PET imaging in prostate cancer: Focus on prostate-specific membrane antigen

Current Topics in Medicinal Chemistry

Volumn 13, Issue 8, 2013, Pages 951-962

  Mease, Ronnie C ^a   Foss, Catherine A ^a   Pomper, Martin G ^a  

^a JOHNS HOPKINS UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

DCFBC; Molecular imaging; Positron emission tomography; PSMA; Radiopharmaceutical

Indexed keywords

2 [3 1 3 DICARBOXYPROPYL)UREIDO]PENTANEDIOIC ACID; APTAMER; BAY 1075553; CAPROMAB PENDETIDE IN 111; CISPLATIN; COPPER 64; DEFEROXAMINE; DOXORUBICIN; FLUORODEOXYGLUCOSE F 18; GALLIUM 68; GLUTAMATE CARBOXYPEPTIDASE II; GLUTAMIC ACID; GLUTARIC ACID; PROSTATE SPECIFIC MEMBRANE ANTIGEN; TENOFOVIR; TETRAXETAN; UNCLASSIFIED DRUG; YTTRIUM 86;

ARTICLE; BONE LESION; BONE METASTASIS; COMPUTER ASSISTED TOMOGRAPHY; HUMAN; ISOTOPE LABELING; MOLECULAR WEIGHT; PHOSPHORYLATION; POSITRON EMISSION TOMOGRAPHY; PROSTATE CANCER; PROTEIN EXPRESSION; RADIOACTIVITY; THERMODYNAMICS; TUMOR XENOGRAFT; URINARY EXCRETION;

ANIMALS; ANTIGENS, SURFACE; GLUTAMATE CARBOXYPEPTIDASE II; HUMANS; MALE; POSITRON-EMISSION TOMOGRAPHY; PROSTATIC NEOPLASMS;

EID: 84878773196     PISSN: 15680266     EISSN: 18734294     Source Type: Journal    
DOI: 10.2174/1568026611313080008     Document Type: Article

References (145)

1. Glunde, K.; Pathak, A.P.; Bhujwalla, Z.M. Molecular-functional imaging of cancer: to image and imagine. Trends. Mol. Med, 2007, 13, 287-97.
2. Higgins, L.J.; Pomper, M.G. The evolution of imaging in cancer: current state and future challenges. Semin. Oncol, 2011, 38, 3-15.
3. Weissleder, R.; Pittet, M.J. Imaging in the era of molecular oncology. Nature, 2008, 452, 580-9.
4. Jemal, A.; Siegel, R.; Ward, E.; Hao, Y.; Xu, J.; Thun, M.J. Cancer statistics, 2009. CA. Cancer. J. Clin, 2009, 59, 225-49.
5. Jadvar, H. Molecular imaging of prostate cancer with 18F-fluorodeoxyglucose PET. Nat. Rev. Urol, 2009, 6, 317-23.
6. Dehdashti, F.; Picus, J.; Michalski, J.M.; Dence, C.S.; Siegel, B.A.; Katzenellenbogen, J.A.; Welch, M.J. Positron tomographic assessment of androgen receptors in prostatic carcinoma. Eur. J. Nucl. Med. Mol. Imaging, 2005, 32, 344-50.
7. Larson, S.M.; Morris, M.; Gunther, I.; Beattie, B.; Humm, J.L.; Akhurst, T.A.; Finn, R.D.; Erdi, Y.; Pentlow, K.; Dyke, J.; Squire, O.; Bornmann, W.; McCarthy, T.; Welch, M.; Scher, H. Tumor localization of 16beta-18F-fluoro-5alpha-dihydrotestosterone versus 18F-FDG in patients with progressive, metastatic prostate cancer. J. Nucl. Med, 2004, 45, 366-73.
8. Kato, T.; Tsukamoto, E.; Kuge, Y.; Takei, T.; Shiga, T.; Shinohara, N.; Katoh, C.; Nakada, K.; Tamaki, N. Accumulation of [11C]acetate in normal prostate and benign prostatic hyperplasia: comparison with prostate cancer. Eur. J. Nucl. Med. Mol. Imaging, 2002, 29, 1492-5.
9. DeGrado, T.R.; Coleman, R.E.; Wang, S.; Baldwin, S.W.; Orr, M.D.; Robertson, C.N.; Polascik, T.J.; Price, D.T. Synthesis and evaluation of 18F-labeled choline as an oncologic tracer for positron emission tomography: initial findings in prostate cancer. Cancer. Res, 2001, 61, 110-7.
10. Bauman, G.; Belhocine, T.; Kovacs, M.; Ward, A.; Beheshti, M.; Rachinsky, I. 18F-fluorocholine for prostate cancer imaging: a systematic review of the literature. Prostate. Cancer. Prostatic. Dis, 2012, 15, 45-55.
11. Schuster, D.M.; Savir-Baruch, B.; Nieh, P.T.; Master, V.A.; Halkar, R.K.; Rossi, P.J.; Lewis, M.M.; Nye, J.A.; Yu, W.; Bowman, F.D.; Goodman, M.M. Detection of recurrent prostate carcinoma with anti-1-amino-3-18F-fluorocyclobutane-1-carboxylic acid PET/CT and 111In-capromab pendetide SPECT/CT. Radiology, 2011, 259, 852-61.
12. Mease, R.C. Radionuclide based imaging of prostate cancer. Curr. Top. Med. Chem, 2010, 10, 1600-16.
13. Hong, H.; Zhang, Y.; Sun, J.; Cai, W. Positron emission tomography imaging of prostate cancer. Amino. Acids, 2010, 39, 11-27.
14. Effert, P.J.; Bares, R.; Handt, S.; Wolff, J.M.; Bull, U.; Jakse, G. Metabolic imaging of untreated prostate cancer by positron emission tomography with 18fluorine-labeled deoxyglucose. J. Urol, 1996, 155, 994-8.
15. Liu, I.J.; Zafar, M.B.; Lai, Y.H.; Segall, G.M.; Terris, M.K. Fluorodeoxyglucose positron emission tomography studies in diagnosis and staging of clinically organ-confined prostate cancer. Urology, 2001, 57, 108-11.
