Abstract
A novel pro-dye approach for the acid-selective staining of the subcellular compartments for better permeability and selectivity was applied. The designed sensor has suitable physicochemical properties such as a large Stokes shift and a long-lived intracellular fluorescence. The Schiff base fragment was used for the acid-sensitive release of a fluorophore without affecting the overall stability of the biological systems. Due to the presence of an imine bond in its structure and its unique fluorescent properties, it can be presented as a “pro-dye” for acidic structures such as lysosomes. As a result of an imine bond cleavage, a new fluorescent compound is released, whose substantially shifted excitation and emission wavelengths enable a more selective and effective imaging of lysosomes and endosomes. The presented report provides the chemical, physicochemical and optical profiles as well as biological assays and theoretical calculations.
Highlights
A novel pro-dye approach for the acid-selective staining of the subcellular compartments for better permeability and selectivity was applied
The investigated compound was prepared by a three-step reaction: (1) the synthesis of a nitrostyrylquinoline derivative in a simple, efficient reaction between quinaldine and p-nitrobenzaldehyde in acetic anhydride conditions
Simple styrylquinolines with an amine group may be desirable as dyes for specific organelles
Summary
A novel pro-dye approach for the acid-selective staining of the subcellular compartments for better permeability and selectivity was applied. Staderini et al presented a 4-aminostyryl derivative of 6-methylquinoline with potential therapeutic and diagnostic properties against Alzheimer’s disease due to its ability to stain Aβ amyloid plaques[10] Another good example is a styrylquinoline dye with the dipicolyamine moiety, which demonstrates a multicolor fluorescence depending on the addition of different metal ions[11]. A quinoline conjugated with benzothiazole moiety (BTVQ) has been used as pH specific dye for lysosomes[15] This probe has large Stokes shift and pKa of 3.5 but low wavelength of absorption maxima and reduction of fluorescence in low pH are drawbacks. We present a comprehensive exploration of the newly synthesized compound BC15, including the chemical, physicochemical and optical profiles as well as biological assays and theoretical calculations
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