3-(4-methylquinolin-1-ium-1-yl)propane-1-sulfonate | 56405-66-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-(4-methylquinolin-1-ium-1-yl)propane-1-sulfonate
• 英文别名: 4-Methyl-1-(3-sulfonatopropyl)quinolin-1-ium
• CAS: 56405-66-4
• 化学式: C₁₃H₁₅NO₃S
• mdl: MFCD00182043
• 分子量: 265.333
• InChiKey: QHORCTJPQGNFIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  69.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-methylquinolin-1-ium-1-yl)propane-1-sulfonate 在 吡啶 、 calcium perchlorate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 20.0h， 生成 3-(4-{2,4-di(2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin-15-yl)-3-[1-(3-sulfonatopropyl)-4-quinoliniumyl]cyclobutyl}-1-quinoliniumyl)-1-propanesulfonate
  参考文献：
  名称：

  Crown-ether styryl dyes

  摘要：

  Styryl dyes (4a,b) containing a 15-crown-5 fragment and isomeric 2- and 4-quinolinium residues with an N-sulfopropyl substituent undergo [2+2] -autophotocycloaddition to give cyclobutane derivatives (9a,b) in acetonitrile only in the presence of Mg(ClO4)(2) or Ca(ClO4)(2). The stereospecificity of both pathways of photocycloaddition and its efficiency are explained by the preorganization of the supramolecular dimers derived from the trans-isomers of the dyes when they are bound into complexes with Mg and Ca cations.

  DOI：

  10.1007/bf00696719
• 作为产物：
  描述：

  1,3-丙烷磺内酯 、 4-甲基喹啉 以 甲苯 为溶剂， 反应 10.0h， 以47.8%的产率得到3-(4-methylquinolin-1-ium-1-yl)propane-1-sulfonate
  参考文献：
  名称：

  系列三光子吸收喹啉衍生物的晶体结构和聚集诱导发射

  摘要：

  合成了三种新型喹啉衍生物（QV-1、QV-2 和 QV-3）。通过单晶X射线衍射分析证实了它们的结构。该晶体结构研究的结果表明，与其他两种晶体QV-1和QV-2相比，晶体QV-3中通过双甲氧基相互作用作用的分子间力最强，导致典型的聚集诱导发射（AIE）特征。研究发现，这些分子间力可以促进分子主链的面外扭曲，并使 QV-3 表现出强光致发光和更长的寿命。此外，还发现QV-3在NIR-II激发下在聚集态下表现出优异的三光子吸收（3PA）活性。

  DOI：

  10.1016/j.molstruc.2022.132964

文献信息

• Simultaneous imaging of lysosomal and mitochondrial viscosity during mitophagy using molecular rotors with dual-color emission
  作者：Wen Chen、Junyan Han、Jiaxin She、Fenglin Wang、Lei Zhu、Ru-Qin Yu、Jian-Hui Jiang

  DOI：10.1039/d0cc00868k

  日期：——

  A schematic illustration of rotors to detect mitochondrial and lysosomal viscosity during mitophagy.

  一个旨在检测线粒体和溶酶体粘度的转子的示意图，用于研究线粒体自噬过程。
• Epicocconone-Hemicyanine Hybrids: Near Infrared Fluorophores for Protein Staining and Cell Imaging
  作者：Peter Karuso、Wendy Loa Kum Cheung、Philippe A. Peixoto、Agathe Boulangé、Xavier Franck

  DOI：10.1002/chem.201604698

  日期：2017.2.3

  The development of new near infrared (NIR) dyes is crucial for diverse applications and especially bioimaging, as they absorb and emit light in the “therapeutic window“ (650–950 nm). We report here a new family of NIR fluorophores that has been obtained by hybridising hemicyanines with epicocconone. Emission wavelengths of these hybrid dyes is in the range 715–795 nm and is combined with large Stokes’

  新近红外（NIR）染料的开发对于多种应用，尤其是生物成像至关重要，因为它们在“治疗窗”（650-950 nm）内吸收和发射光。我们在这里报告了一个新的近红外荧光家族，它是通过将半花青素与环氧可可酮杂交而获得的。这些杂化染料的发射波长在715–795 nm范围内，并与较大的斯托克斯位移（75–95 nm）相结合。吸收和发射波长可根据半菁部分进行调节，加入磺酸部分可增强水溶性。我们证明了它们在凝胶电泳中蛋白质的敏感检测以及共聚焦显微镜中特定细胞器的染色中的应用。这些结果特别令人鼓舞，并为化学生物学提出了新的荧光骨架。
• Unsymmetrical cyanine dyes and their application
  申请人：Ying Laiqiang

