2-aminomethyl-8,10,10-trimethyl-10H-pyrido[1,2-a]indolylium perchlorate | 1093744-68-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-aminomethyl-8,10,10-trimethyl-10H-pyrido[1,2-a]indolylium perchlorate
• 英文别名: 2-(aminomethyl)-8,10,10-trimethyl-10H-pyrido[1,2-a]indolium perchlorate；(8,10,10-Trimethylpyrido[1,2-a]indol-5-ium-2-yl)methanamine;perchlorate；(8,10,10-trimethylpyrido[1,2-a]indol-5-ium-2-yl)methanamine;perchlorate
• CAS: 1093744-68-3
• 化学式: C₁₆H₁₉N₂*ClO₄
• 分子量: 338.791
• InChiKey: XGBVDLOWDDTCKD-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.39
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-aminomethyl-8,10,10-trimethyl-10H-pyrido[1,2-a]indolylium perchlorate 在 碘代三甲硅烷 、 sodium acetate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 hydroxylamine-O-sulfonic acid 作用下， 以 N-甲基吡咯烷酮 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 98.0h， 生成 N-ethyl-N-isopropylpropan-2-aminium 3-(N-((8-((1Z,3E)-1-cyano-4-(1,3-dimethyl-6-oxido-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)buta-1,3-dienyl)-10,10-dimethyl-10H-pyrido[1,2-a]indolium-2-yl)methyl)-2-iodoacetamido)propane-1-sulfonate
  参考文献：
  名称：

  Ratiometric Imaging Using a Single Dye Enables Simultaneous Visualization of Rac1 and Cdc42 Activation

  摘要：

  Biosensors that report endogenous protein activity in vivo can be based on environment-sensing fluorescent dyes. The dyes can be attached to reagents that bind selectively to a specific conformation of the targeted protein, such that binding leads to a fluorescence change. Dyes that are sufficiently bright for use at low, nonperturbing intracellular concentrations typically undergo changes in intensity rather than the shifts in excitation or emission maxima that would enable precise quantitation through ratiometric imaging. We report here mero199, an environment-sensing dye that undergoes a 33 nm solvent-dependent shift in excitation. The dye was used to generate a ratiometric biosensor of Cdc42 (CRIB199) without the need for additional fluorophores. CRIB199 was used in the same cell with a FRET sensor of Rac1 activation to simultaneously observe Cdc42 and Rac1 activity in cellular protrusions, indicating that Rac1 but not Cdc42 activity was reduced during tail retraction, and specific protrusions had reduced Cdc42 activity. A novel program (EdgeProps) used to correlate localized activation with cell edge dynamics indicated that Rac1 was specifically reduced during retraction.

  DOI：

  10.1021/jacs.5b09764
• 作为产物：
  描述：

  2-[(2,3,3-三甲基吲哚-5-基)甲基]异吲哚-1,3-二酮 在 吡啶 、 高氯酸 、 一水合肼 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 17.75h， 生成 2-aminomethyl-8,10,10-trimethyl-10H-pyrido[1,2-a]indolylium perchlorate
  参考文献：
  名称：

  Ratiometric Imaging Using a Single Dye Enables Simultaneous Visualization of Rac1 and Cdc42 Activation

  摘要：

  Biosensors that report endogenous protein activity in vivo can be based on environment-sensing fluorescent dyes. The dyes can be attached to reagents that bind selectively to a specific conformation of the targeted protein, such that binding leads to a fluorescence change. Dyes that are sufficiently bright for use at low, nonperturbing intracellular concentrations typically undergo changes in intensity rather than the shifts in excitation or emission maxima that would enable precise quantitation through ratiometric imaging. We report here mero199, an environment-sensing dye that undergoes a 33 nm solvent-dependent shift in excitation. The dye was used to generate a ratiometric biosensor of Cdc42 (CRIB199) without the need for additional fluorophores. CRIB199 was used in the same cell with a FRET sensor of Rac1 activation to simultaneously observe Cdc42 and Rac1 activity in cellular protrusions, indicating that Rac1 but not Cdc42 activity was reduced during tail retraction, and specific protrusions had reduced Cdc42 activity. A novel program (EdgeProps) used to correlate localized activation with cell edge dynamics indicated that Rac1 was specifically reduced during retraction.

