6'-(2,4-dinitrophenoxy)-3'-methoxy-3H-spiro[isobenzofuran-1,9'-xanthen]-3-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6'-(2,4-dinitrophenoxy)-3'-methoxy-3H-spiro[isobenzofuran-1,9'-xanthen]-3-one
• 英文别名: 3'-(2,4-Dinitrophenoxy)-6'-methoxyspiro[2-benzofuran-3,9'-xanthene]-1-one；3'-(2,4-dinitrophenoxy)-6'-methoxyspiro[2-benzofuran-3,9'-xanthene]-1-one
• 化学式: C₂₇H₁₆N₂O₉
• 分子量: 512.432
• InChiKey: ISMUUAGQUCMWAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  38
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  146
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  6'-(2,4-dinitrophenoxy)-3'-methoxy-3H-spiro[isobenzofuran-1,9'-xanthen]-3-one 在 sodium sulfide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 3-O-methylfluorescein
  参考文献：
  名称：

  2,4-dinitrophenyl ether-containing chemodosimeters for the selective and sensitive ‘in vitro’ and ‘in vivo’ detection of hydrogen sulfide

  摘要：

  Four probes (i.e. D1-D4) for the selective and sensitive fluorogenic detection of HS- have been prepared and characterised. HEPES (10mM, pH 7.4)-DMSO 99:1 v/v solutions of D1-D4 are essentially non-fluorescent. Changes in the emission using D1-D4 in the presence of anions (F-, Cl-, Br-, I-,[GRAPHICS], CN-, SCN-, AcO-,[GRAPHICS],[GRAPHICS],[GRAPHICS], HS- and OH-), biothiols (GSH, Cys, Hcy, Me-Cys and lipoic acid), reducing agents ([GRAPHICS]and[GRAPHICS]) and oxidants (H2O2) demonstrated that only HS- is able to induce the appearance of intense emission bands in the 400-520nm range in the four probes. The selectivity observed was ascribed to a unique hydrogen sulfide-induced hydrolysis of the 2,4-dinitrophenyl ether moiety that yielded the corresponding free highly fluorescent alcohols. The potential detection of intracellular HS- was also studied.

  DOI：

  10.1080/10610278.2014.977286
• 作为产物：
  描述：

  2,4-二硝基氟苯 、 3-O-methylfluorescein 在 三乙胺 作用下， 以 丙酮 为溶剂， 反应 0.5h， 以65%的产率得到6'-(2,4-dinitrophenoxy)-3'-methoxy-3H-spiro[isobenzofuran-1,9'-xanthen]-3-one
  参考文献：
  名称：

  2,4-dinitrophenyl ether-containing chemodosimeters for the selective and sensitive ‘in vitro’ and ‘in vivo’ detection of hydrogen sulfide

  摘要：

  Four probes (i.e. D1-D4) for the selective and sensitive fluorogenic detection of HS- have been prepared and characterised. HEPES (10mM, pH 7.4)-DMSO 99:1 v/v solutions of D1-D4 are essentially non-fluorescent. Changes in the emission using D1-D4 in the presence of anions (F-, Cl-, Br-, I-,[GRAPHICS], CN-, SCN-, AcO-,[GRAPHICS],[GRAPHICS],[GRAPHICS], HS- and OH-), biothiols (GSH, Cys, Hcy, Me-Cys and lipoic acid), reducing agents ([GRAPHICS]and[GRAPHICS]) and oxidants (H2O2) demonstrated that only HS- is able to induce the appearance of intense emission bands in the 400-520nm range in the four probes. The selectivity observed was ascribed to a unique hydrogen sulfide-induced hydrolysis of the 2,4-dinitrophenyl ether moiety that yielded the corresponding free highly fluorescent alcohols. The potential detection of intracellular HS- was also studied.

  DOI：

  10.1080/10610278.2014.977286

文献信息

• 2,4-dinitrophenyl ether-containing chemodosimeters for the selective and sensitive ‘<i>in vitro</i>’ and ‘<i>in vivo</i>’ detection of hydrogen sulfide
  作者：Sameh El Sayed、Cristina de la Torre、Luis E. Santos-Figueroa、Ramón Martínez-Máñez、Félix Sancenón、Mar Orzáez、Ana M. Costero、Margarita Parra、Salvador Gil

  DOI：10.1080/10610278.2014.977286

  日期：2015.4.3

  Four probes (i.e. D1-D4) for the selective and sensitive fluorogenic detection of HS- have been prepared and characterised. HEPES (10mM, pH 7.4)-DMSO 99:1 v/v solutions of D1-D4 are essentially non-fluorescent. Changes in the emission using D1-D4 in the presence of anions (F-, Cl-, Br-, I-,[GRAPHICS], CN-, SCN-, AcO-,[GRAPHICS],[GRAPHICS],[GRAPHICS], HS- and OH-), biothiols (GSH, Cys, Hcy, Me-Cys and lipoic acid), reducing agents ([GRAPHICS]and[GRAPHICS]) and oxidants (H2O2) demonstrated that only HS- is able to induce the appearance of intense emission bands in the 400-520nm range in the four probes. The selectivity observed was ascribed to a unique hydrogen sulfide-induced hydrolysis of the 2,4-dinitrophenyl ether moiety that yielded the corresponding free highly fluorescent alcohols. The potential detection of intracellular HS- was also studied.