Kovalska, Vladyslava and Chernii, Svitlana and Losytskyy, Mykhaylo and Tretyakova, Iryna and Dovbii, Yan and Gorski, Alexandr and Chernii, Victor and Czerwieniec, Rafal and Yarmoluk, Sergiy (2018) Design of functionalized beta-ketoenole derivatives as efficient fluorescent dyes for detection of amyloid fibrils. NEW JOURNAL OF CHEMISTRY, 42 (16). pp. 13308-13318. ISSN 1144-0546, 1369-9261
Full text not available from this repository. (Request a copy)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.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | THIOFLAVIN-T FLUORESCENCE; ESCHERICHIA-COLI; ALPHA-SYNUCLEIN; CYANINE DYES; REACTIVITY; BIOFILMS; INSULIN; BINDING; AMINES; PROBES; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Physikalische und Theoretische Chemie |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 09 Mar 2020 14:54 |
| Last Modified: | 09 Mar 2020 14:54 |
| URI: | https://pred.uni-regensburg.de/id/eprint/14032 |
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