3,6,10,13,17,20,24,27-octaaza-1,15(2,6)-dipyridina-8,22(9,10)-dianthracenacyclooctacosaphane | 1429305-71-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 3,6,10,13,17,20,24,27-octaaza-1,15(2,6)-dipyridina-8,22(9,10)-dianthracenacyclooctacosaphane
• 英文别名: 3,6,14,17,28,31,39,42,57,64-Decazanonacyclo[42.6.6.619,26.18,12.133,37.020,25.045,50.051,56.058,63]tetrahexaconta-1(50),8(64),9,11,19(63),20,22,24,26(58),33,35,37(57),44,46,48,51,53,55,59,61-icosaene
• CAS: 1429305-71-4
• 化学式: C₅₄H₆₂N₁₀
• 分子量: 851.153
• InChiKey: FGEAUZVSWWYYEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  64
• 可旋转键数：
  0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  122
• 氢给体数：
  8
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  zinc perchlorate 、 3,6,10,13,17,20,24,27-octaaza-1,15(2,6)-dipyridina-8,22(9,10)-dianthracenacyclooctacosaphane 、 乙腈 反应 2.0h， 以35%的产率得到
  参考文献：
  名称：

  Highly Selective Recognition and Fluorescence Imaging of Adenosine Polyphosphates in Aqueous Solution

  摘要：

  The design and synthesis of chemosensors for the recognition of a certain nucleoside polyphosphate among various structurally similar nucleoside polyphosphates remain a fundamental challenge. Herein, we report the new fluorescent chemosensor [Zn2L](ClO4)(4) (1; L = (3,6,10,13,17,20,24,27-octaaza-1,15(2,6)-dipyridina-8,22(9,10)-dianthracenacyclooctacosaphane), which can selectively recognize adenosine polyphosphates (ATP and ADP) among various nucleoside polyphosphates, with a large fluorescence enhancement (F-max/F-0 = 70 and 80 for ATP and ADP, respectively) and strong binding affinity (K = 3.1 x 10(11) M-1 for [Zn2HL(H(-1)ATP)(2)](-), 2.8 x 10(11) M-1 for [Zn2L(H(-1)ATP)(2)](2-), and 1.5 x 10(13) M-1 for [Zn2L(H(-1)ADP)(2)](2-)) in aqueous solution at physiological pH 7.40. The structure of [Zn2L] (P2O7) (2) was investigated, which shows that mu(2)-pyrophosphate anions alternately link [Zn2L](4+) cations to generate a 1D coordination polymer. The results of P-31 NMR studies and DFT calculations reveal that the two Zn(II) ions in 1 can interact with ATP/ADP anions through coordination interactions between Zn(II) and the polyphosphate groups, and two anthracene moieties in I can interact with adenine groups from two ATP or ADP anions through stacking interactions to form a sandwichlike structure. These multiple recognition interactions between 1 and ATP/ADP enhance the affinity and selectivity of 1, toward ATP/ADP. Due to its highly selective and sensitive ability to detect adenosine polyphosphates, 1 was successfully applied to fluorescence imaging for ATP and ADP in living cells, demonstrating the potential utility of 1 as a fluorescent chemosensor for detecting ATP and ADP.

  DOI：

  10.1021/ic302435g
• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以46%的产率得到3,6,10,13,17,20,24,27-octaaza-1,15(2,6)-dipyridina-8,22(9,10)-dianthracenacyclooctacosaphane
  参考文献：
  名称：

  Highly Selective Recognition and Fluorescence Imaging of Adenosine Polyphosphates in Aqueous Solution

  摘要：

  The design and synthesis of chemosensors for the recognition of a certain nucleoside polyphosphate among various structurally similar nucleoside polyphosphates remain a fundamental challenge. Herein, we report the new fluorescent chemosensor [Zn2L](ClO4)(4) (1; L = (3,6,10,13,17,20,24,27-octaaza-1,15(2,6)-dipyridina-8,22(9,10)-dianthracenacyclooctacosaphane), which can selectively recognize adenosine polyphosphates (ATP and ADP) among various nucleoside polyphosphates, with a large fluorescence enhancement (F-max/F-0 = 70 and 80 for ATP and ADP, respectively) and strong binding affinity (K = 3.1 x 10(11) M-1 for [Zn2HL(H(-1)ATP)(2)](-), 2.8 x 10(11) M-1 for [Zn2L(H(-1)ATP)(2)](2-), and 1.5 x 10(13) M-1 for [Zn2L(H(-1)ADP)(2)](2-)) in aqueous solution at physiological pH 7.40. The structure of [Zn2L] (P2O7) (2) was investigated, which shows that mu(2)-pyrophosphate anions alternately link [Zn2L](4+) cations to generate a 1D coordination polymer. The results of P-31 NMR studies and DFT calculations reveal that the two Zn(II) ions in 1 can interact with ATP/ADP anions through coordination interactions between Zn(II) and the polyphosphate groups, and two anthracene moieties in I can interact with adenine groups from two ATP or ADP anions through stacking interactions to form a sandwichlike structure. These multiple recognition interactions between 1 and ATP/ADP enhance the affinity and selectivity of 1, toward ATP/ADP. Due to its highly selective and sensitive ability to detect adenosine polyphosphates, 1 was successfully applied to fluorescence imaging for ATP and ADP in living cells, demonstrating the potential utility of 1 as a fluorescent chemosensor for detecting ATP and ADP.

  DOI：

  10.1021/ic302435g