9-(o-carboxyphenyl)-4,5-bis[bis(2-pyridylmethyl)aminomethyl]-6-hydroxy-3-xanthanone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 9-(o-carboxyphenyl)-4,5-bis[bis(2-pyridylmethyl)aminomethyl]-6-hydroxy-3-xanthanone
• 英文别名: 2-[4,5-Bis[[bis(pyridin-2-ylmethyl)amino]methyl]-3-hydroxy-6-oxoxanthen-9-yl]benzoic acid
• 化学式: C₄₆H₃₈N₆O₅
• 分子量: 754.845
• InChiKey: WFUUDJHECFJLCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  57
• 可旋转键数：
  14
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  142
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2,6-二羟基甲苯 在 吡啶 、 1,3-二溴-5,5-二甲基海因 、 三乙酰氧基硼氢化钠 、 碳酸氢钠 、 溶剂黄146 、 二甲基亚砜 、 zinc(II) chloride 、 1,1'-偶氮(氰基环己烷) 作用下， 以 1,2-二氯乙烷 、 氯苯 为溶剂， 反应 90.5h， 生成 9-(o-carboxyphenyl)-4,5-bis[bis(2-pyridylmethyl)aminomethyl]-6-hydroxy-3-xanthanone
  参考文献：
  名称：

  Fluorescent Sensors for Zn²⁺ Based on a Fluorescein Platform:  Synthesis, Properties and Intracellular Distribution

  摘要：

  Two new fluorescent sensors for Zn2+ that utilize fluorescein as a reporting group, Zinpyr-1 and Zinpyr-2, have been synthesized and characterized. Zinpyr-1 is prepared in one step via a Mannich reaction, and Zinpyr-2 is obtained in a multistep synthesis that utilizes 4 ' ,5 ' -fluorescein dicarboxaldehyde as a key intermediate. Both Zinpyr sensors have excitation and emission wavelengths in the visible range (similar to 500 nm), dissociation constants (K-d1) for Zn2+ of <1 nM, quantum yields approaching unity (Phi = similar to0.9), and cell permeability, making them well-suited for intracellular applications. A 3- to 5-fold fluorescent enhancement is observed under simulated physiological conditions corresponding to the binding of the Zn2+ cation to the sensor, which inhibits a photoinduced electron transfer (PET) quenching pathway. The X-ray crystal structure of a 2:1 Zn2+:Zinpyr-1 complex has also been solved, and is the first structurally characterized example of a complex of fluorescein substituted with metal binding ligands.

  DOI：

  10.1021/ja010059l

文献信息

• Zintrodes, multitrodes and uses thereof
  申请人：Frederickson Christopher

  公开号：US20050142067A1

  公开（公告）日：2005-06-30

  Provided herein are zintrodes to measure intracranial free zinc levels in an individual or free zinc levels in solution. The zintrodes and multitrodes comprise a zinc chelator and a fluorophore or may comprise only a zinc-chelating fluorophore, an optical fiber having an optical tip, and a means of entrapping the zinc chelator and the fluorophore or the zinc-chelating fluorophore proximate to the optical tip within the zintrode. The zintrode may comprise a multitrode. Also provided are methods of real-time buffering of zinc ion levels in vivo in brain tissue to treat an excitotoxic neural injury using the zintrodes and multitrodes described herein. Additionally, provided herein are a system and method to measure pZn in solution.

  本文提供了用于测量个体颅内游离锌水平或溶液中游离锌水平的锌电极。锌电极和多电极包括锌螯合剂和荧光团，或仅包括螯合锌的荧光团、具有光学尖端的光纤，以及将锌螯合剂和荧光团或螯合锌的荧光团夹在锌电极内靠近光学尖端处的装置。锌螯合剂可包括一个多电极。本文还提供了实时缓冲体内脑组织中锌离子水平的方法，以使用本文所述的锌电极和多电极治疗兴奋性神经损伤。此外，本文还提供了一种测量溶液中 pZn 的系统和方法。
• Compositions and Methods for Traumatized Tissues Using Zinc Chelators
  申请人：Ohio University

  公开号：US20180071238A1

  公开（公告）日：2018-03-15

  Neuroprotective compositions, methods of making the same, and methods of using the same, are disclosed.
• US7160732B2
  申请人：——

  公开号：US7160732B2

  公开（公告）日：2007-01-09
• [EN] ZINTRODES, MULTITRODES AND USES THEREOF<br/>[FR] ZINTRODES, MULTITRODES ET LEURS UTILISATIONS
  申请人：NEUROBIOTEX INC

  公开号：WO2005032330A2

  公开（公告）日：2005-04-14

  Provided herein are zintrodes to measure intracranial free zinc levels in an individual or free zinc levels in solution. The zintrodes and multitrodes comprise a zinc chelator and a fluorophore or may comprise only a zinc-chelating fluorophore, an optical fiber having an optical tip, and a means of entrapping the zinc chelator and the fluorophore or the zinc-chelating fluorophore proximate to the optical tip within the zintrode. The zintrode may comprise a multitrode. Also provided are methods of real-time buffering of zinc ion levels in vivo in brain tissue to treat an excitotoxic neural injury using the zintrodes and multitrodes described herein. Additionally, provided herein are a system and method to measure pZn in solution.