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Rational Design of Fluorescent Phthalazinone Derivatives for One‐ and Two‐Photon Imaging
Author(s) -
Yang Lingfei,
Zhu Yuanjun,
Shui Mengyang,
Zhou Tongliang,
Cai Yuanbo,
Wang Wei,
Xu Fengrong,
Niu Yan,
Wang Chao,
Zhang JunLong,
Xu Ping,
Yuan Lan,
Liang Lei
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201601499
Subject(s) - fluorescence , two photon excitation microscopy , rational design , alkyl , live cell imaging , fluorescence lifetime imaging microscopy , photochemistry , electron acceptor , acceptor , chemistry , materials science , combinatorial chemistry , nanotechnology , cell , optics , organic chemistry , physics , biochemistry , condensed matter physics
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.