Coumarin- and Rhodamine-Fused Deep Red Fluorescent Dyes: Synthesis, Photophysical Properties, and Bioimaging in Vitro

详细信息    查看全文

• 作者：Jianhong Chen ; Weimin Liu ; Bingjiang Zhou ; Guangle Niu ; Hongyan Zhang ; Jiasheng Wu ; Ying Wang ; Weigang Ju ; Pengfei Wang
• 刊名：The Journal of Organic Chemistry
• 出版年：2013
• 出版时间：June 21, 2013
• 年：2013
• 卷：78
• 期：12
• 页码：6121-6130
• 全文大小：565K
• 年卷期：v.78,no.12(June 21, 2013)
• ISSN：1520-6904

文摘

A series of deep red fluorescent dyes (CR1 to CR3) was developed via introduction of a coumarin moiety into the rhodamine molecular skeleton. The novel dyes possessed the individual advantages of coumarin and rhodamine derivatives, and the emission wavelength was extended to the deep red region (>650 nm) due to the extension of fused-ring conjugate structure simultaneously. To illustrate its value, we designed and conveniently synthesized a series of novel deep red bioimaging dyes (CR1E to CR3E) by esterification of CR1 to CR3, which could selectively stain mitochondria. They were superior to the MitoTrackers for mitochondrial staining in terms of large Stokes shift, excellent contrast for imaging, high photostability, and low cytotoxicity. Furthermore, the fluorescence of the coumarin moiety and rhodamine-like fluorophore could be switched like classical rhodamine. Thus, they could be used as an effective platform in constructing fluorescence sensors. Based on this fact, we constructed a novel ratiometric sensor (CR1S) for Hg²⁺ with good selectivity that could be successfully applied to the imaging of Hg²⁺ in living A549 cells. This design strategy is straightforward and adaptable to various deep red dyes and sensing platforms by simply introducing different fluorophores.