6-aminofluorescein

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-aminofluorescein
• 英文别名: 5-aminofluorescein；4-amino-2-(3-hydroxy-6-oxo-6H-xanthen-9-yl)benzoic acid；4-amino-2-(3-hydroxy-6-oxoxanthen-9-yl)benzoic acid
• 化学式: C₂₀H₁₃NO₅
• 分子量: 347.327
• InChiKey: YHVSFLYWEAWYQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-aminofluorescein 在 硫酸 、 potassium carbonate 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 三氟乙酸 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 101.0h， 生成 tert-butyl 1-{9-[5-(1,2-dithiolan-3-yl)pentanamido]-2-[(ethoxycarbonyl)phenyl]-3-oxo-3H-xanthen-6-yloxy}-2-oxo-6,9,12-trioxa-3-azapentadecan-15-oate
  参考文献：
  名称：

  Synthesis of SERS active nanoparticles for detection of biomolecules

  摘要：

  Surface Enhanced Raman Scattering (SERS) can be used to detect specific DNA sequences by methods based on hybridisation of oligonucleotide functionalized nanoparticles to complementary DNA sequences. The problem, which has to be overcome to use this technique is that DNA is not strongly SERS active. This is due to the lack of a visible chromophore and presence of the highly negatively charged phosphate backbone, which prevents the electrostatic interaction with the metal surface necessary for the enhancement. To obtain SERS active DNA a label containing a surface seeking group, to allow adsorption of DNA on a metal surface, and a chromophore has to be attached to the DNA strand. Here we report the synthesis of three linkers containing a Raman tag [the following fluorophores were used for this purpose due to the fluorescence quenching ability of metallic nanoparticles: fluorescein, 6-aminofluorescein and tetramethylrhodamine (TAMRA)], surface complexing group (cyclic disulphide thioctic acid) and a chemical functionality for attachment of DNA (carboxyl group). Each of the linkers also contain poly(ethylene glycol) (PEG) (3 mer), which reduces non-specific adsorption of molecules to the surface of the nanoparticles and provides colloidal stability. The synthesized linkers were used to functionalize gold citrate (18 and 50 nm), silver citrate (40 nm) and silver EDTA (35 nm) nanoparticles. All of the conjugates exhibit high stability, gave good SERS responses at laser excitation frequencies of 514 and 633 nm and could be conjugated to amino-modified oligonucleotides in the presence of the commonly used (N-(3-dimethylaminopropyl)-N'-ethyl carbodiimide hydrochloride-EDC center dot HCl with N-hydroxysulfosuccinimide or 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride-DMT MM, which has not been used for bioconjugate preparation previously. This approach is less time consuming and less expensive than previously used protocols and does not require the formation of a mixed layer of oligonucleotides and Raman reporter on the metal surface. Additionally the presence of a reactive functionality within the linker structure makes it possible to conjugate the linker to other biomolecules of interest such as proteins. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.053
• 作为产物：
  描述：

  4-硝基邻苯二甲酸 、 间苯二酚 在 zinc(II) chloride 、 sodium hydrogen sulfide 、 sodium sulfide 作用下， 以 melt 为溶剂， 反应 26.0h， 以40%的产率得到5-氨基荧光素
  参考文献：
  名称：

  新型荧光素衍生物的荧光传感器性能：[2-吗啉-4-（6-氯-1,3,5,5-s-三嗪）-氨基]荧光素

  摘要：

  通过亲电取代合成了一种基于5-氨基荧光素的新型反应性荧光染料[2-吗啉-4-（6-氯-1,3,5-三嗪）-氨基]荧光素。研究了这种新型荧光团的光物理性质，溶剂效应，pH值敏感性和金属离子的作用。与5-氨基荧光素相比，新型荧光团显示出更强的荧光和更长的寿命。新型染料的荧光特性明显受溶剂和pH值的影响，并且在质子溶剂或碱性环境中表现出较强的荧光。此外，可以通过与金属离子特别是与Mg 2+形成络合物来增强荧光强度。。结果表明，荧光染料是用于溶剂，质子和金属离子的有前途的高效传感器。

  DOI：

  10.1002/bkcs.10551

文献信息

• Syntheses of Regioisomerically Pure 5- or 6-Halogenated Fluoresceins
  作者：Guan-Sheng Jiao、Jin Wook Han、Kevin Burgess

  DOI：10.1021/jo034724f

  日期：2003.10.1

  Three routes to regioisomerically pure 5- and 6-iodofluoresceins or 5- and 6-bromofluoresceins are described. The first, shown in Scheme 1, involves diazotization/iodination of the corresponding aminofluoresceins. In the second approach (Scheme 2) a mixture of regioisomeric fluoresceins was prepared, and the 5-bromo isomers were isolated as the ring closed diacetates 9b and 11 by fractional crystallization

  描述了区域异构纯的5-和6-碘荧光素或5-和6-溴荧光素的三种途径。方案1中显示的第一个涉及相应的氨基荧光素的重氮化/碘化。在第二种方法（方案2）中，制备了区域异构荧光素的混合物，并通过分步结晶分离了5溴异构体，成为闭环的二乙酸酯9b和11。方案3显示了5-碘荧光素的磺酸衍生物3和4的方法。这是三者中最方便的方法，由于与没有磺酸基的荧光素相比，磺基荧光素的水溶性更好，因此特别有用。
• FLUORESCENT SUBSTRATE FOR DETECTION OF ENZYMATIC ACTIVITY OF NITRILE-RELATED ENZYME
  申请人：Urano Yasuteru

  公开号：US20130065263A1

  公开（公告）日：2013-03-14

  The object of the present invention is to provide a fluorescent substrate for detecting the enzymatic activity of a nitrile-related enzyme. The present invention provides a compound represented by formula (I) and a fluorescent substrate for detecting the enzymatic activity of a nitrile-related enzyme, which comprises the compound.