16. Hofer, C.; Laubenbacher, C.; Block, T.; Breul, J.; Hartung, R.; Schwaiger, M. Fluorine-18-fluorodeoxyglucose positron emission tomography is useless for the detection of local recurrence after radical prostatectomy. Eur. Urol, 1999, 36, 31-5.
17. Shreve, P.D.; Grossman, H.B.; Gross, M.D.; Wahl, R.L. Metastatic prostate cancer: initial findings of PET with 2-deoxy-2-[F-18]fluoro-D-glucose. Radiology, 1996, 199, 751-6.
18. Richter, J.A.; Rodriguez, M.; Rioja, J.; Penuelas, I.; Marti-Climent, J.; Garrastachu, P.; Quincoces, G.; Zudaire, J.; Garcia-Velloso, M.J. Dual tracer 11C-choline and FDG-PET in the diagnosis of biochemical prostate cancer relapse after radical treatment. Mol. Imaging. Biol, 2010, 12, 210-7.
19. Schoder, H.; Herrmann, K.; Gonen, M.; Hricak, H.; Eberhard, S.; Scardino, P.; Scher, H.I.; Larson, S.M. 2-[18F]fluoro-2-deoxyglucose positron emission tomography for the detection of disease in patients with prostate-specific antigen relapse after radical prostatectomy. Clin. Cancer. Res, 2005, 11, 4761-9.
20. Schoder, H.; Larson, S.M. Positron emission tomography for prostate, bladder, and renal cancer. Semin. Nucl. Med, 2004, 34, 274-92.
21. Haseman, M.K.; Rosenthal, S.A.; Polascik, T.J. Capromab Pendetide imaging of prostate cancer. Cancer. Biother. Radiopharm, 2000, 15, 131-40.
22. Seo, Y.; Aparici, C.M.; Cooperberg, M.R.; Konety, B.R.; Hawkins, R.A. In. vivo tumor grading of prostate cancer using quantitative 111In-capromab pendetide SPECT/CT. J. Nucl. Med, 2010, 51, 31-6.
23. Troyer, J.K.; Beckett, M.L.; Wright, G.L., Jr. Location of prostate-specific membrane antigen in the LNCaP prostate carcinoma cell line. Prostate, 1997, 30, 232-42.
24. Ruggiero, A.; Holland, J.P.; Hudolin, T.; Shenker, L.; Koulova, A.; Bander, N.H.; Lewis, J.S.; Grimm, J. Targeting the internal epitope of prostate-specific membrane antigen with 89Zr-7E11 immuno-PET. J. Nucl. Med, 2011, 52, 1608-15.
25. Holland, J.P.; Divilov, V.; Bander, N.H.; Smith-Jones, P.M.; Larson, S.M.; Lewis, J.S. 89Zr-DFO-J591 for immunoPET of prostate-specific membrane antigen expression in. vivo. J. Nucl. Med, 2010, 51, 1293-300.
26. Beattie, B.J.; Smith-Jones, P.M.; Jhanwar, Y.S.; Schoder, H.; Schmidtlein, C.R.; Morris, M.J.; Zanzonico, P.; Squire, O.; Meirelles, G.S.; Finn, R.; Namavari, M.; Cai, S.; Scher, H.I.; Larson, S.M.; Humm, J.L. Pharmacokinetic assessment of the uptake of 16beta-18F-fluoro-5alpha-dihydrotestosterone (FDHT) in prostate tumors as measured by PET. J. Nucl. Med, 2010, 51, 183-92.
27. Oyama, N.; Akino, H.; Kanamaru, H.; Suzuki, Y.; Muramoto, S.; Yonekura, Y.; Sadato, N.; Yamamoto, K.; Okada, K. 11C-acetate PET imaging of prostate cancer. J. Nucl. Med, 2002, 43, 181-6.
28. de Jong, I.J.; Pruim, J.; Elsinga, P.H.; Vaalburg, W.; Mensink, H.J. 11C-choline positron emission tomography for the evaluation after treatment of localized prostate cancer. Eur. Urol, 2003, 44, 32-8; discussion 38-9.
29. Hara, T.; Kosaka, N.; Kishi, H. PET imaging of prostate cancer using carbon-11-choline. J. Nucl. Med, 1998, 39, 990-5.
30. Hara, T.; Kosaka, N.; Kishi, H. Development of (18)F-fluoroethylcholine for cancer imaging with PET: synthesis, biochemistry, and prostate cancer imaging. J. Nucl. Med, 2002, 43, 187-99.
31. Price, D.T.; Coleman, R.E.; Liao, R.P.; Robertson, C.N.; Polascik, T.J.; DeGrado, T.R. Comparison of [18 F]fluorocholine and [18 F]fluorodeoxyglucose for positron emission tomography of androgen dependent and androgen independent prostate cancer. J. Urol, 2002, 168, 273-80.
32. Vallabhajosula S K.L., Kothari PA, Hamacher K, Goldsmith SJ. Pharmacokinetics and biodistribution of radiolabeled choline in human subjects: comparison of [11C]choline and [18F]choline. Journal of Labelled Compounds and Radiopharmaceuticals, 2005, 16th International Symposium on Radiopharmaceutical Chemistry, Iowa City, Iowa, S281.
33. Sutinen, E.; Nurmi, M.; Roivainen, A.; Varpula, M.; Tolvanen, T.; Lehikoinen, P.; Minn, H. Kinetics of [(11)C]choline uptake in prostate cancer: a PET study. Eur. J. Nucl. Med. Mol. Imaging, 2004, 31, 317-24.
34. Connors, T.A.; Elson, L.A.; Haddow, A.; Ross, W.C. The pharmacology and tumour growth inhibitory activity of 1-aminocyclopentane-1-carboxylic acid and related compounds. Biochem. Pharmacol, 1960, 5, 108-29.
35. Okudaira, H.; Shikano, N.; Nishii, R.; Miyagi, T.; Yoshimoto, M.; Kobayashi, M.; Ohe, K.; Nakanishi, T.; Tamai, I.; Namiki, M.; Kawai, K. Putative transport mechanism and intracellular fate of trans-1-amino-3-18F-fluorocyclobutanecarboxylic acid in human prostate cancer. J. Nucl. Med, 2011, 52, 822-9.
