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The series of the β-ketoenoles (2 E ,5 Z ,7 E ,9 E )-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 μg/ml). In complexes with fibrils, the dyes possess fluorescence quantum yield values up to 15% and binding constant values of about 2 × 10 5 M −1 . The excitation and emission maxima of β-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 β-ketoenoles are considered as prospective molecules for the fluorescent detection of amyloid aggregates of proteins. [ABSTRACT FROM AUTHOR]

The effect of various N,N ′-substituents in the molecule of benzothiazole trimethine cyanine dye on its ability to sense the amyloid aggregates of protein was studied. The dyes are low fluorescent when free and in the presence of monomeric proteins, but their emission intensity sharply increases in complexes with aggregated insulin and lysozyme, with the fluorescence quantum yield reaching up to 0.42. The dyes carrying butyl, hydroxyalkyl, and phenylalkyl groups as N,N ′-substituents possess the increased fluorescent sensitivity to fibrillar lysozyme, whereas the ones carrying quaternary amino groups are preferably sensitive to fibrillar insulin. This fluorescent sensitivity preference provided by the N,N ′-functional groups could be explained by the interaction between these groups and protein side chains. The strongest fluorescent response (up to 70 times) and the same sensitivity to aggregates of both proteins were exhibited by the dye D-51 carrying N -sulfoalkyl group. The studied cyanines allow the detection of fibrillar aggregates in the wide range up to 0.8 to 300 μg/ml and permit monitoring the protein aggregation kinetics with high reproducibility. The modification of trimethine cyanine dyes by functional substituents in N,N ′-positions is suggested as a tool for the design of fluorescent molecules with the enhanced fluorescent sensitivity to the fibrillar aggregates of proteins. [ABSTRACT FROM AUTHOR]

Abstract: A series of new symmetrical and asymmetrical squaraines were synthesised and efficiency of their use as fluorescent probes for the specific detection of proteins was studied. Spectral-luminescent properties of the squaraines were measured in presence of bovine serum albumin (BSA), human serum albumin (HSA), ovalbumin, avidin from hen egg white (AVI), lysozyme, and trypsin. All investigated squaraines show considerable (in 24–190 times) emission increase in the presence of BSA. At the same time the fluorescent response of the studied dyes in the presence of other albumins is significantly lower – emission enhances up to 24 times. The 3-oxo-substituted indolenine dye 9(74) demonstrates sufficient fluorescence increasing value and emission intensity level in the presence of BSA as well as of HSA and ovalbumin. Dyes containing N-carboxyalkyl group demonstrate sufficient emission enhancement (up to 16 times) and noticeable fluorescent signal in the presence of avidin from hen egg white. Squaraines slightly increase or even decrease their emission intensity in the presence of hydrolases lysozyme or trypsin. [Copyright &y& Elsevier]

Abstract: The influence of methyl-, 2-hydroxyethyl-, dimethyl-, diethyl- and benzoyl-amino substituents in the 6,6′-positions of benzothiazole heterocycle of trimethine cyanines on their spectral-luminescent properties and behavior in presence of DNA, RNA and BSA was studied. It was shown that incorporation of 6,6′-substituents generally leads to the increase in dyes tendency to aggregation, resulting in the considerable decrease in the emission intensity of the disubstituted dyes as compared to the unsubstituted ones. Emission of the studied 6,6′-disubstited dyes in DNA presence is considerably more intensive than in presence of RNA, that points on the existing of DNA binding preference for the mentioned dyes. Insertion of benzoyl-amino groups into the 6,6′-positions permitted us to design the DNA-sensitive dyes on the basis of symmetric trimethine cyanines with unsubstituted polymethine chain, while typically such dyes slightly respond on the presence of biopolymers. 6,6′-Benzoyl-amino-disubstituted trimethine cyanines are proposed as efficient dyes for DNA detection. [Copyright &y& Elsevier]