Amino acid functionalized benzanthrone dyes: Synthesis and photophysical study

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 i...

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Published inDyes and pigments Vol. 204; p. 110363
Main Authors Konstantinova, Anastasija, Avotiņa, Līga, Ķizāne, Gunta, Pučkins, Aleksandrs, Osipovs, Sergejs, Kirilova, Elena
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 01.08.2022
Subjects
Amino acids
Benzanthrone
Fluorescence spectroscopy
Synthesis
Fluorescence spectroscopy
Amino acids
Synthesis
Benzanthrone
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Summary: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. [Display omitted] •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.
ISSN:0143-7208
1873-3743
DOI:10.1016/j.dyepig.2022.110363