期刊
CHEMISTRY-AN ASIAN JOURNAL
卷 12, 期 2, 页码 233-238出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201601430
关键词
cell imaging; cyanines; DNA recognition; dyes/pigments; fluorescence; structure-activity relationships
资金
- ERATO program from JST
- Japan Advanced Plant Science Network
- JSPS KAKENHI [JP15K14542, JP16H06280, JP16H06465, JP16H06464]
- JSPS
- World Premier International Research Center (WPI) Initiative, Japan
- Grants-in-Aid for Scientific Research [15K14542, 15H05491, 26810057, 16H00907, 15K14559] Funding Source: KAKEN
Unsymmetrical cyanine dyes, such as thiazole orange, are useful for the detection of nucleic acids with fluorescence because they dramatically enhance the fluorescence upon binding to nucleic acids. Herein, we synthesized a series of unsymmetrical cyanine dyes and evaluated their fluorescence properties. A systematic structure-property relationship study has revealed that the dialkylamino group at the 2-position of quinoline in a series of unsymmetrical cyanine dyes plays a critical role in the fluorescence enhancement. Four newly designed unsymmetrical cyanine dyes showed negligible intrinsic fluorescence in the free state and strong fluorescence upon binding to double-stranded DNA (dsDNA) with a quantum yield of 0.53 to 0.90, which is 2 to 3 times higher than previous unsymmetrical cyanine dyes. A detailed analysis of the fluorescence lifetime revealed that the dialkylamino group at the 2-position of quinoline suppressed nonradiative decay in favor of increased fluorescence quantum yield. Moreover, these newly developed dyes were able to stain the nucleus specifically in fixed HeLa cells examined by using a confocal laser-scanning microscope.
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