Synthesis and Biological Evaluation of PSMA Ligands with Aromatic Residues and Fluorescent Conjugates Based on Them
Radik R Shafikov
1, 2
,
Stanislav A Petrov
1
,
Anton P Ber
1
,
Dmitry Skvortsov
1, 3
,
Dmitry A. Skvortsov
1, 3
,
Ekaterina A. Nimenko
1
,
Nikolay U Zyk
1
,
Galina B. Smirnova
4
,
Vadim S. Pokrovsky
4, 5
,
Irina V Saltykova
1
,
Rauf T Akhmirov
7
,
A. S. Garanina
6
,
Anastasiia S Garanina
6
,
Oleg Y Saveliev
8
,
Yan Ivanenkov
1, 6, 9, 10, 11
,
Anastasiya V Aladinskaya
9
,
A V Finko
1
,
Alexander V Finko
1
,
Emil U Yamansarov
1
,
Olga O. Krasnovskaya
1, 6
,
Alexander V. Erofeev
1, 6
,
Alexander S. Erofeev
1, 6
,
Peter Gorelkin
1, 6
,
Petr V. Gorelkin
1, 6
,
Olga A. Dontsova
1, 2
,
Nikolay V. Zyk
1
,
Elena S Khazanova
12
,
Alexander G. Majouga
1, 6, 7
10
12
Izvarino Pharma LLC, v. Vnukovskoe, Vnukovskoe sh., 5th km., Building 1, Moscow 108817, Russian Federation
|
Publication type: Journal Article
Publication date: 2021-04-06
scimago Q1
wos Q1
SJR: 1.801
CiteScore: 11.5
Impact factor: 6.8
ISSN: 00222623, 15204804
PubMed ID:
33822606
Drug Discovery
Molecular Medicine
Abstract
Prostate-specific membrane antigen (PSMA), also known as glutamate carboxypeptidase II (GCPII), is a suitable target for specific delivery of antitumor drugs and diagnostic agents due to its overexpression in prostate cancer cells. In the current work, we describe the design, synthesis, and biological evaluation of novel low-molecular PSMA ligands and conjugates with fluorescent dyes FAM-5, SulfoCy5, and SulfoCy7. In vitro evaluation of synthesized PSMA ligands on the activity of PSMA shows that the addition of aromatic amino acids into a linker structure leads to a significant increase in inhibition. The conjugates of the most potent ligand with FAM-5 as well as SulfoCy5 demonstrated high affinities to PSMA-expressing tumor cells in vitro. In vivo biodistribution in 22Rv1 xenografts in Balb/c nude mice of PSMA-SulfoCy5 and PSMA-SulfoCy7 conjugates with a novel PSMA ligand demonstrated good visualization of PSMA-expressing tumors. Also, the conjugate PSMA-SulfoCy7 demonstrated the absence of any explicit toxicity up to 87.9 mg/kg.
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35
Total citations:
35
Citations from 2024:
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(45%)
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GOST
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Machulkin A. E. et al. Synthesis and Biological Evaluation of PSMA Ligands with Aromatic Residues and Fluorescent Conjugates Based on Them // Journal of Medicinal Chemistry. 2021. Vol. 64. No. 8. pp. 4532-4552.
GOST all authors (up to 50)
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Machulkin A. E., Shafikov R. R., Uspenskaya A. A., Petrov S. B., Petrov S. A., Ber A. P., Skvortsov D., Skvortsov D. A., Nimenko E. A., Zyk N. U., Smirnova G. B., Pokrovsky V. S., Abakumov M. A., Saltykova I. V., Akhmirov R. T., Garanina A. S., Garanina A. S., Polshakov V. I., Saveliev O. Y., Ivanenkov Y., Aladinskaya A. V., Finko A. V., Finko A. V., Yamansarov E. U., Krasnovskaya O. O., Erofeev A. V., Erofeev A. S., Gorelkin P., Gorelkin P. V., Dontsova O. A., Beloglazkina E. K., Zyk N. V., Khazanova E. S., Majouga A. G. Synthesis and Biological Evaluation of PSMA Ligands with Aromatic Residues and Fluorescent Conjugates Based on Them // Journal of Medicinal Chemistry. 2021. Vol. 64. No. 8. pp. 4532-4552.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.jmedchem.0c01935
UR - https://pubs.acs.org/doi/10.1021/acs.jmedchem.0c01935
TI - Synthesis and Biological Evaluation of PSMA Ligands with Aromatic Residues and Fluorescent Conjugates Based on Them
T2 - Journal of Medicinal Chemistry
AU - Machulkin, Aleksei E.
