5-[(2E)-3-methoxyprop-2-enylidene]-1,3-dimethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione | 521060-40-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-[(2E)-3-methoxyprop-2-enylidene]-1,3-dimethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
• 英文别名: 5-[(E)-3-methoxyprop-2-enylidene]-1,3-dimethyl-2-sulfanylidene-1,3-diazinane-4,6-dione
• CAS: 521060-40-2
• 化学式: C₁₀H₁₂N₂O₃S
• 分子量: 240.283
• InChiKey: ZSHOPUNBANTPFM-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  81.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-[(2E)-3-methoxyprop-2-enylidene]-1,3-dimethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione 在 sodium acetate 作用下， 以 甲醇 、 氯仿 、 二甲基亚砜 为溶剂， 反应 12.67h， 生成 sodium 3-[(2Z)-6-(acetylamino)-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
• 作为产物：
  描述：

  1,3,3-三甲氧基丙烯 、 1,3-二甲基-2-硫代巴比妥酸 以 甲醇 、 氯仿 为溶剂， 反应 0.08h， 以75%的产率得到5-[(2E)-3-methoxyprop-2-enylidene]-1,3-dimethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
  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

• METHODS TO INCREASE THE PHOTOSTABILITY OF DYES
  申请人：Hahn Klaus

  公开号：US20110046000A1

  公开（公告）日：2011-02-24

  The presently disclosed subject matter provides dyes having an improved photostability, biosensors comprising such dyes, and methods of use thereof, including methods for detecting target molecules in a sample under test and for live-cell imaging. The dyes can include a binding member, including a biomolecule or fragments thereof, which can interact with target molecules of interest and can be specific to a given conformational state or covalent modification, e.g., phosphorylation, of the target molecule. The presently disclosed dyes can be used for detecting changes in the binding, conformational change, or posttranslational modification of the target molecule.

  所述主题提供了具有改善光稳定性的染料、包括此类染料的生物传感器以及其使用方法，包括用于检测样品中的靶分子和用于活细胞成像的方法。该染料可以包括结合成员，包括生物分子或其片段，其可以与感兴趣的靶分子相互作用，并且可以特定于给定的构象状态或靶分子的共价修饰，例如磷酸化。目前披露的染料可用于检测靶分子的结合、构象变化或后翻译修饰的变化。
• US8835632B2
  申请人：——

  公开号：US8835632B2

  公开（公告）日：2014-09-16
• [EN] SULFHYDRYL-REACTIVE, WATER SOLUBLE DYES<br/>[FR] COLORANTS HYDROSOLUBLES, RÉACTIFS AVEC LE SULFHYDRYLE
  申请人：SCRIPPS RESEARCH INST

  公开号：WO2008027075A2

  公开（公告）日：2008-03-06

  [EN] The invention relates to novel dye compounds and to methods of joining compounds, such as the dye compounds of the invention, to ulfhydryl-containing compounds.
  [FR] L'invention concerne de nouveaux composés colorants et des procédés de liaison de composés, par exemple les composés colorants selon l'invention, à des composés contenant du sulfhydryle.
• [EN] METHODS TO INCREASE THE PHOTOSTABILITY<br/>[FR] PROCÉDÉS POUR ACCROÎTRE LA PHOTOSTABILITÉ
  申请人：UNIV NORTH CAROLINA

  公开号：WO2008157762A2

  公开（公告）日：2008-12-24

  (EN) The presently disclosed subject matter provides dyes having an improved photostability, biosensors comprising such dyes, and methods of use thereof, including methods for detecting target molecules in a sample under test and for live- cell imaging. The dyes can include a binding member, including a biomolecule or fragments thereof, which can interact with target molecules of interest and can be specific to a given conformational state or covalent modification, e.g., phosphorylation, of the target molecule. The presently disclosed dyes can be used for detecting changes in the binding, conformational change, or posttranslational modification of the target molecule.(FR) La présente invention concerne des colorants qui présentent une meilleure photostabilité, des biocapteurs comprenant ces colorants et des procédés d'utilisation de ces derniers, y compris des procédés de détection de molécules cibles dans un échantillon soumis à un essai et pour l'imagerie de cellules vivantes. Les colorants peuvent comprendre un élément de liaison renfermant une biomolécule ou un fragment de cette dernière, qui peut interagir avec des molécules cibles présentant un intérêt et qui peuvent être spécifiques d'un état conformationnel donné ou d'une modification covalente donnée, par exemple, la phosphorylation, de la molécule cible. Les colorants selon la présente invention peuvent être utilisés pour détecter des changements concernant la liaison, le changement conformationnel ou la modification post-traduction de la molécule cible.
• Solvent-Sensitive Dyes to Report Protein Conformational Changes in Living Cells
  作者：Alexei Toutchkine、Vadim Kraynov、Klaus Hahn

  DOI：10.1021/ja0290882

  日期：2003.4.1

  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.