Rational Design of Fluorescent Phthalazinone Derivatives for One‐ and Two‐Photon Imaging |
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| Authors: | 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 Prof. Dr. Lei Liang |
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| Affiliation: | 1. Department of Medicinal Chemistry, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing, P. R. China;2. Medical and Healthy Analysis Center, Peking University, Beijing, P. R. China;3. Department of Molecular and Cellular Pharmacology, School of Pharmaceutical Sciences, Peking University, Beijing, P. R. China;4. Beijing National Laboratory for Molecular Science, State Key Laboratory of Rare Earth Materials Chemistry and Applications, College of Chemistry and Molecular Engineering, Peking University, Beijing, P. R.China |
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| Abstract: | 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. |
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| Keywords: | density functional calculations fluorescence microscopy fluorescent probes imaging agents synthesis design |
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