Bioconjugate Chemistry, volume 31, issue 5, pages 1313-1319
Synthesis and Evaluation of New Trivalent Ligands for Hepatocyte Targeting via the Asialoglycoprotein Receptor
Reshitko Galina S
1
,
Yamansarov Emil Yu
1, 2
,
Evteev Sergei A
1
,
Lopatukhina Elena V.
1
,
Shkil Dmitry O
1
,
Saltykova Irina V
1
,
Lopukhov Anton V
1
,
Kovalev Sergey
1
,
Kislyakov Ivan V
1
,
Burenina Olga Y
4
,
Klyachko Natalia L.
1, 4
,
Garanina A. S.
2
,
Dontsova Olga A.
1, 4
,
Ivanenkov Yan
5, 6
,
Erofeev Alexander V.
1, 2
,
Gorelkin Peter
1, 2
,
Majouga Alexander G.
1, 2, 7
Publication type: Journal Article
Publication date: 2020-05-07
Journal:
Bioconjugate Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 4.7
ISSN: 10431802, 15204812
Organic Chemistry
Pharmacology
Pharmaceutical Science
Biotechnology
Bioengineering
Biomedical Engineering
Abstract
Since the asialoglycoprotein receptor (also known as the 'Ashwell-Morell receptor' or ASGPR) was discovered as the first cellular mammalian lectin, numerous drug delivery systems have been developed and several gene delivery systems associated with multivalent ligands for liver disease targeting are undergoing clinical trials. The success of these systems has facilitated the further study of new ligands with comparable or higher affinity and less synthetic complexity. Herein, we designed two novel trivalent ligands based on the esterification of tris (hydroxymethyl) aminomethane (TRIS) followed by the azide-alkyne Huisgen cycloaddition with azido N-acetyl-D-galactosamine. The presented triazolyl glycoconjugates exhibited good binding to ASGPR, which was predicted using in silico molecular docking and assessed by a surface plasmon resonance (SPR) technique. Moreover, we demonstrated the low level of in vitro cytotoxicity, as well as the optimal spatial geometry and the required amphiphilic balance for new, easily accessible ligands. The conjugate of a new ligand with Cy5 dye exhibited selective penetration into HepG2 cells in contrast to the ASGPR-negative PC3 cell line.
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- We do not take into account publications that without a DOI.
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- Statistics recalculated weekly.
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Reshitko G. S. et al. Synthesis and Evaluation of New Trivalent Ligands for Hepatocyte Targeting via the Asialoglycoprotein Receptor // Bioconjugate Chemistry. 2020. Vol. 31. No. 5. pp. 1313-1319.
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Reshitko G. S., Yamansarov E. Yu., Evteev S. A., Lopatukhina E. V., Shkil D. O., Saltykova I. V., Lopukhov A. V., Kovalev S., Lobov A. N., Kislyakov I. V., Burenina O. Y., Klyachko N. L., Garanina A. S., Dontsova O. A., Ivanenkov Y., Erofeev A. V., Gorelkin P., Beloglazkina E. K., Majouga A. G. Synthesis and Evaluation of New Trivalent Ligands for Hepatocyte Targeting via the Asialoglycoprotein Receptor // Bioconjugate Chemistry. 2020. Vol. 31. No. 5. pp. 1313-1319.
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TY - JOUR
DO - 10.1021/acs.bioconjchem.0c00202
UR - https://doi.org/10.1021%2Facs.bioconjchem.0c00202
TI - Synthesis and Evaluation of New Trivalent Ligands for Hepatocyte Targeting via the Asialoglycoprotein Receptor
T2 - Bioconjugate Chemistry
AU - Reshitko, Galina S
AU - Lopatukhina, Elena V.
AU - Dontsova, Olga A.
AU - Evteev, Sergei A
AU - Shkil, Dmitry O
AU - Yamansarov, Emil Yu
AU - Lopukhov, Anton V
AU - Kovalev, Sergey
AU - Lobov, Alexander Nikolaevich
AU - Kislyakov, Ivan V
AU - Klyachko, Natalia L.
AU - Ivanenkov, Yan
AU - Majouga, Alexander G.
AU - Saltykova, Irina V
AU - Burenina, Olga Y
AU - Garanina, A. S.
AU - Erofeev, Alexander V.
AU - Gorelkin, Peter
AU - Beloglazkina, Elena K.
PY - 2020
DA - 2020/05/07 00:00:00
PB - American Chemical Society (ACS)
SP - 1313-1319
IS - 5
VL - 31
SN - 1043-1802
SN - 1520-4812
ER -
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@article{2020_Reshitko,
author = {Galina S Reshitko and Elena V. Lopatukhina and Olga A. Dontsova and Sergei A Evteev and Dmitry O Shkil and Emil Yu Yamansarov and Anton V Lopukhov and Sergey Kovalev and Alexander Nikolaevich Lobov and Ivan V Kislyakov and Natalia L. Klyachko and Yan Ivanenkov and Alexander G. Majouga and Irina V Saltykova and Olga Y Burenina and A. S. Garanina and Alexander V. Erofeev and Peter Gorelkin and Elena K. Beloglazkina},
title = {Synthesis and Evaluation of New Trivalent Ligands for Hepatocyte Targeting via the Asialoglycoprotein Receptor},
journal = {Bioconjugate Chemistry},
year = {2020},
volume = {31},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021%2Facs.bioconjchem.0c00202},
number = {5},
pages = {1313--1319},
doi = {10.1021/acs.bioconjchem.0c00202}
}
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Reshitko, Galina S., et al. āSynthesis and Evaluation of New Trivalent Ligands for Hepatocyte Targeting via the Asialoglycoprotein Receptor.ā Bioconjugate Chemistry, vol. 31, no. 5, May. 2020, pp. 1313-1319. https://doi.org/10.1021%2Facs.bioconjchem.0c00202.