8-[4-(Benzotriazol-1-yl)phenyl]-2,2-difluoro-4,6,10,12-tetramethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene | 850534-68-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 8-[4-(Benzotriazol-1-yl)phenyl]-2,2-difluoro-4,6,10,12-tetramethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene
• 英文别名: 8-[4-(benzotriazol-1-yl)phenyl]-2,2-difluoro-4,6,10,12-tetramethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene
• CAS: 850534-68-8
• 化学式: C₂₅H₂₂BF₂N₅
• 分子量: 441.291
• InChiKey: DLSFAIAIRZYBNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.27
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  38.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,3,5,7-tetramethyl-8-(4'-aminophenyl-N-(2''-amino)-phenyl)-difluoroboradiaza-s-indacene 、 氧化亚氮 在 氧气 作用下， 以 水 为溶剂， 生成 8-[4-(Benzotriazol-1-yl)phenyl]-2,2-difluoro-4,6,10,12-tetramethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene
  参考文献：
  名称：

  Design, synthesis and characterization of a novel fluorescent probe for nitric oxide based on difluoroboradiaza-s-indacene fluorophore

  摘要：

  Nitric oxide (NO) is a gaseous. free radical, which plays a role as an intracellular second messenger and a diffusible intercellular messenger. To obtain evidence for NO function in vivo, 1,3,5,7-tetramethyl-8-(4'-aminophenyl-N-(2"-amino)-phenzyl)-difluoroboradiaza-s-indacene (TMAPABODIPY) was designed and synthesized as a fluorescent probe for nitric oxide, which features high photostability and no pH dependency over a wide pH range. The fluorescence of TMAPABODIPY itself is very strong. When TMAPABODIPY traps NO in the presence of dioxygen, the weak fluorescent triazole form is obtained, which offers the advantages of specificity, and sensitivity for direct detection of NO. The relationship was obtained between the quenching fluorescence intensity and NO concentration in the range 0.02-4.0 mu mol l(-1). The detection limit is 5 nmol l(-1) (S/N = 3). The proposed method has been used to monitor the release of NO from S-nitrosocysteine, a NO-releasing agent. (c) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2004.05.041

文献信息

• Design, synthesis and characterization of a novel fluorescent probe for nitric oxide based on difluoroboradiaza-s-indacene fluorophore
  作者：Xian Zhang、Hua-shan Zhang

  DOI：10.1016/j.saa.2004.05.041

  日期：2005.4

  Nitric oxide (NO) is a gaseous. free radical, which plays a role as an intracellular second messenger and a diffusible intercellular messenger. To obtain evidence for NO function in vivo, 1,3,5,7-tetramethyl-8-(4'-aminophenyl-N-(2"-amino)-phenzyl)-difluoroboradiaza-s-indacene (TMAPABODIPY) was designed and synthesized as a fluorescent probe for nitric oxide, which features high photostability and no pH dependency over a wide pH range. The fluorescence of TMAPABODIPY itself is very strong. When TMAPABODIPY traps NO in the presence of dioxygen, the weak fluorescent triazole form is obtained, which offers the advantages of specificity, and sensitivity for direct detection of NO. The relationship was obtained between the quenching fluorescence intensity and NO concentration in the range 0.02-4.0 mu mol l(-1). The detection limit is 5 nmol l(-1) (S/N = 3). The proposed method has been used to monitor the release of NO from S-nitrosocysteine, a NO-releasing agent. (c) 2004 Elsevier B.V. All rights reserved.