36. Asano, Y.; Inoue, Y.; Ikeda, Y.; Kikuchi, K.; Hara, T.; Taguchi, C.; Tokushige, T.; Maruo, H.; Takeda, T.; Nakamura, T.; Fujita, T.; Kumagai, Y.; Hayakawa, K. Phase I clinical study of NMK36: a new PET tracer with the synthetic amino acid analogue anti-[18F]FACBC. Ann. Nucl. Med, 2011, 25, 414-8.
37. Nye, J.A.; Schuster, D.M.; Yu, W.; Camp, V.M.; Goodman, M.M.; Votaw, J.R. Biodistribution and radiation dosimetry of the synthetic nonmetabolized amino acid analogue anti-18F-FACBC in humans. J. Nucl. Med, 2007, 48, 1017-20.
38. Schuster, D.M.; Votaw, J.R.; Nieh, P.T.; Yu, W.; Nye, J.A.; Master, V.; Bowman, F.D.; Issa, M.M.; Goodman, M.M. Initial experience with the radiotracer anti-1-amino-3-18F-fluorocyclobutane-1-carboxylic acid with PET/CT in prostate carcinoma. J. Nucl. Med, 2007, 48, 56-63.
39. Chang, S.S.; Reuter, V.E.; Heston, W.D.; Gaudin, P.B. Comparison of anti-prostate-specific membrane antigen antibodies and other immunomarkers in metastatic prostate carcinoma. Urology, 2001, 57, 1179-83.
40. Wright, G.L., Jr.; Grob, B.M.; Haley, C.; Grossman, K.; Newhall, K.; Petrylak, D.; Troyer, J.; Konchuba, A.; Schellhammer, P.F.; Moriarty, R. Upregulation of prostate-specific membrane antigen after androgen-deprivation therapy. Urology, 1996, 48, 326-34.
41. Perner, S.; Hofer, M.D.; Kim, R.; Shah, R.B.; Li, H.; Moller, P.; Hautmann, R.E.; Gschwend, J.E.; Kuefer, R.; Rubin, M.A. Prostate-specific membrane antigen expression as a predictor of prostate cancer progression. Hum. Pathol, 2007, 38, 696-701.
42. Antunes, A.A.; Leite, K.R.; Sousa-Canavez, J.M.; Camara-Lopes, L.H.; Srougi, M. The role of prostate specific membrane antigen and pepsinogen C tissue expression as an adjunctive method to prostate cancer diagnosis. J. Urol, 2009, 181, 594-600.
43. Ghosh, A.; Heston, W.D. Tumor target prostate specific membrane antigen (PSMA) and its regulation in prostate cancer. J. Cell. Biochem, 2004, 91, 528-39.
44. Mhawech-Fauceglia, P.; Zhang, S.; Terracciano, L.; Sauter, G.; Chadhuri, A.; Herrmann, F.R.; Penetrante, R. Prostate-specific membrane antigen (PSMA) protein expression in normal and neo-plastic tissues and its sensitivity and specificity in prostate adenocarcinoma: an immunohistochemical study using mutiple tumour tissue microarray technique. Histopathology, 2007, 50, 472-83.
45. Rovenska, M.; Hlouchova, K.; Sacha, P.; Mlcochova, P.; Horak, V.; Zamecnik, J.; Barinka, C.; Konvalinka, J. Tissue expression and enzymologic characterization of human prostate specific membrane antigen and its rat and pig orthologs. Prostate, 2008, 68, 171-82.
46. Silver, D.A.; Pellicer, I.; Fair, W.R.; Heston, W.D.; Cordon-Cardo C. Prostate-specific membrane antigen expression in normal and malignant human tissues. Clin. Cancer. Res, 1997, 3, 81-5.
47. Samplaski, M.K.; Heston, W.; Elson, P.; Magi-Galluzzi, C.; Hansel, D.E. Folate hydrolase (prostate-specific membrane [corrected] antigen) 1 expression in bladder cancer subtypes and associated tumor neovasculature. Mod. Pathol, 2011, 24, 1521-9.
48. Wang, W.; Tavora, F.; Sharma, R.; Eisenberger, M.; Netto, G.J. PSMA expression in Schwannoma: a potential clinical mimicker of metastatic prostate carcinoma. Urol. Oncol, 2009, 27, 525-8.
49. Chang, S.S.; O'Keefe, D.S.; Bacich, D.J.; Reuter, V.E.; Heston, W.D.; Gaudin, P.B. Prostate-specific membrane antigen is produced in tumor-associated neovasculature. Clin. Cancer. Res, 1999, 5, 2674-81.
50. Chang, S.S.; Reuter, V.E.; Heston, W.D.; Bander, N.H.; Grauer, L.S.; Gaudin, P.B. Five different anti-prostate-specific membrane antigen (PSMA) antibodies confirm PSMA expression in tumor-associated neovasculature. Cancer. Res, 1999, 59, 3192-8.
51. Chang, S.S.; Reuter, V.E.; Heston, W.D.; Gaudin, P.B. Metastatic renal cell carcinoma neovasculature expresses prostate-specific membrane antigen. Urology, 2001, 57, 801-5.
52. Haffner, M.C.; Kronberger, I.E.; Ross, J.S.; Sheehan, C.E.; Zitt, M.; Muhlmann, G.; Ofner, D.; Zelger, B.; Ensinger, C.; Yang, X.J.; Geley, S.; Margreiter, R.; Bander, N.H. Prostate-specific membrane antigen expression in the neovasculature of gastric and colorectal cancers. Hum. Pathol, 2009, 40, 1754-61.
53. Carter, R.E.; Feldman, A.R.; Coyle, J.T. Prostate-specific membrane antigen is a hydrolase with substrate and pharmacologic characteristics of a neuropeptidase. Proc. Natl. Acad. Sci. U. S. A, 1996, 93, 749-53.
54. Robinson, M.B.; Blakely, R.D.; Couto, R.; Coyle, J.T. Hydrolysis of the brain dipeptide N-acetyl-L-aspartyl-L-glutamate. Identification and characterization of a novel N-acetylated alpha-linked acidic dipeptidase activity from rat brain. J. Biol. Chem, 1987, 262, 14498-506.
