N-hydroxysulfosuccinimide ester of ICG derivative | 787529-38-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-hydroxysulfosuccinimide ester of ICG derivative
• 英文别名: ICG-sulfo-OSu
• CAS: 787529-38-8
• 化学式: C₄₉H₅₃N₃O₁₀S₂
• 分子量: 908.106
• InChiKey: IGFQGAQGMSLVQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.08
• 重原子数：
  64.0
• 可旋转键数：
  17.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  181.5
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (3S,7S)-26-amino-5,13,20-trioxo-4,6,12,21-tetraazahexacosane-1,3,7,22-tetracarboxylic acid 、 N-hydroxysulfosuccinimide ester of ICG derivative 在 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以71%的产率得到4-[(2E)-2-[(2E,4E,6E)-7-[3-[6-[[5-carboxy-5-[[8-[[(5S)-5-carboxy-5-[[(1S)-1,3-dicarboxypropyl]carbamoylamino]pentyl]amino]-8-oxooctanoyl]amino]pentyl]amino]-6-oxohexyl]-1,1-dimethylbenzo[e]indol-3-ium-2-yl]hepta-2,4,6-trienylidene]-1,1-dimethylbenzo[e]indol-3-yl]butane-1-sulfonate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Low Molecular Weight Fluorescent Imaging Agents for the Prostate-Specific Membrane Antigen

  摘要：

  Targeted near-infrared (MR) optical imaging can be used in vivo to detect specific tissues, including malignant cells. A series of NIR fluorescent ligands targeting the prostate-specific membrane antigen (PSMA) was synthesized and each compound was tested for its ability to image PSMA+ tissues in experimental models of prostate cancer. The agents were prepared by conjugating commercially available active esters of NIR dyes, including IRDye800CW, IRDye800RS, Cy5.5, Cy7, or a derivative of indocyanine green (ICG) to the terminal amine group of (S)-2-(3-((S)-5-amino-1-carboxypentyl)ureido)pentanedioic acid 1, (14S,18S)-1-amino-8,16-dioxo-3,6-dioxa-9,15,17-triazaicosane-14,18,20-tricarboxylic acid 2 and (3S,7S)-26-amino-5,13,20-trioxo-4,6,12,21-tetraaza-hexacosane-1,3,7,22-tetracarboxylic acid 3. The K-i values for the dye-inhibitor conjugates ranged from 1 to 700 pM. All compounds proved capable of imaging PSMA+ tumors selectively to varying degrees depending on the choice of fluorophore and linker. The highest tumor uptake was observed with IRDye800CW employing a poly(ethylene glycol) or lysine suberate linker, as in 800CW-2 and 800CW-3, while the highest tumor to nontarget tissue ratios were obtained for Cy7 with these same linkers, as in Cy7-2 and Cy7-3. Compounds 2 and 3 provide useful scaffolds for targeting of PSMA+ tissues in vivo and should be useful for preparing NIR dye conjugates designed specifically for clinical intraoperative optical imaging devices.

  DOI：

  10.1021/bc3003919