beta-ketoenole dyes: Synthesis and study as fluorescent sensors for protein amyloid aggregates

Kovalska, Vladyslava and Chernii, Svitlana and Losytskyy, Mykhaylo and Dovbii, Yan and Tretyakova, Iryna and Czerwieniec, Rafal and Chernii, Victor and Yarmoluk, Sergiy and Volkov, Sergiy (2016) beta-ketoenole dyes: Synthesis and study as fluorescent sensors for protein amyloid aggregates. DYES AND PIGMENTS, 132. pp. 274-281. ISSN 0143-7208, 1873-3743

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Abstract

The series of the beta-ketoenoles (2E,5Z,7E,9E)-2-(alkylamino)-6-hydroxy-10-phenyldeca-2,5,7,9-tetraen-4-ones with variation of the alkylamino tail groups was synthesized and studied as potential probes for the sensing of protein insoluble aggregates - amyloid fibrils. Depending on the structure of the alkylamino group, the dyes could increase their fluorescence intensity in the dozens of times in the presence of insulin fibrils. The compound with a 2-hydroxyethylamino substituent demonstrates the highest fluorescence response (up to 60 times) and good range of insulin fibril detection (1-50 mu g/ml). In complexes with fibrils, the dyes possess fluorescence quantum yield values up to 15% and binding constant values of about 2 x 105 M-1. The excitation and emission maxima of beta-ketoenoles are located in the range 407 -427 nm and 500-554 nm correspondingly. These compounds are weakly fluorescent when free and slightly sensitive to the native proteins insulin and bovine serum albumin. Thus beta-ketoenoles are considered as prospective molecules for the fluorescent detection of amyloid aggregates of proteins. (C) 2016 Elsevier Ltd. All rights reserved.

Item Type: Article
Uncontrolled Keywords: TRIMETHINE CYANINE DYES; FIBRILS; REACTIVITY; PROBES; AMINES; beta-Ketoenole dyes; Fluorescent sensing; Probes; Amyloid fibrils; Proteins
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Physikalische und Theoretische Chemie
Depositing User: Dr. Gernot Deinzer
Date Deposited: 05 Apr 2019 08:44
Last Modified: 05 Apr 2019 08:44
URI: https://pred.uni-regensburg.de/id/eprint/3450

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