Development of a series of near-infrared dark quenchers based on Si-rhodamines and their application to fluorescent probes
| Autor: | Shimpei Iwaki, Tasuku Ueno, Toru Komatsu, Yasuteru Urano, Takuya Myochin, Tetsuo Nagano, Kenjiro Hanaoka, Takuya Terai |
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| Rok vydání: | 2015 |
| Předmět: |
Silicon
Absorption spectroscopy Infrared Cell Survival Infrared Rays Photochemistry Biochemistry Catalysis Rhodamines chemistry.chemical_compound Mice Colloid and Surface Chemistry Drug Stability Cell Line Tumor Animals Humans Absorption (electromagnetic radiation) neoplasms Fluorescent Dyes Xanthene Chemistry Near-infrared spectroscopy Optical Imaging technology industry and agriculture Water General Chemistry Darkness equipment and supplies Fluorescence surgical procedures operative Förster resonance energy transfer Solubility Drug Design |
| Zdroj: | Journal of the American Chemical Society. 137(14) |
| ISSN: | 1520-5126 |
| Popis: | Near-infrared (NIR) fluorescent probes based on the Forster resonance energy transfer (FRET) mechanism have various practical advantages, and their molecular design is generally based on the use of NIR dark quenchers, which are nonfluorescent dyes, as cleavable FRET acceptors. However, few NIR dark quenchers can quench fluorescence in the Cy7 region (over 780 nm). Here, we describe Si-rhodamine-based NIR dark quenchers (SiNQs), which show broad absorption covering this region. They are nonfluorescent independently of solvent polarity and pH, probably due to free rotation of the bond between the N atom and the xanthene moiety. SiNQs can easily be structurally modified to tune their water-solubility and absorption spectra, enabling flexible design of appropriate FRET pair for various NIR fluorescent dyes. To demonstrate the usefulness of SiNQs, we designed and synthesized a NIR fluorescent probe for matrix metalloproteinase (MMP) activity using SiNQ780. This probe 1 could detect MMP activity in vitro, in cultured cells and in a tumor-bearing mouse, in which the tumor was clearly visualized, by NIR fluorescence. We believe SiNQs will be useful for the development of a wide range of practical NIR fluorescent probes. |
| Databáze: | OpenAIRE |
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