Synthesis of a new betulinic acid glycoconjugate with N-acetyl-d-galactosamine for the targeted delivery to hepatocellular carcinoma cells
A S Olshanova
1
,
E Yu Yamansarov
1
,
E I Seleznev
1
,
S V Kovalev
1
,
A V Lopuhov
1
,
D A Skvortsov
1
,
S A Evteev
1
,
N L Klyachko
1, 2
,
E K Beloglazkina
1
,
Ya A Ivanenkov
3, 4
,
A G Majouga
1, 5, 6
3
Publication type: Journal Article
Publication date: 2020-01-01
scimago Q3
SJR: 0.305
CiteScore: 2.8
Impact factor: —
ISSN: 10665285, 15739171
General Chemistry
Abstract
A new promising conjugate of betulinic acid with N-acetyl-d-galactosamine was synthesized by the simple reaction sequence: esterification and copper-catalyzed azide-alkyne cycloaddition. The obtained glycoderivative exhibited high activity against hepatocarcinoma cell lines in vitro, selectivity of cytotoxic action, and excellent binding to the asialoglycoprotein receptor (ASGPR) of hepatocytes. Its affinity to the ASGPR was established by surface plasmon resonance spectroscopy and confirmed by molecular docking in silico. An original approach was proposed to enhance the cytotoxic properties of C-28 betulinic esters by introducing a hemioxalate fragment bearing free carboxyl group into the C(3) position of ring A.
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Olshanova A. S. et al. Synthesis of a new betulinic acid glycoconjugate with N-acetyl-d-galactosamine for the targeted delivery to hepatocellular carcinoma cells // Russian Chemical Bulletin. 2020. Vol. 69. No. 1. pp. 158-163.
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Olshanova A. S., Yamansarov E. Yu., Seleznev E. I., Kovalev S. V., Lopuhov A. V., Skvortsov D. A., Evteev S. A., Klyachko N. L., Beloglazkina E. K., Ivanenkov Ya. A., Majouga A. G. Synthesis of a new betulinic acid glycoconjugate with N-acetyl-d-galactosamine for the targeted delivery to hepatocellular carcinoma cells // Russian Chemical Bulletin. 2020. Vol. 69. No. 1. pp. 158-163.
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TY - JOUR
DO - 10.1007/s11172-020-2737-3
UR - http://link.springer.com/10.1007/s11172-020-2737-3
TI - Synthesis of a new betulinic acid glycoconjugate with N-acetyl-d-galactosamine for the targeted delivery to hepatocellular carcinoma cells
T2 - Russian Chemical Bulletin
AU - Olshanova, A S
AU - Yamansarov, E Yu
AU - Seleznev, E I
AU - Kovalev, S V
AU - Lopuhov, A V
AU - Skvortsov, D A
AU - Evteev, S A
AU - Klyachko, N L
AU - Beloglazkina, E K
AU - Ivanenkov, Ya A
AU - Majouga, A G
PY - 2020
DA - 2020/01/01
PB - Springer Nature
SP - 158-163
IS - 1
VL - 69
SN - 1066-5285
SN - 1573-9171
ER -
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BibTex (up to 50 authors)
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@article{2020_Olshanova,
author = {A S Olshanova and E Yu Yamansarov and E I Seleznev and S V Kovalev and A V Lopuhov and D A Skvortsov and S A Evteev and N L Klyachko and E K Beloglazkina and Ya A Ivanenkov and A G Majouga},
title = {Synthesis of a new betulinic acid glycoconjugate with N-acetyl-d-galactosamine for the targeted delivery to hepatocellular carcinoma cells},
journal = {Russian Chemical Bulletin},
year = {2020},
volume = {69},
publisher = {Springer Nature},
month = {jan},
url = {http://link.springer.com/10.1007/s11172-020-2737-3},
number = {1},
pages = {158--163},
doi = {10.1007/s11172-020-2737-3}
}
Cite this
MLA
Copy
Olshanova, A. S., et al. āSynthesis of a new betulinic acid glycoconjugate with N-acetyl-d-galactosamine for the targeted delivery to hepatocellular carcinoma cells.ā Russian Chemical Bulletin, vol. 69, no. 1, Jan. 2020, pp. 158-163. http://link.springer.com/10.1007/s11172-020-2737-3.