1-{3-[(2-aminoethoxy)ethoxy]propyl}-4-(3-methyl-3H-benzothiazol-2-ylidenemethyl)quinolinium | 872045-53-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-{3-[(2-aminoethoxy)ethoxy]propyl}-4-(3-methyl-3H-benzothiazol-2-ylidenemethyl)quinolinium
• CAS: 872045-53-9
• 化学式: C₂₅H₃₀N₃O₂S
• 分子量: 436.598
• InChiKey: JPYUQDAOHWTSCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  31.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  51.6
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-{3-[(2-aminoethoxy)ethoxy]propyl}-4-(3-methyl-3H-benzothiazol-2-ylidenemethyl)quinolinium 、 在 二苯基膦叠氮化物 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以0.75 mg的产率得到N-[2-[[2-[[5-[[5-[[3-hydroxy-3-[2-[2-[3-[4-[(3-methyl-1,3-benzothiazol-3-ium-2-yl)methylidene]quinolin-1-yl]propoxy]ethoxy]ethylimino]propyl]carbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylimidazol-4-yl]carbamoyl]-1-methylimidazol-4-yl]-4-[[1-methyl-4-[[1-methyl-4-[[1-methyl-4-[(1-methylimidazole-2-carbonyl)amino]imidazole-2-carbonyl]amino]pyrrole-2-carbonyl]amino]pyrrole-2-carbonyl]amino]butanimidic acid
  参考文献：
  名称：

  Sequence-Specific Fluorescence Detection of DNA by Polyamide−Thiazole Orange Conjugates

  摘要：

  Fluorescent methods to detect specific double-stranded DNA sequences without the need for denaturation may be useful in the field of genetics. Three hairpin pyrrole-imidazole polyamides 2-4 that target their respective sequences 5'-WGGGWW-3', 5'-WGGCCW-3', and 5'-WGWWCW-3'(W = A or T) were conjugated to thiazole orange dye at the C-termini to examine their fluorescence properties in the presence and absence of match duplex DNA. The conjugates fluoresce weakly in the absence of DNA but showed significant enhancement (> 1000-fold) upon the addition of 1 equiv of match DNA and only slight enhancement with the addition of mismatch DNA. The polyamide-dye conjugates bound specific DNA sequences with high affinity (K-a > 10(8) M-1) and unwound the DNA duplex through intercalation (unwinding angle, Phi, similar to 8 degrees). This new class of polyamides provides a method to specifically detect DNA sequences without denaturation.

  DOI：

  10.1021/ja054650k
• 作为产物：
  描述：

  1-{3-[2-(2-tert-Butoxycarbonylamino-ethoxy)-ethoxy]-propyl}-4-[3-methyl-3H-benzothiazol-(2Z)-ylidenemethyl]-quinolinium; iodide 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以3.7 mg的产率得到1-{3-[(2-aminoethoxy)ethoxy]propyl}-4-(3-methyl-3H-benzothiazol-2-ylidenemethyl)quinolinium
  参考文献：
  名称：

  Sequence-Specific Fluorescence Detection of DNA by Polyamide−Thiazole Orange Conjugates

  摘要：

  Fluorescent methods to detect specific double-stranded DNA sequences without the need for denaturation may be useful in the field of genetics. Three hairpin pyrrole-imidazole polyamides 2-4 that target their respective sequences 5'-WGGGWW-3', 5'-WGGCCW-3', and 5'-WGWWCW-3'(W = A or T) were conjugated to thiazole orange dye at the C-termini to examine their fluorescence properties in the presence and absence of match duplex DNA. The conjugates fluoresce weakly in the absence of DNA but showed significant enhancement (> 1000-fold) upon the addition of 1 equiv of match DNA and only slight enhancement with the addition of mismatch DNA. The polyamide-dye conjugates bound specific DNA sequences with high affinity (K-a > 10(8) M-1) and unwound the DNA duplex through intercalation (unwinding angle, Phi, similar to 8 degrees). This new class of polyamides provides a method to specifically detect DNA sequences without denaturation.

  DOI：

  10.1021/ja054650k