sodium;4-[(2E)-5-carboxy-2-[(2E,4E,6E)-7-[3,3-dimethyl-1-(4-sulfonatobutyl)indol-1-ium-2-yl]hepta-2,4,6-trienylidene]-3,3-dimethylindol-1-yl]butane-1-sulfonate

• 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: sodium;4-[(2E)-5-carboxy-2-[(2E,4E,6E)-7-[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: C₃₆H₄₃N₂O₈S₂*Na
• 分子量: 718.868
• InChiKey: CDICLKLWEFOZCF-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  49
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  175
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  雌二醇 、 sodium;4-[(2E)-5-carboxy-2-[(2E,4E,6E)-7-[3,3-dimethyl-1-(4-sulfonatobutyl)indol-1-ium-2-yl]hepta-2,4,6-trienylidene]-3,3-dimethylindol-1-yl]butane-1-sulfonate 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  乳腺癌的早期检测：用于分子光学成像的新型靶标特异性 NIR 荧光雌激素偶联物的合成和表征

  摘要：

  雌激素诱导的现有突变细胞增殖被广泛认为是乳腺癌发展的主要风险决定因素。因此，雌激素受体 [ER] 状态的确定至关重要。我们已经完成了一种新型 NIR 荧光染料偶联物的合成和表征，旨在测量体内 ER+ve 状态。缀合物通过 17-β 雌二醇和花青染料之间的酯形成合成，即：双-1, 1-(4-磺丁基) indotricarbocyanine-5-羧酸钠盐。发现用较大的葡萄糖铵离子替代酯中的钠离子可增强亲水性并降低对细胞系的毒性作用。染料的激发和发射峰分别记录为 750 和 788 nm；由于这些波长下的组织衰减和自发荧光最小，因此非常适合非侵入性光学成像。染料(NIRDC1) 的血浆蛋白结合显着下降，因此与 ICG 相比，显着改善了药代动力学特征，例如染料清除。此外，相对于 ICG，染料显示出增强的荧光量子产率、摩尔消光系数和荧光线性。这种染料可潜在地用作分子光学成像中的目标特异性外源造影剂，用于乳腺癌的早期检测。

  DOI：

  10.1007/s10895-010-0795-x
• 作为产物：
  描述：

  1-(4-磺基丁基)-2,3,3-三甲基吲哚鎓内盐 在 sodium acetate 、 溶剂黄146 作用下， 以 乙酸酐 为溶剂， 反应 1.0h， 生成 sodium;4-[(2E)-5-carboxy-2-[(2E,4E,6E)-7-[3,3-dimethyl-1-(4-sulfonatobutyl)indol-1-ium-2-yl]hepta-2,4,6-trienylidene]-3,3-dimethylindol-1-yl]butane-1-sulfonate
  参考文献：
  名称：

  纤维素膜上可裂解的肽染料偶联物的高度平行纳米合成

  摘要：

  用预先形成的Fmoc-氨基酸3-溴丙基酯处理巯基官能化的纤维素膜，产生通过稳定的硫醚和可裂解的酯键连接的膜结合氨基酸。这种合成策略允许高度平行地制备可从固体支持物中溶解的肽。我们将这种方法应用于新型肽-花青染料偶联物的合成，这些偶联物可能可用作靶向肿瘤特异性受体的荧光造影剂。

  DOI：

  10.1016/s0040-4039(00)00019-8

文献信息

• Macromolecular Contrast Agents for Optical Imaging of Tumors: Comparison of Indotricarbocyanine-labeled Human Serum Albumin and Transferrin¶
  作者：Andreas Becker、Björn Riefke、Bernd Ebert、Uwe Sukowski、Herbert Rinneberg、Wolfhard Semmler、Kai Licha

