4-bromomethyl-2-(4,5-dimethoxy-2-methoxymethoxyphenyl)benzoxazole | 909415-75-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-bromomethyl-2-(4,5-dimethoxy-2-methoxymethoxyphenyl)benzoxazole
• 英文别名: 4-(bromomethyl)-2-[4,5-dimethoxy-2-(methoxymethoxy)phenyl]-1,3-benzoxazole
• CAS: 909415-75-4
• 化学式: C₁₈H₁₈BrNO₅
• 分子量: 408.249
• InChiKey: UIZVFPHNGKIMAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  63
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-bromomethyl-2-(4,5-dimethoxy-2-methoxymethoxyphenyl)benzoxazole 在 sodium carbonate 、 对甲苯磺酸 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 2-(4,5-dimethoxy-2-hydroxyphenyl)-4-(2-pyridylmethyl)aminomethylbenzoxazole
  参考文献：
  名称：

  Emission Ratiometric Imaging of Intracellular Zinc:  Design of a Benzoxazole Fluorescent Sensor and Its Application in Two-Photon Microscopy

  摘要：

  Zinc and calcium are ubiquitous intracellular metals, and while a variety of quantitative probes have been developed for measuring intracellular changes in calcium concentration, the same is not true of zinc. We describe here the design, synthesis, and properties of the benzoxazole-based, ratiometric zinc probe, Zinbo-5. This bright fluorescent reporter has a quantum yield of 0.1 in the zinc-form, exhibits a Kd for Zn2+ in the nanomolar range, and shows significant changes in both excitation and emission maxima upon zinc binding. The utility of this cell permeable probe is demonstrated in fluorescence microscopy emission ratio imaging experiments on mammalian cells. We further show that Zinbo-5 is well suited for two-photon excitation microscopy ratio imaging and can readily reveal changes in intracellular zinc concentration within optical planes of single cells. To the best of our knowledge, this is the first example of two-photon excitation microscopy applied to ratio imaging of zinc. These methods can be applied to real-time emission or excitation ratio imaging studies of zinc physiology in living cells.

  DOI：

  10.1021/ja039073j
• 作为产物：
  描述：

  (4,5-dimethoxy-2-(methoxymethoxy)benzaldehyde): 在 N-溴代丁二酰亚胺(NBS) 、 barium permanganate 、 偶氮二异丁腈 作用下， 以 四氯化碳 、 苯 为溶剂， 反应 35.0h， 生成 4-bromomethyl-2-(4,5-dimethoxy-2-methoxymethoxyphenyl)benzoxazole
  参考文献：
  名称：

  Emission Ratiometric Imaging of Intracellular Zinc:  Design of a Benzoxazole Fluorescent Sensor and Its Application in Two-Photon Microscopy

  摘要：

  Zinc and calcium are ubiquitous intracellular metals, and while a variety of quantitative probes have been developed for measuring intracellular changes in calcium concentration, the same is not true of zinc. We describe here the design, synthesis, and properties of the benzoxazole-based, ratiometric zinc probe, Zinbo-5. This bright fluorescent reporter has a quantum yield of 0.1 in the zinc-form, exhibits a Kd for Zn2+ in the nanomolar range, and shows significant changes in both excitation and emission maxima upon zinc binding. The utility of this cell permeable probe is demonstrated in fluorescence microscopy emission ratio imaging experiments on mammalian cells. We further show that Zinbo-5 is well suited for two-photon excitation microscopy ratio imaging and can readily reveal changes in intracellular zinc concentration within optical planes of single cells. To the best of our knowledge, this is the first example of two-photon excitation microscopy applied to ratio imaging of zinc. These methods can be applied to real-time emission or excitation ratio imaging studies of zinc physiology in living cells.

  DOI：

  10.1021/ja039073j

文献信息

• Zinc-chelating ratiometric fluorescent probes and related methods
  申请人：Northwestern University

  公开号：US07105680B1

  公开（公告）日：2006-09-12

  Benzoxazole fluorescent sensor compounds and related ratiometric imaging methods for zinc metal ion.

  苯并噁唑荧光传感器化合物及相关的锌金属离子比色成像方法。
• US7105680B1
  申请人：——

  公开号：US7105680B1

  公开（公告）日：2006-09-12
• US7262301B1
  申请人：——

  公开号：US7262301B1

  公开（公告）日：2007-08-28
• Emission Ratiometric Imaging of Intracellular Zinc:  Design of a Benzoxazole Fluorescent Sensor and Its Application in Two-Photon Microscopy
  作者：Masayasu Taki、Janet L. Wolford、Thomas V. O'Halloran

  DOI：10.1021/ja039073j

  日期：2004.1.28

  Zinc and calcium are ubiquitous intracellular metals, and while a variety of quantitative probes have been developed for measuring intracellular changes in calcium concentration, the same is not true of zinc. We describe here the design, synthesis, and properties of the benzoxazole-based, ratiometric zinc probe, Zinbo-5. This bright fluorescent reporter has a quantum yield of 0.1 in the zinc-form, exhibits a Kd for Zn2+ in the nanomolar range, and shows significant changes in both excitation and emission maxima upon zinc binding. The utility of this cell permeable probe is demonstrated in fluorescence microscopy emission ratio imaging experiments on mammalian cells. We further show that Zinbo-5 is well suited for two-photon excitation microscopy ratio imaging and can readily reveal changes in intracellular zinc concentration within optical planes of single cells. To the best of our knowledge, this is the first example of two-photon excitation microscopy applied to ratio imaging of zinc. These methods can be applied to real-time emission or excitation ratio imaging studies of zinc physiology in living cells.