3-[2-[5-[1-(2-carboxyethyl)-3,3-dimethyl-5-sulfoindol-1-ium-2-yl]penta-2,4-dienylidene]-3,3-dimethyl-5-sulfoindol-1-yl]propanoic acid | 774524-85-5

• 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: 3-[2-[5-[1-(2-carboxyethyl)-3,3-dimethyl-5-sulfoindol-1-ium-2-yl]penta-2,4-dienylidene]-3,3-dimethyl-5-sulfoindol-1-yl]propanoic acid
• CAS: 774524-85-5
• 化学式: C₃₁H₃₅N₂O₁₀S₂
• 分子量: 659.758
• InChiKey: PXQMFFKNWQZGFR-UHFFFAOYSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  45
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  206
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  N-(2-(2-(2-aminoethoxy)ethoxy)ethyl)-3-sulfamoylbenzamide 、 3-[2-[5-[1-(2-carboxyethyl)-3,3-dimethyl-5-sulfoindol-1-ium-2-yl]penta-2,4-dienylidene]-3,3-dimethyl-5-sulfoindol-1-yl]propanoic acid 在 O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 0.33h， 以36%的产率得到
  参考文献：
  名称：

  细胞表面荧光代谢物传感器的半合成

  摘要：

  缺乏合适的传感器来跟踪活细胞中的代谢物、第二信使和神经递质，这阻碍了了解信号转导和代谢途径的进展。在这里，我们介绍了一类合理设计的半合成荧光传感器蛋白，称为 Snifits，用于测量哺乳动物细胞表面的代谢物浓度。功能性 Snifits 通过基因编码的蛋白质支架的两个选择性化学标记反应组装在活细胞上。我们最好的 Snifit 在活细胞上显示的荧光强度比变化明显高于之前报道的任何细胞表面靶向荧光传感器蛋白。

  DOI：

  10.1021/ja206915m

文献信息

• SNAP‐Tag‐Targeted MRI‐Fluorescent Multimodal Probes
  作者：Ebaston Thankarajan、Shimrit Oz、Abed Saady、Kseniya Kulbitski、Mykhail O. Kompanets、Moris S. Eisen、Shai Berlin

  DOI：10.1002/cbic.202300172

  日期：2023.8.15

  Magnetic resonance imaging (MRI) is a powerful imaging modality, widely employed in research and clinical settings. However, MRI images suffer from low signals and a lack of target specificity. We aimed to develop a multimodal imaging probe to detect targeted cells by MRI and fluorescence microscopy. We synthesized a trifunctional imaging probe consisting of a SNAP‐tag substrate for irreversible and specific labelling of cells, cyanine dyes for bright fluorescence, and a chelated Gd^III molecule for enhancing MRI contrast. Our probes exhibit specific and efficient labelling of genetically defined cells (expressing SNAP‐tag at their membrane), bright fluorescence and MRI signal. Our synthetic approach provides a versatile platform for the production of multimodal imaging probes, particularly for light microscopy and MRI.

  摘要 磁共振成像（MRI）是一种功能强大的成像模式，广泛应用于研究和临床。然而，核磁共振成像存在信号低和缺乏靶标特异性的问题。我们旨在开发一种多模态成像探针，通过核磁共振成像和荧光显微镜检测靶细胞。我们合成了一种三功能成像探针，包括用于不可逆和特异性标记细胞的 SNAP 标记底物、用于发出明亮荧光的氰基染料以及用于增强核磁共振成像对比度的螯合 GdIII 分子。我们的探针能对基因定义的细胞（在细胞膜上表达 SNAP-tag）进行特异性高效标记，并发出明亮的荧光和磁共振成像信号。我们的合成方法为生产多模态成像探针（尤其是用于光学显微镜和核磁共振成像）提供了一个多功能平台。
• A Fluorescent Sensor for GABA and Synthetic GABA_B Receptor Ligands
  作者：Anastasiya Masharina、Luc Reymond、Damien Maurel、Keitaro Umezawa、Kai Johnsson

  DOI：10.1021/ja306320s

  日期：2012.11.21

  While gamma-aminobutyric acid (GABA) is the main inhibitory neurotransmitter, suitable tools to measure its concentration in living cells with high spatiotemporal resolution are missing. Herein, we describe the first ratiometric fluorescent sensor for GABA, dubbed GABA-Snifit, which senses GABA with high specificity and spatiotemporal resolution on the surface of living mammalian cells. GABA-Snifit is a semisynthetic fusion protein containing the GABA(B) receptor, SNAP- and CLIP-tag, a synthetic fluorophore and a fluorescent GABA(B) receptor antagonist. When assembled on cell surfaces, GABA-Snifit displays a GABA-dependent fluorescence emission spectrum in the range of 500-700 nm that permits sensing micromolar to millimolar GABA concentrations. The ratiometric change of the sensor on living cells is 1.8. Furthermore, GABA-Snifit can be utilized to quantify the relative binding affinities of GABA(B) receptor agonists, antagonists and the effect of allosteric modulators. These properties make GABA-Snifit a valuable tool to investigate the role of GABA and GABA(B) in biological systems.
• REAGENT FOR MEASUREMENT OF REACTIVE OXYGEN
  申请人：Nagano Tetsuo

  公开号：US20110111515A1

  公开（公告）日：2011-05-12

  A reagent for measurement of reactive oxygen, which can be used with a light of the near infrared region showing superior biological tissue permeability, wherein (i) a first cyanine compound residue and a second cyanine compound residue are bound to each other, (ii) the first cyanine compound residue has a property that it easily reacts with a reactive oxygen species and is thereby decomposed, and (iii) the second cyanine compound residue either equals or surpasses the first cyanine compound residue in its stability to the reactive oxygen species, and the first cyanine compound residue acts as a quenching group for the second cyanine compound residue.
• Semisynthesis of Fluorescent Metabolite Sensors on Cell Surfaces
  作者：Matthias A. Brun、Rudolf Griss、Luc Reymond、Kui-Thong Tan、Joachim Piguet、Ruud J.R.W. Peters、Horst Vogel、Kai Johnsson

  DOI：10.1021/ja206915m

  日期：2011.10.12

  Progress in understanding signal transduction and metabolic pathways is hampered by a shortage of suitable sensors for tracking metabolites, second messengers, and neurotransmitters in living cells. Here we introduce a class of rationally designed semisynthetic fluorescent sensor proteins, called Snifits, for measuring metabolite concentrations on the cell surface of mammalian cells. Functional Snifits

  缺乏合适的传感器来跟踪活细胞中的代谢物、第二信使和神经递质，这阻碍了了解信号转导和代谢途径的进展。在这里，我们介绍了一类合理设计的半合成荧光传感器蛋白，称为 Snifits，用于测量哺乳动物细胞表面的代谢物浓度。功能性 Snifits 通过基因编码的蛋白质支架的两个选择性化学标记反应组装在活细胞上。我们最好的 Snifit 在活细胞上显示的荧光强度比变化明显高于之前报道的任何细胞表面靶向荧光传感器蛋白。