1-methyl-2,6-bis[2-(1-methylpyrrol-2-yl)vinyl]pyridinium iodide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-methyl-2,6-bis[2-(1-methylpyrrol-2-yl)vinyl]pyridinium iodide
• 英文别名: 1-methyl-2,6-bis((E)-2-(1-methylpyrrol-2-yl)vinyl)pyridinium iodide；1-methyl-2,6-bis[2-(1-methylpyrrol-2-yl)ethenyl]pyridin-1-ium;iodide
• 化学式: C₂₀H₂₂N₃*I
• 分子量: 431.319
• InChiKey: XBPPQTNHSJCPPU-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.53
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  13.7
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,6-二甲基吡啶 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 40.0h， 生成 1-methyl-2,6-bis[2-(1-methylpyrrol-2-yl)vinyl]pyridinium iodide
  参考文献：
  名称：

  Synthesis, absorption and fluorescence spectral characteristics of trinucleus dimethine cyanine dyes as fluorescent probes for DNA detection

  摘要：

  The preparation of six trinucleus dimethine cyanine dyes with pyridine nucleus obtained by the condensation of trimethylpyridinium iodides with heterocyclic aromatic aldehyde was described. The absorption and fluorescence properties of the dyes were studied in different polarity solvents. Blue shift of the maxima absorption of the dyes was observed with the increase of solvents polarity. The fluorescence properties of the dyes in solution and in presence of DNA were studied. Significant enhancement of the fluorescent quantum yield was observed in four dyes in the presence of DNA. Specially, one of six dyes emitted weak fluorescence in Tris-HCl buffer, but displayed bright fluorescence in the presence of DNA.

  DOI：

  10.1590/s0103-50532011000100009

文献信息

• Identification of optimal fluorescent probes for G-quadruplex nucleic acids through systematic exploration of mono- and distyryl dye libraries
  作者：Xiao Xie、Michela Zuffo、Marie-Paule Teulade-Fichou、Anton Granzhan

  DOI：10.3762/bjoc.15.183

  日期：——

  A library of 52 distyryl and 9 mono-styryl cationic dyes was synthesized and investigated with respect to their optical properties, propensity to aggregation in aqueous medium, and capacity to serve as fluorescence “light-up” probes for G-quadruplex (G4) DNA and RNA structures. Among the 61 compounds, 57 dyes showed preferential enhancement of fluorescence intensity in the presence of one or another G4-DNA or RNA structure, while no dye displayed preferential response to double-stranded DNA or single-stranded RNA analytes employed at equivalent nucleotide concentration. Thus, preferential fluorimetric response towards G4 structures appears to be a common feature of mono- and distyryl dyes, including long-known mono-styryl dyes used as mitochondrial probes or protein stains. However, the magnitude of the G4-induced “light-up” effect varies drastically, as a function of both the molecular structure of the dyes and the nature or topology of G4 analytes. Although our results do not allow to formulate comprehensive structure–properties relationships, we identified several structural motifs, such as indole- or pyrrole-substituted distyryl dyes, as well as simple mono-stryryl dyes such as DASPMI [2-(4-(dimethylamino)styryl)-1-methylpyridinium iodide] or its 4-isomer, as optimal fluorescent light-up probes characterized by high fluorimetric response (I/I₀ of up to 550-fold), excellent selectivity with respect to double-stranded DNA or single-stranded RNA controls, high quantum yield in the presence of G4 analytes (up to 0.32), large Stokes shift (up to 150 nm) and, in certain cases, structural selectivity with respect to one or another G4 folding topology. These dyes can be considered as promising G4-responsive sensors for in vitro or imaging applications. As a possible application, we implemented a simple two-dye fluorimetric assay allowing rapid topological classification of G4-DNA structures.

  合成了52种二亚基和9种单亚基阳离子染料库，并对它们的光学性质、在水介质中的聚集倾向以及作为荧光“点亮”探针用于G-四链体（G4）DNA和RNA结构的能力进行了研究。在这61种化合物中，有57种染料显示出在存在某种G4-DNA或RNA结构时荧光强度的优先增强，而没有染料显示出对等核苷酸浓度下使用的双链DNA或单链RNA分析物的优先响应。因此，对G4结构的优先荧光响应似乎是单亚基和二亚基染料的共同特征，包括长期以来用作线粒体探针或蛋白质染料的已知单亚基染料。然而，G4诱导的“点亮”效应的幅度变化很大，这取决于染料的分子结构和G4分析物的性质或拓扑结构。尽管我们的结果不能提供全面的结构-性质关系，但我们确定了几种结构基元，如吲哚或吡咯取代的二亚基染料，以及简单的单亚基染料，如DASPMI [2-(4-(二甲基氨基)亚基)-1-甲基吡啶碘化物]或其4-异构体，作为具有高荧光响应（I/I0高达550倍）、对双链DNA或单链RNA控制具有优异选择性、在G4分析物存在时具有高量子产率（高达0.32）、大Stokes位移（高达150 nm）以及在某些情况下对一种或另一种G4折叠拓扑结构具有结构选择性的最佳荧光点亮探针。这些染料可以被视为有前途的G4响应传感器，用于体外或成像应用。作为一个可能的应用，我们实施了一个简单的双染料荧光测定，可以快速对G4-DNA结构进行拓扑分类。
• Studies on the Interactions of the New 2,6-Bis[2-(heteroaryl)vinyl]1-methylpyridinium Cations with the Decamer d(CGTACGTACG)2
  作者：Maria Fichera、Cosimo G. Fortuna、Giuseppe Impallomeni、Giuseppe Musumarra

  DOI：10.1002/1099-0690(20021)2002:1<145::aid-ejoc145>3.0.co;2-3

  日期：2002.1

  The synthesis and spectroscopic characterization of 2,6-bis[2-(heteroaryl)vinyl]-1-methylpyridinium iodides (heteroaryl = 1-methylpyrrol-2-yl, furan-2-yl, thiazol-2-yl, imidazol-2-yl, 5-bromofuran-2-yl) is reported. Interactions of furan and pyrrole derivatives with the decamer duplex d(CGTACGTACG)(2) were clearly detectable by UV/Vis, CD, and H-1 NMR spectroscopy, and attention is drawn to the complementarity of the above techniques in such studies. The NMR evidence is consistent with literature data ascribed to intercalation.
• Synthesis, absorption and fluorescence spectral characteristics of trinucleus dimethine cyanine dyes as fluorescent probes for DNA detection
  作者：Jun-Jie Su、Lan-Ying Wang、Xiang-Han Zhang、Yi-Le Fu、Yi Huang、Yong-Sheng Wei

  DOI：10.1590/s0103-50532011000100009

  日期：——

  The preparation of six trinucleus dimethine cyanine dyes with pyridine nucleus obtained by the condensation of trimethylpyridinium iodides with heterocyclic aromatic aldehyde was described. The absorption and fluorescence properties of the dyes were studied in different polarity solvents. Blue shift of the maxima absorption of the dyes was observed with the increase of solvents polarity. The fluorescence properties of the dyes in solution and in presence of DNA were studied. Significant enhancement of the fluorescent quantum yield was observed in four dyes in the presence of DNA. Specially, one of six dyes emitted weak fluorescence in Tris-HCl buffer, but displayed bright fluorescence in the presence of DNA.