6-N,N-dimethylamino-2,3-naphthalenedicarboxylic acid | 858932-53-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-N,N-dimethylamino-2,3-naphthalenedicarboxylic acid
• 英文别名: 6-(Dimethylamino)naphthalene-2,3-dicarboxylic acid
• CAS: 858932-53-3
• 化学式: C₁₄H₁₃NO₄
• 分子量: 259.262
• InChiKey: KKWJIWYWIGUKJT-UHFFFAOYSA-N

物化性质

• 沸点：
  465.5±45.0 °C(Predicted)
• 密度：
  1.389±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  77.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-N,N-dimethylamino-2,3-naphthalenedicarboxylic acid 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 methyl 2-[6-(dimethylamino)-2,3-naphthalimido]acetate
  参考文献：
  名称：

  Photophysics and Biological Applications of the Environment-Sensitive Fluorophore 6-N,N-Dimethylamino-2,3-naphthalimide

  摘要：

  We have synthesized a new environment-sensitive fluorophore, 6-N,N-dimethylamino-2,3-naphthalimide (6DMN). This chromophore exhibits valuable fluorescent properties as a biological probe with emission in the 500-600 nm range and a marked response to changes in the environment polarity. The 6DMN fluorescence is red-shifted in polar protic environments, with the maximum emission intensity shifting more than 100 nm from 491 nm in toluene to 592 nm in water. Additionally, the fluorescence quantum yield decreases more than 100-fold from chloroform (Phi = 0.225) to water (Phi = 0.002). The scope and applications of the 6DMN probe are expanded with the synthesis of an Fmoc-protected amino acid derivative (5), which contains the fluorophore. This unnatural amino acid has been introduced into several peptides, demonstrating that it can be manipulated under standard solid-phase peptide synthesis conditions. Peptides incorporating the new residue can be implemented for monitoring protein-protein interactions as exemplified in studies with Sire homology 2 (SH2) phosphotyrosine binding domains. The designed peptides exhibit a significant increase in the quantum yield of the long wavelength fluorescence emission band (596 nm) upon binding to selected SH2 domains (e.g., Crk SH2, Abl SH2, and PI3K SH2). The peptides can be used as ratiometric sensors, since the short wavelength band (460 nm) was found almost invariable throughout the titrations.

  DOI：

  10.1021/ja0449168
• 作为产物：
  描述：

  diethyl 6-N,N-dimethylamino-2,3-naphthalenedicarboxylate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 6-N,N-dimethylamino-2,3-naphthalenedicarboxylic acid
  参考文献：
  名称：

  Photophysics and Biological Applications of the Environment-Sensitive Fluorophore 6-N,N-Dimethylamino-2,3-naphthalimide

  摘要：

  We have synthesized a new environment-sensitive fluorophore, 6-N,N-dimethylamino-2,3-naphthalimide (6DMN). This chromophore exhibits valuable fluorescent properties as a biological probe with emission in the 500-600 nm range and a marked response to changes in the environment polarity. The 6DMN fluorescence is red-shifted in polar protic environments, with the maximum emission intensity shifting more than 100 nm from 491 nm in toluene to 592 nm in water. Additionally, the fluorescence quantum yield decreases more than 100-fold from chloroform (Phi = 0.225) to water (Phi = 0.002). The scope and applications of the 6DMN probe are expanded with the synthesis of an Fmoc-protected amino acid derivative (5), which contains the fluorophore. This unnatural amino acid has been introduced into several peptides, demonstrating that it can be manipulated under standard solid-phase peptide synthesis conditions. Peptides incorporating the new residue can be implemented for monitoring protein-protein interactions as exemplified in studies with Sire homology 2 (SH2) phosphotyrosine binding domains. The designed peptides exhibit a significant increase in the quantum yield of the long wavelength fluorescence emission band (596 nm) upon binding to selected SH2 domains (e.g., Crk SH2, Abl SH2, and PI3K SH2). The peptides can be used as ratiometric sensors, since the short wavelength band (460 nm) was found almost invariable throughout the titrations.

  DOI：

  10.1021/ja0449168

文献信息

• Spectroscopic investigation of bio-mimetic solvolysis of 6-(N,N-dimethylamino)-2,3-naphthalic anhydride in confined nanocavities
  作者：Falguni Chandra、Suman Mallick、Apurba L. Koner

  DOI：10.1039/c6cp08009j

  日期：——

  the reaction as compared to that without catalyst. The solvolysis reaction of a 6-(N,N-dimethylamino)-2,3-naphthalic anhydride probe is investigated using UV-Vis and fluorescence spectroscopy in pure alcohols and in bio-mimetic nano-sized environments like surfactants, macrocyclic hosts and protein nanocavities. The solvolysis rate in alcohols is found to be regulated directly by the alkyl chain length

  酶是生物催化剂，可以通过将其容纳在活性位点来极大地加快其反应速度。与没有催化剂的情况相比，由天然催化剂的活性位点提供的局部环境导致反应的显着速率提高。6-（N，N-UV-Vis和荧光光谱法在纯醇和仿生纳米大小的环境（例如表面活性剂，大环主体和蛋白质纳米腔）中使用UV-Vis和荧光光谱法研究了-二甲氨基）-2,3-萘酸酐探针。发现在醇中的溶剂分解速率直接由烷基链长调节，并且遵循阿累尼乌斯依赖性。在生理条件下（pH 7.4，在25°C下），探针在水中的水解速率非常慢。但是，在相同条件下，蛋白质和超分子纳米腔可以显着提高该速率。因此，对这种仿生溶剂分解理解的这种基本动力学分析将使我们能够设计出具有有效控释和功能的新型探针-药物偶联物。
• Unusual large Stokes shift and solvatochromic fluorophore: Synthesis, spectra, and solvent effect of 6-substituted 2,3-naphthalimide
  作者：Kishore Baathulaa、Yufang Xu、Xuhong Qian

  DOI：10.1016/j.jphotochem.2010.09.002

  日期：2010.11

  In this article four new series of 6-substituted 2 3-naphthalimides (1a-d 2a-d 3a-d 4a-d and 4 e-h) have been designed and synthesized through the formation of key cyclic anhydride intermediate which was the precursor of the well known environment-sensitive fluorophore [6-N,N-dimethylammonaphthalimides (6-DMN)] and other 6-substituted 2 3-naphthalimide series (2 3 4) Based on 6-amino-2 3-naphthalimide (6-ANP) compound a new type of fluorophore was found to exhibit moderate to unusual large Stokes shift (297-303 nm) 6-ANP derivatives display relatively low fluorescence quantum yields in high polar protic solvents such as water (Phi(F) similar to 0 004 571-576 nm) and a significant unusual red shift due to (1) hydrogen bonding interaction of the excited state of the molecule with the solvents which presumably enhance the intersystem crossing process in the system to quench fluorescence (2) this large Stokes shift was assumed to be the consequence of a substantial change of the geometric structure from the ground state (S-0) to the first excited state (S-1)) Compared with the other compounds studied the fluorescence of the nitro- and halo-derivatives was rather weak probably due to the efficient intersystem crossing leading to a non-reactive triplet state (C) 2010 Elsevier B V All rights reserved