4-(di(2-picolyl)aminomethyl)-2-(2'-methoxymethyloxy-3'-naphthyl)benzoxazole | 1374460-08-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(di(2-picolyl)aminomethyl)-2-(2'-methoxymethyloxy-3'-naphthyl)benzoxazole
• CAS: 1374460-08-8
• 化学式: C₃₂H₂₈N₄O₃
• 分子量: 516.599
• InChiKey: VOHLHOUJZJCANC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.62
• 重原子数：
  39.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  73.51
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-(di(2-picolyl)aminomethyl)-2-(2'-methoxymethyloxy-3'-naphthyl)benzoxazole 在 对甲苯磺酸 、 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 以49%的产率得到4-(di(2-picolyl)aminomethyl)-2-(2'-hydroxy-3'-naphthyl)-benzoxazole
  参考文献：
  名称：

  Fluorescent Zinc Sensor with Minimized Proton-Induced Interferences: Photophysical Mechanism for Fluorescence Turn-On Response and Detection of Endogenous Free Zinc Ions

  摘要：

  A new fluorescent zinc sensor (HNBO-DPA) consisting of 2-(2'-hydroxy-3'-naphthyl)benzoxazole (HNBO) chromophore and a di(2-picolyl)amine (DPA) metal chelator has been prepared and examined for zinc bioimaging. The probe exhibits zinc-induced fluorescence turn-on without any spectral shifts. Its crystal structure reveals that HNBO DPA binds a zinc ion in a pentacoordinative fashion through the DPA and HNBO moieties. Steady-state photophysical studies establish zinc-induced deprotonation of the HNBO group. Nanosecond and femtosecond laser flash photolysis and electrochemical measurements provide evidence for zinc-induced modulation of photoinduced electron transfer (PeT) from DPA to HNBO. Thus, the zinc-responsive fluorescence turn-on is attributed to suppression of PeT exerted by deprotonation of HNBO and occupation of the electron pair of DPA, a conclusion that is further supported by density functional theory and time-dependent density functional theory (DFT/TD-DFT) calculations. Under physiological conditions (pH 7.0), the probe displays a 44-fold fluorescence turn-on in response to zinc ions with a K-d value of 12 pM. The fluorescent response of the probe to zinc ions is conserved over a broad pH range with its excellent selectivity for zinc ions among biologically relevant metal ions. In particular, its sensing ability is not altered by divalent transition metal ions such as Fe(II), Cu(II), Cd(II), and Hg(II). Cell experiments using HNBO DPA show its suitability for monitoring intracellular zinc ions. We have also demonstrated applicability of the probe to visualize intact zinc ions released from cells that undergo apoptosis. More interestingly, zinc-rich pools in zebrafish embryos are traced with HNBO DPA during early developmental stages. The results obtained from the in vitro and in vivo imaging studies demonstrate the practical usefulness of the probe to detect zinc ions.

  DOI：

  10.1021/ic300476e
• 作为产物：
  描述：

  2-(2'-hydroxy-3'-naphthyl)-4-methylbenzoxazole 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 sodium carbonate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 为溶剂， 生成 4-(di(2-picolyl)aminomethyl)-2-(2'-methoxymethyloxy-3'-naphthyl)benzoxazole
  参考文献：
  名称：

  Fluorescent Zinc Sensor with Minimized Proton-Induced Interferences: Photophysical Mechanism for Fluorescence Turn-On Response and Detection of Endogenous Free Zinc Ions

  摘要：

  A new fluorescent zinc sensor (HNBO-DPA) consisting of 2-(2'-hydroxy-3'-naphthyl)benzoxazole (HNBO) chromophore and a di(2-picolyl)amine (DPA) metal chelator has been prepared and examined for zinc bioimaging. The probe exhibits zinc-induced fluorescence turn-on without any spectral shifts. Its crystal structure reveals that HNBO DPA binds a zinc ion in a pentacoordinative fashion through the DPA and HNBO moieties. Steady-state photophysical studies establish zinc-induced deprotonation of the HNBO group. Nanosecond and femtosecond laser flash photolysis and electrochemical measurements provide evidence for zinc-induced modulation of photoinduced electron transfer (PeT) from DPA to HNBO. Thus, the zinc-responsive fluorescence turn-on is attributed to suppression of PeT exerted by deprotonation of HNBO and occupation of the electron pair of DPA, a conclusion that is further supported by density functional theory and time-dependent density functional theory (DFT/TD-DFT) calculations. Under physiological conditions (pH 7.0), the probe displays a 44-fold fluorescence turn-on in response to zinc ions with a K-d value of 12 pM. The fluorescent response of the probe to zinc ions is conserved over a broad pH range with its excellent selectivity for zinc ions among biologically relevant metal ions. In particular, its sensing ability is not altered by divalent transition metal ions such as Fe(II), Cu(II), Cd(II), and Hg(II). Cell experiments using HNBO DPA show its suitability for monitoring intracellular zinc ions. We have also demonstrated applicability of the probe to visualize intact zinc ions released from cells that undergo apoptosis. More interestingly, zinc-rich pools in zebrafish embryos are traced with HNBO DPA during early developmental stages. The results obtained from the in vitro and in vivo imaging studies demonstrate the practical usefulness of the probe to detect zinc ions.

  DOI：

  10.1021/ic300476e