6-O-(carboxymethyl)fluorescein ethyl ester | 191791-17-0

• 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-O-(carboxymethyl)fluorescein ethyl ester
• 英文别名: 2-((9-(2-(ethoxycarbonyl)phenyl)-3-oxo-3H-xanthen-6-yl)oxy)acetic acid；2-[9-(2-ethoxycarbonylphenyl)-6-oxoxanthen-3-yl]oxyacetic acid
• CAS: 191791-17-0
• 化学式: C₂₄H₁₈O₇
• 分子量: 418.403
• InChiKey: PUGOKYOQJONOGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  99.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-O-(carboxymethyl)fluorescein ethyl ester 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 96.03h， 生成 2-aminoethoxy-6-O-(carbonylmethyl)fluorecein ethyl ester
  参考文献：
  名称：

  A new selective fluorogenic probe for trivalent cations

  摘要：

  报告了一种新的选择性变色荧光探针，用于检测Fe3+、Cr3+和Al3+。检测限在微摩尔范围内，当用紫外光照射时，可用肉眼观察到荧光响应。二价阳离子未观察到反应。

  DOI：

  10.1039/c2cc17184h
• 作为产物：
  描述：

  fluorescein free acid 在 硫酸 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.67h， 生成 6-O-(carboxymethyl)fluorescein ethyl ester
  参考文献：
  名称：

  A new selective fluorogenic probe for trivalent cations

  摘要：

  报告了一种新的选择性变色荧光探针，用于检测Fe3+、Cr3+和Al3+。检测限在微摩尔范围内，当用紫外光照射时，可用肉眼观察到荧光响应。二价阳离子未观察到反应。

  DOI：

  10.1039/c2cc17184h

文献信息

• Fluorogenic probes to monitor cytosolic phospholipase A₂ activity
  作者：Cheng Yang Ng、Timothy Xiong Wei Kwok、Francis Chee Kuan Tan、Chian-Ming Low、Yulin Lam

  DOI：10.1039/c6cc09305a

  日期：——

  Arachidonic acid derivatives equipped with either one or two fluorescent groups attached to the tip of the alkyl chains were synthesized and shown to function as inhibitor and substrate probes...

  合成了带有一个或两个连接在烷基链末端的荧光基团的花生四烯酸衍生物，并显示出其作为抑制剂和底物探针的功能。
• 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。
• A “Ready-To-Use” fluorescent-labelled-cysteine-TBTP (4-thiobutyltriphenylphosphonium) synthon to investigate the delivery of non-permeable PNA (peptide nucleic acids)-based compounds to cells
  作者：Mohamed Mehiri、Sergio Caldarelli、Audrey Di Giorgio、Thibault Barouillet、Alain Doglio、Roger Condom、Nadia Patino

  DOI：10.1016/j.bioorg.2007.01.002

  日期：2007.8

  This paper reports: (i) the facile synthesis of a cysteine synthon incorporating both a fluorescent group and a triphenylphosphonium derivative (TBTP) via the formation of a disulphide bond, which can subsequently undergo facile intracellular scission, (ii) the direct conjugation of this synthon to a non-permeable drug, (a cyclic PNA (peptide nucleic acid)-based compound has been chosen as a model), and (iii) that this conjugation enables the efficient homogenous delivery of the otherwise non-permeable cyclic PNA into the cytoplasm of cells, as demonstrated by fluorescence microscopy. Our results indicate that this fluorescent-labelled cysteine-TBTP synthon can provide a very useful tool for exploring the cellular uptake of a large range of molecules of biological interest, containing only a single reactive function. The preparation of an activated TBTP derivative is also described and this procedure could be widely used to introduce a TBTP cation to any thio-containing molecule. (c) 2007 Elsevier Inc. All rights reserved.
• Synthesis of SERS active nanoparticles for detection of biomolecules
  作者：Joanna Wrzesien、Duncan Graham

  DOI：10.1016/j.tet.2011.11.053

  日期：2012.1

  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.
• A new selective fluorogenic probe for trivalent cations
  作者：Andrea Barba-Bon、Ana M. Costero、Salvador Gil、Margarita Parra、Juan Soto、Ramón Martínez-Máñez、Félix Sancenón

  DOI：10.1039/c2cc17184h

  日期：——

  A new selective chromo-fluorogenic probe for Fe3+, Cr3+ and Al3+ is reported. Detection limits are in the μM range and the fluorogenic sensing ability could be observed by the naked eye when illuminated with UV-light. No response is observed with divalent cations.

  报告了一种新的选择性变色荧光探针，用于检测Fe3+、Cr3+和Al3+。检测限在微摩尔范围内，当用紫外光照射时，可用肉眼观察到荧光响应。二价阳离子未观察到反应。