3-acetoxy-6,8-difluoro-7-hydroxycoumarin

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-acetoxy-6,8-difluoro-7-hydroxycoumarin
• 英文别名: Pacific Blue；6,8-difluoro-7-hydroxy-4-methylcoumarin-3-acetic acid；(6,8-difluoro-7-hydroxy-4-methyl-2-oxo-2H-chromen-3-yl)acetic acid；2-(6,8-difluoro-7-hydroxy-4-methyl-2-oxochromen-3-yl)acetic acid
• 化学式: C₁₂H₈F₂O₅
• 分子量: 270.189
• InChiKey: LOOHJLFUKMXKKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-羟基丁二酰亚胺 、 N-trifluoroacetoxy succinimide 、 3-acetoxy-6,8-difluoro-7-hydroxycoumarin 在 三氟乙酸酐 作用下， 以 吡啶 为溶剂， 以0.41 g (62%)的产率得到Marina Blue succinimidyl ester
  参考文献：
  名称：

  Derivatives of 6,8-difluoro-7-hydroxycoumarin

  摘要：

  本发明包括6,8-二氟-7-羟基香豆素及其衍生物，包括反应染料、染料共轭物和酶底物。这些氟取代的荧光染料通常具有比其非氟取代的类似物在生理pH范围内更高的光稳定性和较低的pH敏感性，当与物质结合时，表现出较少的荧光猝灭，具有吸收和发射光谱与其非氟取代的类似物非常接近，并且比其非氟取代的类似物具有更高的量子产率。

  公开号：

  US05830912A1
• 作为产物：
  描述：

  乙酰琥珀酸二乙酯 、 2,4-二氟邻苯二酚 在 甲烷磺酸 作用下， 生成 3-acetoxy-6,8-difluoro-7-hydroxycoumarin
  参考文献：
  名称：

  Synthesis of novel fluorinated coumarins: Excellent UV-light excitable fluorescent dyes

  摘要：

  Two new fluorinated fluorescent dyes, 6,8-difluoro-7-hydroxy-4-methylcoumarin (Marina Blue(TM)) and 3-carboxy-6,8-difluoro-7-hydroxycoumarin (Pacific Blue(TM)), exhibit excellent photophysical properties among a series of novel fluorinated 7-hydroxycoumarins. Most of these fluorinated coumarins have quantum yields (0.63 to 0.89) equal to or higher than that of the parent compound (0.63), which, in combination with their lower pK(a)s and higher photostability, make them superior fluorescent dyes fbr use as reporter molecules in biological systems. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00578-2

文献信息

• SITE-SPECIFIC LABELING OF AFFINITY TAGS IN FUSION PROTEINS
  申请人：LIFE TECHNOLOGIES CORPORATION

  公开号：US20160025713A1

  公开（公告）日：2016-01-28

  The present invention provides methods and fluorescent compounds that facilitate detecting and labeling of a fusion protein by being capable of selectively binding to an affinity tag. The fluorescent compounds have the general formula A(B)n, wherein A is a fluorophore, B is a binding domain that is a charged chemical moiety, a protein or fragment thereof and n is an integer from 1-6 with the proviso that the protein or fragment thereof not be an antibody or generated from an antibody. The present invention provides specific fluorescent compounds and methods used to detect and label fusion proteins that contain a poly-histidine affinity tag. These compounds have the general formula A(L)m(B)n wherein A is a fluorophore, L is a linker, B is an acetic acid binding domain, m is an integer from 1 to 4 and n is an integer from 1 to 6. The acetic acid groups interact directly with the positively charged histidine residues of the affinity tag to effectively label and detect a fusion protein containing such an affinity tag when present in an acidic or neutral environment.

  本发明提供了一种方法和荧光化合物，通过选择性地与亲和标签结合，从而促进融合蛋白的检测和标记。所述荧光化合物具有通式A(B)n，其中A是荧光团，B是带电化学基团、蛋白质或其片段的绑定域，n是1-6的整数，但该蛋白质或其片段不是抗体或由抗体产生的。本发明还提供了特定的荧光化合物和方法，用于检测和标记含有聚组氨酸亲和标签的融合蛋白。这些化合物具有通式A(L)m(B)n，其中A是荧光团，L是连接器，B是醋酸绑定域，m是1到4的整数，n是1到6的整数。醋酸基团直接与亲和标签中的正电荷组氨酸残基相互作用，有效地标记和检测含有此类亲和标签的融合蛋白，当其存在于酸性或中性环境中时。
• METHOD FOR IMAGING CELL USING FLUORESCENCE-LABELED SUGAR DERIVATIVE HAVING COUMARIN DERIVATIVE BOUND THERETO, AND IMAGING AGENT
  申请人：Hirosaki University

  公开号：US20150369797A1

  公开（公告）日：2015-12-24

  The present invention has an object of providing a sugar derivative emitting blue fluorescence color which can be used for imaging of cells or intracellular molecules and a method for imaging cells using the derivative. Further, the present invention has an object of providing a method for detecting cancer cells at high accuracy by imaging, and an imaging agent used for this method. The present invention provides a fluorescently labeled sugar derivative having 3-carboxy-6,8-difluoro-7-hydroxycoumarin or 3-carboxymethyl-6,8-difluoro-7-hydroxy-4-methylcoumarin as a fluorescent molecular group in its molecule, and a cell imaging agent and an imaging method using the derivative. Further, the present invention provides an imaging agent and an imaging method for cancer cells using an L-glucose derivative having the above-described fluorescent molecular group in its molecule.

