2‑Aminoadipic Acid–C(O)–Glutamate Based Prostate-Specific Membrane Antigen Ligands for Potential Use as Theranostics

2‑Aminoadipic Acid–C(O)–Glutamate Based Prostate-Specific Membrane Antigen Ligands for Potential Use as Theranostics

The design and synthesis of prostate specific membrane antigen (PSMA) ligands derived from 2-aminoadipic acid, a building block that has not previously been used to construct PSMA ligands, are reported. The effects of both the linker length and of an N-substituent of our PSMA ligands were probed, an...

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Veröffentlicht in:ACS medicinal chemistry letters 2018-11, Vol.9 (11), p.1099-1104
Hauptverfasser: Nakajima, Ryo, Nováková, Zora, Tueckmantel, Werner, Motlová, Lucia, Bařinka, Cyril, Kozikowski, Alan P
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container_end_page 1104
container_issue 11
container_start_page 1099
container_title ACS medicinal chemistry letters
container_volume 9
creator Nakajima, Ryo
Nováková, Zora
Tueckmantel, Werner
Motlová, Lucia
Bařinka, Cyril
Kozikowski, Alan P
description The design and synthesis of prostate specific membrane antigen (PSMA) ligands derived from 2-aminoadipic acid, a building block that has not previously been used to construct PSMA ligands, are reported. The effects of both the linker length and of an N-substituent of our PSMA ligands were probed, and X-ray structures of five of these ligands bound to PSMA were obtained. Among the ligands disclosed herein, 13b showed the highest inhibitory activity for PSMA. As ligand 13b can readily be radiolabeled since its fluorine atom is adjacent to the nitrogen atom of its pyridine ring, the use of this and related compounds as theranostics can be pursued.
doi_str_mv 10.1021/acsmedchemlett.8b00318
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title 2‑Aminoadipic Acid–C(O)–Glutamate Based Prostate-Specific Membrane Antigen Ligands for Potential Use as Theranostics
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