9H-fluoren-9-ylmethyl 2-methyl-3-(3-sulfonatopropyl)-1,3-benzothiazol-6-ylcarbamate | 521060-43-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9H-fluoren-9-ylmethyl 2-methyl-3-(3-sulfonatopropyl)-1,3-benzothiazol-6-ylcarbamate
• CAS: 521060-43-5
• 化学式: C₂₆H₂₄N₂O₅S₂
• 分子量: 508.619
• InChiKey: FCFZQYPYEYUZMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.79
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  99.41
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  9H-fluoren-9-ylmethyl 2-methyl-3-(3-sulfonatopropyl)-1,3-benzothiazol-6-ylcarbamate 在 sodium acetate 作用下， 以 甲醇 、 氯仿 、 二甲基亚砜 为溶剂， 反应 0.67h， 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
• 作为产物：
  描述：

  1,3-丙烷磺内酯 、 9H-fluoren-9-ylmethyl 2-methyl-1,3-benzothiazol-6-ylcarbamate 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以87%的产率得到9H-fluoren-9-ylmethyl 2-methyl-3-(3-sulfonatopropyl)-1,3-benzothiazol-6-ylcarbamate
  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