A phosphoramidate-based prostate-specific membrane antigen-targeted SPECT agent

Prostate

Volumn 72, Issue 8, 2012, Pages 904-912

  Nedrow Byers, Jessie R ^a   Jabbes, Mohamed ^a   Jewett, Cayla ^a   Ganguly, Tanushree ^a   He, Haiyang ^a   Liu, Tiancheng ^a   Benny, Paul ^a   Bryan, Jeffrey N ^b   Berkman, Clifford E ^a,c  

^a WASHINGTON STATE UNIVERSITY   (United States)

^b UNIVERSITY OF MISSOURI   (United States)

^c Cancer Targeted Technology   (United States)

Author keywords

prostate cancer; PSMA; radioimaging

Indexed keywords

LEVO2 [[2 (4 AMINO 4 CARBOXY BUTYRYLAMINO) 2 CARBOXYETHOXY] HYDROXY PHOSPHORYLAMINO] PENTANEDIOICACID PENTAPOTASSIUM SALT; PENTETATE TECHNETIUM TC 99M; PROSTATE SPECIFIC MEMBRANE ANTIGEN; TRACER; UNCLASSIFIED DRUG;

ARTICLE; BINDING KINETICS; BIOACCUMULATION; CELL STRAIN LNCAP; DISTRIBUTION VOLUME; HUMAN; HUMAN CELL; HUMAN TISSUE; IN VIVO STUDY; PRIORITY JOURNAL; PROSTATE CANCER; SINGLE PHOTON EMISSION COMPUTER TOMOGRAPHY;

ADENOCARCINOMA; AMIDES; ANIMALS; CELL LINE, TUMOR; HUMANS; MALE; MICE; MICE, NUDE; PENTETIC ACID; PHOSPHORIC ACIDS; PROSTATE-SPECIFIC ANTIGEN; PROSTATIC NEOPLASMS; SENSITIVITY AND SPECIFICITY; TECHNETIUM; TIME FACTORS; TOMOGRAPHY, EMISSION-COMPUTED, SINGLE-PHOTON; TRANSPLANTATION, HETEROLOGOUS;

EID: 84860321272     PISSN: 02704137     EISSN: 10970045     Source Type: Journal    
DOI: 10.1002/pros.21493     Document Type: Article

References (38)

