Synthesis and initial in vitro evaluation of PSMA-targeting ligands with a modified aromatic moiety at the lysine ε-nitrogen atom

被引：4

作者：

Zyk, Nikolai Y. ^{[1
]}

Ber, Anton P. ^{[1
]}

Nimenko, Ekaterina A. ^{[1
]}

Shafikov, Radik R. ^{[1
,2
]}

Evteev, Sergei A. ^{[3
]}

Petrov, Stanislav A. ^{[1
]}

Uspenskaya, Anastasia A. ^{[1
]}

Dashkova, Natalia S. ^{[1
]}

Ivanenkov, Yan A. ^{[1
,3
]}

Skvortsov, Dmitry A. ^{[1
]}

Beloglazkina, Elena K. ^{[1
]}

Majouga, Alexander G. ^{[1
,4
]}

Machulkin, Aleksei E. ^{[1
,5
]}

机构：

[1] Lomonosov Moscow State Univ, Chem Dept, Bldg 1-3,GSP-1, Moscow 119991, Russia

[2] Russian Acad Sci, Shemyakin & Ovchinnikov Inst Bioorgan Chem, GSP-7,Ulitsa Miklukho Maklaya 16-10, Moscow 117997, Russia

[3] Fed State Unitary Enterprise Dukhov Automat Res In, Moscow 127055, Russia

[4] Dmitry Mendeleev Univ Chem Technol Russia, Miusskaya Sq 9, Moscow 125047, Russia

[5] RUDN Univ, Miklukho Maklaya Str 6, Moscow 117198, Russia

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2022年 / 71卷

基金：

俄罗斯基础研究基金会;

关键词：

Prostate cancer; Prostate-specific membrane antigen; Drug delivery; Ligands; Sulfo-Cy5; GLUTAMATE CARBOXYPEPTIDASE-II; MEMBRANE ANTIGEN PSMA; PRECLINICAL EVALUATION; INHIBITORS; DESIGN;

D O I：

10.1016/j.bmcl.2022.128840

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

We report an improved series of ligands targeting prostate specific membrane antigen (PSMA). The new compounds were designed by the introduction of changes in the structure of the aromatic fragment at epsilon-nitrogen atom of lysine that resulted in improved biological parameters. Some of them demonstrated high selectivity and nanomolar IC50 values. We synthesized and tested two conjugates with a fluorescent label Sulfo-Cy5 as an example of the use of the obtained PSMA inhibitors as a basis for the creation of diagnostic preparations.

