Synthesis and preclinical evaluation of DOTAGA-conjugated PSMA ligands for functional imaging and endoradiotherapy of prostate cancer

EJNMMI Research

Volumn 4, Issue 1, 2014, Pages

  Weineisen, Martina ^a   Simecek, Jakub ^a   Schottelius, Margret ^a   Schwaiger, Markus ^b   Wester, Hans Jürgen ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^b TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Endoradiotherapy; PET; Prostate cancer; Prostate specific membrane antigen; PSMA; PSMA ligand; Theranostic; 177Lu DOTAGA ffk(Sub KuE); 68Ga DOTAGA ffk(Sub KuE)

Indexed keywords

DEXTRO AMINO ACID; GADOTERIC ACID; GALLIUM; LIGAND; LUTETIUM; PROSTATE SPECIFIC MEMBRANE ANTIGEN; TETRAXETAN; TRACER;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BINDING AFFINITY; BINDING KINETICS; CANCER RADIOTHERAPY; CELL COUNT; CELL VIABILITY; CHELATION; COMPLEX FORMATION; CONTROLLED STUDY; DIAGNOSTIC IMAGING; DRUG DISTRIBUTION; DRUG STABILITY; DRUG SYNTHESIS; ENDORADIOTHERAPY; FEMALE; HUMAN; HUMAN CELL; HYDROPHILICITY; IC50; ISOTOPE LABELING; LIGAND BINDING; LIPOPHILICITY; LIQUID CHROMATOGRAPHY; LNCAP CELL LINE; MALE; MASS SPECTROMETRY; MOUSE; NONHUMAN; PHOTOCHEMICAL INTERNALIZATION; POSITRON EMISSION TOMOGRAPHY; PRECURSOR; PROSTATE CANCER; RADIOCHEMISTRY; RADIOIODINATION; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

EID: 84914695684     PISSN: None     EISSN: 2191219X     Source Type: Journal    
DOI: 10.1186/s13550-014-0063-1     Document Type: Article

References (40)

