(2,2,5-trimethyl-1,3-dioxan-5-yl)methyl 4-(3-(4-cyanophenyl)-5-(4-(3,3,13,13-tetramethyl-2,4,12,14-tetraoxa-8,17,23-trithia-20-azadispiro[5.3.5.9]tetracosan-20-yl)phenyl)-4,5-dihydro-1H-pyrazol-1-yl)benzene-1-sulfonate | 1335107-43-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2,2,5-trimethyl-1,3-dioxan-5-yl)methyl 4-(3-(4-cyanophenyl)-5-(4-(3,3,13,13-tetramethyl-2,4,12,14-tetraoxa-8,17,23-trithia-20-azadispiro[5.3.5.9]tetracosan-20-yl)phenyl)-4,5-dihydro-1H-pyrazol-1-yl)benzene-1-sulfonate
• 英文别名: (2,2,5-Trimethyl-1,3-dioxan-5-yl)methyl 4-[5-(4-cyanophenyl)-3-[4-(3,3,13,13-tetramethyl-2,4,12,14-tetraoxa-8,17,23-trithia-20-azadispiro[5.3.510.96]tetracosan-20-yl)phenyl]-3,4-dihydropyrazol-2-yl]benzenesulfonate；(2,2,5-trimethyl-1,3-dioxan-5-yl)methyl 4-[5-(4-cyanophenyl)-3-[4-(3,3,13,13-tetramethyl-2,4,12,14-tetraoxa-8,17,23-trithia-20-azadispiro[5.3.510.96]tetracosan-20-yl)phenyl]-3,4-dihydropyrazol-2-yl]benzenesulfonate
• CAS: 1335107-43-1
• 化学式: C₅₀H₆₆N₄O₉S₄
• 分子量: 995.359
• InChiKey: UMQYUHKZDULDIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  67
• 可旋转键数：
  8
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  226
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  (2,2,5-trimethyl-1,3-dioxan-5-yl)methyl 4-(3-(4-cyanophenyl)-5-(4-(3,3,13,13-tetramethyl-2,4,12,14-tetraoxa-8,17,23-trithia-20-azadispiro[5.3.5.9]tetracosan-20-yl)phenyl)-4,5-dihydro-1H-pyrazol-1-yl)benzene-1-sulfonate 在 水 、 三氟乙酸 、 氨 、 potassium tert-butylate 作用下， 以 水 、 四氢呋喃 、 二甲基亚砜 、 叔丁醇 为溶剂， 反应 1.23h， 以61%的产率得到4-(3-(4-cyanophenyl)-5-(4-(9,9,13,13-tetrakis(hydroxymethyl)-1,7,11-trithia-4-azacyclotetradecan-4-yl)phenyl)-4,5-dihydro-1H-pyrazol-1-yl)benzene-1-sulfonic acid ammonium salt
  参考文献：
  名称：

  Designed To Dissolve: Suppression of Colloidal Aggregation of Cu(I)-Selective Fluorescent Probes in Aqueous Buffer and In-Gel Detection of a Metallochaperone

  摘要：

  Due to the lipophilicity of the metal-ion receptor, previously reported Cu(I)-selective fluorescent probes form colloidal aggregates, as revealed by dynamic light scattering. To address this problem, we have developed a hydrophilic triarylpyrazoline-based fluorescent probe, CTAP-2, that dissolves directly in water and shows a rapid, reversible, and highly selective 65-fold fluorescence turn-on response to Cu(I) in aqueous solution. CTAP-2 proved to be sufficiently sensitive for direct in-gel detection of Cu(I) bound to the metallochaperone Atoxl, demonstrating the potential for cation-selective fluorescent probes to serve as tools in metalloproteomics for identifying proteins with readily accessible metal-binding sites.

  DOI：

  10.1021/ja207004v
• 作为产物：
  描述：

  N,N-二羟乙基苯胺 在 四氢吡咯 、 吡啶 、 4-甲基苯磺酸吡啶 、 caesium carbonate 、 sodium iodide 、 三氯氧磷 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 丁酮 、 苯 为溶剂， 反应 106.0h， 生成 (2,2,5-trimethyl-1,3-dioxan-5-yl)methyl 4-(3-(4-cyanophenyl)-5-(4-(3,3,13,13-tetramethyl-2,4,12,14-tetraoxa-8,17,23-trithia-20-azadispiro[5.3.5.9]tetracosan-20-yl)phenyl)-4,5-dihydro-1H-pyrazol-1-yl)benzene-1-sulfonate
  参考文献：
  名称：

  Designed To Dissolve: Suppression of Colloidal Aggregation of Cu(I)-Selective Fluorescent Probes in Aqueous Buffer and In-Gel Detection of a Metallochaperone

  摘要：

  Due to the lipophilicity of the metal-ion receptor, previously reported Cu(I)-selective fluorescent probes form colloidal aggregates, as revealed by dynamic light scattering. To address this problem, we have developed a hydrophilic triarylpyrazoline-based fluorescent probe, CTAP-2, that dissolves directly in water and shows a rapid, reversible, and highly selective 65-fold fluorescence turn-on response to Cu(I) in aqueous solution. CTAP-2 proved to be sufficiently sensitive for direct in-gel detection of Cu(I) bound to the metallochaperone Atoxl, demonstrating the potential for cation-selective fluorescent probes to serve as tools in metalloproteomics for identifying proteins with readily accessible metal-binding sites.

  DOI：

  10.1021/ja207004v

文献信息

• Designed To Dissolve: Suppression of Colloidal Aggregation of Cu(I)-Selective Fluorescent Probes in Aqueous Buffer and In-Gel Detection of a Metallochaperone
  作者：M. Thomas Morgan、Pritha Bagchi、Christoph J. Fahrni

  DOI：10.1021/ja207004v

  日期：2011.10.12

  Due to the lipophilicity of the metal-ion receptor, previously reported Cu(I)-selective fluorescent probes form colloidal aggregates, as revealed by dynamic light scattering. To address this problem, we have developed a hydrophilic triarylpyrazoline-based fluorescent probe, CTAP-2, that dissolves directly in water and shows a rapid, reversible, and highly selective 65-fold fluorescence turn-on response to Cu(I) in aqueous solution. CTAP-2 proved to be sufficiently sensitive for direct in-gel detection of Cu(I) bound to the metallochaperone Atoxl, demonstrating the potential for cation-selective fluorescent probes to serve as tools in metalloproteomics for identifying proteins with readily accessible metal-binding sites.