Molecular Design Strategies for Near-Infrared Ratiometric Fluorescent Probes Based on the Unique Spectral Properties of Aminocyanines

被引：121

作者：

Kiyose, Kazuki ^{[1
,2
]}

Aizawa, Sakiko ^{[1
,2
]}

Sasaki, Eita ^{[1
,2
]}

Kojima, Hirotatsu ^{[2
,4
]}

Hanaoka, Kenjiro ^{[1
,2
]}

Terai, Takuya ^{[1
,2
]}

Urano, Yasuteru ^{[1
,3
]}

Nagano, Tetsuo ^{[1
,2
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

[2] Japan Sci & Technol Agcy, CREST, Kawaguchi, Saitama 3320012, Japan

[3] Japan Sci & Technol Agcy, PRESTO, Kawaguchi, Saitama 3320012, Japan

[4] Univ Tokyo, Chem Biol Res Inst, Bunkyo Ku, Tokyo 1130033, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2009年 / 15卷 / 36期

关键词：

enzymes; esterase; fluorescent probes; IR spectroscopy; pH probes; sensors; HEPTAMETHINE CYANINE DYES; INTRAMOLECULAR CHARGE-TRANSFER; RESONANCE ENERGY-TRANSFER; ELECTRON-TRANSFER; PROTEINS; RECEPTOR; PHOSPHODIESTERASE; FLUOROCHROMES; CHROMOPHORE; XENOGRAFTS;

D O I：

10.1002/chem.200900035

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In spite of the wide availability of various near-infrared (NIR) fluorophores as labeling reagents, there are few functional NIR fluorescent probes for which change in the absorption and/or fluorescence spectra upon specific reaction with biomolecules is seen. The widely used photoinduced electron-transfer mechanism is unsuitable for NIR fluorophores, such as tricarbocyanines, because their long excitation wavelength results in a small singlet ex-citation energy. We have reported the unique spectral properties of amine-substituted tricarbocyanines, which were utilized to develop two design strategies. One approach was based on control of the absorption wavelength by using the difference in electron-donating ability before and after a specific reaction with a biomolecule, and the other approach was based on control of the fluorescence intensity by modulating the Forster resonance energy-transfer efficiency through a change in the overlap integral that arises from the change in absorption under acidic conditions. These strategies were validated by obtaining tricarbocyanine-based ratiometric NIR fluorescent probes for esterase and for pH level.

引用

页码：9191 / 9200

页数：10

共 43 条

[41] Design, synthesis and evaluation of near-infrared fluorescent pH indicators in a physiologically relevant range [J].