N-(2-(2-(2-(4-(5-(4-methylpiperazin-1-yl)-1H,1'H-[2,5'-bibenzo[d]imidazol]-2'-yl)phenoxy)ethoxy)ethoxy)ethyl)-4-(pyren-1-yl)-N-(2-(2-(2-(2,2,2-trifluoroacetamido)ethoxy)ethoxy)ethyl)butanamide | 1189543-45-0

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: N-(2-(2-(2-(4-(5-(4-methylpiperazin-1-yl)-1H,1'H-[2,5'-bibenzo[d]imidazol]-2'-yl)phenoxy)ethoxy)ethoxy)ethyl)-4-(pyren-1-yl)-N-(2-(2-(2-(2,2,2-trifluoroacetamido)ethoxy)ethoxy)ethyl)butanamide
• CAS: 1189543-45-0
• 化学式: C₅₉H₆₃F₃N₈O₇
• 分子量: 1053.19
• InChiKey: IBSZZNXPVMDCNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  77.0
• 可旋转键数：
  26.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  159.4
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  N-(2-(2-(2-(4-(5-(4-methylpiperazin-1-yl)-1H,1'H-[2,5'-bibenzo[d]imidazol]-2'-yl)phenoxy)ethoxy)ethoxy)ethyl)-4-(pyren-1-yl)-N-(2-(2-(2-(2,2,2-trifluoroacetamido)ethoxy)ethoxy)ethyl)butanamide 在 水 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以12 mg的产率得到HPA
  参考文献：
  名称：

  Triple Recognition of B-DNA by a Neomycin−Hoechst 33258−Pyrene Conjugate

  摘要：

  Recent developments have indicated that aminoglycoside binding is not limited to RNA, but to nucleic acids that, like RNA, adopt conformations similar to its A-form. We further sought to expand the utility of aminoglycoside binding to B-DNA structures by conjugating neomycin, an aminoglycoside antibiotic, with the B-DNA minor groove binding ligand Hoechst 33258. Envisioning a dual groove binding mode, we have extended the potential recognition process to include I third, intercalative moiety. Similar conjugates. which vary ill the number of binding moieties but maintain Identical linkages to allow direct comparisons to be made, have also been prepared. We report herein novel neomycin- and Hoechst 33258-based conjugates developed Ill our laboratories for exploring the recognition potential with B-DNA. Spectroscopic studies Such as UV melting, differential scanning calorimetry, isothermal fluorescence titrations, and circular dichroism together illustrate the triple recognition of the novel conjugate containing neomycin, Hoechst 33258, and pyrene. This study represents the first example of DNA molecular recognition capable of minor versus major groove recognition in conjunction with intercalation.

  DOI：

  10.1021/bi9016796
• 作为产物：
  描述：

  、 2-(3,4-diaminophenyl)-6-(1-methyl-4-piperazinyl)benzimidazole 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 N-(2-(2-(2-(4-(5-(4-methylpiperazin-1-yl)-1H,1'H-[2,5'-bibenzo[d]imidazol]-2'-yl)phenoxy)ethoxy)ethoxy)ethyl)-4-(pyren-1-yl)-N-(2-(2-(2-(2,2,2-trifluoroacetamido)ethoxy)ethoxy)ethyl)butanamide
  参考文献：
  名称：

  Triple Recognition of B-DNA by a Neomycin−Hoechst 33258−Pyrene Conjugate

  摘要：

  Recent developments have indicated that aminoglycoside binding is not limited to RNA, but to nucleic acids that, like RNA, adopt conformations similar to its A-form. We further sought to expand the utility of aminoglycoside binding to B-DNA structures by conjugating neomycin, an aminoglycoside antibiotic, with the B-DNA minor groove binding ligand Hoechst 33258. Envisioning a dual groove binding mode, we have extended the potential recognition process to include I third, intercalative moiety. Similar conjugates. which vary ill the number of binding moieties but maintain Identical linkages to allow direct comparisons to be made, have also been prepared. We report herein novel neomycin- and Hoechst 33258-based conjugates developed Ill our laboratories for exploring the recognition potential with B-DNA. Spectroscopic studies Such as UV melting, differential scanning calorimetry, isothermal fluorescence titrations, and circular dichroism together illustrate the triple recognition of the novel conjugate containing neomycin, Hoechst 33258, and pyrene. This study represents the first example of DNA molecular recognition capable of minor versus major groove recognition in conjunction with intercalation.

  DOI：

  10.1021/bi9016796

文献信息

• Triple recognition of B-DNA
  作者：Bert Willis、Dev P. Arya

  DOI：10.1016/j.bmcl.2009.07.079

  日期：2009.9

  A novel conjugate of Hoechst 33258, pyrene and neomycin was synthesized and examined for its binding and stabilization of A-T rich DNA duplexes using spectroscopic and viscometric techniques. The conjugate, containing three well known ligands that bind nucleic acids albeit in different binding modes, was found to significantly stabilize DNA over parent conjugates containing only one or both of the other recognition elements. The study represents the first example of DNA molecular recognition capable of minor/major groove recognition in conjunction with intercalation. (C) 2009 Elsevier Ltd. All rights reserved.