A high-affinity [18F]-labeled phosphoramidate peptidomimetic PSMA-targeted inhibitor for PET imaging of prostate cancer
Abstract
Here in this study, a structurally modified phosphoramidate scaffold, with improved prostate-specific membrane antigen (PSMA) avidity, stability and in vivo characteristics, as a PET imaging agent for prostate cancer (PCa), was prepared and evaluated. p-Fluorobenzoyl-aminohexanoate and 2-(3-hydroxypropyl)glycine were introduced into the PSMA-targeting scaffold yielding phosphoramidate 5. X-ray crystallography was performed on the PSMA/5 complex. [18F]5 was synthesized, and cell uptake and internalization studies were conducted in PSMA(+) LNCaP and CWR22Rv1 cells and PSMA(-) PC-3 cells. In vivo PET imaging and biodistribution studies were performed at 1 and 4 h post injection in mice bearing CWR22Rv1 tumor, with or without blocking agent. The crystallographic data showed interaction of the p-fluorobenzoyl group with an arene-binding cleft on the PSMA surface. In vitro studies revealed elevated uptake of [18F]5 in PSMA(+) cells (2.2% in CWR22Rv1 and 12.1% in LNCaP) compared to PSMA(-) cells (0.08%) at 4 h. In vivo tumor uptake of 2.33% ID/g and tumor-to-blood ratio of 265:1 was observed at 4 h. In conclusion, we have successfully synthesized, radiolabeled and evaluated a new PSMA-targeted PET agent. The crystal structure of the PSMA/5 complex highlighted the interactions within the arene-binding cleft contributing to the overall complex stability. The high target uptake andmore »
- Authors:
-
- Washington State Univ., Pullman, WA (United States). Dept. of Chemistry
- Univ. of California, San Francisco, CA (United States). Dept. of Radiology and Biomedical Imaging
- Inst. of Biotechnology, Prague (Czech Republic)
- Washington State Univ., Pullman, WA (United States). Dept. of Chemistry; Cancer Targeted Technology, Woodinville, WA (United States)
- Publication Date:
- Research Org.:
- Argonne National Laboratory (ANL), Argonne, IL (United States). Advanced Photon Source (APS)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES)
- OSTI Identifier:
- 1214298
- Alternate Identifier(s):
- OSTI ID: 1252095
- Grant/Contract Number:
- W-31-109-Eng-38; R01 CA140617; W81XWH-11-1-0464; 301/12/1513; CZ.1.05/1.1.00/02.0109
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Nuclear Medicine and Biology
- Additional Journal Information:
- Journal Volume: 42; Journal Issue: 10; Journal ID: ISSN 0969-8051
- Publisher:
- Elsevier
- Country of Publication:
- United States
- Language:
- ENGLISH
- Subject:
- 62 RADIOLOGY AND NUCLEAR MEDICINE; 59 BASIC BIOLOGICAL SCIENCES; Flourine-18; PET; PSMA; Phosphoramidate
Citation Formats
Ganguly, Tanushree, Dannoon, Shorouk, Hopkins, Mark R., Murphy, Stephanie, Cahaya, Hendry, Blecha, Joseph E., Jivan, Salma, Drake, Christopher R., Barinka, Cyril, Jones, Ella F., VanBrocklin, Henry F., and Berkman, Clifford E. A high-affinity [18F]-labeled phosphoramidate peptidomimetic PSMA-targeted inhibitor for PET imaging of prostate cancer. United States: N. p., 2015.
Web. doi:10.1016/j.nucmedbio.2015.06.003.
Ganguly, Tanushree, Dannoon, Shorouk, Hopkins, Mark R., Murphy, Stephanie, Cahaya, Hendry, Blecha, Joseph E., Jivan, Salma, Drake, Christopher R., Barinka, Cyril, Jones, Ella F., VanBrocklin, Henry F., & Berkman, Clifford E. A high-affinity [18F]-labeled phosphoramidate peptidomimetic PSMA-targeted inhibitor for PET imaging of prostate cancer. United States. https://doi.org/10.1016/j.nucmedbio.2015.06.003
Ganguly, Tanushree, Dannoon, Shorouk, Hopkins, Mark R., Murphy, Stephanie, Cahaya, Hendry, Blecha, Joseph E., Jivan, Salma, Drake, Christopher R., Barinka, Cyril, Jones, Ella F., VanBrocklin, Henry F., and Berkman, Clifford E. Tue .
"A high-affinity [18F]-labeled phosphoramidate peptidomimetic PSMA-targeted inhibitor for PET imaging of prostate cancer". United States. https://doi.org/10.1016/j.nucmedbio.2015.06.003. https://www.osti.gov/servlets/purl/1214298.
@article{osti_1214298,
title = {A high-affinity [18F]-labeled phosphoramidate peptidomimetic PSMA-targeted inhibitor for PET imaging of prostate cancer},
author = {Ganguly, Tanushree and Dannoon, Shorouk and Hopkins, Mark R. and Murphy, Stephanie and Cahaya, Hendry and Blecha, Joseph E. and Jivan, Salma and Drake, Christopher R. and Barinka, Cyril and Jones, Ella F. and VanBrocklin, Henry F. and Berkman, Clifford E.},
abstractNote = {Here in this study, a structurally modified phosphoramidate scaffold, with improved prostate-specific membrane antigen (PSMA) avidity, stability and in vivo characteristics, as a PET imaging agent for prostate cancer (PCa), was prepared and evaluated. p-Fluorobenzoyl-aminohexanoate and 2-(3-hydroxypropyl)glycine were introduced into the PSMA-targeting scaffold yielding phosphoramidate 5. X-ray crystallography was performed on the PSMA/5 complex. [18F]5 was synthesized, and cell uptake and internalization studies were conducted in PSMA(+) LNCaP and CWR22Rv1 cells and PSMA(-) PC-3 cells. In vivo PET imaging and biodistribution studies were performed at 1 and 4 h post injection in mice bearing CWR22Rv1 tumor, with or without blocking agent. The crystallographic data showed interaction of the p-fluorobenzoyl group with an arene-binding cleft on the PSMA surface. In vitro studies revealed elevated uptake of [18F]5 in PSMA(+) cells (2.2% in CWR22Rv1 and 12.1% in LNCaP) compared to PSMA(-) cells (0.08%) at 4 h. In vivo tumor uptake of 2.33% ID/g and tumor-to-blood ratio of 265:1 was observed at 4 h. In conclusion, we have successfully synthesized, radiolabeled and evaluated a new PSMA-targeted PET agent. The crystal structure of the PSMA/5 complex highlighted the interactions within the arene-binding cleft contributing to the overall complex stability. The high target uptake and rapid non-target clearance exhibited by [18F]5 in PSMA(+) xenografts substantiates its potential use for PET imaging of PCa.},
doi = {10.1016/j.nucmedbio.2015.06.003},
journal = {Nuclear Medicine and Biology},
number = 10,
volume = 42,
place = {United States},
year = {Tue Jun 09 00:00:00 EDT 2015},
month = {Tue Jun 09 00:00:00 EDT 2015}
}
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