N-(2-aminoethyl)-4-((4-(dimethylamino)phenyl)diazenyl) benzenesulfonamide | 72720-26-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: N-(2-aminoethyl)-4-((4-(dimethylamino)phenyl)diazenyl) benzenesulfonamide
• 英文别名: dabsyl-ED；N-(2-aminoethyl)-4-[[4-(dimethylamino)phenyl]diazenyl]benzenesulfonamide
• CAS: 72720-26-4
• 化学式: C₁₆H₂₁N₅O₂S
• 分子量: 347.441
• InChiKey: WWRSKYGABFUKBM-UHFFFAOYSA-N

物化性质

• 沸点：
  556.1±60.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(2-aminoethyl)-4-((4-(dimethylamino)phenyl)diazenyl) benzenesulfonamide 、 叔丁氧羰基氨氧基乙酸 在 N-羟基-7-氮杂苯并三氮唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以38%的产率得到tert-butyl 2-((2-(4-((4-(dimethylamino)phenyl)diazenyl)phenylsulfonamido)ethyl)amino)-2-oxoethoxycarbamate
  参考文献：
  名称：

  Fluorescence Quenchers for Hydrazone and Oxime Orthogonal Bioconjugation

  摘要：

  We describe the synthesis and properties of new fluorescence quenchers containing aldehyde, hydrazine, and aminooxy groups, allowing convenient bioconjugation as oximes or hydrazones. Conjugation to oligonucleotides proceeded in high yield with aniline as catalyst. Kinetics studies of conjugation show that, under optimal conditions, a hydrazine or aminooxy quencher can react with aldehyde-modified DNA to form a stable hydrazone or oxime adduct in as little as five minutes. The resulting quencher-containing DNAs were assessed for their ability to quench the emission of fluorescein in labeled complements and compared to the commercially available dabcyl and Black Hole Quencher 2 (BHQ2), which were conjugated as phosphoramidites. Results show that the new quenchers possess slightly different absorbance properties compared to dabcyl and are as efficient as the commercial quenchers in quenching fluorescein emission. Hydrazone-based quenchers were further successfully incorporated into molecular beacons and shown to give high signal to background ratios in single nucleotide polymorphism detection in vitro. Finally, aminooxy and hydrazine quenchers were applied to quenching of an aldehyde-containing fluorophore associated with living cells, demonstrating cellular quenching within one hour.

  DOI：

  10.1021/bc300344b
• 作为产物：
  描述：

  4-二甲胺基苯基偶氮苯磺酰氯 、 乙二胺 以 二氯甲烷 为溶剂， 反应 0.25h， 以80%的产率得到N-(2-aminoethyl)-4-((4-(dimethylamino)phenyl)diazenyl) benzenesulfonamide
  参考文献：
  名称：

  Novel applications of acridinium compounds and derivatives in homogeneous assays

  摘要：

  公开号：

  EP1403254B1

文献信息

• Novel applications of acridinium compounds and derivatives in homogeneous assays
  申请人：Siemens Healthcare Diagnostics Inc.

  公开号：EP1403254B1

  公开（公告）日：2014-09-17
• JP2019527744A5
  申请人：——

  公开号：JP2019527744A5

  公开（公告）日：2019-10-03
• Fluorescence Quenchers for Hydrazone and Oxime Orthogonal Bioconjugation
  作者：Pete Crisalli、Armando R. Hernández、Eric T. Kool

  DOI：10.1021/bc300344b

  日期：2012.9.19

  We describe the synthesis and properties of new fluorescence quenchers containing aldehyde, hydrazine, and aminooxy groups, allowing convenient bioconjugation as oximes or hydrazones. Conjugation to oligonucleotides proceeded in high yield with aniline as catalyst. Kinetics studies of conjugation show that, under optimal conditions, a hydrazine or aminooxy quencher can react with aldehyde-modified DNA to form a stable hydrazone or oxime adduct in as little as five minutes. The resulting quencher-containing DNAs were assessed for their ability to quench the emission of fluorescein in labeled complements and compared to the commercially available dabcyl and Black Hole Quencher 2 (BHQ2), which were conjugated as phosphoramidites. Results show that the new quenchers possess slightly different absorbance properties compared to dabcyl and are as efficient as the commercial quenchers in quenching fluorescein emission. Hydrazone-based quenchers were further successfully incorporated into molecular beacons and shown to give high signal to background ratios in single nucleotide polymorphism detection in vitro. Finally, aminooxy and hydrazine quenchers were applied to quenching of an aldehyde-containing fluorophore associated with living cells, demonstrating cellular quenching within one hour.
• High performance liquid chromatographic determination of naturally occurring primary and secondary amines with dabsyl chloride
  作者：Jen-Kun. Lin、Chen-Ching. Lai

  DOI：10.1021/ac50054a008

  日期：1980.4.1