eosin 5-isothiocyanate | 890090-90-1

• 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: eosin 5-isothiocyanate
• 英文别名: EITC；eosin isothiocyanate；Eosin-5-isothiocyanate；5-isothiocyanato-2-(2,4,5,7-tetrabromo-3-hydroxy-6-oxoxanthen-9-yl)benzoic acid
• CAS: 890090-90-1
• 化学式: C₂₁H₇Br₄NO₅S
• 分子量: 704.972
• InChiKey: MCXYFYWNOWPDMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  128
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  eosin 5-isothiocyanate 、 L-谷胱甘肽 (氧化型) 以 aq. phosphate buffer 为溶剂， 以80%的产率得到dieosinglutathione disulfide
  参考文献：
  名称：

  Activity assays of mammalian thioredoxin and thioredoxin reductase: Fluorescent disulfide substrates, mechanisms, and use with tissue samples

  摘要：

  Thioredoxin (Trx) is a protein disulfide reductase that, together with nicotinamide adenine dinucleotide phosphate (NADPH) and thioredoxin reductase (TrxR), controls oxidative stress or redox signaling via thiol redox control. Human cytosolic Trx1 has Cys32 and Cys35 as the active site and three additional cysteine residues (Cys62, Cys69, and Cys73), which by oxidation generates inactive Cys62 to Cys69 two-disulfide Trx. This, combined with TrxR with a broad substrate specificity, complicates assays of mammalian Trx and TrxR. We sought to understand the autoregulation of Trx and TrxR and to generate new methods for quantification of Trx and TrxR. We optimized the synthesis of two fluorescent substrates, di-eosin-glutathione disulfide (Di-E-GSSG) and fluorescein isothiocyanate-labeled insulin (FiTC-insulin), which displayed higher fluorescence on disulfide reduction. Di-E-GSSG showed a very large increase in fluorescence quantum yield but had a relatively low affinity for Trx and was also a weak direct substrate for TrxR, in contrast to GSSG. FiTC-insulin was used to develop highly sensitive assays for TrxR and Trx. Reproducible conditions were developed for reactivation of modified Trx, commonly present in frozen or oxidized samples. Trx in cell extracts and tissue samples, including plasma and serum, were subsequently analyzed, showing highly reproducible results and allowing measurement of trace amounts of Trx. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.ab.2013.12.025

文献信息

• Site-directed attachment of photoexcitable spin labels for light-induced pulsed dipolar spectroscopy
  作者：Lara Williams、Sonja Tischlik、Andreas Scherer、Jörg Wolfram Anselm Fischer、Malte Drescher

  DOI：10.1039/d0cc03101a

  日期：——

  Photoexcited triplet states are gaining popularity as spin labels in pulsed electron paramagnetic resonance (EPR) spectroscopy. Here, we demonstrate that the fluorophores Eosin Y, Rose Bengal and Atto Thio12 are suitable markers for distance determination by laser-induced magnetic dipole (LaserIMD) spectroscopy in proteins that lack an intrinsic photoexcitable center.

  光激发的三重态在脉冲电子顺磁共振（EPR）光谱中作为自旋标记物越来越受欢迎。在这里，我们证明荧光团曙红Y，孟加拉红和Atto Thio12是合适的标记物，用于通过激光诱导的磁偶极（LaserIMD）光谱法在缺乏固有光激发中心的蛋白质中确定距离。
• Photoinduced Electron Transfer for an Eosin-Tyrosine Conjugate. Activity of the Tyrosinate Anion in Long Range Electron Transfer in a Protein-like Polymer Matrix
  作者：Guilford Jones、Zhiming Feng、Churl Oh

  DOI：10.1021/j100012a001

  日期：1995.3

  The xanthene dye eosin Y has been modified via a thiohydantoin link to the amine terminus of the amino acid L-tyrosine. Photochemical electron transfer involving the singlet state of the dye and the attached phenol-containing residue led to a reduction in eosin fluorescence quantum yield and lifetime for aqueous solutions at elevated pH. The conjugate provided an electron transfer product of relatively long lifetime (1 mu s range) observed by flash photolysis of solutions at pH 12.0, conditions under which the tyrosine moiety is ionized. The effects of binding of the conjugate in the polymer poly(vinylpyrrolidone) (PVP) on the rates of electron transfer of species of different charge type were examined.
• METHODS AND COMPOSITIONS RELATED TO NUCLEIC ACID BINDING ASSAYS
  申请人：Nubad, LLC

  公开号：US20140024137A1

  公开（公告）日：2014-01-23

  Small molecule fluorescent probes for established drug targets such as nucleic acids including DNA and RNA has been developed and disclosed herein. These nucleic acid probes bind to multiple DNA and RNA structures, and to sites crucial for nucleic acid function, such as DNA and RNA major grooves. Displacement of the probes by other binders such as small molecule compounds and/or proteins illicits a fluorescence change in the probe that once detected and analyzed provide binding information of these other binders of interest. Similarly, changes in fluorescence upon binding of the probes to nucleic acid have been applied to screen nucleic acid of different sequence and conformation. The nucleic acid probes and method of uses disclosed herein are advantageously suitable for high-through put screening of libraries of small molecule compounds, proteins, and nucleic acids.
• US8652778B2
  申请人：——

  公开号：US8652778B2

  公开（公告）日：2014-02-18
• US9017943B2
  申请人：——

  公开号：US9017943B2

  公开（公告）日：2015-04-28