6-硝基-二乙酸荧光素 | 53299-21-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 6-硝基-二乙酸荧光素
• 英文名称: 3',6'-bis(acetyloxy)-4-nitrospiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one
• 英文别名: 6-nitrofluorescein diacetate；6-nitrofluoresceindiacetate；3',6'-di-O-acetyl-4-nitrofluorescein；3',6'-diacetoxy-6-nitro-spiro[phthalan-1,9'-xanthen]-3-one；3',6'-Diacetoxy-6-nitro-spiro[phthalan-1,9'-xanthen]-3-on；5-Nitro-fluorescein-diacetat；(6'-acetyloxy-6-nitro-3-oxospiro[2-benzofuran-1,9'-xanthene]-3'-yl) acetate
• CAS: 53299-21-1
• 化学式: C₂₄H₁₅NO₉
• 分子量: 461.384
• InChiKey: VYIGESZPYCCIHE-UHFFFAOYSA-N

物化性质

• 沸点：
  674.5±55.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、可溶于二氯甲烷、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  134
• 氢给体数：
  0
• 氢受体数：
  9

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  6-硝基-二乙酸荧光素 在 sodium hydrogensulfide 、 sodiumsulfide nonahydrate 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 生成 6-氨基荧光素
  参考文献：
  名称：

  Fluorescent Human EP₃ Receptor Antagonists

  摘要：

  Exchange of the lipophilc part of ortho-substituted cinnamic acid lead structures with different small molecule fluorophoric moieties via a dimethylene spacer resulted in hEP(3)R ligands with affinities in the nanomolar concentration range. Synthesized compounds emit fluorescence in the blue, green, and red range of light and have been tested concerning their potential as a pharmacological tool. hEP(3)Rs were visualized by confocal laser scanning microscopy on HT-29 cells, on murine kidney tissues, and on human brain tissues and functionally were characterized as antagonists on human platelets. Inhibition of PGE(2) and collagen-induced platelet aggregation was measured after preincubation with novel hEP(3)R ligands. The pyryllium-labeled ligand 8 has been shown as one of the most promising structures, displaying a useful fluorescence and highly affine hEP(3)R antagonists.

  DOI：

  10.1021/ml300191g
• 作为产物：
  描述：

  5-硝基荧光素 、 乙酸酐 生成 6-硝基-二乙酸荧光素
  参考文献：
  名称：

  ABRAMOCHKIN, EH. S.;KADYRMATOVA, T. P.;PETROVA, G. S.;RODIONOVA, N. A.;FA+, XIMIYA ORGAN. SOEDIN. AZOTA, PERM, 1981, 97-103

  摘要：

  DOI：

文献信息

• Nucleotides. Part LXXI
  作者：Harald Sigmund、Wolfgang Pfleiderer

  DOI：10.1002/hlca.200390186

  日期：2003.7

  A new labelling technique attaching fluorescein via a carbamoyl linker directly to the amino groups of the nucleobases was developed. The amino groups were first converted to the phenoxycarbonyl derivatives (10, 15, 19, 58), which reacted under mild conditions with 5-aminofluorescein to give the corresponding N-[(fluorescein-5-ylamino)carbonyl] derivatives (11–14, 16, 17, 20, 59, 60). The introduction

  开发了一种新的标记技术，该技术通过氨基甲酰基接头将荧光素直接连接到核碱基的氨基上。氨基首先转化为苯氧基羰基衍生物（10，15，19，58），它在温和条件下反应，用5-氨基荧光素，得到相应的Ñ - [（荧光素-5-基氨基）羰基]衍生物（11 - 14 ，16，17，20，59，60）。将5-氨基荧光素残基引入适当保护的腺苷-腺苷二聚体（39，40）和三聚体（50）工作良好，并且这些均一地封闭的前体的最终脱保护导致用DBU（1,8-二氮杂双环[5.4.0] undec-7-ene）处理，一步到二聚体41和三聚体51。适当保护的单体亚磷酰胺结构单元（75）的合成更加困难，因为将2-（4-硝基苯基）乙基残基引入59中的荧光素部分主要导致三取代，从而得到包括尿素官能团的61。腺苷二聚体66和三聚体67的形成通过亚磷酰胺化学反应以通常的方式进行；参见表1。然而，脱保护67与DBU是不完整的，因为Ø发现
• Synthesis and fluorescence properties of six fluorescein-nitroxide radical hybrid-compounds
  作者：Shingo Sato、Susumu Endo、Yusuke Kurokawa、Masaki Yamaguchi、Akio Nagai、Tomohiro Ito、Tateaki Ogata

  DOI：10.1016/j.saa.2016.06.021

  日期：2016.12

  with DPROXYL-3-ylmethyl methanesulfonate (5). Fluorescence intensities (around 520nm) after reduction of the radical increased to 1.43-, 1.38-, and 1.61-folds for 2a, 2b and 3b respectively; 3a alone exhibited a decrease in intensity on reduction. Since 4 was readily solvolyzed in PBS or even methanol to afford fluorescein and 4-carboxy-TEMPO, its fluorescence change could not be measured. Hybrid compound

  通过5-或6-羧基荧光素与4-氨基-TEMPO（2ab），5-或6-氨基荧光素和4的缩合反应，合成了六种荧光素-硝基氧自由基杂化化合物（2ab，3ab，4和5）。 -羧基-TEMPO（3ab），以及荧光素和4-羧基-TEMPO（4），或使荧光素的3-羟基与DPROXYL-3-基甲基甲磺酸酯反应（5）。自由基还原后的荧光强度（约520nm）分别为2a，2b和3b的1.43倍，1.38倍和1.61倍；单独的3a显示出还原强度降低。由于4容易溶于PBS或什至甲醇中以提供荧光素和4-羧基-TEMPO，因此无法测量其荧光变化。在荧光素酚和3-羟甲基-DPROXYL羟基中心之间包含醚键的杂化化合物5是稳定的，并且在还原时，
• Fluorescent Human EP₃ Receptor Antagonists
  作者：Miriam Tomasch、J. Stephan Schwed、Karina Kuczka、Sascha Meyer dos Santos、Sebastian Harder、Rolf M. Nüsing、Alexander Paulke、Holger Stark

  DOI：10.1021/ml300191g

  日期：2012.9.13

  Exchange of the lipophilc part of ortho-substituted cinnamic acid lead structures with different small molecule fluorophoric moieties via a dimethylene spacer resulted in hEP(3)R ligands with affinities in the nanomolar concentration range. Synthesized compounds emit fluorescence in the blue, green, and red range of light and have been tested concerning their potential as a pharmacological tool. hEP(3)Rs were visualized by confocal laser scanning microscopy on HT-29 cells, on murine kidney tissues, and on human brain tissues and functionally were characterized as antagonists on human platelets. Inhibition of PGE(2) and collagen-induced platelet aggregation was measured after preincubation with novel hEP(3)R ligands. The pyryllium-labeled ligand 8 has been shown as one of the most promising structures, displaying a useful fluorescence and highly affine hEP(3)R antagonists.
• ABRAMOCHKIN, EH. S.;KADYRMATOVA, T. P.;PETROVA, G. S.;RODIONOVA, N. A.;FA+, XIMIYA ORGAN. SOEDIN. AZOTA, PERM, 1981, 97-103
  作者：ABRAMOCHKIN, EH. S.、KADYRMATOVA, T. P.、PETROVA, G. S.、RODIONOVA, N. A.、FA+

  DOI：——

  日期：——