Design and development of a fluorescent probe for monitoring hydrogen peroxide using photoinduced electron transfer
Design and development of a fluorescent probe for monitoring hydrogen peroxide using photoinduced electron transfer
复制标题
DOI：
10.1016/j.bmc.2004.11.023
复制
发表时间：
2005-02-15
影响因子：
3.5
通讯作者：
Imato, T
中科院分区：
文献类型：
--
作者：
Soh, N;Sakawaki, O;Imato, T
开发了一种新的荧光探针7-羟基-2-氧代-N-（2-（二苯基膦基）乙基）-2H-色烯-3-甲酰胺（DPPEA-HC），用于监测过氧化氢（H2 O2）的生成。DPPEA-HC由二苯基膦部分和7-羟基香豆素部分组成，与H2 O2反应形成DPPEA-HC氧化物，这类似于三苯基膦与氢过氧化物（如H2 O2）反应形成三苯基膦氧化物。将光诱导电子转移（PET）应用于DPPEA-HC的设计。由于二苯基膦部分和7-羟基香豆素部分将分别充当PET供体和受体，基于使用B3 LYP/6- 31 G *//AM 1方法计算的供体和受体部分的能级，预期DPPEA-HC将通过形成DPPEA-HC氧化物合理地取消PET过程。DPPEA-HC的荧光强度在加入100 mM磷酸钠缓冲液（pH7.4）中的H2 O2溶液时增加，如从能级计算预测的，并且观察到DPPEA-HC的荧光增加与H2 O2浓度之间的良好相关性。黄嘌呤/黄嘌呤氧化酶/超氧化物歧化酶（XA/XOD/SOD）体系中酶促产生的H_2O_2也能使DPPEA-HC产生荧光。在H2 O2存在下DPPEA-HC的荧光增加在加入催化H2 O2分解的过氧化氢酶（CAT）后立即停止。此外，DPPEA-HC对H_2O_2的选择性和抗氧化性均高于2 ′，7 ′-二氯二氢荧光素。DPPEA-HC和DPPEA-HC氧化物的时间分辨荧光测量证实DPPEA-HC的荧光关/开切换机制是基于PET开/关控制。(C)2004爱思唯尔有限公司保留所有权利。
A novel fluorescent probe, 7-hydroxy-2-oxo-N-(2-(diphenylphosphino)ethyl)-2H-chromene-3-carboxamide (DPPEA-HC) was developed for use in monitoring hydrogen peroxide (H2O2) production. DPPEA-HC, which consists of a diphenylphosphine moiety and a 7-hydroxycoumarin moiety, reacts with H2O2 to form DPPEA-HC oxide, which is analogous to the reaction of triphenylphosphine with hydroperoxides such as H2O2 to form triphenylphosphine oxide. Photoinduced electron transfer (PET) was applied in the design of DPPEA-HC. Since the diphenylphosphine moiety and the 7-hydroxycoumarin moiety would act as the PET donor and the acceptor, respectively, it would be expected that DPPEA-HC would rationally cancel the PET process via the formation of DPPEA-HC oxide, based on the calculated energy levels of the donor and the acceptor moieties using the B3LYP/6-31G*//AM1 method. The fluorescence intensity of DPPEA-HC increased on the addition of a H2O2 solution in 100 mM sodium phosphate buffer (pH7.4), as predicted from the energy level calculation and a good correlation between increase in the fluorescence of DPPEA-HC and the concentration of H2O2 was observed. DPPEA-HC was also fluoresced by H2O2, which was enzymatically produced in xanthine/xanthine oxidase/superoxide dismutase (XA/XOD/SOD) system. The increase in the fluorescence of DPPEA-HC in the presence of H2O2 immediately ceased on the addition of catalase (CAT), which catalyzes the disproportionation of H2O2. In addition, DPPEA-HC was found to have a much higher selectivity for H2O2 and a greater resistance to autoxidation than 2',7'-dichlorodihydrofluoresein (DCFH). Time-resolved fluorescence measurements of DPPEA-HC and DPPEA-HC oxide confirmed that the fluorescence off/on switching mechanism of DPPEA-HC is based on the PET on/off control. (C) 2004 Elsevier Ltd. All rights reserved.