  本发明的目的是提供一种用于检测腈相关酶的酶活性的荧光底物。本发明提供了一种由公式（I）表示的化合物和一种用于检测腈相关酶的酶活性的荧光底物，该荧光底物包括该化合物。
• Fluorescence Probes for Imaging Basic Carboxypeptidase Activity in Living Cells with High Intracellular Retention
  作者：Hirohisa Iwaki、Mako Kamiya、Minoru Kawatani、Ryosuke Kojima、Tatsuya Yamasoba、Yasuteru Urano

  DOI：10.1021/acs.analchem.0c04793

  日期：2021.2.23

  Basic carboxypeptidases (basic CPs) cleave the C-terminal basic amino acid of peptides, and their activity is upregulated in some types of cancers. Therefore, detecting the activity of basic CPs in living cells would be important not only for studying the physiological functions of these enzymes but also for visualization of cancerous tissues. Here, we report two fluorescein diacetate (FDA)-based activatable fluorescence probes, named 5ArgAF-FDA and 5LysAF-FDA, in which the substrate amino acid arginine or lysine is conjugated to the benzene moiety via an azoformyl linker. In live-cell fluorescence imaging of CPM, one of the seven basic CPs, 5ArgAF-FDA showed a larger intracellular fluorescence increase than did 5LysAF-FDA within a few minutes. This increase was inhibited by coincubation with 2-mercaptomethyl-3-guanidinoethylthiopropanoic acid (MGTA), an inhibitor of basic CPs. When 5ArgAF-FDA was applied to a coculture of two breast cancer cell lines with different CPM activities, the fluorescence increase in individual cells was correlated with the expression level of CPM, suggesting that 5ArgAF-FDA has the ability to distinguish cell lines having different levels of CPM activity, owing to its high intracellular retention. We believe these probes will be useful for imaging cancers with upregulated basic CP activity.

  碱性羧肽酶（碱性 CPs）能裂解肽的 C 端碱性氨基酸，在某些类型的癌症中，碱性 CPs 的活性会升高。因此，检测活细胞中碱性羧肽酶的活性不仅对研究这些酶的生理功能很重要，而且对癌症组织的可视化也很重要。在这里，我们报告了两种基于双乙酸荧光素（FDA）的可激活荧光探针，分别命名为 5ArgAF-FDA 和 5LysAF-FDA，其中底物氨基酸精氨酸或赖氨酸通过偶氮甲酰基连接物与苯分子共轭。在七种基本 CPs 之一 CPM 的活细胞荧光成像中，5ArgAF-FDA 在几分钟内显示出比 5LysAF-FDA 更大的细胞内荧光增加。与碱性氯化石蜡抑制剂 2-巯甲基-3-胍基乙基硫代丙酸（MGTA）同时使用可抑制这种增加。当将 5ArgAF-FDA 应用于两种具有不同 CPM 活性的乳腺癌细胞系的共培养时，单个细胞的荧光增加与 CPM 的表达水平相关，这表明 5ArgAF-FDA 由于其在细胞内的高滞留性，能够区分具有不同 CPM 活性水平的细胞系。我们相信，这些探针将有助于对基本 CP 活性上调的癌症进行成像。
• Fluorescein-Based Compounds And Their Use For Peptide Synthesis
  申请人：Balakirev Maxim

  公开号：US20080275215A1

  公开（公告）日：2008-11-06

  The present invention is related to new fluorescein derivatives, the method for producing such derivatives and their use for the synthesis of fluorogenic peptides and in particular protease substrates and peptide ligands.

  本发明涉及新的荧光素衍生物，以及制备这些衍生物的方法及其用于合成荧光基肽和特别是蛋白酶底物和肽配体的用途。
• Visible-Light-Mediated Radical Arylations Using a Fluorescein-Derived Diazonium Salt: Reactions Proceeding via an Intramolecular Forth and Back Electron Transfer
  作者：Nina Diesendorf、Pia Wenisch、Janina Oppl、Markus R. Heinrich

  DOI：10.1021/acs.orglett.2c03877

  日期：2023.1.13

  Functionalizations of arenes and alkenes via additive-free radical reactions using highly photosensitive, fluorescein-derived diazonium salts are described. The particular properties of the diazonium salts enable unique Meerwein-type carbohydroxylations of non-activated alkenes, which can be rationalized by a reaction mechanism involving forth and back electron transfer from and to the xanthene subunit

  描述了使用高光敏性、荧光素衍生的重氮盐通过加成自由基反应实现芳烃和烯烃的功能化。重氮盐的特殊性质使非活化烯烃能够进行独特的 Meerwein 型羧基化，这可以通过涉及荧光素部分的呫吨亚基的来回电子转移的反应机制来合理化。