55. Halsted, C.H. The intestinal absorption of folates. Am. J. Clin. Nutr, 1979, 32, 846-55.
56. Sirotnak, F.M.; Tolner, B. Carrier-mediated membrane transport of folates in mammalian cells. Annu. Rev. Nutr, 1999, 19, 91-122.
57. DeMarzo, A.M.; Nelson, W.G.; Isaacs, W.B.; Epstein, J.I. Pathological and molecular aspects of prostate cancer. Lancet, 2003, 361, 955-64.
58. Grauer, L.S.; Lawler, K.D.; Marignac, J.L.; Kumar, A.; Goel, A.S.; Wolfert, R.L. Identification, purification, and subcellular localization of prostate-specific membrane antigen PSM' protein in the LNCaP prostatic carcinoma cell line. Cancer. Res, 1998, 58, 4787-9.
59. Heston, W.D. Characterization and glutamyl preferring carboxypeptidase function of prostate specific membrane antigen: a novel folate hydrolase. Urology, 1997, 49, 104-12.
60. Su, S.L.; Huang, I.P.; Fair, W.R.; Powell, C.T.; Heston, W.D. Alternatively spliced variants of prostate-specific membrane antigen RNA: ratio of expression as a potential measurement of progression. Cancer. Res, 1995, 55, 1441-3.
61. Wright, G.L., Jr.; Haley, C.; Beckett, M.L.; Schellhammer, P.F. Expression of prostate-specific membrane antigen in normal, benign, and malignant prostate tissues. Urol. Oncol, 1995, 1, 18-28.
62. Birtle, A.J.; Freeman, A.; Masters, J.R.; Payne, H.A.; Harland, S.J. Tumour markers for managing men who present with metastatic prostate cancer and serum prostate-specific antigen levels of <10 ng/mL. BJU. Int, 2005, 96, 303-7.
63. Denmeade, S.R.; Sokoll, L.J.; Dalrymple, S.; Rosen, D.M.; Gady, A.M.; Bruzek, D.; Ricklis, R.M.; Isaacs, J.T. Dissociation between androgen responsiveness for malignant growth vs. expression of prostate specific differentiation markers PSA, hK2, and PSMA in human prostate cancer models. Prostate, 2003, 54, 249-57.
64. Evans, M.J.; Smith-Jones, P.M.; Wongvipat, J.; Navarro, V.; Kim, S.; Bander, N.H.; Larson, S.M.; Sawyers, C.L. Noninvasive measurement of androgen receptor signaling with a positron-emitting radiopharmaceutical that targets prostate-specific membrane antigen. Proc. Natl. Acad. Sci. U. S. A, 2011, 108, 9578-82.
65. Lambert, L.A.; Mitchell, S.L. Molecular evolution of the transferrin receptor/glutamate carboxypeptidase II family. J. Mol. Evol, 2007, 64, 113-28.
66. Mahadevan, D.; Saldanha, J.W. The extracellular regions of PSMA and the transferrin receptor contain an aminopeptidase domain: implications for drug design. Protein. Sci, 1999, 8, 2546-9.
67. Dautry-Varsat, A. Receptor-mediated endocytosis: the intracellular journey of transferrin and its receptor. Biochimie, 1986, 68, 375-81.
68. Schulke, N.; Varlamova, O.A.; Donovan, G.P.; Ma, D.; Gardner, J.P.; Morrissey, D.M.; Arrigale, R.R.; Zhan, C.; Chodera, A.J.; Surowitz, K.G.; Maddon, P.J.; Heston, W.D.; Olson, W.C. The homodimer of prostate-specific membrane antigen is a functional target for cancer therapy. Proc. Natl. Acad. Sci. U. S. A, 2003, 100, 12590-5.
69. Carrasquillo, J. Imaging and dosimetry determinations using radiolabeled antibodies. Cancer. Treat. Res, 1993, 68, 65-97.
70. Commandeur, L.C.; Parsons, J.R. Degradation of halogenated aromatic compounds. Biodegradation, 1990, 1, 207-20.
71. Grant, B.D.; Donaldson, J.G. Pathways and mechanisms of endocytic recycling. Nat. Rev. Mol. Cell. Biol, 2009, 10, 597-608.
72. Yao, V.; Bacich, D.J. Prostate specific membrane antigen (PSMA) expression gives prostate cancer cells a growth advantage in a physiologically relevant folate environment in. vitro. Prostate, 2006, 66, 867-75.
73. Yao, V.; Berkman, C.E.; Choi, J.K.; O'Keefe, D.S.; Bacich, D.J. Expression of prostate-specific membrane antigen (PSMA), increases cell folate uptake and proliferation and suggests a novel role for PSMA in the uptake of the non-polyglutamated folate, folic acid. Prostate, 2010, 70, 305-16.
74. Yao, V.; Parwani, A.; Maier, C.; Heston, W.D.; Bacich, D.J. Moderate expression of prostate-specific membrane antigen, a tissue differentiation antigen and folate hydrolase, facilitates prostate carcinogenesis. Cancer. Res, 2008, 68, 9070-7.
75. Vallabhajosula, S.; Kuji, I.; Hamacher, K.A.; Konishi, S.; Kostakoglu, L.; Kothari, P.A.; Milowski, M.I.; Nanus, D.M.; Bander, N.H.; Goldsmith, S.J. Pharmacokinetics and biodistribution of 111In-and 177Lu-labeled J591 antibody specific for prostate-specific membrane antigen: prediction of 90Y-J591 radiation dosimetry based on 111In or 177Lu? J. Nucl. Med, 2005, 46, 634-41.
76. Bander, N.H.; Trabulsi, E.J.; Kostakoglu, L.; Yao, D.; Vallabhajosula, S.; Smith-Jones, P.; Joyce, M.A.; Milowsky, M.; Nanus, D.M.; Goldsmith, S.J. Targeting metastatic prostate cancer with radiolabeled monoclonal antibody J591 to the extracellular domain of prostate specific membrane antigen. J. Urol, 2003, 170, 1717-21.