  DOI：10.1562/0031-8655(2000)072<0234:mcafoi>2.0.co;2

  日期：——

  Macromolecules accumulate in solid tumors and can thus be used as carriers for the delivery of attached contrast agents to tumors. We report the synthesis and use of serum protein-dye conjugates consisting of transferrin (Tf) or human serum albumin (HSA) and an indotricarbocyanine (ITCC) derivative as contrast agents for the optical imaging of tumors. The compounds were characterized with respect to their photophysical properties and tested in vitro for their ability to bind to tumor cells and in vivo for their potential to delineate experimental tumors. In contrast to HAS-ITTC, Tf-ITCC showed receptor-mediated uptake by HT29 human colon cancer cells in vitro. After intravenous injection into HT29 tumor-bearing nude mice both compounds induced increased fluorescence contrast of tumors in vivo. After 24 h the contrast between tumor and normal tissue was significantly higher for Tf-ITCC than for HAS-ITCC. Dye-induced fluorescence was found to be predominantly located in perinecrotic areas of the tumor. Furthermore, Tf-ITCC produced fluorescence of viable tumor cells, whereas HAS-ITCC fluorescence was recorded along connective tissue. We conclude that ITCC-labeled Tf and HSA can serve as macromolecular contrast agents for the optical imaging of tumors, with Tf-ITCC showing higher efficiency.
• 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.
• 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
• Highly parallel nano-synthesis of cleavable peptide-dye conjugates on cellulose membranes
  作者：Kai Licha、Sarah Bhargava、Christiane Rheinländer、Andreas Becker、Jens Schneider-Mergener、Rudolf Volkmer-Engert

  DOI：10.1016/s0040-4039(00)00019-8

  日期：2000.3

  mercapto-functionalized cellulose membranes with preformed Fmoc-amino acid 3-bromopropyl esters yielded membrane-bound amino acids connected via a stable thioether and a cleavable ester bond. This synthesis strategy allows the highly parallel preparation of peptides that can be solubilized from the solid support. We apply this approach to the synthesis of novel peptide–cyanine dye conjugates which are

  用预先形成的Fmoc-氨基酸3-溴丙基酯处理巯基官能化的纤维素膜，产生通过稳定的硫醚和可裂解的酯键连接的膜结合氨基酸。这种合成策略允许高度平行地制备可从固体支持物中溶解的肽。我们将这种方法应用于新型肽-花青染料偶联物的合成，这些偶联物可能可用作靶向肿瘤特异性受体的荧光造影剂。
• Early Detection of Breast Cancer: Synthesis and Characterization of Novel Target Specific NIR-Fluorescent Estrogen Conjugate for Molecular Optical Imaging
  作者：Iven Jose、Kodand Dinakar Deodhar、Uday B. Desai、Shubhadeep Bhattacharjee

  DOI：10.1007/s10895-010-0795-x

  日期：2011.5

  importance. We have carried out the synthesis and characterization of a novel NIR fluorescent dye conjugate aimed at measuring ER+ve status in-vivo. The conjugate was synthesized by ester formation between 17-β estradiol and a cyanine dye namely: bis-1, 1-(4-sulfobutyl) indotricarbocyanine-5-carboxylic acid, sodium salt. The replacement of the sodium ion in the ester by a larger glucosammonium ion was found

  雌激素诱导的现有突变细胞增殖被广泛认为是乳腺癌发展的主要风险决定因素。因此，雌激素受体 [ER] 状态的确定至关重要。我们已经完成了一种新型 NIR 荧光染料偶联物的合成和表征，旨在测量体内 ER+ve 状态。缀合物通过 17-β 雌二醇和花青染料之间的酯形成合成，即：双-1, 1-(4-磺丁基) indotricarbocyanine-5-羧酸钠盐。发现用较大的葡萄糖铵离子替代酯中的钠离子可增强亲水性并降低对细胞系的毒性作用。染料的激发和发射峰分别记录为 750 和 788 nm；由于这些波长下的组织衰减和自发荧光最小，因此非常适合非侵入性光学成像。染料(NIRDC1) 的血浆蛋白结合显着下降，因此与 ICG 相比，显着改善了药代动力学特征，例如染料清除。此外，相对于 ICG，染料显示出增强的荧光量子产率、摩尔消光系数和荧光线性。这种染料可潜在地用作分子光学成像中的目标特异性外源造影剂，用于乳腺癌的早期检测。