Publication details
DESIGN AND SYNTHESIS OF NEW FLUOROPHORES FOR THE DETECTION OF BIOMOLECULES
| Authors | |
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| Year of publication | 2023 |
| Type | Appeared in Conference without Proceedings |
| MU Faculty or unit | |
| Citation | |
| Description | Changes in the composition of glycans correlate with the progression of many diseases, therefore they are investigated as disease markers. On the other hand, their analysis is difficult because they do not contain a chromophore or charges that would enable their electrophoretic separation. Our goal was to develop a new fluorescent marker covalently bound to glycans providing fast labeling kinetics, high quantum yield, increased detection sensitivity using MS, and at the same time carrying a charge in the structure, which will enable the studied glycans to be separated electrophoretically. The basic skeleton of this fluorophore is based on pyrrole and indolizine. The synthesis was based on two building blocks, synthon A and synthon B, which were subsequently connected. The plan was to prepare variants of the fluorophore carrying electron-donating or electron-accepting groups on synthon A. These substitutions allow for variability in the wavelength of the absorption maximum and thus the wavelength of fluorescence. The molecule also carries a trimethylammonium functional group and a propanoate chain, which is necessary for the attachment of the fluorophore to the glycan. Synthon B and synthon A were prepared without substitution at the 4-phenyl position and with methyl and methoxycarbonyl groups at this position. The methyl derivative was used for the synthesis of the fluorophore backbone. This structure showed fluorescence in the UV region of the spectrum. The substance was subsequently oxidized to an aldehyde, which will have to be further converted to a quaternary ammonium compound. Also, the side chain carrying the methyl ester function will need to be converted to a hydrazide. The prepared substances will also be characterized in cooperation with the Institute of Analytical Chemistry of the Academy of Sciences of the Czech Republic. The usability of the newly developed fluorophores will be demonstrated by profiling glycoproteins associated with breast cancer. |
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