Huan-bao Fa, Jingting Zhou, Dong Zhang
May 1, 2015
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Influential Citations
3
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Quality indicators
Journal
Research on Chemical Intermediates
Abstract
A novel 4-(2-{[6-(1,1-dicyanoprop-1-en-2-yl)naphthalen-2-yl](methyl)amino} ethoxy)-4-oxobutanoic acid (5) fluorescent probe for β-amyloids was synthesized by catalytic acylation using 4-dimethylaminopyridine between succinic anhydride and (1-{6-[(2-hydroxyethyl)(methyl) amino]-2-naphthyl}ethylidene)malononitrile (4). The structures of all compounds were identified by proton nuclear magnetic resonance spectroscopy, infrared spectroscopy, mass spectrometry, and ultraviolet–visible (UV–Vis) spectroscopy. The UV–Vis and fluorescence spectra of 1-{6-[(2-hydroxyethyl)(methyl) amino]-2-naphthyl}ethan-1-one (3), 4, and 5 in solvents with different polarities were investigated, and the effects of solvent polarity on the optical properties of the three compounds were studied. The objective product 5 showed high binding affinities toward Aβ(1–40) aggregates in vitro (Kd = 29.4 nmol/L) by fluorophotometry. This study provides a powerful fluorescent probe for the molecular diagnosis of Alzheimer’s disease.