AU - Shafikov, Radik R
AU - Uspenskaya, Anastasia A.
AU - Petrov, Stanislav B.
AU - Petrov, Stanislav A
AU - Ber, Anton P
AU - Skvortsov, Dmitry
AU - Skvortsov, Dmitry A.
AU - Nimenko, Ekaterina A.
AU - Zyk, Nikolay U
AU - Smirnova, Galina B.
AU - Pokrovsky, Vadim S.
AU - Abakumov, Maxim A.
AU - Saltykova, Irina V
AU - Akhmirov, Rauf T
AU - Garanina, A. S.
AU - Garanina, Anastasiia S
AU - Polshakov, Vladimir I.
AU - Saveliev, Oleg Y
AU - Ivanenkov, Yan
AU - Aladinskaya, Anastasiya V
AU - Finko, A V
AU - Finko, Alexander V
AU - Yamansarov, Emil U
AU - Krasnovskaya, Olga O.
AU - Erofeev, Alexander V.
AU - Erofeev, Alexander S.
AU - Gorelkin, Peter
AU - Gorelkin, Petr V.
AU - Dontsova, Olga A.
AU - Beloglazkina, Elena K.
AU - Zyk, Nikolay V.
AU - Khazanova, Elena S
AU - Majouga, Alexander G.
PY - 2021
DA - 2021/04/06
PB - American Chemical Society (ACS)
SP - 4532-4552
IS - 8
VL - 64
PMID - 33822606
SN - 0022-2623
SN - 1520-4804
ER -
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@article{2021_Machulkin,
author = {Aleksei E. Machulkin and Radik R Shafikov and Anastasia A. Uspenskaya and Stanislav B. Petrov and Stanislav A Petrov and Anton P Ber and Dmitry Skvortsov and Dmitry A. Skvortsov and Ekaterina A. Nimenko and Nikolay U Zyk and Galina B. Smirnova and Vadim S. Pokrovsky and Maxim A. Abakumov and Irina V Saltykova and Rauf T Akhmirov and A. S. Garanina and Anastasiia S Garanina and Vladimir I. Polshakov and Oleg Y Saveliev and Yan Ivanenkov and Anastasiya V Aladinskaya and A V Finko and Alexander V Finko and Emil U Yamansarov and Olga O. Krasnovskaya and Alexander V. Erofeev and Alexander S. Erofeev and Peter Gorelkin and Petr V. Gorelkin and Olga A. Dontsova and Elena K. Beloglazkina and Nikolay V. Zyk and Elena S Khazanova and Alexander G. Majouga},
title = {Synthesis and Biological Evaluation of PSMA Ligands with Aromatic Residues and Fluorescent Conjugates Based on Them},
journal = {Journal of Medicinal Chemistry},
year = {2021},
volume = {64},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://pubs.acs.org/doi/10.1021/acs.jmedchem.0c01935},
number = {8},
pages = {4532--4552},
doi = {10.1021/acs.jmedchem.0c01935}
}
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MLA
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Machulkin, Aleksei E., et al. āSynthesis and Biological Evaluation of PSMA Ligands with Aromatic Residues and Fluorescent Conjugates Based on Them.ā Journal of Medicinal Chemistry, vol. 64, no. 8, Apr. 2021, pp. 4532-4552. https://pubs.acs.org/doi/10.1021/acs.jmedchem.0c01935.