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用于糖类信号传导的含硼酸基团的查尔酮类似物荧光探针。

Chalcone-analogue fluorescent prfobes for saccharides signaling using the boronic acid group.

作者信息

DiCesare Nicolas, Lakowicz Joseph R

机构信息

Center for Fluorescence Spectroscopy, University of Maryland, School of Medicine, 725 W. Lombard St., Baltimore, MD 21201, USA.

出版信息

Tetrahedron Lett. 2002 Apr 1;43(14):2615-2618. doi: 10.1016/s0040-4039(02)00312-x. Epub 2002 Mar 6.

DOI:10.1016/s0040-4039(02)00312-x
PMID:33828341
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8022852/
Abstract

Two new fluorescent probes based on 1,3-diphenylprop-2-en-1-one and on 1,5-diphenylpenta-2,4-dien-1-one structures are presented. Both probes posses one electron-donating dimethylamino group and one boronic acid group (electron-withdrawing group). The change between the neutral and the anionic form of the boronic acid group induced at high pH and/or in presence of sugar, induces optical changes for both probes. Spectroscopic data, p and dissociation constants for different monosaccharides are presented and discussed in terms of sugar detection.

摘要

本文介绍了两种基于1,3 - 二苯基丙 - 2 - 烯 - 1 - 酮和1,5 - 二苯基戊 - 2,4 - 二烯 - 1 - 酮结构的新型荧光探针。两种探针均具有一个供电子的二甲氨基基团和一个硼酸基团(吸电子基团)。在高pH值和/或存在糖的情况下,硼酸基团的中性和阴离子形式之间的变化会引起两种探针的光学变化。文中给出了光谱数据、不同单糖的pKa和离解常数,并就糖检测方面进行了讨论。

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本文引用的文献

1
Wavelength-ratiometric probes for saccharides based on donor-acceptor diphenylpolyenes.基于供体-受体二苯基多烯的糖类波长比率探针。
J Photochem Photobiol A Chem. 2001 Oct 1;143(1):39-47. doi: 10.1016/S1010-6030(01)00471-3. Epub 2001 Sep 5.
2
Spectral Properties of Fluorophores Combining the Boronic Acid Group with Electron Donor or Withdrawing Groups. Implication in the Development of Fluorescence Probes for Saccharides.结合硼酸基团与供电子或吸电子基团的荧光团的光谱性质。对糖类荧光探针开发的启示。
J Phys Chem A. 2001 Jul 1;105(28):6834-6840. doi: 10.1021/jp010076x. Epub 2001 Jun 23.
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A new highly fluorescent probe for monosaccharides based on a donor-acceptor diphenyloxazole.一种基于供体-受体二苯基恶唑的新型高荧光单糖探针。
Chem Commun (Camb). 2001 Oct 7(19):2022-3. doi: 10.1039/b106763j.
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Implanted electrochemical glucose sensors for the management of diabetes.用于糖尿病管理的植入式电化学葡萄糖传感器。
Annu Rev Biomed Eng. 1999;1:153-75. doi: 10.1146/annurev.bioeng.1.1.153.
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Computer-Guided Design in Molecular Recognition: Design and Synthesis of a Glucopyranose Receptor This work was supported by the National Institutes of Health (grant DK5523402).分子识别中的计算机辅助设计:吡喃葡萄糖受体的设计与合成 本研究得到美国国立卫生研究院资助(基金编号DK5523402)。
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