77. Bander, N.H.; Milowsky, M.I.; Nanus, D.M.; Kostakoglu, L.; Vallabhajosula, S.; Goldsmith, S.J. 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, 4591-601.
78. Elsasser-Beile, U.; Wolf, P.; Gierschner, D.; Buhler, P.; Schultze-Seemann, W.; Wetterauer, U. A new generation of monoclonal and recombinant antibodies against cell-adherent prostate specific membrane antigen for diagnostic and therapeutic targeting of prostate cancer. Prostate, 2006, 66, 1359-70.
79. Alt, K.; Wiehr, S.; Ehrlichmann, W.; Reischl, G.; Wolf, P.; Pichler, B.J.; Elsasser-Beile, U.; Buhler, P. High-resolution animal PET imaging of prostate cancer xenografts with three different 64Culabeled antibodies against native cell-adherent PSMA. Prostate, 2010, 70, 1413-21.
80. Viola-Villegas, N., Evans, H., Bartlett, D., Wu, A, Lewis, J. Preclinical development of Zr-89 labeled anti-PSMA minibody and cys-diabody. Abstracts. of. the. Society. of. Nuclear. Medicine. Annual. Meeting, June. 9-13, 2012. Miami. Beach, Florida
81. Cerchia, L.; Giangrande, P.H.; McNamara, J.O.; de Franciscis, V. Cell-specific aptamers for targeted therapies. Methods. Mol. Biol, 2009, 535, 59-78.
82. Lupold, S.E.; Hicke, B.J.; Lin, Y.; Coffey, D.S. Identification and characterization of nuclease-stabilized RNA molecules that bind human prostate cancer cells via the prostate-specific membrane antigen. Cancer. Res, 2002, 62, 4029-33.
83. Bagalkot, V.; Farokhzad, O.C.; Langer, R.; Jon, S. An aptamer-doxorubicin physical conjugate as a novel targeted drug-delivery platform. Angew. Chem. Int. Ed. Engl, 2006, 45, 8149-52.
84. Dassie, J.P.; Liu, X.Y.; Thomas, G.S.; Whitaker, R.M.; Thiel, K.W.; Stockdale, K.R.; Meyerholz, D.K.; McCaffrey, A.P.; McNamara, J.O., 2nd; Giangrande, P.H. Systemic administration of optimized aptamer-siRNA chimeras promotes regression of PSMA-expressing tumors. Nat. Biotechnol, 2009, 27, 839-49.
85. Kim, D.; Jeong, Y.Y.; Jon, S. A drug-loaded aptamer-gold nanoparticle bioconjugate for combined CT imaging and therapy of prostate cancer. ACS. Nano, 2010, 4, 3689-96.
86. Ni, X.; Zhang, Y.; Ribas, J.; Chowdhury, W.H.; Castanares, M.; Zhang, Z.; Laiho, M.; DeWeese, T.L.; Lupold, S.E. Prostate-targeted radiosensitization via aptamer-shRNA chimeras in human tumor xenografts. J. Clin. Invest, 2011, 121, 2383-90.
87. Chu, T.C.; Marks, J.W., 3rd; Lavery, L.A.; Faulkner, S.; Rosenblum, M.G.; Ellington, A.D.; Levy, M. Aptamer:toxin conjugates that specifically target prostate tumor cells. Cancer. Res, 2006, 66, 5989-92.
88. Dhar, S.; Gu, F.X.; Langer, R.; Farokhzad, O.C.; Lippard, S.J. Targeted delivery of cisplatin to prostate cancer cells by aptamer functionalized Pt(IV) prodrug-PLGA-PEG nanoparticles. Proc. Natl. Acad. Sci. U. S. A, 2008, 105, 17356-61.
89. Farokhzad, O.C.; Cheng, J.; Teply, B.A.; Sherifi, I.; Jon, S.; Kantoff, P.W.; Richie, J.P.; Langer, R. Targeted nanoparticle-aptamer bioconjugates for cancer chemotherapy in. vivo. Proc. Natl. Acad. Sci. U. S. A, 2006, 103, 6315-20.
90. Farokhzad, O.C.; Jon, S.; Khademhosseini, A.; Tran, T.N.; Lavan, D.A.; Langer, R. Nanoparticle-aptamer bioconjugates: a new approach for targeting prostate cancer cells. Cancer. Res, 2004, 64, 7668-72.
91. Wang, A.Z.; Bagalkot, V.; Vasilliou, C.C.; Gu, F.; Alexis, F.; Zhang, L.; Shaikh, M.; Yuet, K.; Cima, M.J.; Langer, R.; Kantoff, P.W.; Bander, N.H.; Jon, S.; Farokhzad, O.C. Superparamagnetic iron oxide nanoparticle-aptamer bioconjugates for combined prostate cancer imaging and therapy. ChemMedChem, 2008, 3, 1311-5.
92. Zhang, L.; Radovic-Moreno, A.F.; Alexis, F.; Gu, F.X.; Basto, P.A.; Bagalkot, V.; Jon, S.; Langer, R.S.; Farokhzad, O.C. Codelivery of hydrophobic and hydrophilic drugs from nanoparticle-aptamer bioconjugates. ChemMedChem, 2007, 2, 1268-71.
93. Bagalkot, V.; Zhang, L.; Levy-Nissenbaum, E.; Jon, S.; Kantoff, P.W.; Langer, R.; Farokhzad, O.C. Quantum dot-aptamer conjugates for synchronous cancer imaging, therapy, and sensing of drug delivery based on bi-fluorescence resonance energy transfer. Nano. Lett, 2007, 7, 3065-70.
94. Wu, X.; Ding, B.; Gao, J.; Wang, H.; Fan, W.; Wang, X.; Zhang, W.; Ye, L.; Zhang, M.; Ding, X.; Liu, J.; Zhu, Q.; Gao, S. Second-generation aptamer-conjugated PSMA-targeted delivery system for prostate cancer therapy. Int. J. Nanomedicine, 2011, 6, 1747-56.
95. Rockey, W.M.; Huang, L.; Kloepping, K.C.; Baumhover, N.J.; Giangrande, P.H.; Schultz, M.K. Synthesis and radiolabeling of chelator-RNA aptamer bioconjugates with copper-64 for targeted molecular imaging. Bioorg. Med. Chem, 2011, 19, 4080-90.
