NIR664 succinimidyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: NIR664 succinimidyl ester
• 英文别名: 4-[2-[(1E,3E,5E)-5-[5-[2-(2,5-dioxopyrrolidin-1-yl)oxy-2-oxoethyl]-1-ethyl-3,3-dimethylindol-2-ylidene]penta-1,3-dienyl]-1,1-dimethylbenzo[e]indol-3-ium-3-yl]butane-1-sulfonate
• 化学式: C₄₁H₄₅N₃O₇S
• 分子量: 723.89
• InChiKey: OPIIZKCLUIZXHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  52
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  136
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  NIR664 succinimidyl ester 在 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 2.08h， 以68%的产率得到4-[2-[5-[5-[2-[4-[[2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetyl]amino]butylamino]-2-oxoethyl]-1-ethyl-3,3-dimethylindol-2-ylidene]penta-1,3-dienyl]-1,1-dimethylbenzo[e]indol-3-ium-3-yl]butane-1-sulfonate
  参考文献：
  名称：

  Methods and compositions for diagnostic and therapeutic targeting of COX-2

  摘要：

  目前公开的主题提供了选择性结合环氧合酶-2并包含治疗和/或诊断基团的组合物。还提供了使用公开的组合物进行诊断（即通过成像）目标细胞和/或治疗与环氧合酶-2生物活性相关的疾病的方法。

  公开号：

  US20070292352A1
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 4-[2-[5-[5-(Carboxymethyl)-1-ethyl-3,3-dimethylindol-2-ylidene]penta-1,3-dienyl]-1,1-dimethylbenzo[e]indol-3-ium-3-yl]butane-1-sulfonate 在 N,N'-二环己基碳二亚胺 作用下， 以 乙腈 为溶剂， 生成 NIR664 succinimidyl ester
  参考文献：
  名称：

  Visible Diode Laser-Induced Fluorescence Detection in Liquid Chromatography after Precolumn Derivatization of Amines

  摘要：

  To fully exploit the attractive visible diode laser-induced fluorescence (LIF) detection technique in column liquid chromatography (LC), covalent labeling procedures need to be developed which are compatible with near-infrared fluorescence. For this purpose, several red-absorbing labels containing a single succinimidyl ester functionality were synthesized and used for the derivatization of primary and secondary amines. Oxazines/thiazines, squaraines, and dicarbocyanines were examined as red-absorbing fluorophores. The quality of the LC-diode LIF system for the analytes concerned is illustrated by the concentration detection limit of the labeled n-octylamine (a test compound), which was as low as 2 x 10(-12) M. As expected in view of the limited reactivity of the succinimidyl ester group, the analyte concentrations required to obtain quantitative reaction with the label were equal to or higher than 2 x 10(-8) M. To show the applicability of the method to biological samples, urine was spiked with 5 x 10(-7) M. 1-adamantanamine, extracted, derivatized with a dicarbocyanine-based label, and analyzed by LC-diode LIF.

  DOI：

  10.1021/ac00106a015

文献信息

• Divergent Oriented Synthesis For the Design of Reagents for Protein Conjugation
  作者：Elisabeth Garanger、Joseph Blois、Scott A. Hilderbrand、Fangwei Shao、Lee Josephson

  DOI：10.1021/cc900141b

  日期：2010.1.11

  Instead of using diversity oriented syntheses (DOS) to obtain compounds with biological activities, we employed the DOS method to efficiently obtain multifunctional single attachment point (MSAP) reagents for the conjugation to proteins. Acid insensitive functional groups (chelators, fluorochromes) were attached to Lys-Cys-NH2 or Lys-Lys-βAla-Cys-NH2 peptide scaffolds. After cleavage from solid supports

  我们没有使用面向多样性的合成（DOS）来获得具有生物活性的化合物，而是采用DOS方法来有效地获得多功能单连接点（MSAP）试剂以与蛋白质结合。酸不敏感的官能团（螯合剂，荧光染料）附着于赖氨酸的Cys-NH 2或Lys-赖氨酸βAla-的Cys-NH 2肽支架。从固体支持物上裂解后，将修饰的肽中间体分开并进一步通过两个溶液相进行修饰，使用存在于中间体上的单胺和单硫醇进行化学选择性反应。获得了基于MSAP的荧光铬螯合物，其中一些具有第三官能团，例如聚乙二醇（PEG）聚合物或“点击化学”反应性炔烃和叠氮化物。MSAP试剂的DOS可以高效生成MSAP试剂组，可用于获得具有单个修饰氨基酸（单个连接点）的多功能蛋白质。