Amino acid functionalized benzanthrone dyes: Synthesis and photophysical study. (August 2022)

• Record Type: Journal Article
• Authors: Konstantinova, Anastasija; Avotiņa, Līga; Ķizāne, Gunta; Pučkins, Aleksandrs; Osipovs, Sergejs; Kirilova, Elena
• Is Part Of: Dyes and pigments. Volume 204(2022)
• Publication Date: 2022-08
• Subjects: Amino acids -- Benzanthrone -- Synthesis -- Fluorescence spectroscopy; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2022.110363
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: The substitution reaction of 3- N -(2-chloroacetamido)benzanthrone with a number of the amino acids is reported. The possibility of using this halogenated benzanthrone for fluorescent labelling of amino acids has been studied. Arginine is the most reactive amino acid in the reaction, as it was found in the study. The spectral behavior of new benzanthrone derivatives depends on the polarity of the medium, exhibiting fluorescent solvatochromism due to intramolecular charge transfer from the substituted amino group to the carbonyl group. The results obtained indicate that the synthesized compounds are promising for studying peptides and proteins, as well as for visualizing biological objects. Graphical abstract: Image 1 Highlights: The reaction between 3- N -(2-chloroacetamido)benzanthrone and amino acids were studied. Spectroscopic properties of the newly synthesized luminescent dyes were examined. The synthesized dyes are promising for studying peptides and proteins, as well as for visualizing biological objects.