New Small-Molecule Glycoconjugates of Docetaxel and GalNAc for Targeted Delivery to Hepatocellular Carcinoma
Rostislav A Petrov
1, 2
,
Sofiia R Mefedova
1
,
Emil Yu Yamansarov
1, 3
,
Svetlana Maklakova
1, 3
,
Elena V. Lopatukhina
1
,
Olga Y Burenina
4
,
Anton V Lopukhov
1
,
Sergey Kovalev
1
,
Yury V Timchenko
1
,
Evgenia E Ondar
1
,
Yan Ivanenkov
2, 5
,
Sergei A Evteev
1
,
Alexander N. Vaneev
1, 3
,
Natalia L. Klyachko
1, 4
,
Alexander V. Erofeev
1, 3
,
Alexander S. Erofeev
1, 3
,
Peter Gorelkin
1, 3
,
Petr V. Gorelkin
1, 3
,
Alexander G. Majouga
1, 3, 6
Publication type: Journal Article
Publication date: 2020-12-02
scimago Q1
wos Q1
SJR: 0.968
CiteScore: 7.8
Impact factor: 4.5
ISSN: 15438384, 15438392
PubMed ID:
33264010
Drug Discovery
Pharmaceutical Science
Molecular Medicine
Abstract
In this work, we have developed covalent and low molecular weight docetaxel delivery systems based on conjugation with N-acetyl-d-galactosamine and studied their properties related to hepatocellular carcinoma cells. The resulting glycoconjugates have an excellent affinity to the asialoglycoprotein receptor (ASGPR) in the nanomolar range of concentrations and a high cytotoxicity level comparable to docetaxel. Likewise, we observed the 21-75-fold increase in water solubility in comparison with parent docetaxel and prodrug lability to intracellular conditions with half-life values from 25.5 to 42 h. We also found that the trivalent conjugate possessed selective toxicity against hepatoma cells vs control cell lines (20-35 times). The absence of such selectivity in the case of monovalent conjugates indicates the effect of ligand valency. Specific ASGPR-mediated cellular uptake of conjugates was proved in vitro using fluorescent-labeled analogues. In addition, we showed an enhanced generation of reactive oxygen species in the HepG2 cells, which could be inhibited by the natural ligand of ASGPR. Overall, the obtained results highlight the potential of ASGPR-directed cytostatic taxane drugs for selective therapy of hepatocellular carcinoma.
Found
Nothing found, try to update filter.
Found
Nothing found, try to update filter.
Top-30
Journals
|
1
2
3
|
|
|
Journal of Medicinal Chemistry
3 publications, 7.5%
|
|
|
RSC Medicinal Chemistry
2 publications, 5%
|
|
|
Russian Journal of Organic Chemistry
2 publications, 5%
|
|
|
ŠŃŃŠ½Š°Š» Š¾ŃŠ³Š°Š½ŠøŃŠµŃŠŗŠ¾Š¹ Ń
ŠøŠ¼ŠøŠø
2 publications, 5%
|
|
|
Inorganic Chemistry Frontiers
1 publication, 2.5%
|
|
|
Journal of Nanobiotechnology
1 publication, 2.5%
|
|
|
International Journal of Molecular Sciences
1 publication, 2.5%
|
|
|
Journal of Cluster Science
1 publication, 2.5%
|
|
|
Molecular Pharmaceutics
1 publication, 2.5%
|
|
|
European Journal of Organic Chemistry
1 publication, 2.5%
|
|
|
Advanced healthcare materials
1 publication, 2.5%
|
|
|
Molecules
1 publication, 2.5%
|
|
|
International Journal of Nanomedicine
1 publication, 2.5%
|
|
|
Molecular Therapy - Nucleic Acids
1 publication, 2.5%
|
|
|
SSRN Electronic Journal
1 publication, 2.5%
|
|
|
Cells
1 publication, 2.5%
|
|
|
Moscow University Chemistry Bulletin
1 publication, 2.5%
|
|
|
Lomonosov chemistry journal
1 publication, 2.5%
|
|
|
Colloid Journal
1 publication, 2.5%
|
|
|
Analytical Chemistry
1 publication, 2.5%
|
|
|
Science China Life Sciences
1 publication, 2.5%
|
|
|
Colloids and Surfaces A: Physicochemical and Engineering Aspects
1 publication, 2.5%
|
|
|
Life Sciences
1 publication, 2.5%
|
|
|
Critical Reviews in Oncology/Hematology
1 publication, 2.5%
|
|
|
Journal of Ethnopharmacology
1 publication, 2.5%
|
|
|
ŠŠ¾Š»Š»Š¾ŠøŠ“Š½ŃŠ¹ Š¶ŃŃŠ½Š°Š»
1 publication, 2.5%
|
|
|
Drug Development Research
1 publication, 2.5%
|
|
|
Drug Delivery and Translational Research
1 publication, 2.5%
|
|
|
Carbohydrate Research
1 publication, 2.5%
|
|
|
Asian Journal of Pharmaceutical Sciences
1 publication, 2.5%
|
|
|
1
2
3
|
Publishers
|
1
2
3
4
5
6
7
8
9
|
|
|
Elsevier
9 publications, 22.5%
|
|
|
American Chemical Society (ACS)
6 publications, 15%
|
|
|
Pleiades Publishing
5 publications, 12.5%
|
|
|
Royal Society of Chemistry (RSC)
4 publications, 10%
|
|
|
Springer Nature
4 publications, 10%
|
|
|
MDPI
3 publications, 7.5%
|
|
|
Wiley
3 publications, 7.5%
|
|
|
Akademizdatcenter Nauka
2 publications, 5%
|
|
|
Taylor & Francis
1 publication, 2.5%
|
|
|
Social Science Electronic Publishing
1 publication, 2.5%
|
|
|
Moscow University Press
1 publication, 2.5%
|
|
|
The Russian Academy of Sciences
1 publication, 2.5%
|
|
|
1
2
3
4
5
6
7
8
9
|
- We do not take into account publications without a DOI.