1. Jemal A, Clegg LX, Ward E, Ries LA, Wu X, Jamison PM, Wingo PA, Howe HL, Anderson RN, Edwards BK,. Annual report to the nation on the status of cancer, 1975-2001 with a special feature regarding survival. Cancer 2004; 101 (1): 3-27. (Pubitemid 38812419)
2. Bacich DJ, Pinto JT, Tong WP, Heston WD,. Cloning, expression, genomic localization, and enzymatic activities of the mouse homolog of prostate-specific membrane antigen/NAALADase/folate hydrolase. Mamm Genome 2001; 12 (2): 117-123. (Pubitemid 32147666)
3. Perner S, Hofer MD, Kim R, Shah RB, Li H, Moller P, Hautmann RE, Gschwend JE, Kuefer R, Rubin MA,. Prostate-specific membrane antigen expression as a predictor of prostate cancer progression. Hum Pathol 2007; 38 (5): 696-701. (Pubitemid 46560805)
4. Bradford TJ, Tomlins SA, Wang X, Chinnaiyan AM,. Molecular markers of prostate cancer. Urol Oncol 2006; 24 (6): 538-551. (Pubitemid 44810016)
5. Rosenthal SA, Haseman MK, Polascik TJ,. Division of Radiation Oncology RAoSMGICUSA. Utility of capromab pendetide (ProstaScint) imaging in the management of prostate cancer. Tech Urol 2001; 7 (1): 27-37. (Pubitemid 32162808)
6. Bander NH, Milowsky MI, Nanus DM, Kostakoglu L, Vallabhajosula S, Goldsmith SJ,. Phase I trial of 177lutetium-labeled J591, a monoclonal antibody to prostate-specific membrane antigen, in patients with androgen-independent prostate cancer. J Clin Oncol 2005; 23 (21): 4591-4601. (Pubitemid 46224061)
7. Chu TC, Shieh F, Lavery LA, Levy M, Richards-Kortum R, Korgel BA, Ellington AD,. Labeling tumor cells with fluorescent nanocrystal-aptamer bioconjugates. Biosens Bioelectron 2006; 21 (10): 1859-1866.
8. Farokhzad OC, Khademhosseini A, Jon S, Hermmann A, Cheng J, Chin C, Kiselyuk A, Teply B, Eng G, Langer R,. Microfluidic system for studying the interaction of nanoparticles and microparticles with cells. Anal Chem 2005; 77 (17): 5453-5459. (Pubitemid 41266036)
9. Foss CA, Mease RC, Fan H, Wang Y, Ravert HT, Dannals RF, Olszewski RT, Heston WD, Kozikowski AP, Pomper MG,. Radiolabeled small-molecule ligands for prostate-specific membrane antigen: In vivo imaging in experimental models of prostate cancer. Clin Cancer Res 2005; 11 (11): 4022-4028. (Pubitemid 40791565)
10. Gao X, Cui Y, Levenson RM, Chung LW, Nie S,. In vivo cancer targeting and imaging with semiconductor quantum dots. Nat Biotechnol 2004; 22 (8): 969-976. (Pubitemid 39014473)
11. Guilarte TR, McGlothan JL, Foss CA, Zhou J, Heston WD, Kozikowski AP, Pomper MG, Department of Environmental Health Sciences JHSoPHBMDUSA. Glutamate carboxypeptidase II levels in rodent brain using [125I]DCIT quantitative autoradiography. Neurosci Lett 2005; 387 (3): 141-144. (Pubitemid 41160545)
12. Humblet V, Lapidus R, Williams LR, Tsukamoto T, Rojas C, Majer P, Hin B, Ohnishi S, De Grand AM, Zaheer A, Renze JT, Nakayama A, Slusher BS, Frangioni JV,. High-affinity near-infrared fluorescent small-molecule contrast agents for in vivo imaging of prostate-specific membrane antigen. Mol Imaging 2005; 4 (4): 448-462. (Pubitemid 43143785)
13. Milowsky MI, Nanus DM, Kostakoglu L, Sheehan CE, Vallabhajosula S, Goldsmith SJ, Ross JS, Bander NH,. Vascular targeted therapy with anti-prostate-specific membrane antigen monoclonal antibody J591 in advanced solid tumors. J Clin Oncol 2007; 25 (5): 540-547. (Pubitemid 350002961)
14. Pomper MG, Musachio JL, Zhang J, Scheffel U, Zhou Y, Hilton J, Maini A, Dannals RF, Wong DF, Kozikowski AP,. 11C-MCG: Synthesis, uptake selectivity, and primate PET of a probe for glutamate carboxypeptidase II (NAALADase). Mol Imaging 2002; 1 (2): 96-101.
15. Smith MR, Nelson JB,. Future therapies in hormone-refractory prostate cancer. Urology 2005; 65 (5 Suppl): 9-16 (discussion 17).
16. Smith-Jones PM, Vallabhajosula S, Navarro V, Bastidas D, Goldsmith SJ, Bander NH,. Radiolabeled monoclonal antibodies specific to the extracellular domain of prostate-specific membrane antigen: Preclinical studies in nude mice bearing LNCaP human prostate tumor. J Nucl Med 2003; 44 (4): 610-617. (Pubitemid 40003748)
17. Tsukamoto T, Wozniak KM, Slusher BS,. Progress in the discovery and development of glutamate carboxypeptidase II inhibitors. Drug Discov Today 2007; 12 (17-18): 767-776. (Pubitemid 47362787)
18. Tasch J, Gong M, Sadelain M, Heston WD, Department of Urology MHMS-KCCNYNYUSA. A unique folate hydrolase, prostate-specific membrane antigen (PSMA): A target for immunotherapy? Crit Rev Immunol 2001; 21 (1-3): 249-261. (Pubitemid 32959364)
