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ID: ALA5096171

Journal: J Med Chem

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

Authors: Machulkin AE, Shafikov RR, Uspenskaya AA, Petrov SA, Ber AP, Skvortsov DA, Nimenko EA, Zyk NU, Smirnova GB, Pokrovsky VS, Abakumov MA, Saltykova IV, Akhmirov RT, Garanina AS, Polshakov VI, Saveliev OY, Ivanenkov YA, Aladinskaya AV, Finko AV, Yamansarov EU, Krasnovskaya OO, Erofeev AS, Gorelkin PV, Dontsova OA, Beloglazkina EK, Zyk NV, Khazanova ES, Majouga AG.

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.

CiteXplore: 33822606

DOI: 10.1021/acs.jmedchem.0c01935