Synthesis of daunorubicin conjugates with fragments of H type 5, Lea, Lex antigens and N-fucoglycan
- Авторы: Likhosherstov L.1, Novikova O.1, Kolotyrkina N.1, Piskarev V.2
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Учреждения:
- N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
- A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences
- Выпуск: Том 68, № 12 (2019)
- Страницы: 2339-2343
- Раздел: Full Articles
- URL: https://journals.rcsi.science/1066-5285/article/view/243568
- DOI: https://doi.org/10.1007/s11172-019-2708-8
- ID: 243568
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Аннотация
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.
Об авторах
L. Likhosherstov
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Автор, ответственный за переписку.
Email: likhosherstov@mail.ru
Россия, 47 Leninsky prosp., Moscow, 119991
O. Novikova
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: likhosherstov@mail.ru
Россия, 47 Leninsky prosp., Moscow, 119991
N. Kolotyrkina
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: likhosherstov@mail.ru
Россия, 47 Leninsky prosp., Moscow, 119991
V. Piskarev
A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences
Email: likhosherstov@mail.ru
Россия, 28 ul. Vavilova, Moscow, 119991