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Synthesis, Evaluation, and Computational Studies of Naphthalimide‐Based Long‐Wavelength Fluorescent Boronic Acid Reporters
Author(s) -
Jin Shan,
Wang Junfeng,
Li Minyong,
Wang Binghe
Publication year - 2008
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.200701785
Subject(s) - fluorescence , boronic acid , chemistry , combinatorial chemistry , solubility , amino acid , organic chemistry , biochemistry , physics , quantum mechanics
Abstract Boronic acids that change fluorescence properties upon sugar binding are very useful for the synthesis of carbohydrate sensors. Along this line, boronic acids that fluoresce beyond 500 nm are especially useful. A series of boronic acid fluorescent reporter compounds based on the 4‐amino‐1,8‐naphthalimide structure have been synthesized ( 1 a – d ) and evaluated under near physiological conditions. These compounds showed good water solubility and significant changes in fluorescence properties after binding with sugars, with the emission wavelength being at around 570 nm. Analogues in this series with different substitutions showed similar properties. We have also examined the mechanism of the observed fluorescence changes for these compounds.