An Autoimmolative Spacer Allows First-Time Incorporation of a Unique Solid-State Fluorophore into a Detection Probe for Acyl Hydrolases

被引：55
作者：
Zhang, Xiao-bing [1 ,2 ]
Waibel, Michael [1 ]
Hasserodt, Jens [1 ]
机构：
[1] Univ Lyon, ENS, Chim Lab, F-69364 Lyon, France
[2] Hunan Univ, Coll Chem & Chem Engn, State Key Lab Chemobiosensing & Chemometr, Changsha 410082, Hunan, Peoples R China
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 03期
基金：
中国国家自然科学基金;
关键词：
autoimmolative spacers; diagnostic agents; fluorescent probes; peptidases; prodrugs; IN-VITRO EVALUATION; PRODRUG STRATEGIES; BETA-GLUCURONIDASE; ENZYMATIC-ACTIVITY; COUPLING REACTION; PROTON-TRANSFER; TRIMETHYL LOCK; PHENOLS; MECHANISM; SUBSTRATE;
D O I：
10.1002/chem.200902412
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A study was conducted to demonstrate the use of an autoimmolative spacer to incorporate a unique solid-state fluorophore into a detection probe for acyl hydrolases. The molecule effectively detected a model peptidase and showed elevated robustness that allowed for the adaptation to diffusion-resistant sequence-specific detection of peptidases for maximal spatial control. A cyclization linker was selected that immolated through an energetically favorable five- or six-membered transition state, taking into account the acylated O,O-acetal moiety. A GABA model compound was prepared to whether a GABA-based three-component system fragmented reliably.
引用
收藏
页码：792 / 795
页数：4
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