引用

页数：7

共 13 条

[1] Synthesis and biological evaluation of PSMA-targeting paclitaxel conjugates
Machulkin, Alexey E.
Skvortsov, Dmitry A.
Ivanenkov, Yan A.
Ber, Anton P.
Kavalchuk, Mikhail, V
Aladinskaya, Anastasia, V
Uspenskaya, Anastasia A.
Shafikov, Radik R.
Plotnikova, Ekaterina A.
Yakubovskaya, Raisa, I
Nimenko, Ekaterina A.
Zyk, Nikolay U.
Beloglazkina, Elena K.
Zyk, Nikolay, V
Koteliansky, Victor E.
Majouga, Alexander G.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2019, 29 (16) : 2229 - 2235
[2] Design, Synthesis, and Evaluation of Linker-Optimised PSMA-Targeting Radioligands
Lundmark, Fanny
Olanders, Gustav
Rinne, Sara Sophie
Abouzayed, Ayman
Orlova, Anna
Rosenstrom, Ulrika
PHARMACEUTICS, 2022, 14 (05)
[3] Synthesis and Biological Evaluation of PSMA Ligands with Aromatic Residues and Fluorescent Conjugates Based on Them
Machulkin, Aleksei E.
Shafikov, Radik R.
Uspenskaya, Anastasia A.
Petrov, Stanislav A.
Ber, Anton P.
Skvortsov, Dmitry A.
Nimenko, Ekaterina A.
Zyk, Nikolay U.
Smirnova, Galina B.
Pokrovsky, Vadim S.
Abakumov, Maxim A.
Saltykova, Irina, V
Akhmirov, Rauf T.
Garanina, Anastasiia S.
Polshakov, Vladimir, I
Saveliev, Oleg Y.
Ivanenkov, Yan A.
Aladinskaya, Anastasiya, V
Finko, Alexander, V
Yamansarov, Emil U.
Krasnovskaya, Olga O.
Erofeev, Alexander S.
Gorelkin, Petr, V
Dontsova, Olga A.
Beloglazkina, Elena K.
Zyk, Nikolay, V
Khazanova, Elena S.
Majouga, Alexander G.
JOURNAL OF MEDICINAL CHEMISTRY, 2021, 64 (08) : 4532 - 4552
[4] Optimization of the dipeptide motifs in the PSMA ligands linker structure: synthesis and in vitro evaluation
Uspenskaya, Anastasiia A. A.
Nimenko, Ekaterina A. A.
Shafikov, Radik R. R.
Zyk, Nikolay Y. Y.
Evteev, Sergei A. A.
Dashkova, Natalia S. S.
Ivanenkov, Yan A. A.
Majouga, Alexander G. G.
Skvortsov, Dmitry A. A.
Garanina, Anastasiia S. S.
Beloglazkina, Elena K. K.
Machulkin, Aleksei E. E.
MEDICINAL CHEMISTRY RESEARCH, 2023, 32 (01) : 32 - 37
[5] Optimization of the dipeptide motifs in the PSMA ligands linker structure: synthesis and in vitro evaluation
Anastasiia A. Uspenskaya
Ekaterina A. Nimenko
Radik R. Shafikov
Nikolay Y. Zyk
Sergei A. Evteev
Natalia S. Dashkova
Yan A. Ivanenkov
Alexander G. Majouga
Dmitry A. Skvortsov
Anastasiia S. Garanina
Elena K. Beloglazkina
Aleksei E. Machulkin
Medicinal Chemistry Research, 2023, 32 : 32 - 37
[6] Synthesis and evaluation of novel radioiodinated PSMA targeting ligands for potential radiotherapy of prostate cancer
Yao, Xinyue
Zha, Zhihao
Ploessl, Karl
Choi, Seok Rye
Zhao, Ruiyue
Alexoff, David
Zhu, Lin
Kung, Hank F.
BIOORGANIC & MEDICINAL CHEMISTRY, 2020, 28 (05)
[7] First-in-human study of PSMA-targeting agent, [18F]AlF-P16-093: dosimetry and initial evaluation in prostate cancer patients
Ruiyue Zhao
Miao Ke
Jie Lv
Shaoyu Liu
Yuheng Liu
Jing Zhang
Lifu Xu
Di Gu
Mingzhao Li
Chao Cai
Yongda Liu
Guohua Zeng
David Alexoff
Karl Ploessl
Lin Zhu
Hank F. Kung
Xinlu Wang
European Journal of Nuclear Medicine and Molecular Imaging, 2024, 51 : 1753 - 1762
[8] First-in-human study of PSMA-targeting agent, [18F]AlF-P16-093: dosimetry and initial evaluation in prostate cancer patients
Zhao, Ruiyue
Ke, Miao
Lv, Jie
Liu, Shaoyu
Liu, Yuheng
Zhang, Jing
Xu, Lifu
Gu, Di
Li, Mingzhao
Cai, Chao
Liu, Yongda
Zeng, Guohua
Alexoff, David
Ploessl, Karl
Zhu, Lin
Kung, Hank F.
Wang, Xinlu
EUROPEAN JOURNAL OF NUCLEAR MEDICINE AND MOLECULAR IMAGING, 2024, 51 (06) : 1753 - 1762
[9] Tween 80-modified hyaluronic acid-ss-curcumin micelles for targeting glioma: Synthesis, characterization and their in vitro evaluation
Tian, Cihui
Asghar, Sajid
Xu, Yurui
Chen, Zhipeng
Zhang, Jingwei
Ping, Qineng
Xiao, Yanyu
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, 2018, 120 : 2579 - 2588
[10] Design, Synthesis, In Vitro, and Initial In Vivo Evaluation of Heterobivalent Peptidic Ligands Targeting Both NPY(Y1)- and GRP-Receptors-An Improvement for Breast Cancer Imaging?
Vall-Sagarra, Alicia
Litau, Shanna
Decristoforo, Clemens
Waengler, Bjoern
Schirrmacher, Ralf
Fricker, Gert
Waengler, Carmen
PHARMACEUTICALS, 2018, 11 (03)

← 1 2 →