N-[2-(2-aminooxyethoxy)ethoxy]-5-(dimethylamino)naphthalene-1-sulfonamide | 190249-82-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-[2-(2-aminooxyethoxy)ethoxy]-5-(dimethylamino)naphthalene-1-sulfonamide
• CAS: 190249-82-2
• 化学式: C₁₆H₂₃N₃O₅S
• 分子量: 369.442
• InChiKey: DQSAFSOBFJXPCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-脱氧-D-核糖 、 N-[2-(2-aminooxyethoxy)ethoxy]-5-(dimethylamino)naphthalene-1-sulfonamide 以 acetate buffer 为溶剂， 生成
  参考文献：
  名称：

  A Simple and Sensitive Method for in Vitro Quantitation of Abasic Sites in DNA

  摘要：

  A novel method for the quantitation of abasic sites (AP sites) in DNA is described. As abasic sites can be generated by controlled thermal treatment of base-modified DNA, this method can be used for estimation of the extent of DNA damage resulting from exposure to genotoxic agents. The method involves use of probe molecules 1 and 2 that contain a fluorescent label linked to an aminooxy group which reacts specifically with the aldehydic function of the ring-opened form of abasic sites. The two fluorescent probes 1 and 2 were found to react with 2-deoxyribose, a model substrate, at the optimum of PH 4.0. As spontaneous depurination occurs at low PH, the reactions with abasic DNA were carried out at neutral PH with an excess concentration of the probes. Studies with alkylated, depurinated calf thymus DNA showed that the method is selective and quantitative. Good correlations were found between the level of 7-methylguanine (7-MeGua), generated in vitro in DNA by the methylating agent dimethyl sulfate, and the amount of AP sites as determined by the method presented here. In addition, similar correlations were found when the assay was used to detect abasic sites in DNA isolated from rats treated with carcinogenic alkylating agents. In each case, the level of abasic sites, as expected, is slightly higher than the level of 7-MeGua which is known to represent about 70% of the total modifications of DNA following exposure to the methylating agent. This method may be useful not only in experimental settings but also in studies of DNA damage in humans resulting from chemotherapy or exposure to environmental agents.

  DOI：

  10.1021/tx980275g
• 作为产物：
  描述：

  N-(9-fluorenylmethoxycarbonyl)-N'-(5-dimethylamino-1-naphthalenesulfonamido)-3-oxapentane-1,5-dioxyamine 在 哌啶 作用下， 以 二氯甲烷 为溶剂， 生成 N-[2-(2-aminooxyethoxy)ethoxy]-5-(dimethylamino)naphthalene-1-sulfonamide
  参考文献：
  名称：

  Site-specific unnatural base excision via visible light

  摘要：

  在这篇论文中，我们报告了一种可见光诱导的方法来构建位点特异性的非天然碱基切除（BE），并展示了其调节转录和翻译水平的影响。

  DOI：

  10.1039/d2cc03664a

文献信息

• Synthesis of fluorescent probes for the detection of abasic sites in DNA
  作者：Didier Boturyn、Ali Boudali、Jean-François Constant、Eric Defrancq、Jean Lhomme

  DOI：10.1016/s0040-4020(97)00235-4

  日期：1997.4

  The three luminescent molecules 1-3 were prepared as highly sensitive and specific probes for the quantification of a major DNA lesion, the abasic site. These molecules incorporate in their structure the reactive oxyamino function linked to the Dansyl or Lissamine-Rhodamine fluorophores through amido or polyether chains. (C) 1997 Elsevier Science Ltd.
• The oxyamino-aldehyde coupling reaction: An efficient method for the derivatization of oligonucleotides
  作者：Emmanuelle Trévisiol、Annabelle Renard、Eric Defrancq、Jean Lhomme

  DOI：10.1016/s0040-4039(97)10335-5

  日期：1997.12

  Oligonucleotides containing an aldehydic function at any preselected position in the sequence have been prepared using post-synthetic oxidation of an alkene as the key reaction. These were efficiently coupled to a reporter molecule tethered to an oxyamino linker. (C) 1997 Elsevier Science Ltd.