bis-1,1‘-(4-sulfobutyl)indotricarbocyanine-5,5‘-dicarboxylic acid sodium salt

• 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: bis-1,1‘-(4-sulfobutyl)indotricarbocyanine-5,5‘-dicarboxylic acid sodium salt
• 英文别名: monosodium bis(1,1-(4-sulfobutyl)indotricarbocyanine-5-carboxylic acid)；sodium bis-1,1'-(4-sulfobutyl)indoletricarbocyanine-5,5'-dicarboxylic acid；sodium;4-[5-carboxy-2-[7-[5-carboxy-3,3-dimethyl-1-(4-sulfonatobutyl)indol-1-ium-2-yl]hepta-2,4,6-trienylidene]-3,3-dimethylindol-1-yl]butane-1-sulfonate
• 化学式: C₃₇H₄₃N₂O₁₀S₂*Na
• 分子量: 762.878
• InChiKey: RKUODBYIZYLIDP-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.46
• 重原子数：
  52
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  212
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  雌二醇 、 bis-1,1‘-(4-sulfobutyl)indotricarbocyanine-5,5‘-dicarboxylic acid sodium salt 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以10%的产率得到
  参考文献：
  名称：

  Conjugate of estradiol and applications thereof

  摘要：

  本发明涉及17-β雌二醇与吲哚青绿染料类似物的共轭物，用于癌症检测。该发明还提供了共轭物的制备方法和癌细胞检测方法。

  公开号：

  US10054602B2
• 作为产物：
  描述：

  4-肼基苯甲酸 在 sodium acetate 、 乙酸酐 、 溶剂黄146 作用下， 以 邻二氯苯 为溶剂， 反应 13.75h， 生成 bis-1,1‘-(4-sulfobutyl)indotricarbocyanine-5,5‘-dicarboxylic acid sodium salt
  参考文献：
  名称：

  A polyamine-modified near-infrared fluorescent probe for selective staining of live cancer cells

  摘要：

  已开发出一种新型聚胺修饰的近红外荧光探针，可在非癌细胞存在的情况下选择性地标记活体癌细胞。

  DOI：

  10.1039/c5cc01637a

文献信息

• Accessing Structurally Diverse Near-Infrared Cyanine Dyes for Folate Receptor-Targeted Cancer Cell Staining
  作者：Sandra G. König、Roland Krämer

  DOI：10.1002/chem.201700026

  日期：2017.7.12

  for the development of small‐molecule‐based cancer imaging agents considering that the FR is highly overexpressed on the surface of many cancer cell types. FR‐targeted conjugates of near‐infrared (NIR) emissive cyanine dyes are in advanced clinical trials for fluorescence‐guided surgery and are valuable research tools for optical molecular imaging in animal models. Only a small number of promising conjugates

  叶酸受体（FR）靶向是发展基于小分子的癌症显像剂的最有前途的策略之一，考虑到FR在许多癌细胞类型的表面上高度过量表达。FR靶向的近红外（NIR）发射花菁染料的共轭物正在荧光引导手术的高级临床试验中，并且是在动物模型中进行光学分子成像的有价值的研究工具。迄今为止，仅评估了少量有希望的缀合物。为了确定进一步优化的目标，分析结构与性能的关系以识别调节目标结合物性能的关键因素是至关重要的。该贡献解决了需要方便地合成获得结构多样的NIR发射性花青染料以与叶酸共轭的需求。尤其是通过C-C偶联反应，包括Suzuki和（首次使用这些类型的染料）Sonogashira交叉偶联，将结构变化引入到容易获得的花菁前体中。诸如最大吸收度，亮度和光稳定性的光物理性质高度依赖于分子结构。将选定的修饰的花菁与叶酸缀合，用于癌细胞靶向。几种结合物显示出高荧光亮度和光稳定性以及对FR阳性癌细胞具有高亲和力的良好组合，并能够对
• Synthesis and fluorescent characteristics of imidazole–indocyanine green conjugates
  作者：Christopher Pavlik、Nrusingh C. Biswal、Faith Corbo Gaenzler、Martha D. Morton、Liisa T. Kuhn、Kevin P. Claffey、Quing Zhu、Michael B. Smith