96. Barinka, C.; Byun, Y.; Dusich, C.L.; Banerjee, S.R.; Chen, Y.; Castanares, M.; Kozikowski, A.P.; Mease, R.C.; Pomper, M.G.; Lubkowski, J. Interactions between human glutamate carboxypeptidase II and urea-based inhibitors: structural characterization. J. Med. Chem, 2008, 51, 7737-43.
97. Barinka, C.; Rovenska, M.; Mlcochova, P.; Hlouchova, K.; Plechanovova, A.; Majer, P.; Tsukamoto, T.; Slusher, B.S.; Konvalinka, J.; Lubkowski, J. Structural insight into the pharmacophore pocket of human glutamate carboxypeptidase II. J. Med. Chem, 2007, 50, 3267-73.
98. Barinka, C.; Starkova, J.; Konvalinka, J.; Lubkowski, J. A high-resolution structure of ligand-free human glutamate carboxypeptidase II. Acta. Crystallogr. Sect. F. Struct. Biol. Cryst. Commun, 2007, 63, 150-3.
99. Davis, M.I.; Bennett, M.J.; Thomas, L.M.; Bjorkman, P.J. Crystal structure of prostate-specific membrane antigen, a tumor marker and peptidase. Proc. Natl. Acad. Sci. U. S. A, 2005, 102, 5981-6.
100. Mesters, J.R.; Barinka, C.; Li, W.; Tsukamoto, T.; Majer, P.; Slusher, B.S.; Konvalinka, J.; Hilgenfeld, R. Structure of glutamate carboxypeptidase II, a drug target in neuronal damage and prostate cancer. EMBO. J, 2006, 25, 1375-84.
101. Mesters, J.R.; Henning, K.; Hilgenfeld, R. Human glutamate carboxypeptidase II inhibition: structures of GCPII in complex with two potent inhibitors, quisqualate and 2-PMPA. Acta. Crystallogr. D. Biol. Crystallogr, 2007, 63, 508-13.
102. Wang, H.; Byun, Y.; Barinka, C.; Pullambhatla, M.; Bhang, H.E.; Fox, J.J.; Lubkowski, J.; Mease, R.C.; Pomper, M.G. Bioisosterism of urea-based GCPII inhibitors: Synthesis and structure-activity relationship studies. Bioorg. Med. Chem. Lett, 2010, 20, 392-7.
103. Byun, Y., Mease, R.C., Lupold, S.E., Pomper, M.G., Chapter. 36. Recent. Development. of. Diagnostic. and. Therapeutic. Agents. Targeting. Glutamate. Carboxylpeptidase. II. (GCPII). John Wiley & Sons: 2009.
104. Zhou, J.; Neale, J.H.; Pomper, M.G.; Kozikowski, A.P. NAAG peptidase inhibitors and their potential for diagnosis and therapy. Nat. Rev. Drug. Discov, 2005, 4, 1015-26.
105. Slusher, B.S.; Vornov, J.J.; Thomas, A.G.; Hurn, P.D.; Harukuni, I.; Bhardwaj, A.; Traystman, R.J.; Robinson, M.B.; Britton, P.; Lu, X.C.; Tortella, F.C.; Wozniak, K.M.; Yudkoff, M.; Potter, B.M.; Jackson, P.F. Selective inhibition of NAALADase, which converts NAAG to glutamate, reduces ischemic brain injury. Nat. Med, 1999, 5, 1396-402.
106. Jackson, P.F.; Cole, D.C.; Slusher, B.S.; Stetz, S.L.; Ross, L.E.; Donzanti, B.A.; Trainor, D.A. Design, synthesis, and biological activity of a potent inhibitor of the neuropeptidase N-acetylated alpha-linked acidic dipeptidase. J. Med. Chem, 1996, 39, 619-22.
107. Majer, P.; Jackson, P.F.; Delahanty, G.; Grella, B.S.; Ko, Y.S.; Li, W.; Liu, Q.; Maclin, K.M.; Polakova, J.; Shaffer, K.A.; Stoermer, D.; Vitharana, D.; Wang, E.Y.; Zakrzewski, A.; Rojas, C.; Slusher, B.S.; Wozniak, K.M.; Burak, E.; Limsakun, T.; Tsukamoto, T. Synthesis and biological evaluation of thiol-based inhibitors of glutamate carboxypeptidase II: discovery of an orally active GCP II inhibitor. J. Med. Chem, 2003, 46, 1989-96.
108. Anderson, M.O.; Wu, L.Y.; Santiago, N.M.; Moser, J.M.; Rowley, J.A.; Bolstad, E.S.; Berkman, C.E. Substrate specificity of prostate-specific membrane antigen. Bioorg. Med. Chem, 2007, 15, 6678-86.
109. Liu, T.; Wu, L.Y.; Kazak, M.; Berkman, C.E. Cell-Surface labeling and internalization by a fluorescent inhibitor of prostate-specific membrane antigen. Prostate, 2008, 68, 955-64.
110. Maung, J.; Mallari, J.P.; Girtsman, T.A.; Wu, L.Y.; Rowley, J.A.; Santiago, N.M.; Brunelle, A.N.; Berkman, C.E. Probing for a hydrophobic a binding register in prostate-specific membrane antigen with phenylalkylphosphonamidates. Bioorg. Med. Chem, 2004, 12, 4969-79.
111. Kozikowski, A.P.; Nan, F.; Conti, P.; Zhang, J.; Ramadan, E.; Bzdega, T.; Wroblewska, B.; Neale, J.H.; Pshenichkin, S.; Wroblewski, J.T. Design of remarkably simple, yet potent ureabased inhibitors of glutamate carboxypeptidase II (NAALADase). J. Med. Chem, 2001, 44, 298-301.
112. Kozikowski, A.P.; Zhang, J.; Nan, F.; Petukhov, P.A.; Grajkowska, E.; Wroblewski, J.T.; Yamamoto, T.; Bzdega, T.; Wroblewska, B.; Neale, J.H. Synthesis of urea-based inhibitors as active site probes of glutamate carboxypeptidase II: efficacy as analgesic agents. J. Med. Chem, 2004, 47, 1729-38.