  本发明旨在提供一种发出蓝色荧光颜色的糖衍生物，可用于细胞或细胞内分子的成像，以及使用该衍生物成像细胞的方法。此外，本发明旨在提供一种通过成像高精度检测癌细胞的方法，以及用于该方法的成像剂。本发明提供一种含有3-羧基-6,8-二氟-7-羟基香豆素或3-羧甲基-6,8-二氟-7-羟基-4-甲基香豆素作为其分子中的荧光分子基团的荧光标记糖衍生物，以及使用该衍生物的细胞成像剂和成像方法。此外，本发明提供一种使用具有上述荧光分子基团的L-葡萄糖衍生物的成像剂和成像方法，用于癌细胞。
• Multimers of MHC-peptide complexes and uses thereof in Borrelia infectious diseases
  申请人：Dako Denmark A/S

  公开号：EP2361930A2

  公开（公告）日：2011-08-31

  The present application concerns multimers of MHC-peptide complexes, in particular, dextramers, wherein the peptide is a 9-mer derived from a Borrelia outer surface protein antigen. The application is also directed to compositions, kits and vaccines comprising said MHC multimers and uses thereof in immuno-monitoring, diagnosis, and therapy, especially to detect specific T cells.

  本申请涉及 MHC-肽复合物的多聚体，特别是右旋聚体，其中的肽是源自包柔氏外表面蛋白抗原的 9 聚体。本申请还涉及包含上述 MHC 多聚体的组合物、试剂盒和疫苗，以及它们在免疫监测、诊断和治疗中的用途，特别是用于检测特异性 T 细胞。
• IMPROVED METHODS FOR GENERATION, LABELING AND USE OF MHC MULTIMERS
  申请人：Dako Denmark A/S

  公开号：EP3023436A1

  公开（公告）日：2016-05-25

  The present invention describes novel methods to generate MHC multimers and methods to improve existing and new MHC multimers. The invention also describes improved methods for the use of MHC multimers in analysis of T-cells in samples including diagnostic and prognostic methods. Furthermore the use of MHC multimers in therapy are described, e.g. anti-tumour and anti-virus therapy, including isolation of antigen specific T-cells capable of inactivation or elimination of undesirable targeT-cells or isolation of specific T-cells capable of regulation of other immune cells.

  本发明描述了生成 MHC 多聚物的新方法以及改进现有和新 MHC 多聚物的方法。本发明还描述了在分析样本中的 T 细胞时使用 MHC 多聚物的改进方法，包括诊断和预后方法。此外，本发明还描述了 MHC 多聚体在治疗中的应用，例如抗肿瘤和抗病毒治疗，包括分离抗原特异性 T 细胞，使其能够灭活或消除不需要的 T 细胞，或分离能够调节其他免疫细胞的特异性 T 细胞。
• NOVEL GLUCOSE DERIVATIVE, AND CELL IMAGING METHOD AND IMAGING AGENT USING SAID DERIVATIVE
  申请人：Hirosaki University

  公开号：EP3130596A1

  公开（公告）日：2017-02-15

  A purpose of the present invention is to provide a novel glucose derivative, which is taken into cells via a membrane sugar transport system and is represented by formula (1). Another purpose of the present invention is to provide an imaging agent and an imaging method for a cell or intracellular molecule using said glucose derivative. Yet another purpose of the present invention is to provide a method for detecting cancer cells with good accuracy using said glucose derivative and an imaging agent to be used in said method. The present invention provides D-glucose derivatives and L-glucose derivatives in which glucose is bound to the 7-position of a fluorescent molecular group with a coumarin backbone or a quinolone backbone. Also provided are a cell imaging agent and imaging method using the derivative. A cancer cell imaging agent and imaging method using the L-glucose derivative is also provided. G is a group selected from formulas (G1) - (G4) below.

  本发明的一个目的是提供一种新型葡萄糖衍生物，它可通过膜糖转运系统被带入细胞，由式（1）表示。本发明的另一个目的是提供一种成像剂和一种使用所述葡萄糖衍生物的细胞或细胞内分子成像方法。本发明的另一个目的是提供一种使用所述葡萄糖衍生物准确检测癌细胞的方法和用于所述方法的成像剂。本发明提供了 D-葡萄糖衍生物和 L-葡萄糖衍生物，其中葡萄糖与具有香豆素骨架或醌骨架的荧光分子基团的 7 位结合。还提供了一种细胞成像剂和使用该衍生物的成像方法。还提供了一种癌细胞成像剂和使用 L-葡萄糖衍生物的成像方法。G 是选自以下式 (G1) - (G4) 的基团。