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

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• 作者：Lingfei Yang ; Dr. Yuanjun Zhu ; Mengyang Shui ; Tongliang Zhou ; Yuanbo Cai ; Wei Wang ; Fengrong Xu ; Yan Niu ; Chao Wang ; Prof. Dr. Jun-Long Zhang ; Prof. Dr. Ping Xu ; Dr. Lan Yuan and Prof. Dr. Lei Liang
• 刊名：Chemistry - A European Journal
• 出版年：2016
• 出版时间：August 22, 2016
• 年：2016
• 卷：22
• 期：35
• 页码：12363-12370
• 全文大小：3396K
• ISSN：1521-3765

文摘

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.