4',5'-fluoresceindicarboxaldehyde

• 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: 4',5'-fluoresceindicarboxaldehyde
• 英文别名: 4',5'-fluorescein dialdehyde；2-(4,5-diformyl-3-hydroxy-6-oxoxanthen-9-yl)benzoic acid
• 化学式: C₂₂H₁₂O₇
• 分子量: 388.333
• InChiKey: LKLOGSNUDDRQEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  121.88
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4',5'-fluoresceindicarboxaldehyde 在 三乙酰氧基硼氢化钠 作用下， 以 乙酸乙酯 、 1,2-二氯乙烷 为溶剂， 反应 17.0h， 生成 2-[6-hydroxy-3-oxo-4,5-bis(quinolin-8-ylaminomethyl)-3H-xanthen-9-yl]benzoic acid
  参考文献：
  名称：

  QZ1 and QZ2:  Rapid, Reversible Quinoline-Derivatized Fluoresceins for Sensing Biological Zn(II)

  摘要：

  QZ1, 2-[2-chloro-6-hydroxy-3-oxo-5-(quinolin-8-ylaminomethyl)-3H-xanthen-9-yl]benzoic acid, and QZ2, 2-[6-hydroxy-3-oxo-4,5-bis-(quinolin-8-ylaminomethyl)-3H-xanthen-9-yl]benzoic acid, two fluorescein-based dyes derivatized with 8-aminoquinoline, have been prepared and their photophysical, thermodynamic, and zinc-binding kinetic properties determined. Because of their low background fluorescence and highly emissive Zn(II) complexes, QZ1 and QZ2 have a large dynamic range, with similar to 42- and similar to 150-fold fluorescence enhancements upon Zn(II) coordination, respectively. These dyes have micromolar K-d values for Zn(II) and are selective for Zn(II) over biologically relevant concentrations of the alkali and alkaline earth metals. The Zn(II) complexes also fluoresce brightly in the presence of excess Mn(II), Fe(II), Co(II), Cd(II), and Hg(II), offering improved specificity for Zn(II) over di(2-picolyl)amine-based Zn(II) sensors. Stopped-flow kinetic investigations indicate that QZ1 and QZ2 bind Zn(II) with k(on) values of (3-4) x 10(6) M-1 s(-1), compared to(6-8) x 10(5) M-1 s(-1) for select ZP (Zinpyr) dyes, at 4.3 degrees C. Dissociation of Zn(ll) from QZ1 and QZ2 occurs with k(off) values of 150 and 160 s(-1), over 5 orders of magnitude larger than those for ZP probes, achieving reversibility on the biological (millisecond) time scale. Laser scanning confocal and two-photon microscopy studies reveal that QZ2 is cell-permeable and Zn(II)-responsive in vivo. Because of its weaker affinity for Zn(II), QZ2 responds to higher concentrations of intracellular Zn(ll) than members of the ZP family, illustrating that binding affinity is an important parameter for Zn(II) detection in vivo.

  DOI：

  10.1021/ja052184t
• 作为产物：
  描述：

  氯仿 、 荧光素 在 sodium hydroxide 、 15-冠醚-5 作用下， 反应 5.0h， 以34.1%的产率得到4-fluoresceincarboxaldehyde
  参考文献：
  名称：

  Detection of Homocysteine and Cysteine

  摘要：

  At elevated levels, homocysteine (Hey, 1) is a risk factor for cardiovascular diseases, Alzheimer's disease, neural tube defects, and osteoporosis. Both 1 and cysteine (Cys, 3) are linked to neurotoxicity. The biochemical mechanisms by which 1 and 3 are involved in disease states are relatively unclear. Herein, we describe simple methods for detecting either Hey or Cys in the visible spectral region with the highest selectivity reported to date without using biochemical techniques or preparative separations. Simple methods and readily available reagents allow for the detection of Cys and Hey in the range of their physiologically relevant levels. New HPLC postcolumn detection methods for biological thiols are reported. The potential biomedical relevance of the chemical mechanisms involved in the detection of 1 is described.

  DOI：

  10.1021/ja054962n

文献信息

• Visualization of nitric oxide production in the mouse main olfactory bulb by a cell-trappable copper(II) fluorescent probe
  作者：Lindsey E. McQuade、Jie Ma、Graeme Lowe、Ambarish Ghatpande、Alan Gelperin、Stephen J. Lippard

  DOI：10.1073/pnas.0914794107

  日期：2010.5.11

  We report the visualization of NO production using fluorescence in tissue slices of the mouse main olfactory bulb. This discovery was possible through the use of a novel, cell-trappable probe for intracellular nitric oxide detection based on a symmetric scaffold with two NO-reactive sites. Ester moieties installed onto the fluorescent probe are cleaved by intracellular esterases to yield the corresponding negatively charged, cell-impermeable acids. The trappable probe Cu ₂ (FL2E) and the membrane-impermeable acid derivative Cu ₂ (FL2A) respond rapidly and selectively to NO in buffers that simulate biological conditions, and application of Cu ₂ (FL2E) leads to detection of endogenously produced NO in cell cultures and olfactory bulb brain slices.

