fluorescein-5-EX succinimidyl ester

• 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: fluorescein-5-EX succinimidyl ester
• 英文别名: 5-[[2-[3-(2,5-Dioxocyclopentyl)oxy-3-oxopropyl]sulfanylacetyl]amino]-2-(3-hydroxy-6-oxoxanthen-9-yl)benzoic acid；5-[[2-[3-(2,5-dioxocyclopentyl)oxy-3-oxopropyl]sulfanylacetyl]amino]-2-(3-hydroxy-6-oxoxanthen-9-yl)benzoic acid
• 化学式: C₃₀H₂₃NO₁₀S
• 分子量: 589.579
• InChiKey: BDMNVZJHBMSQTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  199
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  fluorescein-5-EX succinimidyl ester 、 tert-butyl N-[(2R,3R,4R,5S,6S)-2-[(2S,3S,4R,5R)-2-(2-aminoethylsulfanylmethyl)-5-[(1R,2R,3S,5R,6S)-2-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-6-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]oxan-2-yl]oxy-6-hydroxy-3,5-bis[(2-methylpropan-2-yl)oxycarbonylamino]cyclohexyl]oxy-4-hydroxyoxolan-3-yl]oxy-4,5-dihydroxy-6-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]oxan-3-yl]carbamate 在 4-二甲氨基吡啶 作用下， 以10 mg的产率得到
  参考文献：
  名称：

  Thermodynamics of Nucleic Acid “Shape Readout” by an Aminosugar

  摘要：

  Recognition of nucleic acids is important for our understanding of nucleic acid structure as well as for our understanding of nucleic acid protein interactions. In addition to the direct readout mechanisms of nucleic acids such as H-bonding, shape recognition of nucleic acids is being increasingly recognized as playing an equally important role in DNA recognition. Competition dialysis, UV, flourescent intercalator displacement (FID), computational docking, and calorimetry studies were conducted to study the interaction of neomycin with a variety of nucleic acid conformations (shapes). At pH 5.5, the results suggest the following. (1) Neomycin binds three RNA structures [16S A site rRNA, poly(rA).poly(rA), and poly(rA).poly(rU)] with high affinities (K-a similar to 10(7) M-1). (2) The binding of neomycin to A-form GC-rich oligomer d(A(2)G(15)C(15)T(2))(2) has an affinity comparable to those of RNA structures. (3) The binding of neomycin to DNA.RNA hybrids shows a 3-fold variance that can be attributed to their structural differences [for poly(dA).poly(rU), K-a = 9.4 x 10(6) M-1 and for poly(rA).poly(dT), K-a = 3.1 X 10(6) M-1. (4) The interaction of neomycin with DNA triplex poly(dA).2poly(dT) yields a binding affinity (K-a) of 2.4 X 10(5) M-1. (5) Poly(dA-dT)(2) shows the lowest association constant for all nucleic acids studied (K-a < 10(5)). (6) Neomycin binds to G-quadruplexes with Ka values of similar to 10(4)-10(5) M-1. (7) Computational studies show that the decrease in major groove width in the B to A transition correlates with increasing neomycin affinity. Neomycin's affinity for various nucleic acid structures can be ranked as follows: RNAs and GC-rich d(A(2)G(15)C(15)T(2))(2) structures > poly(dA).poly(rU) > poly(rA).poly(dT) > T-A-T triplex, G-quadruplex, B-form AT-rich, or GC-rich DNA sequences. The results illustrate the first example of a small molecule-based "shape readout" of different nucleic acid conformations.

  DOI：

  10.1021/bi201077h

文献信息

• Methods and compositions related to nucleic acid binding assays
  申请人：Nubad, LLC

  公开号：US10203334B2

  公开（公告）日：2019-02-12

  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.

  本文开发并公开了针对核酸（包括 DNA 和 RNA）等既定药物靶点的小分子荧光探针。这些核酸探针与多种 DNA 和 RNA 结构以及对核酸功能至关重要的位点（如 DNA 和 RNA 主要沟槽）结合。探针被其他结合剂（如小分子化合物和/或蛋白质）置换后，探针的荧光会发生变化，这种变化一旦被检测和分析，就会提供这些其他相关结合剂的结合信息。同样，探针与核酸结合后的荧光变化也可用于筛选不同序列和构象的核酸。本文公开的核酸探针和使用方法非常适用于小分子化合物、蛋白质和核酸文库的高通量筛选。
• Noninvasive Imaging of Cell Death Using an Hsp90 Ligand
  作者：Danielle Park、Anthony S. Don、Tania Massamiri、Amol Karwa、Beth Warner、Jan MacDonald、Christine Hemenway、Arati Naik、Kah-Tiong Kuan、Pierre J. Dilda、Jason W. H. Wong、Kevin Camphausen、Lori Chinen、Mary Dyszlewski、Philip J. Hogg

  DOI：10.1021/ja110226y

  日期：2011.3.9

  Cell death plays a central role in normal physiology and in disease. Common to apoptotic and necrotic cell death is the eventual loss of plasma membrane integrity. We have produced a small organoarsenical compound, 4-(N-(S-glutathionylacetyl)amino)phenylarsonous add, that rapidly accumulates in the cytosol of dying cells coincident with loss of plasma membrane integrity. The compound is retained in the cytosol predominantly by covalent reaction with the 90 kDa heat shock protein (Hsp90), the most abundant molecular chaperone of the eukaryotic cytoplasm. The organoarsenical was tagged with either optical or radioisotope reporting groups to image cell death in cultured cells and in murine tumors ex vivo and in situ. Tumor cell death in mice was noninvasively imaged by SPECT/CT using an (111)In-tagged compound. This versatile compound should enable the imaging of cell death in most experimental settings.
• 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.
• US9017943B2
  申请人：——

  公开号：US9017943B2

  公开（公告）日：2015-04-28
• US9410186B2
  申请人：——

  公开号：US9410186B2

  公开（公告）日：2016-08-09