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

URN to cite this document:

urn:nbn:de:bvb:355-epub-383996 Copy

DOI to cite this document:

10.5283/epub.38399 Copy

Kovalska, Vladislava ; Chernii, Svitlana ; Losytskyy, Mykhaylo ; Dovbii, Yan ; Tretyakova, Iryna ; Czerwieniec, Rafal ; Gorskii, Aleksandr ; Chernii, Victor ; Yarmoluk, Sergiy

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Date of publication of this fulltext: 01 Mar 2019 09:13

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Details

Item type:	Article
Journal or Publication Title:	New Journal of Chemistry
Publisher:	ROYAL SOC CHEMISTRY
Place of Publication:	CAMBRIDGE
Volume:	42
Page Range:	pp. 13308-13318
Date:	12 July 2018
Institutions:	Chemistry and Pharmacy > Institut für Physikalische und Theoretische Chemie
Identification Number:	Value Type 10.1039/c8nj01020j DOI
Keywords:	THIOFLAVIN-T FLUORESCENCE; ESCHERICHIA-COLI; ALPHA-SYNUCLEIN; CYANINE DYES; REACTIVITY; BIOFILMS; INSULIN; BINDING; AMINES; PROBES;
Dewey Decimal Classification:	500 Science > 540 Chemistry & allied sciences
Status:	Published
Refereed:	Yes, this version has been refereed
Created at the University of Regensburg:	Partially
Item ID:	38399

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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 ...

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.

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Metadata last modified: 18 Feb 2021 10:56

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