  我们报告了使用荧光技术在小鼠主嗅球组织切片中观察NO产生的结果。这项发现是通过使用一种基于对称支架的新型细胞可捕获探针来检测细胞内一氧化氮而实现的。将酯基安装到荧光探针上，细胞内酯酶将其裂解为相应的带负电、不可渗透的酸。可捕获的探针Cu ₂ (FL2E)和膜不可渗透的酸衍生物Cu ₂ (FL2A)在模拟生物条件的缓冲液中对NO做出快速、选择性的反应，应用Cu ₂ (FL2E)可检测到细胞培养和嗅球脑片中内源性产生的NO。
• Visual Detection of Cysteine and Homocysteine
  作者：Oleksandr Rusin、Nadia N. St. Luce、Rezik A. Agbaria、Jorge O. Escobedo、Shan Jiang、Isiah M. Warner、Fareed B. Dawan、Kun Lian、Robert M. Strongin

  DOI：10.1021/ja036297t

  日期：2004.1.1

  The determination of cysteine and homocysteine levels is of great current interest for the monitoring of desease states. A new colorimetric method for the simultaneous detection of l-cysteine and l-homocysteine has been developed. A fluorescein derivative reacts with the above amino acids, producing their respective thiazolidines resulting in color changes. Interference from other amino acids and proteins is minimal.
• Zinspy Sensors with Enhanced Dynamic Range for Imaging Neuronal Cell Zinc Uptake and Mobilization
  作者：Elizabeth M. Nolan、Jubin W. Ryu、Jacek Jaworski、Rodney P. Feazell、Morgan Sheng、Stephen J. Lippard

  DOI：10.1021/ja065759a

  日期：2006.12.1

  Thiophene moieties were incorporated into previously described Zinspy (ZS) fluorescent Zn(II) sensor motifs (Nolan, E. M.; Lippard, S. J. Inorg. Chem. 2004, 43, 8310-8317) to provide enhanced fluorescence properties, low-micromolar dissociation constants for Zn(II), and improved Zn(II) selectivity. Halogenation of the xanthenone and benzoate moieties of the fluorescein platform systematically modulates the excitation and emission profiles, pH-dependent fluorescence, Zn(II) affinity, and Zn(II) complexation rates, offering a general strategy for tuning multiple properties of xanthenone- based metal ion sensors. Extensive biological studies in cultured cells and primary neuronal cultures demonstrate 2-6-hydroxy-3-oxo- 4,5-bis[(pyridin-2-ylmethylthiophen-2-ylmethylamino)methyl]-3H-xanthen-9-yl}benzoic acid (ZS5) to be a versatile imaging tool for detecting Zn(II) in vivo. ZS5 localizes to the mitochondria of HeLa cells and allows visualization of glutamate-mediated Zn(II) uptake in dendrites and Zn(II) release resulting from nitrosative stress in neurons.
• Fluorescence-Based Nitric Oxide Sensing by Cu(II) Complexes That Can Be Trapped in Living Cells
  作者：Lindsey E. McQuade、Stephen J. Lippard

  DOI：10.1021/ic100802q

  日期：2010.8.16

  A series of symmetrical, fluorescein-derived ligands appended with two derivatized 2-methyl-8-aminoquinolines were prepared and spectroscopically characterized. The ligands FL2, FL2E, and FL2A were designed to improve the dynamic range of previously described asymmetric systems, and the copper complex Cu-2(FL2E) was constructed as a trappable NO probe that is hydrolyzed intracellularly to form Cu-2(FL2A). The ligands themselves are only weakly emissive, and the completely quenched Cu(II) complexes, generated in situ by combining each ligand with 2 equiv of CuCl2, were investigated as fluorescent probes for nitric oxide. Upon introduction of excess NO under anaerobic conditions to buffered solutions of Cu-2(FL2), Cu-2(FL2E), and Cu-2(FL2A), the fluorescence increased by factors of 23 +/- 3, 17 +/- 2, and 27 +/- 3, respectively. The corresponding rate constants for fluorescence turn-on were determined to be 0.4 +/- 0, 0.35 +/- 0.05, and 0.6 +/- 0.1 min(-1). The probes are highly specific for NO over other biologically relevant reactive oxygen and nitrogen species, as well as Zn(II), the metal ion for which similar probes were designed to detect.
• Colorimetric and Fluorometric Determination of Homocysteine and Cysteine
  申请人：Strongin Robert M.

  公开号：US20080261315A1

  公开（公告）日：2008-10-23

  Colorimetric and fluorometric methods are disclosed for the rapid, accurate, selective, and inexpensive detection of homocysteine, or of homocysteine and cysteine, or of cysteine. The methods may be employed with materials that are readily available commercially. The novel methods are selective for homocysteine, for cysteine, or for total homocysteine and cysteine, and do not cross-react substantially with chemically-related species such as glutathione. The homocysteine-selective method does not have substantial cross-reactivity to the very closely related species cysteine. The cysteine-selective method does not have substantial cross-reactivity to the very closely related species homocysteine. The methods may be used, for example, in a direct assay of human blood plasma for homocysteine levels.