Synthesis of daunorubicin conjugates with fragments of H type 5, Lea, Lex antigens and N-fucoglycan
| Autor: | Leonid M. Likhosherstov, Olga Novikova, V. E. Piskarev, Natalya G. Kolotyrkina |
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| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
Daunorubicin Hydrochloride Hemagglutination assay biology 010405 organic chemistry Chemistry Stereochemistry Daunorubicin Laburnum anagyroides General Chemistry Lotus tetragonolobus Oligosaccharide 010402 general chemistry biology.organism_classification 01 natural sciences Ulex europaeus 0104 chemical sciences medicine Conjugate medicine.drug |
| Zdroj: | Russian Chemical Bulletin. 68:2339-2343 |
| ISSN: | 1573-9171 1066-5285 |
| Popis: | Daunorubicin was conjugated with spacered N-glycosides of di- and trisaccharides containing terminal α-l-fucopyranose residues. The synthesis was carried out by N-monoalkylation of daunorubicin hydrochloride (1) in aqueous DMF in the presence of NaHCO3 using N-β-glycoside N-bromoacetylglycyl derivatives, namely, α-l-Fucp-(1→2)-β-d-Galp-(1→4)-β-d-Glcp-NHCOCH2NHCOCH2Br (2a), α-l-Fucp-(1→4)-[β-d-Galp-(1→3)]-β-d-GlcpNAc-NHCOCH2NHCOCH2Br (3a), α-l-Fucp-(1→3)-β-d-GlcpNAc-NHCOCH2NHCOCH2Br (4a), and α-l-Fucp-(1→6)-β-d-GlcpNAc-NHCOCH2NHCOCH2Br (5a). The conjugates of daunorubicin were obtained as hydrochlorides (2b-5b) in 40% yield. Their oligosaccharide components are fragments of H type 5, Lea, Lex antigens and N-fucolglycan, respectively. 0(I) Erythrocytes hemagglutination inhibition assay was performed with conjugates 2b–5b and Ulex europaeus (UEA 1), Lotus tetragonolobus (LTA), and Laburnum anagyroides (LAA) plant fucolectins. |
| Databáze: | OpenAIRE |
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