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Rational Design of Fluorescent Phthalazinone Derivatives for One- and Two-Photon Imaging

机译:一和二光子成像的荧光酞菁衍生物的合理设计

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摘要

Phthalazinone derivatives were designed as optical probes for one- and two-photon fluorescence microscopy imaging. The design strategy involves stepwise extension and modification of pyridazinone by 1)expansion of pyridazinone to phthalazinone, a larger conjugated system, as the electron acceptor, 2)coupling of electron-donating aromatic groups such as N,N-diethylaminophenyl, thienyl, naphthyl, and quinolyl to the phthalazinone, and 3)anchoring of an alkyl chain to the phthalazinone with various terminal substituents such as triphenylphosphonio, morpholino, triethylammonio, N-methylimidazolio, pyrrolidino, and piperidino. Theoretical calculations were utilized to verify the initial design. The desired fluorescent probes were synthesized by two different routes in considerable yields. Twenty-two phthalazinone derivatives were synthesized and their photophysical properties were measured. Selected compounds were applied in cell imaging, and valuable information was obtained. Furthermore, the designed compounds showed excellent performance in two-photon microscopic imaging of mouse brain slices.
机译:酞嗪酮衍生物被设计为用于单光子和双光子荧光显微镜成像的光学探针。设计策略包括逐步扩展和修饰哒嗪酮,方法是:1)将哒嗪酮扩展为酞菁酮(一种较大的共轭体系,作为电子受体); 2)给电子芳族基团(如N,N-二乙基氨基苯基),噻吩基,萘基, 3)将烷基链固定在具有各种末端取代基的酞菁酮上,所述取代基例如为三苯基膦酰基,吗啉代,三乙基铵基,N-甲基咪唑基,吡咯烷基和哌啶子基。理论计算用于验证初始设计。通过两种不同的途径以可观的产率合成了所需的荧光探针。合成了22种酞嗪酮衍生物,并对其光物理性质进行了测定。选择的化合物应用于细胞成像,并获得了有价值的信息。此外,设计的化合物在小鼠脑切片的双光子显微成像中显示出优异的性能。

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