5-(dimethylamino)-(3-[4-(3-aminopropyl)-piperazin-1-yl]propyl)-1-naphthalenesulfonamide | 330163-26-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-(dimethylamino)-(3-[4-(3-aminopropyl)-piperazin-1-yl]propyl)-1-naphthalenesulfonamide
• 英文别名: Ds-HAPP；N-[3-[4-(3-aminopropyl)piperazin-1-yl]propyl]-5-(dimethylamino)naphthalene-1-sulfonamide
• CAS: 330163-26-3
• 化学式: C₂₂H₃₅N₅O₂S
• 分子量: 433.618
• InChiKey: CLSUMSBNEOQICI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  90.3
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-(dimethylamino)-(3-[4-(3-aminopropyl)-piperazin-1-yl]propyl)-1-naphthalenesulfonamide 、 copper(II) bis(trifluoromethanesulfonate) 以 乙醚 、 二氯甲烷 为溶剂， 生成 [Cu(5-(dimethylamino)-(3-[4-(3-aminopropyl)-piperazin-1-yl]propyl)-1-naphthalenesulfonamidato)(triflato)]
  参考文献：
  名称：

  Fluorescent Nitric Oxide Detection by Copper Complexes Bearing Anthracenyl and Dansyl Fluorophore Ligands

  摘要：

  Anthrancenyl and dansyl fluorophore ligands [AnCH(2)pipCS(2)K (1), Ds-Hen (2), Ds-HAMP (3), Ds-HAQ (4), and Ds-HAPP (5)] were prepared for coordination to Cu-II. Five Cu complexes, [Cu(AnCH(2)pipCS(2))(2)] (6), [Cu(Ds-en)(2)] (7), [Cu(Ds-AMP)(2)] (8), [Cu(Ds-AQ)(2)] (9), and [Cu(Ds-APP)(OTf)] (10), were synthesized as candidates for detecting nitric oxide (NO) by fluorescence and characterized by X-ray crystallography. A decrease in fluorescence compared to that of the free ligands (1-5) was measured following the formation of the corresponding five Cu-II complexes 6-10. Fluorescence was restored in the presence of NO in CH3OH/CH2Cl2 solutions of the compounds. Complexes 7, 8, and 10 exhibited a fluorescence response to NO in pH 7.0 or 9.0 buffered aqueous solutions. Spectroscopic studies revealed that NO-induced fluorescence enhancement in these Cu-II complexes occurs by reduction to Cu-I. The present studies demonstrate that Cu-II complexes are effective as fluorescent probes for detecting NO in both organic and aqueous environments.

  DOI：

  10.1021/ic0609913

文献信息

• Fluorescent Nitric Oxide Detection by Copper Complexes Bearing Anthracenyl and Dansyl Fluorophore Ligands
  作者：Mi Hee Lim、Stephen J. Lippard

  DOI：10.1021/ic0609913

  日期：2006.10.30

  Anthrancenyl and dansyl fluorophore ligands [AnCH(2)pipCS(2)K (1), Ds-Hen (2), Ds-HAMP (3), Ds-HAQ (4), and Ds-HAPP (5)] were prepared for coordination to Cu-II. Five Cu complexes, [Cu(AnCH(2)pipCS(2))(2)] (6), [Cu(Ds-en)(2)] (7), [Cu(Ds-AMP)(2)] (8), [Cu(Ds-AQ)(2)] (9), and [Cu(Ds-APP)(OTf)] (10), were synthesized as candidates for detecting nitric oxide (NO) by fluorescence and characterized by X-ray crystallography. A decrease in fluorescence compared to that of the free ligands (1-5) was measured following the formation of the corresponding five Cu-II complexes 6-10. Fluorescence was restored in the presence of NO in CH3OH/CH2Cl2 solutions of the compounds. Complexes 7, 8, and 10 exhibited a fluorescence response to NO in pH 7.0 or 9.0 buffered aqueous solutions. Spectroscopic studies revealed that NO-induced fluorescence enhancement in these Cu-II complexes occurs by reduction to Cu-I. The present studies demonstrate that Cu-II complexes are effective as fluorescent probes for detecting NO in both organic and aqueous environments.