Synthesis, Labeling and Preclinical Evaluation of a Squaric Acid Containing PSMA Inhibitor Labeled with
Animals
Cyclobutanes
/ chemistry
Dipeptides
/ chemical synthesis
Edetic Acid
/ analogs & derivatives
Gallium Isotopes
Gallium Radioisotopes
/ chemistry
Heterocyclic Compounds, 1-Ring
/ chemical synthesis
Humans
Male
Mice
Mice, Nude
Molecular Structure
Oligopeptides
/ chemical synthesis
Positron Emission Tomography Computed Tomography
Prostate-Specific Antigen
/ antagonists & inhibitors
Prostatic Neoplasms
/ drug therapy
Radiopharmaceuticals
/ chemical synthesis
Tumor Cells, Cultured
68Ga
PET
PSMA
prostate cancer
squaric acid
Journal
ChemMedChem
ISSN: 1860-7187
Titre abrégé: ChemMedChem
Pays: Germany
ID NLM: 101259013
Informations de publication
Date de publication:
20 04 2020
20 04 2020
Historique:
received:
03
10
2019
revised:
19
12
2019
pubmed:
15
2
2020
medline:
21
5
2021
entrez:
15
2
2020
Statut:
ppublish
Résumé
The L-lysine urea-L-glutamate (KuE) represents a key motif in recent diagnostic and therapeutic radiopharmaceuticals targeting the prostate specific membrane antigen (PSMA). Using a squaric acid moiety for coupling of KuE with a radioactive label, the squaric acid as a linker in the PSMA ligand seems to mimic the aromatic structure of the naphthylalanine unit on PSMA-617. In this work, we investigate the influence of squaric acid moiety on the biological activity of the compound carrying a KuE motif and three typical chelates. The derivatives TRAM.SA.KuE, DOTAGA.SA.KuE and NODAGA.SA.KuE were all synthesized in straightforward organic reactions and purified by HPLC afterward. Different amounts of tracer were labeled at different temperatures with
Identifiants
pubmed: 32057189
doi: 10.1002/cmdc.201900559
doi:
Substances chimiques
Cyclobutanes
0
Dipeptides
0
Gallium Isotopes
0
Gallium Radioisotopes
0
Heterocyclic Compounds, 1-Ring
0
Oligopeptides
0
PSMA-617
0
Radiopharmaceuticals
0
gallium 68 PSMA-11
0
Edetic Acid
9G34HU7RV0
Prostate-Specific Antigen
EC 3.4.21.77
squaric acid
SVR9D0VODW
Types de publication
Comparative Study
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
695-704Informations de copyright
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Références
L. A. Torre, R. L. Siegel, Cancer J Clin 2015, 65, 87-108.
A. Afshar-Oromieh, A. Malcer, J Nucl Med Mol Imaging 2013, 40, 486-495.
P. J. Davidson, D. van den Ouden, Eur. Urol. 1996, 29, 168-173.
M. R. A. Pillai, R. Nanabala, Nucl. Med. Biol. 2016, 43, 692-720.
D. A. Silver, I. Pellicer, Cli Cancer Res 1997, 3, 81-85.
S. Perner, M. D. Hofer, Hum. Pathol. 2007, 38, 696-701.
J.-M. Mosquera, S. Perner, I Pathol 2007, 212, 91-101.
C. Barinka, C. Rojas, Curr. Med. Chem. 2012, 19, 856-870.
T. Wüstermann, U. Bauder-Wüst, Theranostics 2016, 6, 1085-1095.
A. X. Zhang, R. P. Murelli, J. Am. Chem. Soc. 2010, 132, 12711-12716.
S. Lütje, S. Heskamp, Theranostics 2015, 1388-1401.
E. Witkowska-Patena, A. Mazurek, Cent European J Urol 2017, 70, 37-43.
A. P. Kozikowski, J. Zhang, J. Med. Chem. 2004, 47, 1729-1738.
M. Eder, M. Schäfer, Bioconjugate Chem. 2012, 23, 668-697.
R. Ian Store, C. Aciro, Chem. Soc. Rev. 2011, 40, 2330-2346.
E. Neuse, B. Green, Justus Liebigs Ann. Chem. 1973, 1973, 619-632.
F. R. Wurm, H.-A. Klok, Chem. Soc. Rev. 2013, 42, 8220-8236.
L. F. Tietze, M. Arlt, Chem. Ber. 1991, 124, 1215-1221.
D. Quinonero, A. Frontera, Tetrahedron Lett. 2000, 41, 2001-2005.
B. Davis, J. Chem. Soc. 1999, 1, 3215-3237.
D. P. Gamblin, E. M. Scanlan, Chem. Rev. 2016, 109, 131-163.
S. E. Rudd, P. Roselt, Chem. Commun. 2016, 52, 11889-11892.
S. Yoganathan, C. S. Sit, Org. Biomol. Chem., 2011, 9, 2133-2141.
K. Sato, K. Seio, J. Am. Chem. Soc. 2002, 124, 12715-12724.
A. Rostami, A. Colin, J. Org. Chem. 2010, 75, 3983-3992.
C. W. Lee, K. Ichiyama, Bioorg. Med. Chem. Lett. 2005, 15, 4243-4246.
J. Gauger, G. Manecke, Chem. Ber. 1970, 103, 3553-3562.
M. Eder, M. Schäfer, Bioconjugate Chem. 2012, 23, 688-697.
J. Cardinale, M. Schäfer, J. Nucl. Med. 2015, 58, 425-431.
M. Benesova, M. Schäfer, J. Nucl. Med. 2015, 56, 914-920.
A. Afshar-Oromiehm, A. Malcher, Eur. J. Nucl. Med. Mol. Imaging 2013, 40, 486-495.
M. Benesova, U. Bauder-Wüst, J. Med. Chem. 2016, 59, 1761-1775.
M. Benesova, M. Schäfer, J. Nucl. Med. 2015, 56, 914-920.
K. P. Zhernosekov, D. V. Filosofov, J. Nucl. Med. 2007, 48, 1741-1748.
M. Asti, G. Pietri, Nucl. Med. Biol. 2018, 35, 721-724.