- Statistics recalculated weekly.
Are you a researcher?
Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
40
Total citations:
40
Citations from 2024:
16
(40%)
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
Petrov R. A. et al. New Small-Molecule Glycoconjugates of Docetaxel and GalNAc for Targeted Delivery to Hepatocellular Carcinoma // Molecular Pharmaceutics. 2020. Vol. 18. No. 1. pp. 461-468.
GOST all authors (up to 50)
Copy
Petrov R. A., Mefedova S. R., Yamansarov E. Yu., Maklakova S., Grishin D. A., Lopatukhina E. V., Burenina O. Y., Lopukhov A. V., Kovalev S., Timchenko Y. V., Ondar E. E., Ivanenkov Y., Evteev S. A., Vaneev A. N., Timoshenko R. V., Klyachko N. L., Erofeev A. V., Erofeev A. S., Gorelkin P., Gorelkin P. V., Beloglazkina E. K., Majouga A. G. New Small-Molecule Glycoconjugates of Docetaxel and GalNAc for Targeted Delivery to Hepatocellular Carcinoma // Molecular Pharmaceutics. 2020. Vol. 18. No. 1. pp. 461-468.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.molpharmaceut.0c00980
UR - https://pubs.acs.org/doi/10.1021/acs.molpharmaceut.0c00980
TI - New Small-Molecule Glycoconjugates of Docetaxel and GalNAc for Targeted Delivery to Hepatocellular Carcinoma
T2 - Molecular Pharmaceutics
AU - Petrov, Rostislav A
AU - Mefedova, Sofiia R
AU - Yamansarov, Emil Yu
AU - Maklakova, Svetlana
AU - Grishin, Dmitrii A
AU - Lopatukhina, Elena V.
AU - Burenina, Olga Y
AU - Lopukhov, Anton V
AU - Kovalev, Sergey
AU - Timchenko, Yury V
AU - Ondar, Evgenia E
AU - Ivanenkov, Yan
AU - Evteev, Sergei A
AU - Vaneev, Alexander N.
AU - Timoshenko, Roman V
AU - Klyachko, Natalia L.
AU - Erofeev, Alexander V.
AU - Erofeev, Alexander S.
AU - Gorelkin, Peter
AU - Gorelkin, Petr V.
AU - Beloglazkina, Elena K.
AU - Majouga, Alexander G.
PY - 2020
DA - 2020/12/02
PB - American Chemical Society (ACS)
SP - 461-468
IS - 1
VL - 18
PMID - 33264010
SN - 1543-8384
SN - 1543-8392
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2020_Petrov,
author = {Rostislav A Petrov and Sofiia R Mefedova and Emil Yu Yamansarov and Svetlana Maklakova and Dmitrii A Grishin and Elena V. Lopatukhina and Olga Y Burenina and Anton V Lopukhov and Sergey Kovalev and Yury V Timchenko and Evgenia E Ondar and Yan Ivanenkov and Sergei A Evteev and Alexander N. Vaneev and Roman V Timoshenko and Natalia L. Klyachko and Alexander V. Erofeev and Alexander S. Erofeev and Peter Gorelkin and Petr V. Gorelkin and Elena K. Beloglazkina and Alexander G. Majouga},
title = {New Small-Molecule Glycoconjugates of Docetaxel and GalNAc for Targeted Delivery to Hepatocellular Carcinoma},
journal = {Molecular Pharmaceutics},
year = {2020},
volume = {18},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://pubs.acs.org/doi/10.1021/acs.molpharmaceut.0c00980},
number = {1},
pages = {461--468},
doi = {10.1021/acs.molpharmaceut.0c00980}
}
Cite this
MLA
Copy
Petrov, Rostislav A., et al. āNew Small-Molecule Glycoconjugates of Docetaxel and GalNAc for Targeted Delivery to Hepatocellular Carcinoma.ā Molecular Pharmaceutics, vol. 18, no. 1, Dec. 2020, pp. 461-468. https://pubs.acs.org/doi/10.1021/acs.molpharmaceut.0c00980.