Design and Synthesis of a BODIPY-Tetrazole Based "Off-On" in-Cell Fluorescence Reporter of Hydrogen Peroxide

被引：18

作者：

An, Peng ^{[1
]}

Lewandowski, Tracey M. ^{[1
]}

Lin, Qing ^{[1
]}

机构：

[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA

来源：

CHEMBIOCHEM | 2018年 / 19卷 / 12期

基金：

美国国家卫生研究院;

关键词：

bioorthogonal; BODIPY; fluorescent probes; hydrogen peroxide; tetrazole; PHOTOINDUCED ELECTRON-TRANSFER; PHOTOCLICK-CHEMISTRY; BIOORTHOGONAL CHEMISTRY; PHOTOACTIVATABLE DIARYLTETRAZOLES; OXIDATIVE AROMATIZATION; PROTEIN; PROBES; PYRAZOLINES; DERIVATIVES; DISCOVERY;

D O I：

10.1002/cbic.201700656

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

BODIPY-linked bithiophene-tetrazoles were designed and synthesized for bioorthogonal photoclick reactions in vitro and in vivo. The reactivity of these tetrazoles toward dimethyl fumarate was found to depend on the BODIPY attachment site, with the meta-linked BODIPY-tetrazole being the most reactive. The resulting pyrazoline cycloadduct showed drastically reduced BODIPY fluorescence. However, BODIPY fluorescence recovered after treatment with hydrogen peroxide. This turn-on effect was attributed to conversion from the pyrazoline to a pyrazole. Finally, we showed that this unique BODIPY-tetrazole off-on fluorescence probe can be used to detect hydrogen peroxide inside HeLa cells.

引用

页码：1326 / 1333

页数：8

共 51 条

[1] Design and Synthesis of Laser-Activatable Tetrazoles for a Fast and Fluorogenic Red-Emitting 1,3-Dipolar Cycloaddition Reaction [J].