Journal of Medicinal Chemistry, volume 64, issue 8, pages 4532-4552

Synthesis and Biological Evaluation of PSMA Ligands with Aromatic Residues and Fluorescent Conjugates Based on Them

Shafikov Radik R 1, 2
Ber Anton P 1
Skvortsov Dmitry 1, 3
Nimenko Ekaterina A. 1
Zyk Nikolay U 1
Smirnova Galina B. 4
Saltykova Irina V 1
Akhmirov Rauf T 7
Saveliev Oleg Y 8
Ivanenkov Yan 1, 6, 9, 10, 11
Aladinskaya Anastasiya V 11
Finko A V 1
Yamansarov Emil U 1
Gorelkin Peter 1, 6
Dontsova Olga A. 1, 2
Zyk Nikolay V. 1
Khazanova Elena S 12
12
 
Izvarino Pharma LLC, v. Vnukovskoe, Vnukovskoe sh., 5th km., Building 1, Moscow 108817, Russian Federation
Publication typeJournal Article
Publication date2021-04-06
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor7.3
ISSN00222623, 15204804
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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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) Copy
Machulkin A. E., Shafikov R. R., Uspenskaya A. A., Petrov S. B., Ber A. P., Skvortsov D., Nimenko E. A., Zyk N. U., Smirnova G. B., Pokrovsky V. S., Abakumov M. A., Saltykova I. V., Akhmirov R. T., Garanina A. S., Polshakov V. I., Saveliev O. Y., Ivanenkov Y., Aladinskaya A. V., Finko A. V., Yamansarov E. U., Krasnovskaya O. O., Erofeev A. V., Gorelkin P., 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.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1021/acs.jmedchem.0c01935
UR - https://doi.org/10.1021%2Facs.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 - Ber, Anton P
AU - Nimenko, Ekaterina A.
AU - Zyk, Nikolay U
AU - Smirnova, Galina B.
AU - Akhmirov, Rauf T
AU - Saveliev, Oleg Y
AU - Aladinskaya, Anastasiya V
AU - Yamansarov, Emil U
AU - Dontsova, Olga A.
AU - Zyk, Nikolay V.
AU - Khazanova, Elena S
AU - Abakumov, Maxim A.
AU - Ivanenkov, Yan
AU - Majouga, Alexander G.
AU - Machulkin, Aleksei E.
AU - Shafikov, Radik R
AU - Uspenskaya, Anastasia A.
AU - Petrov, Stanislav B.
AU - Skvortsov, Dmitry
AU - Pokrovsky, Vadim S.
AU - Saltykova, Irina V
AU - Garanina, A. S.
AU - Polshakov, Vladimir I.
AU - Finko, A V
AU - Krasnovskaya, Olga O.
AU - Erofeev, Alexander V.
AU - Gorelkin, Peter
AU - Beloglazkina, Elena K.
PY - 2021
DA - 2021/04/06 00:00:00
PB - American Chemical Society (ACS)
SP - 4532-4552
IS - 8
VL - 64
SN - 0022-2623
SN - 1520-4804
ER -
BibTex |
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BibTex Copy
@article{2021_Machulkin
author = {Anton P Ber and Ekaterina A. Nimenko and Nikolay U Zyk and Galina B. Smirnova and Rauf T Akhmirov and Oleg Y Saveliev and Anastasiya V Aladinskaya and Emil U Yamansarov and Olga A. Dontsova and Nikolay V. Zyk and Elena S Khazanova and Maxim A. Abakumov and Yan Ivanenkov and Alexander G. Majouga and Aleksei E. Machulkin and Radik R Shafikov and Anastasia A. Uspenskaya and Stanislav B. Petrov and Dmitry Skvortsov and Vadim S. Pokrovsky and Irina V Saltykova and A. S. Garanina and Vladimir I. Polshakov and A V Finko and Olga O. Krasnovskaya and Alexander V. Erofeev and Peter Gorelkin and Elena K. Beloglazkina},
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://doi.org/10.1021%2Facs.jmedchem.0c01935},
number = {8},
pages = {4532--4552},
doi = {10.1021/acs.jmedchem.0c01935}
}
MLA
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MLA Copy
Machulkin, Aleksei E., et al. ā€œSynthesis 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://doi.org/10.1021%2Facs.jmedchem.0c01935.
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