2′-deoxy-5’-O-(4,4'-dimethoxytrityl)-6-N-{2-[(1,3-diaza-3-methyl-2-oxophenoxazin-9-yl)oxy]ethyl}-2-(phenoxyacetylamino)adenosin-3′-yl 2-cyanoethyl N,N-diisopropylphosphoramidite | 1572289-19-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2′-deoxy-5’-O-(4,4'-dimethoxytrityl)-6-N-{2-[(1,3-diaza-3-methyl-2-oxophenoxazin-9-yl)oxy]ethyl}-2-(phenoxyacetylamino)adenosin-3′-yl 2-cyanoethyl N,N-diisopropylphosphoramidite
• CAS: 1572289-19-0
• 化学式: C₆₁H₆₆N₁₁O₁₁P
• 分子量: 1160.24
• InChiKey: MZHWAUGRDDHTTF-GZCBYOGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.25
• 重原子数：
  84.0
• 可旋转键数：
  26.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  241.75
• 氢给体数：
  3.0
• 氢受体数：
  21.0

反应信息

• 作为产物：
  描述：

  3',5'-bis-O-[(tert-butyl)dimethylsilyl]-2'-deoxy-O⁶-[(2,4,6-triisopropylphenyl)sulfonyl]guanosine 在 吡啶 、 triethylamine tris(hydrogen fluoride) 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 丙醇 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 2′-deoxy-5’-O-(4,4'-dimethoxytrityl)-6-N-{2-[(1,3-diaza-3-methyl-2-oxophenoxazin-9-yl)oxy]ethyl}-2-(phenoxyacetylamino)adenosin-3′-yl 2-cyanoethyl N,N-diisopropylphosphoramidite
  参考文献：
  名称：

  2,6-Diaminopurine nucleoside derivative of 9-ethyloxy-2-oxo-1,3-diazaphenoxazine (2-amino-Adap) for recognition of 8-oxo-dG in DNA

  摘要：

  8-Oxo-2'-deoxyguanosine (8-oxo-dG) is a nucleoside resulting from oxidative damage and is known to be mutagenic. 8-Oxo-dG has been related to aging and diseases, including neurological disorders and cancer. Recently, we reported that a fluorescent nucleoside derivative, adenosine-1,3-diazaphenoxazine (Adap), forms a stable base pair with 8-oxo-dG in DNA with accompanying efficient quenching. In this study, a new Adap derivative having an additional 2-amino group on the adenosine moiety (2-amino-Adap) was designed with the anticipation of additional hydrogen bonding with the 8-oxo group of 8-oxo-dG. The properties of the ODN containing 2-amino-Adap were evaluated by measuring thermal stability and fluorescence quenching. In contrast to the previously designed Adap, the base-pairing and fluorescence quenching properties of 2-amino-Adap varied depending on the ODN sequence, and there was no clear indication of an additional hydrogen bond with 8-oxo-dG. Instead, the base pairing of 2-amino-Adap with dG was significantly destabilized compared with that of Adap with dG, resulting in improved selectivity for 8-oxo-dG in the human telomere DNA sequence. Thus, the telomere-targeting ODN probe containing 2-amino-Adap displayed selective, sensitive and quantitative detection of 8-oxo-dG in the human telomere DNA sequence in a light-up detection system using SYBR Green. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2014.01.024