Fluorescence Assisted Capillary Electrophoresis of Glycans Enabled by the Negatively Charged Auxochromes in 1-Aminopyrenes.

A compact and negatively charged acceptor group, N-(cyanamino)sulfonyl, is introduced for dye design and its influence on the absorption and emission spectra of the "push-pull" chromophores is demonstrated with 1,3,6-tris[(cyanamino)sulfonyl]-8-aminopyrene. The new sulfonamides, including O-phosphorylated (3-hydroxyazetidine)-N-sulfonyl, are negatively charged electron acceptors and auxochromes. 1-Aminopyrenes decorated with the new sulfonamides have three or six negative charges (pH ≥8), low m/z ratios, high mobilities in an electric field, and yellow to orange emission. We labeled maltodextrin oligomers by reductive amination, separated the products by electrophoresis, and demonstrated their high brightness in a commercial DNA analyzer and the distribution of the emission signal among the detection channels.

Negatively Charged Yellow-Emitting 1-Aminopyrene Dyes for Reductive Amination and Fluorescence Detection of Glycans.

1-Aminopyrenes with three ω-hydroxylated N-alkylsulfonamido or alkylsulfonyl residues in positions 3, 6, and 8 were prepared, O-phosphorylated, and applied for reductive amination of oligosaccharides. The dyes (ϵ≈20 000 m-1 cm-1 ) with six negative charges (pH≥8) and low m/z ratios enable labeling and fluorescence detection of reducing sugars (glycans) related to the most structurally and functionally diverse class of natural products. Under excitation with a 488 nm laser, the new glycoconjugates emit yellow light of about 560 nm, outperforming (with respect to brightness and faster electrophoretic mobilities) the corresponding APTS derivatives (benchmark dye with green emission in conjugates).

Novel non-toxic high efficient antibacterial azido chitosan derivatives with potential application in food coatings.

In this work, we developed a simple method for the preparation of N-(3-azido-2-hydroxypropyl)chitosan. We compared the antibacterial activity of N-(3-azido-2-hydroxypropyl)chitosans and previously synthesized N-(2-azidoethyl)chitosans. N-(3-azido-2-hydroxypropyl)chitosans possess higher antibacterial effect which is comparable with that of ampicillin and gentamicin. The effect is due to azido pharmacophore -CH2-CH(OH)-CH2-N3 (for N-(3-azido-2-hydroxypropyl)chitosan) or -CH2-CH2-N3 (for N-(2-azidoethyl)chitosan) introduced in chitosan chain, since the corresponding organic azides NH2-CH2-CH2-N3 and NH2-CH2-CH2-N3 are characterized by high antibacterial activity. However, high antibacterial organic azides NH2-CH2-CH2-N3 and NH2-CH2-CH2-N3 are characterized by high toxicity. Their conjugation to the chitosan chain saves their antibacterial effect, but strongly diminishes their toxicity, and the toxicity of the resulting derivatives is comparable with that of the starting chitosan. These findings are of interest to food science, since novel effective food coatings can be developed on basis of prepared derivatives.