8-(3',4'-diaminophenyl)-difluoroboradiaza-s-indacene

• 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: 8-(3',4'-diaminophenyl)-difluoroboradiaza-s-indacene
• 英文别名: 8-(3',4'-diaminophenyl)-difluoroboradiaza-S-indacence；DABODIPY；4-(2,2-Difluoro-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaen-8-yl)benzene-1,2-diamine；4-(2,2-difluoro-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaen-8-yl)benzene-1,2-diamine
• 化学式: C₁₅H₁₃BF₂N₄
• 分子量: 298.103
• InChiKey: GFAQASMPTPDWCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  8-(3',4'-diaminophenyl)-difluoroboradiaza-s-indacene 、 N-(N-L-γ-谷氨酰基-S-亚硝基-L-半胱氨酰----甘氨酸 在 phosphate buffered saline 、 氧气 、 mercury dichloride 作用下， 以 水 为溶剂， 生成 DABODIPY-T
  参考文献：
  名称：

  Ultra-trace determination of S-nitrosothiols in blood samples by spectrofluorimetry with 8-(3′,4′-diaminophenyl)-difluoroboradiaza-s-indacene

  摘要：

  increasing evidence suggests that S-nitrosothiols (RSNO) may represent naturally occurring nitric oxide (NO) surrogates and function as intermediates in NO metabolism. In this work, a simple, sensitive, and selective micromethod is developed and validated for quantification of RSNO. A fluorescent probe 8-(3',4'-diaminophenyl)-difluoroboradiaza-s-indacence (DABODIPY) is firstly used to label RSNO. The derivatization reaction is performed in aqueous medium at 30 degrees C for 15 min in the presence of 6 x 10(-5) mol L-1 Hg2+ and the derivative is detected by fluorescence at lambda(ex)/lambda(em) = 500/510 nm. A linear function of concentration in the range of (2.0-600.0) x 10(-8) mol L-1 is observed with a correlation coefficient of 0.9992 and detection limit of 1.2 x 10(-9) mol L-1 (S/N = 3). This technique has been successfully applied to quantify RSNO in some human blood samples including healthy persons and patients suffering from cardiovascular diseases. (C) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2007.04.020
• 作为产物：
  描述：

  盐酸 、 、 一水合肼 在 catalyst: Pd-C 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 8-(3',4'-diaminophenyl)-difluoroboradiaza-s-indacene
  参考文献：
  名称：

  Development of a novel fluorescent probe for nitric oxide detection: 8-(3′,4′-diaminophenyl)-difluoroboradiaza-S-indacence

  摘要：

  A novel fluorescent probe, 8-(3',4'-diaminophenyl)-difluoroboradiaza-S-indacence (DABODIPY), was designed and synthesized for monitoring nitric oxide production, which features high photostability and no pH dependency over a wide pH range. The fluorescence of 8-(3',4'-diaminophenyl)-difluoroboradiaza-S-indacence is very low, however, when the probe traps nitric oxide (NO) in the presence of dioxygen, the strong fluorescent triazole form is obtained, which offers the advantages of specificity, and sensitivity for direct detection of NO. Calibration using various concentrations of NO showed the method has good linearity (0.08-4.00 mumol l(-1)) and its detection limit is 10 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 Published by Elsevier B.V.

  DOI：

  10.1016/j.saa.2004.02.028

文献信息

• Ultra-trace determination of S-nitrosothiols in blood samples by spectrofluorimetry with 8-(3′,4′-diaminophenyl)-difluoroboradiaza-s-indacene
  作者：Ke-Jing Huang、Chun-Xuan Xu、Wan-Zhen Xie、Hua-Shan Zhang、Hong Wang

  DOI：10.1016/j.saa.2007.04.020

  日期：2008.2

  increasing evidence suggests that S-nitrosothiols (RSNO) may represent naturally occurring nitric oxide (NO) surrogates and function as intermediates in NO metabolism. In this work, a simple, sensitive, and selective micromethod is developed and validated for quantification of RSNO. A fluorescent probe 8-(3',4'-diaminophenyl)-difluoroboradiaza-s-indacence (DABODIPY) is firstly used to label RSNO. The derivatization reaction is performed in aqueous medium at 30 degrees C for 15 min in the presence of 6 x 10(-5) mol L-1 Hg2+ and the derivative is detected by fluorescence at lambda(ex)/lambda(em) = 500/510 nm. A linear function of concentration in the range of (2.0-600.0) x 10(-8) mol L-1 is observed with a correlation coefficient of 0.9992 and detection limit of 1.2 x 10(-9) mol L-1 (S/N = 3). This technique has been successfully applied to quantify RSNO in some human blood samples including healthy persons and patients suffering from cardiovascular diseases. (C) 2007 Elsevier B.V. All rights reserved.
• Development of a novel fluorescent probe for nitric oxide detection: 8-(3′,4′-diaminophenyl)-difluoroboradiaza-S-indacence
  作者：Xian Zhang、Ru’an Chi、Jing Zou、Hua-Shan Zhang

  DOI：10.1016/j.saa.2004.02.028

  日期：2004.11

  A novel fluorescent probe, 8-(3',4'-diaminophenyl)-difluoroboradiaza-S-indacence (DABODIPY), was designed and synthesized for monitoring nitric oxide production, which features high photostability and no pH dependency over a wide pH range. The fluorescence of 8-(3',4'-diaminophenyl)-difluoroboradiaza-S-indacence is very low, however, when the probe traps nitric oxide (NO) in the presence of dioxygen, the strong fluorescent triazole form is obtained, which offers the advantages of specificity, and sensitivity for direct detection of NO. Calibration using various concentrations of NO showed the method has good linearity (0.08-4.00 mumol l(-1)) and its detection limit is 10 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 Published by Elsevier B.V.