113. Liu, T.; Wu, L.Y.; Hopkins, M.R.; Choi, J.K.; Berkman, C.E. A targeted low molecular weight near-infrared fluorescent probe for prostate cancer. Bioorg. Med. Chem. Lett, 2010, 20, 7124-6.
114. Nedrow-Byers, J.R.; Jabbes, M.; Jewett, C.; Ganguly, T.; He, H.; Liu, T.; Benny, P.; Bryan, J.N.; Berkman, C.E. A phosphorami-date-based prostate-specific membrane antigen-targeted SPECT agent. Prostate, 2012, 72, 904-12.
115. Nedrow-Byers, J.R.; Moore, A.L.; Ganguly, T.; Hopkins, M.R.; Fulton, M.D.; Benny, P.D.; Berkman, C.E. PSMA-targeted SPECT agents: Mode of binding effect on in. vitro performance. Prostate, 2012
116. Hao, G.K.A., Gore, C., Dobin, T., Singh, A., Oz, O., Hsieh, J-T., Sun, X.,. PET signal amplification via bifunctional chelator scaf-fold for the prostate specific membrane antigen (PSMA) detection. Abstracts. of. the. Society. of. Nuclear. Medicine. Annual. Meeting, June. 9-13, 2012. Miami. Beach, Florida,
117. Graham, K., Kettschau, G., Gromov, A., Friebe, M., Gekeler, V., Dinkelborg, L.,.[18F]-labeled PET tracer BAY1075553, small molecule inhibitor of PSMA for molecular Imaging of prostate cancer. World. Molecular. Imaging. Conference, 2011, Sept. 7-10, San Diego, California, P235.
118. Pomper, M.G.; Musachio, J.L.; Zhang, J.; Scheffel, U.; Zhou, Y.; Hilton, J.; Maini, A.; Dannals, R.F.; Wong, D.F.; Kozikowski, A.P. 11C-MCG: synthesis, uptake selectivity, and primate PET of a probe for glutamate carboxypeptidase II (NAALADase). Mol. Imaging, 2002, 1, 96-101.
119. Foss, C.A.; Mease, R.C.; Fan, H.; Wang, Y.; Ravert, H.T.; Dannals, R.F.; Olszewski, R.T.; Heston, W.D.; Kozikowski, A.P.; Pomper, M.G. Radiolabeled small-molecule ligands for prostate-specific membrane antigen: in. vivo imaging in experimental models of prostate cancer. Clin. Cancer. Res, 2005, 11, 4022-8.
120. 18F]fluorobenzyl triarylphosphoniums ions. J. Label. Compd. Radiopharm, 2004, 47, 469-476.
121. Mease, R.C.; Dusich, C.L.; Foss, C.A.; Ravert, H.T.; Dannals, R.F.; Seidel, J.; Prideaux, A.; Fox, J.J.; Sgouros, G.; Kozikowski, A.P.; Pomper, M.G. N-[N-[(S)-1,3-Dicarboxypropyl]carbamoyl]-4-[18F]fluorobenzyl-L-cysteine, [18F]DCFBC: a new imaging probe for prostate cancer. Clin. Cancer. Res, 2008, 14, 3036-43.
122. Holt, D.P., Ravert, H.T., Mathews, W.B., Horti, A., Mease, R., Dannals, R.F. A semi-automated microwave chemistry system for complete radiosynthesis, purification, and formulation of F-18 radiotracers. J. Label. Compd. Radiopharm, 2011, 54, S426.
123. 18F-DCFBC, a low molecular weight inhibitor of PSMA, in patients with metastatic prostate cancer. J. Nucl. Med, 2012, 53, 1883-91.
124. Chen, Y.; Foss, C.A.; Byun, Y.; Nimmagadda, S.; Pullambhatla, M.; Fox, J.J.; Castanares, M.; Lupold, S.E.; Babich, J.W.; Mease, R.C.; Pomper, M.G. Radiohalogenated prostate-specific membrane antigen (PSMA)-based ureas as imaging agents for prostate cancer. J. Med. Chem, 2008, 51, 7933-43.
125. Olberg, D.E.; Arukwe, J.M.; Grace, D.; Hjelstuen, O.K.; Solbakken, M.; Kindberg, G.M.; Cuthbertson, A. One step radiosynthesis of 6-[(18)F]fluoronicotinic acid 2,3,5,6-tetrafluorophenyl ester ([(18)F]F-Py-TFP): a new prosthetic group for efficient labeling of biomolecules with fluorine-18. J. Med. Chem, 2010, 53, 1732-40.
126. Chen, Y.; Pullambhatla, M.; Foss, C.A.; Byun, Y.; Nimmagadda, S.; Senthamizhchelvan, S.; Sgouros, G.; Mease, R.C.; Pomper, M.G. 2-(3-{1-Carboxy-5-[(6-[18F]fluoro-pyridine-3-carbonyl)-amino]-pentyl}-ureido)-pen tanedioic acid, [18F]DCFPyL, a PSMA-based PET imaging agent for prostate cancer. Clin. Cancer. Res, 2011, 17, 7645-53.
127. Kothari, P., Vallabhajosula, S., Schoendorf, M., Lu, G., Zimmerman, C., Hillier, S., Maresca, K., Eckelman, W., Joyal, J., Babich, J. 18F-labeled small molecule inhibitors of prostate specific membrane antigen (PSMA) for PET imaging of prostate cancer. Abstracts of the Society of Nuclear Medicine Annual Meeting, June 9-13, 2012. Miami Beach, Florida.
128. Banerjee, S.R.; Pullambhatla, M.; Byun, Y.; Nimmagadda, S.; Green, G.; Fox, J.J.; Horti, A.; Mease, R.C.; Pomper, M.G. 68Galabeled inhibitors of prostate-specific membrane antigen (PSMA) for imaging prostate cancer. J. Med. Chem, 2010, 53, 5333-41.