19. Salit RB, Kast WM, Velders MP,. Ins and outs of clinical trials with peptide-based vaccines. Front Biosci 2002; 7: e204-e213.
20. Lu J, Celis E,. Recognition of prostate tumor cells by cytotoxic T lymphocytes specific for prostate-specific membrane antigen. Cancer Res 2002; 62 (20): 5807-5812. (Pubitemid 35204739)
21. Fracasso G, Bellisola G, Cingarlini S, Castelletti D, Prayer-Galetti T, Pagano F, Tridente G, Colombatti M,. Anti-tumor effects of toxins targeted to the prostate specific membrane antigen. Prostate 2002; 53 (1): 9-23. (Pubitemid 34966860)
22. Ren G, Zhang R, Liu Z, Webster JM, Miao Z, Gambhir SS, Syud FA, Cheng Z,. A 2-helix small protein labeled with 68Ga for PET imaging of HER2 expression. J Nucl Med 2009; 50 (9): 1492-1499.
23. Weiner RE, Thakur ML,. Radiolabeled peptides in the diagnosis and therapy of oncological diseases. Appl Radiat Isot 2002; 57 (5): 749-763. (Pubitemid 35279166)
24. Banerjee SR, Foss CA, Castanares M, Mease RC, Byun Y, Fox JJ, Hilton J, Lupold SE, Kozikowski AP, Pomper MG,. Synthesis and evaluation of technetium-99m- and rhenium-labeled inhibitors of the prostate-specific membrane antigen (PSMA). J Med Chem 2008; 51 (15): 4504-4517.
25. Chen Y, Foss CA, Byun Y, Nimmagadda S, Pullambhatla M, Fox JJ, Castanares M, Lupold SE, Babich JW, Mease RC, Pomper MG,. Radiohalogenated prostate-specific membrane antigen (PSMA)-based ureas as imaging agents for prostate cancer. J Med Chem 2008; 51 (24): 7933-7943.
26. Nagda SN, Mohideen N, Lo SS, Khan U, Dillehay G, Wagner R, Campbell S, Flanigan R,. Long-term follow-up of 111In-capromab pendetide (ProstaScint) scan as pretreatment assessment in patients who undergo salvage radiotherapy for rising prostate-specific antigen after radical prostatectomy for prostate cancer. Int J Radiat Oncol Biol Phys 2007; 67 (3): 834-840. (Pubitemid 46215867)
27. Liu T, Wu LY, Kazak M, Berkman CE,. Cell-Surface labeling and internalization by a fluorescent inhibitor of prostate-specific membrane antigen. Prostate 2008; 68 (9): 955-964. (Pubitemid 351794160)
28. Liu T, Toriyabe Y, Kazak M, Berkman CE,. Pseudoirreversible inhibition of prostate-specific membrane antigen by phosphoramidate peptidomimetics. Biochemistry 2008; 47 (48): 12658-12660.
29. Lapi SE, Wahnishe H, Pham D, Wu LY, Nedrow-Byers JR, Liu T, Vejdani K, VanBrocklin HF, Berkman CE, Jones EF,. Assessment of an 18F-labeled phosphoramidate peptidomimetic as a new prostate-specific membrane antigen-targeted imaging agent for prostate cancer. J Nucl Med 2009; 50 (12): 2042-2048.
30. Liu T, Toriyabe Y, Berkman CE,. Purification of prostate-specific membrane antigen using conformational epitope-specific antibody-affinity chromatography. Protein Expr Purif 2006; 49 (2): 251-255. (Pubitemid 44416227)
31. Kuppuswamy D, Pike LJ,. Ligand-induced desensitization of 125I-epidermal growth factor internalization. J Biol Chem 1989; 264 (6): 3357-3363. (Pubitemid 19063391)
32. Schottelius M, Berger S, Poethko T, Schwaiger M, Wester HJ,. Development of novel 68Ga- and 18F-labeled GnRH-I analogues with high GnRHR-targeting efficiency. Bioconjug Chem 2008; 19 (6): 1256-1268. (Pubitemid 351874949)
33. Pinto JT, Suffoletto BP, Berzin TM, Qiao CH, Lin S, Tong WP, May F, Mukherjee B, Heston WD,. Prostate-specific membrane antigen: A novel folate hydrolase in human prostatic carcinoma cells. Clin Cancer Res 1996; 2 (9): 1445-1451. (Pubitemid 126447436)
34. Uekita T, Itoh Y, Yana I, Ohno H, Seiki M,. Cytoplasmic tail-dependent internalization of membrane-type 1 matrix metalloproteinase is important for its invasion-promoting activity. J Cell Biol 2001; 155 (7): 1345-1356. (Pubitemid 34286282)
35. Copeland RA,. Testing for reversibility. Evaluation of enzyme inhibitors in drug discovery: A guide for Medicinal Chemists and Pharmacologists. Hoboken: John Wiley & Sons; 2005. pp. 125-128.
36. Liu H, Rajasekaran AK, Moy P, Xia Y, Kim S, Navarro V, Rahmati R, Bander NH,. Constitutive and antibody-induced internalization of prostate-specific membrane antigen. Cancer Res 1998; 58 (18): 4055-4060. (Pubitemid 28440554)
37. Troyer JK, Beckett ML, Wright GL Jr., Detection and characterization of the prostate-specific membrane antigen (PSMA) in tissue extracts and body fluids. Int J Cancer 1995; 62 (5): 552-558.
38. Israeli RS, Powell CT, Corr JG, Fair WR, Heston WD,. Expression of the prostate-specific membrane antigen. Cancer Res 1994; 54 (7): 1807-1811. (Pubitemid 24116191)