Design and synthesis of a novel BODIPY-labeled PSMA inhibitor

• Published in: Bioorganic & medicinal chemistry letters Vol. 30; no. 3; p. 126894
• Main Authors: Son, Sang-Hyun, Kwon, Hongmok, Ahn, Hye-Hyun, Nam, Hwanhee, Kim, Kyul, Nam, SangJin, Choi, Doyoung, Ha, Hyunsoo, Minn, Il, Byun, Youngjoo
• Format: Journal Article
• Language: English
• Published: England Elsevier Ltd 01-02-2020
• Subjects: Animals; Antigens, Surface - metabolism; Binding Sites; BODIPY; Boron Compounds - chemistry; Cell Line, Tumor; Drug Design; Fluorescent Dyes - chemical synthesis; Fluorescent Dyes - chemistry; Glutamate Carboxypeptidase II - antagonists & inhibitors; Glutamate Carboxypeptidase II - metabolism; Humans; Ligands; Male; Mice; Molecular Dynamics Simulation; Optical Imaging; Polyethylene Glycols - chemistry; Prostate cancer; Prostatic Neoplasms - diagnostic imaging; Prostatic Neoplasms - pathology; PSMA; Transplantation, Heterologous; Optical imaging; PSMA; BODIPY; Prostate cancer
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2019.126894

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Prostate-specific membrane antigen (PSMA) is a zinc-bound metalloprotease which is highly expressed in metastatic prostate cancer. It has been considered an excellent target protein for prostate cancer imaging and targeted therapy because it is a membrane protein and its active site is located in the extracellular region. We successfully synthesized and evaluated a novel PSMA ligand conjugated with BODIPY650/665. Compound 1 showed strong PSMA-inhibitory activity and selective uptake into PSMA-expressing tumors. Compound 1 has the potential to be utilized as a near infrared (NIR) optical imaging probe targeting PSMA-expressing cancers.