  DOI：

  10.1021/jacs.5b09764

文献信息

• METHODS TO INCREASE THE PHOTOSTABILITY OF DYES
  申请人：Hahn Klaus

  公开号：US20110046000A1

  公开（公告）日：2011-02-24

  The presently disclosed subject matter provides dyes having an improved photostability, biosensors comprising such dyes, and methods of use thereof, including methods for detecting target molecules in a sample under test and for live-cell imaging. The dyes can include a binding member, including a biomolecule or fragments thereof, which can interact with target molecules of interest and can be specific to a given conformational state or covalent modification, e.g., phosphorylation, of the target molecule. The presently disclosed dyes can be used for detecting changes in the binding, conformational change, or posttranslational modification of the target molecule.

  所述主题提供了具有改善光稳定性的染料、包括此类染料的生物传感器以及其使用方法，包括用于检测样品中的靶分子和用于活细胞成像的方法。该染料可以包括结合成员，包括生物分子或其片段，其可以与感兴趣的靶分子相互作用，并且可以特定于给定的构象状态或靶分子的共价修饰，例如磷酸化。目前披露的染料可用于检测靶分子的结合、构象变化或后翻译修饰的变化。
• [EN] METHODS TO INCREASE THE PHOTOSTABILITY OF DYES<br/>[FR] PROCÉDÉS POUR ACCROÎTRE LA PHOTOSTABILITÉ
  申请人：UNIV NORTH CAROLINA

  公开号：WO2008157762A8

  公开（公告）日：2009-03-19
• US8835632B2
  申请人：——

  公开号：US8835632B2

  公开（公告）日：2014-09-16
• [EN] METHODS TO INCREASE THE PHOTOSTABILITY<br/>[FR] PROCÉDÉS POUR ACCROÎTRE LA PHOTOSTABILITÉ
  申请人：UNIV NORTH CAROLINA

  公开号：WO2008157762A2

  公开（公告）日：2008-12-24

  (EN) The presently disclosed subject matter provides dyes having an improved photostability, biosensors comprising such dyes, and methods of use thereof, including methods for detecting target molecules in a sample under test and for live- cell imaging. The dyes can include a binding member, including a biomolecule or fragments thereof, which can interact with target molecules of interest and can be specific to a given conformational state or covalent modification, e.g., phosphorylation, of the target molecule. The presently disclosed dyes can be used for detecting changes in the binding, conformational change, or posttranslational modification of the target molecule.(FR) La présente invention concerne des colorants qui présentent une meilleure photostabilité, des biocapteurs comprenant ces colorants et des procédés d'utilisation de ces derniers, y compris des procédés de détection de molécules cibles dans un échantillon soumis à un essai et pour l'imagerie de cellules vivantes. Les colorants peuvent comprendre un élément de liaison renfermant une biomolécule ou un fragment de cette dernière, qui peut interagir avec des molécules cibles présentant un intérêt et qui peuvent être spécifiques d'un état conformationnel donné ou d'une modification covalente donnée, par exemple, la phosphorylation, de la molécule cible. Les colorants selon la présente invention peuvent être utilisés pour détecter des changements concernant la liaison, le changement conformationnel ou la modification post-traduction de la molécule cible.
• Ratiometric Imaging Using a Single Dye Enables Simultaneous Visualization of Rac1 and Cdc42 Activation
  作者：Christopher J. MacNevin、Alexei Toutchkine、Daniel J. Marston、Chia-Wen Hsu、Denis Tsygankov、Li Li、Bei Liu、Timothy Qi、Dan-Vinh Nguyen、Klaus M. Hahn

  DOI：10.1021/jacs.5b09764

  日期：2016.3.2

  Biosensors that report endogenous protein activity in vivo can be based on environment-sensing fluorescent dyes. The dyes can be attached to reagents that bind selectively to a specific conformation of the targeted protein, such that binding leads to a fluorescence change. Dyes that are sufficiently bright for use at low, nonperturbing intracellular concentrations typically undergo changes in intensity rather than the shifts in excitation or emission maxima that would enable precise quantitation through ratiometric imaging. We report here mero199, an environment-sensing dye that undergoes a 33 nm solvent-dependent shift in excitation. The dye was used to generate a ratiometric biosensor of Cdc42 (CRIB199) without the need for additional fluorophores. CRIB199 was used in the same cell with a FRET sensor of Rac1 activation to simultaneously observe Cdc42 and Rac1 activity in cellular protrusions, indicating that Rac1 but not Cdc42 activity was reduced during tail retraction, and specific protrusions had reduced Cdc42 activity. A novel program (EdgeProps) used to correlate localized activation with cell edge dynamics indicated that Rac1 was specifically reduced during retraction.