2-[(2,3,3-三甲基吲哚-5-基)甲基]异吲哚-1,3-二酮 | 149980-68-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 中文名称: 2-[(2,3,3-三甲基吲哚-5-基)甲基]异吲哚-1,3-二酮
• 英文名称: 2-((2,3,3-trimethyl-3H-indol-5-yl)methyl)isoindoline-1,3-dione
• 英文别名: 2-[(2,3,3-Trimethyl-3H-indol-5-yl)methyl]-1H-isoindole-1,3(2H)-dione；2-[(2,3,3-trimethylindol-5-yl)methyl]isoindole-1,3-dione
• CAS: 149980-68-7
• 化学式: C₂₀H₁₈N₂O₂
• 分子量: 318.375
• InChiKey: JFYCOHKLACJNBY-UHFFFAOYSA-N

物化性质

• 沸点：
  470.3±45.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  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 、 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 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 66.25h， 生成 2-(tert-butoxycarbonylamino-methyl)-8-cyanomethyl-10,10-dimethyl-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
• 作为产物：
  描述：

  2,3,3-三甲基-3H-吲哚 、 N-羟甲基邻苯二甲酰亚胺 在 硫酸 作用下， 反应 144.0h， 以88.3%的产率得到2-[(2,3,3-三甲基吲哚-5-基)甲基]异吲哚-1,3-二酮
  参考文献：
  名称：

  [EN] LIPID DERIVATIVES FOR IN VITRO OR IN VIVO DELIVERY
  [FR] DÉRIVÉS LIPIDIQUES POUR ADMINISTRATION IN VITRO OU IN VIVO

  摘要：

  本发明涉及允许将生物活性剂递送入细胞的新颖构建体。在某些实施例中，构建体包括脂溶性膜染料或其衍生物或类似物的偶联物与生物活性剂的结合。

  公开号：

  WO2019126565A1

文献信息

• Rigidized trimethine cyanine dyes
  申请人：Carnegie Mellon University

  公开号：US06686145B1

  公开（公告）日：2004-02-03

  Disclosed are analogues of trimethine cyanine dyes which are useful for imparting fluorescent properties to target materials by covalent and non-covalent association. The compounds have general formula (2) optionally substituted by groups R2-R9 wherein groups R6, R7, R8 and R9 are attached to the rings containing X and Y or, optionally are attached to atoms of the Za and Zb ring structures and groups R1-R9 are chosen to provide desired solubility, reactivity and spectralproperties to the fluorescent compounds; A is selected from O, S and NR11 where R11 is the substituted amino radical (a), where R′ is selected from hydrogen, a C1-4 alkyl and aryl and R″ is selected from C1-18 alkyl, aryl, heteroaryl, an acyl radical having from 2-7 carbon atoms, and a thiocarbamoyl radical; Za and Zb each represent a bond or the atoms necessary to complete one, two fused or three fused aromatic rings each ring having five or six atoms, selected from carbon atoms and, optionally, non more than two oxygen, nitrogen and sulphur atoms.

  披露了三亚甲基青霉素染料的类似物，这些类似物通过共价和非共价结合对目标材料赋予荧光特性。这些化合物具有一般式（2），可选择地由基团R2-R9取代，其中基团R6、R7、R8和R9附着在含有X和Y的环上，或者可选择地附着在Za和Zb环结构的原子上，基团R1-R9被选择以为荧光化合物提供所需的溶解性、反应性和光谱特性；A从O、S和NR11中选择，其中R11是取代氨基基团（a），其中R′从氢、C1-4烷基和芳基中选择，R″从C1-18烷基、芳基、杂环芳基、具有2-7个碳原子的酰基基团和硫代氨基基团中选择；Za和Zb分别代表一个键或完成一个、两个融合或三个融合的芳香环所需的原子，每个环有五个或六个原子，选自碳原子，并且可选择地不超过两个氧、氮和硫原子。
• Water soluble fluorescent compounds
  申请人：Reddington Mark

  公开号：US20070021621A1

  公开（公告）日：2007-01-25

  The invention provides a novel class of fluorescent compounds. Also provided are conjugates of the fluorescent compounds, methods of using the fluorescent compounds and their conjugates as well as kits including the fluorescent compounds and their conjugates.

  这项发明提供了一类新型荧光化合物。还提供了荧光化合物的共轭物，使用荧光化合物及其共轭物的方法，以及包括荧光化合物及其共轭物的试剂盒。
• [EN] MOLECULAR PROBES FOR MULTIMODALITY IMAGING AND TRACKING OF STEM CELLS<br/>[FR] SONDES MOLÉCULAIRES POUR IMAGERIE MULTIMODES ET SUIVI DE CELLULES SOUCHES
  申请人：UNIV MASSACHUSETTS MEDICAL

  公开号：WO2013181119A1

  公开（公告）日：2013-12-05

  The invention relates to novel multi-modality probes for imaging, tracking and analyzing stem cells and related biological samples, and methods of preparation and use thereof. The molecular probes of the invention are constructed, for example, by utilizing (a) the high selectivity of long hydrocarbon chains for binding to plasma membranes of cells, (b) a near-infrared (NIR) dye for optical imaging, and (c) a radionuclide for PET or SPECT imaging. The in vitro and in vivo data of the optical and radiolabeled probes demonstrated their utility for detecting the presence of stem cells with multiple imaging modalities.

  本发明涉及新型多模式探针，用于成像、追踪和分析干细胞及相关生物样品，以及其制备和使用方法。本发明的分子探针是通过利用(a)长烃链对细胞质膜的高选择性结合，(b)近红外（NIR）染料进行光学成像，以及(c)正电子发射断层扫描（PET）或单光子发射计算机体层摄影（SPECT）成像的放射性核素构建的。光学和放射性标记探针的体外和体内数据证明了它们在多种成像模式下检测干细胞存在的实用性。
• MOLECULAR PROBES FOR MULTIMODALITY IMAGING AND TRACKING OF STEM CELLS
  申请人：University of Massachusetts Medical School

  公开号：US20150125388A1

  公开（公告）日：2015-05-07

  The invention relates to novel multi-modality probes for imaging, tracking and analyzing stem cells and related biological samples, and methods of preparation and use thereof. The molecular probes of the invention are constructed, for example, by utilizing (a) the high selectivity of long hydrocarbon chains for binding to plasma membranes of cells, (b) a near-infrared (NIR) dye for optical imaging, and (c) a radionuclide for PET or SPECT imaging. The in vitro and in vivo data of the optical and radiolabeled probes demonstrated their utility for detecting the presence of stem cells with multiple imaging modalities.

  本发明涉及一种新型的多模态探针，用于成像、跟踪和分析干细胞及相关生物样品，以及其制备和使用方法。本发明的分子探针是通过利用（a）长碳链对细胞质膜的高选择性结合，（b）近红外（NIR）染料进行光学成像，以及（c）放射性核素进行PET或SPECT成像，构建而成的。光学和放射性标记探针的体外和体内数据证明了它们在多种成像模式下检测干细胞存在的实用性。
• 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。