件下是稳定的。水溶性荧光探针2对H 2 S表现出超快的特异性响应，在不使用有机溶剂或表面活性剂的辅助下，其NIR荧光的开启限为115倍，检出限为11 nM。细胞成像实验表明，探头2是细胞渗透性的，并能检测ħ 2在溶酶体灵敏S上。此外，我们的探针能够检测ħ 2 s本质产生ħ 2通过从半胱氨酸/ GSH的酶/非酶促生物合成途径S上。此外，我们应用了探针2检测ħ 2 S IN活小鼠并证实H的快速代谢2 S.因此，探针2示出了很有希望作为对H A记者2 S.