Russian Chemical Bulletin

, том 69 , издание 1 , страницы 158-163

Synthesis of a new betulinic acid glycoconjugate with N-acetyl-d-galactosamine for the targeted delivery to hepatocellular carcinoma cells

Тип публикации: Journal Article

Дата публикации: 2020-01-01

Springer Nature

Russian Chemical Bulletin

scimago Q3

БС2

SJR: 0.305

CiteScore: 2.8

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ISSN: 10665285, 15739171

DOI: 10.1007/s11172-020-2737-3

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General Chemistry

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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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@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}

}

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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, vol. 69, no. 1, Jan. 2020, pp. 158-163. http://link.springer.com/10.1007/s11172-020-2737-3.