129. Banerjee, S.R.; Foss, C.A.; Castanares, M.; Mease, R.C.; Byun, Y.; Fox, J.J.; Hilton, J.; Lupold, S.E.; Kozikowski, A.P.; Pomper, M.G. Synthesis and evaluation of technetium-99m-and rhenium-labeled inhibitors of the prostate-specific membrane antigen (PSMA). J. Med. Chem, 2008, 51, 4504-17.
130. Kularatne, S.A.; Zhou, Z.; Yang, J.; Post, C.B.; Low, P.S. Design, synthesis, and preclinical evaluation of prostate-specific membrane antigen targeted (99m)Tc-radioimaging agents. Mol. Pharm, 2009, 6, 790-800.
131. Roesch, F.; Riss, P.J. The renaissance of the (6)(8)Ge/(6)(8)Ga radionuclide generator initiates new developments in (6)(8)Ga radiopharmaceutical chemistry. Curr. Top. Med. Chem, 2010, 10, 1633-68.
132. Eder, M.; Schafer, M.; Bauder-Wust, U.; Hull, W.E.; Wangler, C.; Mier, W.; Haberkorn, U.; Eisenhut, M. 68Ga-complex lipophilicity and the targeting property of a urea-based PSMA inhibitor for PET imaging. Bioconjug. Chem, 2012, 23, 688-97.
133. Schafer, M.; Bauder-Wust, U.; Leotta, K.; Zoller, F.; Mier, W.; Haberkorn, U.; Eisenhut, M.; Eder, M. A dimerized urea-based inhibitor of the prostate-specific membrane antigen for 68Ga-PET imaging of prostate cancer. EJNMMI. Res, 2012, 2, 23.
134. Banerjee, S.R., Pullambhatla, M., Byun, Y., Foss, C., Nimmagadda, S., Ferdani, R., Anderson, C.J., Mease, R.C., Pomper, M.G. 64Cu-labeled inhibitors of prostate specific membrane antigen for PET imaging of prostate cancer. J. Label. Compd. Radiopharm, 2011, 54, S369.
135. Banerjee, S.R., Pullambhatla, M., Byun, Y., Nimmagadda, S., Baidoo, K., Brechbiel, M.W., Mease, R.C., Pomper, M.G. Preclinical evaluation of 86Y-labeled inhibitors of prostate specific membrane antigen. J. Label. Compd. Radiopharm, 2011, 54, S65.
136. Chen, Y.; Dhara, S.; Banerjee, S.R.; Byun, Y.; Pullambhatla, M.; Mease, R.C.; Pomper, M.G. A low molecular weight PSMA-based fluorescent imaging agent for cancer. Biochem. Biophys. Res. Commun, 2009, 390, 624-9.
137. Chandran, S.S.; Banerjee, S.R.; Mease, R.C.; Pomper, M.G.; Denmeade, S.R. Characterization of a targeted nanoparticle functionalized with a urea-based inhibitor of prostate-specific membrane antigen (PSMA). Cancer. Biol. Ther, 2008, 7, 974-82.
138. Hrkach, J.; Von Hoff, D.; Mukkaram Ali, M.; Andrianova, E.; Auer, J.; Campbell, T.; De Witt, D.; Figa, M.; Figueiredo, M.; Horhota, A.; Low, S.; McDonnell, K.; Peeke, E.; Retnarajan, B.; Sabnis, A.; Schnipper, E.; Song, J.J.; Song, Y.H.; Summa, J.; Tompsett, D.; Troiano, G.; Van Geen Hoven, T.; Wright, J.; LoRusso, P.; Kantoff, P.W.; Bander, N.H.; Sweeney, C.; Farokhzad, O.C.; Langer, R.; Zale, S. Preclinical development and clinical translation of a PSMA-targeted docetaxel nanoparticle with a differentiated pharmacological profile. Sci. Transl. Med, 2012, 4, 128ra39.
139. Kularatne, S.A.; Wang, K.; Santhapuram, H.K.; Low, P.S. Prostate-specific membrane antigen targeted imaging and therapy of prostate cancer using a PSMA inhibitor as a homing ligand. Mol. Pharm, 2009, 6, 780-9.
140. Malik, N., Zlatopolskiy, B., Solbach, C., Machulla, H-J., Reske, S. One pot radiosynthesis of a new PSMA ligand [Al18F]NOTA-DUPA-Pep. Abstracts. of. the. Annual. Meeting. of. the. Society. of. Nyclear. Medicine, June. 9-13, Miami. Beach, Florida, 2012
141. Afshar-Oromieh, A., Zechmann, C., Eder, M., Eisenhut, M., Haberkorn, U. [68Ga]Gallium labelled PSMA ligand as new PET-tracer for the diagnosis of prostate cancer: Normal uptake of healthy tissue. Abstracts. of. the. Society. of. Nuclear. Medicine. Annual. Meeting, June. 9-13, 2012. Miami. Beach, Florida.
142. Afshar-Oromieh, A.; Haberkorn, U.; Eder, M.; Eisenhut, M.; Zechmann, C.M. [68Ga]Gallium-labelled PSMA ligand as superior PET tracer for the diagnosis of prostate cancer: comparison with 18F-FECH. Eur. J. Nucl. Med. Mol. Imaging, 2012, 39, 1085-6.
143. Langsteger, W., Kunit, T., Haim, S., Nader, M., Valencia, R., Lesche, R., Sega, W., Piert, M., Loidl, W., Beheshti, M. BAY 1075553 PET/CT in the assessment of prostate cancer: Safety, tolerability and biodistribution - Phase I first in human study results. J. Nucl. Med, 2012, 53, 1125.
144. Beheshti, M., Langsteger, W., Sommerhuber, A., Steinmair, M., Wolf, I., Valencia, R., Lesche, R., Nader, M., Piert, M., Loidl, W. BAY 1075553 in staging and re-staging of prostate cancer patients - Phase I study and comparison to 18F-FCH. J. Nucl. Med, 2012, 53, 272.
145. Hillier, S.M., Kern, A.M., Maresca, K.P., Marquis, J.C., Eckelman, W.C., Joyal, J.L., Babich, J.W. 123I-MIP-1072, a small-molecule inhibitor of prostate-specific membrane antigen, is effective at monitoring tumor response to taxane therapy. J. Nucl. Med, 2011, 52, 1082-93.