1. Mesters JR, Barinka C, Li W, Tsukamoto T, Majer P, Slusher BS, Konvalinka J, Hilgenfeld R: Structure of glutamate carboxypeptidase II, a drug target in neuronal damage and prostate cancer.EMBO J 2006, 25:1375–1384.
2. Ghosh A, Heston WD: Tumor target prostate specific membrane antigen (PSMA) and its regulation in prostate cancer.J Cell Biochem 2004, 91:528–539.
3. Silver DA, Pellicer I, Fair WR, Heston WD, Cordon-Cardo C: Prostate-specific membrane antigen expression in normal and malignant human tissues.Clin Cancer Res 1997, 3:81–85.
4. Pinto JT, Suffoletto BP, Berzin TM, Qiao CH, Lin S, Tong WP, May F, Mukherjee B, Heston WDW: Prostate-specific membrane antigen: a novel folate hydrolase in human prostatic carcinoma cells.Clin Cancer Res 1996, 2:1445–1451.
5. Carter RE, Feldman AR, Coyle JT: Prostate-specific membrane antigen is a hydrolase with substrate and pharmacologic characteristics of a neuropeptidase.Proc Natl Acad Sci USA 1996, 93:749–753.
6. Schulke N, Varlamova OA, Donovan GP, Ma D, Gardner JP, Morrissey DM, Arrigale RR, Zhan C, Chodera AJ, Surowitz KG, Maddon PJ, Heston WD, Olson WC: The homodimer of prostate-specific membrane antigen is a functional target for cancer therapy.Proc Natl Acad Sci USA 2003, 100:12590–12595.
7. Kozikowski AP, Nan F, Conti P, Zhang J, Ramadan E, Bzdega T, Wroblewska B, Neale JH, Pshenichkin S, Wroblewski JT: Design of remarkably simple, yet potent urea-based inhibitors of glutamate carboxypeptidase II (NAALADase).J Med Chem 2001, 44:298–301.
8. 11C-MCG: synthesis, uptake selectivity, and primate PET of a probe for glutamate carboxypeptidase II (NAALADase).Mol Imaging 2002, 1:96–101.
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, 11:4022–4028.
10. 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, 51:7933–7943.
11. 18 F]DCFBC: a new imaging probe for prostate cancer.Clin Cancer Res 2008, 14:3036–3043.
12. Maresca KP, Hillier SM, Femia FJ, Keith D, Barone C, Joyal JL, Zimmerman CN, Kozikowski AP, Barrett JA, Eckelman WC, Babich JW: A series of halogenated heterodimeric inhibitors of prostate specific membrane antigen (PSMA) as radiolabeled probes for targeting prostate cancer.J Med Chem 2009, 52:347–357.
13. Hillier SM, Maresca KP, Femia FJ, Marquis JC, Foss CA, Nguyen N, Zimmerman CN, Barrett JA, Eckelman WC, Pomper MG, Joyal JL, Babich JW: Preclinical evaluation of novel glutamate-urea-lysine analogues that target prostate-specific membrane antigen as molecular imaging pharmaceuticals for prostate cancer.Cancer Res 2009, 69:6932–6940.
14. 99mTc and Re-labeled inhibitors of the prostate-specific membrane antigen (PSMA).J Med Chem 2008, 51:4504–4517.
15. 99mTc-radioimaging agents.Mol Pharm 2009, 6:790–800.
16. Zhang AX, Murelli RP, Barinka C, Michel J, Cocleaza A, Jorgensen WL, Lubkowski J, Spiegel DA: A remote arene-binding site on prostate specific membrane antigen revealed by antibody-recruiting small molecules.J Am Chem Soc 2010, 132:12711–12716.
17. 68Ga-labeled inhibitors of prostate-specific membrane antigen (PSMA) for imaging prostate cancer.J Med Chem 2010, 53:5333–5341.
18. 68Ga-complex lipophilicity and the targeting property of a urea-based PSMA inhibitor for PET imaging.Bioconj Chem 2012, 23:688–697.
19. Akhtar NH, Pail O, Saran A, Tyrell L, Tagawa ST: Prostate-specific membrane antigen-based therapeutics.Adv Urol 2012, 2012:973820.
20. 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, 25:540–547.
21. Tagawa ST, Milowsky MI, Morris MJ, Vallabhajosula S, Christos PJ, Akhtar NH, Goldsmith SJ, Osborne J, Larson SM, Pandit-Taskar N, Scher HI, Bander NH, Nanus DM: Phase II study of Lutetium-177-labeled anti-prostate-specific membrane antigen (PSMA) monoclonal antibody J591 for metastatic castration-resistant prostate cancer.Clin Cancer Res 2013, 19:5182–5191.
22. Milowsky MI, Nanus DM, Kostakoglu L, Vallabhajosula S, Goldsmith SJ, Bander NH: Phase I trial of yttrium-90-labeled anti-prostate-specific membrane antigen monoclonal antibody J591 for androgen-independent prostate cancer.J Clin Oncol 2004, 22:2522–2531.
23. 131I]MIP-1375, a small molecule prostate-specific membrane antigen (PSMA) inhibitor for targeted therapy of prostate cancer (PCa).J Nucl Med 2011, 52(Supplement 1):361.
24. 131I]MIP-1466, a small molecule prostate-specific membrane antigen (PSMA) inhibitor for targeted radiotherapy of prostate cancer (PCa).J Nucl Med 2012, 53(Supplement 1):170.
25. 131I-labelled small molecule (MIP-1095) targeting PSMA for prostate cancer therapy.Eur J Nucl Med Mol Imaging 2014, 41:1280–1292.
26. Bernhard C, Moreau M, Lhenry D, Goze C, Boschetti F, Rousselin Y, Brunotte F, Denat F: DOTAGA-anhydride: a valuable building block for the preparation of DOTA-like chelating agents.Chemistry 2012, 18:7834–7841.
27. Eisenwiener KP, Powell P, Macke HR: A convenient synthesis of novel bifunctional prochelators for coupling to bioactive peptides for radiometal labelling.Bioorg Med Chem Lett 2000, 10:2133–2135.
28. Heppeler A, Froidevaux S, Macke HR, Jermann E, Behe M, Powell P, Hennig M: Radiometal-labelled macrocyclic chelator-derivatized somatostatin analogue with superb tumour-targeting properties and potential for receptor-mediated internal radiotherapy.Chemistry 1999, 5:1974–1981.
29. 68Ga.Chem Med Chem 2012, 7:1375–1378.
30. Schottelius M, Reubi JC, Eltschinger V, Schwaiger M, Wester HJ: N-terminal sugar conjugation and C-terminal Thr-for-Thr(ol) exchange in radioiodinated Tyr3-octreotide: effect on cellular ligand trafficking in vitro and tumor accumulation in vivo.J Med Chem 2005, 48:2778–2789.
31. Dekker B, Keen H, Shaw D, Disley L, Hastings D, Hadfield J, Reader A, Allan D, Julyan P, Watson A, Zweit J: Functional comparison of annexin V analogues labelled indirectly and directly with iodine-124.Nucl Med Biol 2005, 32:403–413.
32. Vaidyanathan G, Zalutsky MR: Preparation of N-succinimidyl 3-[*I]iodobenzoate: an agent for the indirect radioiodination of proteins.Nat Protoc 2006, 1:707–713.
33. 68Ga]CPCR4.2.Nucl Med Biol 2014, 41:84–89.
34. 68Ga radiopharmaceuticals in high radiochemical purity.Bioconj Chem 2012, 23:1712–1717.
35. 68Ga radiopharmaceuticals.Chemistry 2011, 17:14718–14722.
36. 68Ga-labelled PSMA ligand for the diagnosis of prostate cancer: biodistribution in humans and first evaluation of tumour lesions.Eur J Nucl Med Mol Imaging 2013, 40:486–495.
37. 18F-DCFBC, a low-molecular-weight inhibitor of prostate-specific membrane antigen, in patients with metastatic prostate cancer.J Nucl Med 2012, 53(Supplement 1):1883–1891.
38. 177Lu-labelled PSMA ligand, CHX-A''-DTPA-DUPA-Pep.Pharmaceuticals (Basel) 2014, 7:517–529.
39. 68Ga-DOTA-DUPA-Pep as a new peptide conjugate for molecular imaging of prostate carcinoma.J Nucl Med 2011, 52:1597.
40. Benesova M, Schaefer M, Bauder-Wuest U, Mier W, Haberkorn U, Eder M, Kopka K: Preclinical evaluation of a naphthyl-containing DOTA-conjugated PSMA inhibitor with improved targeting and pharmacokinetic properties.Eur J Nucl Med Mol Imaging 2014, 2(Supplement):438.