4-((4-(dimethylamino)naphthalen-1-yl)diazenyl)benzaldehyde | 132252-72-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-((4-(dimethylamino)naphthalen-1-yl)diazenyl)benzaldehyde
• CAS: 132252-72-3
• 化学式: C₁₉H₁₇N₃O
• 分子量: 303.363
• InChiKey: QZDHJNMKEAXRSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.13
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  45.03
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  对氨基苯甲醛 、 N,N-二甲基-1-萘胺 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 1.5h， 生成 4-((4-(dimethylamino)naphthalen-1-yl)diazenyl)benzaldehyde
  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