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  Negatively charged red-emitting acridine dyes for facile reductive amination, separation and fluorescent detection of glycans.

Fomin, M., Seikowski, J., Belov, V. N., & Hell, S. W. (2020). Negatively charged red-emitting acridine dyes for facile reductive amination, separation and fluorescent detection of glycans. Analytical Chemistry, (in press). doi:10.1021/acs.analchem.9b05863.

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Item Permalink: http://hdl.handle.net/21.11116/0000-0005-DFC0-7 Version Permalink: http://hdl.handle.net/21.11116/0000-0005-DFC4-3
Genre: Journal Article

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Fomin, M.1, Author              
Seikowski, J.2, Author              
Belov, V. N.1, Author              
Hell, S. W.1, Author              
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1Department of NanoBiophotonics, MPI for Biophysical Chemistry, Max Planck Society, ou_578627              
2Research Group of Nucleic Acid Chemistry, MPI for Biophysical Chemistry, Max Planck Society, ou_578605              

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 Abstract: The capillary gel electrophoresis with laser-induced fluorescence detection (CGE-LIF) has become a key method in high-throughput glycan analysis. At present, CGE-LIF relies on 8-aminopyrene-1,3,6-trisulfonic acid (APTS). However, APTS has moderate reactivity in labeling of glycans, fixed selectivity profile and renders the detection to only green color. Here, we report synthesis of red-emitting and highly reactive fluo-rescent tags for glycan derivatization. The design is based on a 9-aminoacridine scaffold with various acceptor groups at C-2 (CN, SO2R) and a primary amino group at C-7 for conjugation via reductive amination. These reactive dyes exhibit absorption maxima close to 450 nm and emis-sion above 600 nm. They readily undergo conjugation with reducing sugars at the desired 1:1 stoichiometry. The red emission of conjugates with a maximum at 610-630 nm can be observed under excitation with 488 nm light and detected separately from the APTS-labeled oligosaccharides. Phosphorylated 7,9-diaminoacridine-2-SO2R derivatives with variable amounts of negative charges provide high mobilities of glycoconjugates on polyacrylamide gel electrophoresis (PAGE), as compared to those of APTS. We further demonstrate their utility by labeling and separating a maltodextrin ladder and sialyllactose isomers. The new dyes are expected to cross-validate and increase the glycan identification precision in CGE-LIF and help to reveal "heavy" glycans, yet undetectable with APTS label.

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Language(s): eng - English
 Dates: 2020-03-10
 Publication Status: Published online
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 Rev. Method: Peer
 Identifiers: DOI: 10.1021/acs.analchem.9b05863
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Title: Analytical Chemistry
Source Genre: Journal
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