  DOI：10.1016/j.dyepig.2010.08.008

  日期：2011.4

  We have successfully synthesized imidazole-dye conjugates by linking imidazole and nitroimidazoleacetic acids to an indocyanine green (ICG) carboxylic acid derivative using an ethanolamine linker These dye-conjugates show absorbance peaks at 754-756 nm and fluorescence peaks at 780 rim The dye-conjugates show a blue shift of 25 nm and 30 nm in the absorption and fluorescence spectra respectively when compared to that of standard cardiogreen There is no change in absorption and fluorescence spectral profiles between the ICG derivative and imidazole conjugates The extinction coefficients of new ICG derivative and imidazole conjugates are 1 8 times higher than that of standard ICG The relative quantum yields of the new compounds are 4 5-5 5 times higher than that of the Sigma-Aldrich s ICG The dyes are tested for hypoxia in-vitro with 4T1 luc cell lines and it is found that the cells treated with 2-nitroimidazole ICG show a contrast of fluorescence signal of 2 5-30 for the cells under hypoxic to that of cells under normoxic However pure ICG shows no significant difference between hypoxic and normoxic cells (C) 2010 Elsevier Ltd All rights reserved
• Hydrophilic Cyanine Dyes as Contrast Agents for Near-infrared Tumor Imaging: Synthesis, Photophysical Properties and Spectroscopic In vivo Characterization¶
  作者：Kai Licha、Björn Riefke、Vasilis Ntziachristos、Andreas Becker、Britton Chance、Wolfhard Semmler

  DOI：10.1562/0031-8655(2000)072<0392:hcdaca>2.0.co;2

  日期：——

  We have synthesized a group of glucamine and gluosamine-substituted cyanine dyes structurally related to indocyanine green (ICG) and have characterized these compounds with regard to their potential as contrast agents for biomedical optical imaging. The compounds reported herein exhibit increased hydrophilicity and less plasma protein binding (<50%), and are thus expected to have different pharmacokinetic properties compared with ICG. Furthermore, we measured enhanced fluorescence quantum yields (7-15%) in a physiological environment with respect to ICG, For the derivative with the highest hydrophilicity (5a) the efflux from tumor and normal tissue was monitored by intensity-modulated diffuse optical spectroscopy after intravenous injection into tumor-bearing rats. in comparison with ICG, 5a exhibited a considerably enhanced tissue-efflux half-life (73 min versus less than 10 min for ICG in tumor tissue), a hue-fold higher initial tissue absorption coefficient compared to ICG, and finally, it generated an elevated tumor-to-tissue concentration gradient up to 1 h after injection. In conclusion, compounds such as 5a are promising contrast agents for optical imaging, and could facilitate highly sensitive and specific detection of breast cancer or other malignancies by utilizing mechanisms similar to contrast-enhanced magnetic resonance imaging or computerized tomography.
• Synthesis of a 4-nitroimidazole indocyanine dye-conjugate and imaging of tumor hypoxia in BALB/c tumor-bearing female mice
  作者：Akram Abuteen、Feifei Zhou、Christopher Dietz、Innus Mohammad、Michael B. Smith、Quing Zhu

  DOI：10.1016/j.dyepig.2015.12.010

  日期：2016.3

  Extending our previous work with 2-nitroimidazole-indocyanine dye-conjugate 4, we prepared the 4-nitroimidazole-piperazine-indocyanine derivative (6). We also prepared imidazole derivative 5 as a control. We compared the in vivo hypoxia targeting performance of both 5 and 6 with the previously tested 4, and 6 showed a higher fluorescent intensity after 15 min post-injection, about 1.5-fold higher than 4 and 2.5-fold higher than 5. Cells treated with 6 under hypoxic conditions showed a higher fluorescence yield when compared to the cells kept under normoxic conditions. All findings were supported with fluorescence images of histological sections of tumor samples using a Li-COR scanner and an immunohistochemistry technique for tumor hypoxia. (C) 2015 Elsevier Ltd. All rights reserved.
• Polyamine-modified near-infrared cyanine dyes for targeting the nuclei and nucleoli of cells
  作者：Sandra G. König、Roland Krämer

  DOI：10.1016/j.dyepig.2017.05.041

  日期：2017.10