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Design of functionalized β-ketoenole derivatives as efficient fluorescent dyes for detection of amyloid fibrils

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Abstract

The self-association of proteins into insoluble filamentous aggregates – amyloid fibrils – is associated with a range of protein deposition disorders. With the aim of developing fluorescent probes sensitive to amyloid aggregates, a new series of derivatives of (2Z,5Z,7E)-6-hydroxy-2-(alkylamino)-8-arylocta-2,5,7-trien-4-one dyes was synthesized. These dyes are less sensitive to native amyloidogenic proteins, such as insulin or lysozyme, while they have the ability to exhibit a pronounced fluorescence response in the presence of amyloid fibrils of these proteins depending on the structure of the dye tail groups. The dyes associated with the fibrils show green-yellow emission (495–540 nm) and rather large Stokes shift values (68–125 nm). Upon binding to the fibrils, the fluorescence quantum yields of the dyes could increase by a hundred times up to 0.18–0.47, and the fluorescence intensity decay time strongly enhances up to 0.9–1.3 ns. These features make ketoenoles attractive as probes for the detection of amyloid fibrils; besides, the efficiency of these dyes for real-time monitoring of the kinetics of protein aggregation is shown. The best sensing properties were shown by dyes 2 and 9 bearing short amino tail groups (correspondingly 2-methoxyethyl and 2-hydroxyethyl) and a 4-substituted phenyl moiety at the other end of the ketoenole backbone.

Graphical abstract: Design of functionalized β-ketoenole derivatives as efficient fluorescent dyes for detection of amyloid fibrils

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Publication details

The article was received on 01 Mar 2018, accepted on 11 Jun 2018 and first published on 12 Jul 2018


Article type: Paper
DOI: 10.1039/C8NJ01020J
Citation: New J. Chem., 2018, Advance Article
  • Open access: Creative Commons BY-NC license
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    Design of functionalized β-ketoenole derivatives as efficient fluorescent dyes for detection of amyloid fibrils

    V. Kovalska, S. Chernii, M. Losytskyy, I. Tretyakova, Y. Dovbii, A. Gorski, V. Chernii, R. Czerwieniec and S. Yarmoluk, New J. Chem., 2018, Advance Article , DOI: 10.1039/C8NJ01020J

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