  公开号：US09850382B1

  公开（公告）日：2017-12-26

  The invention describes the preparation and use of fluorescent stains for nucleic acids derived from unsymmetrical cyanine dyes. The dyes of the invention possess superior fluorescent properties when complexed with nucleic acids, and have utility in any application which requires detection of nucleic acids, such as detection of nucleic acids in solution, in gels, in blots, in microarrays, and in bacteria and cells, and for use in analysis of cell structure, membrane integrity, and function. The dyes of the invention have the formula where X is O, S, or C(CH3)2; Each of R1 and R6 is independently hydrogen, carboxy, sulfo, sulfonamide, halogen, CN, or alkoxy; Each of t and s is an integer from 0 to 4; R2 is an alkyl, or alkyl group substituted by a carboxy, or a sulfo; R3 is H, C6H4CO2R7, or C6H4CH2N(R7)2, where R7 is an alkyl; R4 is H, alkyl, aryl, halogen, alkoxy, alkylamino, or alkylthio; R5 is an alkyl, aryl, alkyl group substituted by a carboxy, or a sulfo, or —(CH2)a—[O—(CH2)b]m—O—Z, where Z is H, alkyl, or carboxy; each of a and b is an integer from 1 to 4; m is an integer selected from 0 to 4.

  该发明描述了从非对称靛蓝染料中衍生的核酸荧光染料的制备和使用。该发明的染料在与核酸形成复合物时具有优越的荧光性能，并在任何需要检测核酸的应用中具有实用性，例如在溶液中检测核酸、在凝胶中检测核酸、在印迹中检测核酸、在微阵列中检测核酸、在细菌和细胞中检测核酸，并用于细胞结构、膜完整性和功能的分析。该发明的染料具有下列结构式：其中X为O、S或C(CH3)2；R1和R6中的每一个独立地为氢、羧基、磺酸基、磺酰胺基、卤素、CN或烷氧基；t和s各自为0到4的整数；R2为烷基或通过羧基或磺酸基取代的烷基基团；R3为H、C6H4CO2R7或C6H4CH2N(R7)2，其中R7为烷基；R4为H、烷基、芳基、卤素、烷氧基、烷基氨基或烷基硫基；R5为烷基、芳基、通过羧基或磺酸基取代的烷基基团，或—(CH2)a—[O—(CH2)b]m—O—Z，其中Z为H、烷基或羧基；a和b各自为1到4的整数；m为从0到4选取的整数。
• 不对称花青素染料及其应用
  申请人：安迪福诺生物科技（武汉）有限公司

  公开号：CN108440987A

  公开（公告）日：2018-08-24

  本发明提出了一种不对称花青素染料结构的化合物，具有化学结构通式(I)。该化合物本身没有荧光，但与RNA复合时可以产生强烈的荧光信号，并且荧光信号强度与RNA浓度成正比，且对RNA具有高度选择性。因此，利用该化合物可以简单快速测定生物样品中RNA的浓度。
• Molecular Tuning of Styryl Dyes Leads to Versatile and Efficient Plasma Membrane Probes for Cell and Tissue Imaging
  作者：Mayeul Collot、Emmanuel Boutant、Kyong Tkhe Fam、Lydia Danglot、Andrey S. Klymchenko

  DOI：10.1021/acs.bioconjchem.0c00023

  日期：2020.3.18

  The plasma membrane (PM) plays a major role in many biological processes; therefore, its proper fluorescence staining is required in bioimaging. Among the commercially available PM probes, styryl dye FM1-43 is one of the most widely used. In this work, we demonstrated that fine chemical modifications of FM1-43 can dramatically improve the PM staining. The newly developed probes, SP-468 and SQ-535, were found to display enhanced photophysical properties (reduced cross-talk, higher brightness, improved photostability) and, unlike FM1-43, provided excellent and immediate PM staining in 5 different mammalian cell types including neurons (primary culture and tissue imaging). Taking advantage of these features, we successfully used SP-468 in STED super resolution neuronal imaging. Additionally, we showed that the new probes displayed differences in their internalization pathways compared to their parent FM1-43. Finally, we showed that the new probes kept the ability to stain the PM of plant cells. Overall, this work presents new useful probes for PM imaging in cells and tissues and provides insights on the molecular design of new PM targeting molecules.

  质膜（PM）在许多生物过程中发挥着重要作用，因此在生物成像中需要对其进行适当的荧光染色。在市售的质膜探针中，苯乙烯基染料 FM1-43 是应用最广泛的探针之一。在这项工作中，我们证明了对 FM1-43 进行精细化学修饰可显著改善 PM 染色效果。与 FM1-43 不同，新开发的探针 SP-468 和 SQ-535 显示出更强的光物理特性（减少串扰、提高亮度、改善光稳定性），并能在包括神经元在内的 5 种不同哺乳动物细胞类型（原代培养和组织成像）中提供出色的即时 PM 染色。利用这些特点，我们成功地将 SP-468 用于 STED 超分辨率神经元成像。此外，我们还发现，与母体 FM1-43 相比，新探针的内化途径有所不同。最后，我们还发现新探针保持了对植物细胞PM染色的能力。总之，这项工作为细胞和组织中的 PM 成像提供了新的有用探针，并为新的 PM 靶向分子的分子设计提供了启示。