N,N-bis[(6-methoxyquinolin-2-yl)methyl]-N’,N’-bis[2-(b-d-glucopyranosyloxy)ethyl]ethylenediamine | 1402556-16-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N,N-bis[(6-methoxyquinolin-2-yl)methyl]-N’,N’-bis[2-(b-d-glucopyranosyloxy)ethyl]ethylenediamine
• 英文别名: 2-{(2-{bis[(6-methoxyquinolin-2-yl)methyl]amino}ethyl)[2-(β-D-glucopyranosyloxy)ethyl]amino}ethyl β-D-glucopyranoside；(2R,3R,4S,5S,6R)-2-[2-[2-[bis[(6-methoxyquinolin-2-yl)methyl]amino]ethyl-[2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]amino]ethoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1402556-16-4
• 化学式: C₄₀H₅₄N₄O₁₄
• 分子量: 814.887
• InChiKey: RDYHUPLSVASZGW-AELZGUPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  58
• 可旋转键数：
  19
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  250
• 氢给体数：
  8
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  6-methoxy-2-chloromethylquinoline 在 盐酸 、 sodium methylate 、 potassium carbonate 、 potassium iodide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 176.0h， 生成 N,N-bis[(6-methoxyquinolin-2-yl)methyl]-N’,N’-bis[2-(b-d-glucopyranosyloxy)ethyl]ethylenediamine
  参考文献：
  名称：

  Quinoline‐Based, Glucose‐Pendant Fluorescent Zinc Probes

  摘要：

  AbstractQuinoline‐based tetradentate ligands with glucose pendants, N,N′‐bis[2‐(β‐d‐glucopyranosyloxy)ethyl]‐N,N′‐bis[(6‐methoxyquinolin‐2‐yl)methyl]ethylenediamine (N,N′‐6‐MeOBQBGEN) and its N,N‐counterpart, N,N‐6‐MeOBQBGEN, have been prepared, and their fluorescence‐spectral changes upon Zn binding were investigated. Upon excitation at 336 nm, N,N′‐6‐MeOBQBGEN showed weak fluorescence (ϕ≈ 0.016) in HEPES buffer (HEPES 50 mM, KCl 100 mM, pH 7.5). In the presence of Zn, N,N′‐6‐MeOBQBGEN exhibited a significant increase in fluorescence (ϕ=0.096) at 414 nm. The fluorescence enhancement is specific for Zn and Cd (ICd/IZn of 50% at 414 nm). On the other hand, N,N‐6‐MeOBQBGEN exhibited a smaller fluorescence enhancement upon Zn complexation (ϕ=0.043, λex=334 nm, λem=407 nm) compared with N,N′‐6‐MeOBQBGEN. Fluorescence microscopic analysis using PC‐12 rat adrenal cells revealed that N,N′‐6‐MeOBQBGEN exhibits a 1.8‐fold higher fluorescence‐signal response to Zn ion concentration compared with sugar‐depleted compound 2 (N,N′‐bis[(6‐methoxyquinolin‐2‐yl)methyl]ethylenediamine), due to its enhanced uptake into cells due to the targeting ability of the attached carbohydrates.

  DOI：

  10.1002/cbdv.201100445

文献信息

• Quinoline‐Based, Glucose‐Pendant Fluorescent Zinc Probes
  作者：Yuji Mikata、Anna Ugai、Keiko Yasuda、Saori Itami、Satoshi Tamotsu、Hideo Konno、Satoshi Iwatsuki

  DOI：10.1002/cbdv.201100445

  日期：2012.9

  AbstractQuinoline‐based tetradentate ligands with glucose pendants, N,N′‐bis[2‐(β‐d‐glucopyranosyloxy)ethyl]‐N,N′‐bis[(6‐methoxyquinolin‐2‐yl)methyl]ethylenediamine (N,N′‐6‐MeOBQBGEN) and its N,N‐counterpart, N,N‐6‐MeOBQBGEN, have been prepared, and their fluorescence‐spectral changes upon Zn binding were investigated. Upon excitation at 336 nm, N,N′‐6‐MeOBQBGEN showed weak fluorescence (ϕ≈ 0.016) in HEPES buffer (HEPES 50 mM, KCl 100 mM, pH 7.5). In the presence of Zn, N,N′‐6‐MeOBQBGEN exhibited a significant increase in fluorescence (ϕ=0.096) at 414 nm. The fluorescence enhancement is specific for Zn and Cd (ICd/IZn of 50% at 414 nm). On the other hand, N,N‐6‐MeOBQBGEN exhibited a smaller fluorescence enhancement upon Zn complexation (ϕ=0.043, λex=334 nm, λem=407 nm) compared with N,N′‐6‐MeOBQBGEN. Fluorescence microscopic analysis using PC‐12 rat adrenal cells revealed that N,N′‐6‐MeOBQBGEN exhibits a 1.8‐fold higher fluorescence‐signal response to Zn ion concentration compared with sugar‐depleted compound 2 (N,N′‐bis[(6‐methoxyquinolin‐2‐yl)methyl]ethylenediamine), due to its enhanced uptake into cells due to the targeting ability of the attached carbohydrates.