sodium 3-[(2Z)-6-amino-2-[(2E)-4-(1,3-dimethyl-4,6-dioxo-2-thioxotetrahydropyrimidin-5(2H)-ylidene)but-2-enylidene]-1,3-benzothiazol-3(2H)-yl]propane-1-sulfonate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: sodium 3-[(2Z)-6-amino-2-[(2E)-4-(1,3-dimethyl-4,6-dioxo-2-thioxotetrahydropyrimidin-5(2H)-ylidene)but-2-enylidene]-1,3-benzothiazol-3(2H)-yl]propane-1-sulfonate
• 英文别名: sodium;3-[(2Z)-6-amino-2-[(E)-4-(1,3-dimethyl-4,6-dioxo-2-sulfanylidene-1,3-diazinan-5-ylidene)but-2-enylidene]-1,3-benzothiazol-3-yl]propane-1-sulfonate
• 化学式: C₂₀H₂₁N₄O₅S₃*Na
• 分子量: 516.598
• InChiKey: NFZLYSSNNPKICO-DOGFWTGWSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.34
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  193
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  sodium 3-[(2Z)-6-amino-2-[(2E)-4-(1,3-dimethyl-4,6-dioxo-2-thioxotetrahydropyrimidin-5(2H)-ylidene)but-2-enylidene]-1,3-benzothiazol-3(2H)-yl]propane-1-sulfonate 在 三乙胺 、 sodium iodide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 sodium 3-[(2Z)-2-[(2E)-4-(1,3-dimethyl-4,6-dioxo-2-thioxotetrahydropyrimidin-5(2H)-ylidene)but-2-enylidene]-6-[(iodoacetyl)amino]-1,3-benzothiazol-3(2H)-yl]propane-1-sulfonate
  参考文献：
  名称：

  Solvent-Sensitive Dyes to Report Protein Conformational Changes in Living Cells

  摘要：

  Covalent attachment of solvent-sensitive fluorescent dyes to proteins is a powerful tool for studying protein conformational changes, ligand binding, or posttranslational modifications. We report here new merocyanine dyes that make possible the quantitation of such protein activities in individual living cells. The quantum yield of the new dyes is sharply dependent on solvent polarity or viscosity, enabling them to report changes in their protein environment. This is combined with other stringent requirements needed in a live cell imaging dye, including appropriate photophysical properties (excitation >590 nm, high fluorescence quantum yield, high extinction coefficient), good photostability, minimal aggregation in water, and excellent water solubility. The dyes were derivatized with iodoacetamide and succinimidyl ester side chains for site-selective covalent attachment to proteins. A novel biosensor of Cdc42 activation made with one of the new dyes showed a 3-fold increase in fluorescence intensity in response to GTP-binding by Cdc42. The dyes reported here should be useful in the preparation of live cell biosensors for a diverse range of protein activities.

  DOI：

  10.1021/ja0290882
• 作为产物：
  描述：

  1,3-二甲基-2-硫代巴比妥酸 在 sodium acetate 作用下， 以 甲醇 、 氯仿 、 二甲基亚砜 为溶剂， 反应 0.75h， 生成 sodium 3-[(2Z)-6-amino-2-[(2E)-4-(1,3-dimethyl-4,6-dioxo-2-thioxotetrahydropyrimidin-5(2H)-ylidene)but-2-enylidene]-1,3-benzothiazol-3(2H)-yl]propane-1-sulfonate
  参考文献：
  名称：

  Solvent-Sensitive Dyes to Report Protein Conformational Changes in Living Cells

  摘要：

  Covalent attachment of solvent-sensitive fluorescent dyes to proteins is a powerful tool for studying protein conformational changes, ligand binding, or posttranslational modifications. We report here new merocyanine dyes that make possible the quantitation of such protein activities in individual living cells. The quantum yield of the new dyes is sharply dependent on solvent polarity or viscosity, enabling them to report changes in their protein environment. This is combined with other stringent requirements needed in a live cell imaging dye, including appropriate photophysical properties (excitation >590 nm, high fluorescence quantum yield, high extinction coefficient), good photostability, minimal aggregation in water, and excellent water solubility. The dyes were derivatized with iodoacetamide and succinimidyl ester side chains for site-selective covalent attachment to proteins. A novel biosensor of Cdc42 activation made with one of the new dyes showed a 3-fold increase in fluorescence intensity in response to GTP-binding by Cdc42. The dyes reported here should be useful in the preparation of live cell biosensors for a diverse range of protein activities.

  DOI：

  10.1021/ja0290882

文献信息

• Live cell biosensors
  申请人：Hahn M. Klaus

  公开号：US20060029946A1

  公开（公告）日：2006-02-09

  The invention provides dyes, biosensors, and methods for using the dyes and biosensors to detect selected target molecules. The biosensors have a binding domain and a dye, or a dye which is attached directly to the target of interest. Binding domains contemplated by the invention include biomolecules or fragments of biomolecules that interact with target molecules of interest and can be specific to a given conformational state or covalent modification of the molecule (e.g. phosphorylation). In one embodiment, the binding domain of a biosensor is a single chain variable fragment (scFv) with a dye of the invention linked to a CDR3 region. The invention also provides environmentally sensitive dyes useful for detecting changes in the binding, conformational change, or posttranslational modification of the selected target.

  本发明提供染料、生物传感器及其使用方法，用于检测选定的目标分子。生物传感器具有结合域和染料，或者染料直接附着于感兴趣的目标上。本发明考虑的结合域包括与目标分子相互作用的生物分子或生物分子片段，可以特异性地针对分子的给定构象状态或共价修饰（例如磷酸化）。在一种实施方式中，生物传感器的结合域是单链可变片段（scFv），具有本发明的染料链接到CDR3区域。本发明还提供对环境敏感的染料，用于检测选定目标的结合、构象变化或翻译后修饰的变化。
• US7592188B2
  申请人：——

  公开号：US7592188B2

  公开（公告）日：2009-09-22