Radiofluorination of PSMA-HBED via Al18F2+ Chelation and Biological Evaluations In Vitro

Molecular Imaging and Biology

Volumn 17, Issue 6, 2015, Pages 777-785

  Malik, Noeen ^a   Baur, Benjamin ^a   Winter, Gordon ^a   Reske, Sven N ^a   Beer, Ambros J ^a   Solbach, Christoph ^a  

^a UNIVERSITY HOSPITAL ULM   (Germany)

Author keywords

Al18F labeling; F 18; Prostate cancer; PSMA; PSMA HBED

Indexed keywords

ALUMINUM OXIDE; FLUORINE 18; PROSTATE SPECIFIC MEMBRANE ANTIGEN N,N' BIS(2 HYDROXYBENZYL)ETHYLENEDIAMINE N,N' DIACETIC ACID ALUMINUM F 18; RADIOPHARMACEUTICAL AGENT; UNCLASSIFIED DRUG; ANTIBODY CONJUGATE; CHELATING AGENT; FLUORINE; GLUTAMATE CARBOXYPEPTIDASE II; GLUTAMATE CARBOXYPEPTIDASE II, HUMAN; MEMBRANE ANTIGEN;

ARTICLE; CHELATION; CONTROLLED STUDY; DRUG PURIFICATION; DRUG STABILITY; DRUG STRUCTURE; FLUORINATION; HUMAN; HUMAN CELL; IN VITRO STUDY; ISOTOPE LABELING; LNCAP CELL LINE; MALE; ONE POT SYNTHESIS; PH; PRIORITY JOURNAL; RADIOACTIVITY; RADIOCHEMISTRY; RADIOFLUORINATION; RADIOSYNTHESIS; REACTION TIME; SOLID PHASE EXTRACTION; CHEMISTRY;

ANTIGENS, SURFACE; CHELATING AGENTS; FLUORINE RADIOISOTOPES; GLUTAMATE CARBOXYPEPTIDASE II; HUMANS; HYDROGEN-ION CONCENTRATION; IMMUNOCONJUGATES; IN VITRO TECHNIQUES;

EID: 84945225434     PISSN: 15361632     EISSN: 18602002     Source Type: Journal    
DOI: 10.1007/s11307-015-0844-6     Document Type: Article

References (30)

1. Ghosh A, Heston WD (2004) Tumor target prostate specific membrane antigen (PSMA) and its regulation in prostate cancer. J Cell Biochem 91:528–539
2. Elsasser-B U, Reischl G, Wiehr S et al (2009) PET imaging of prostate cancer xenografts prostate-specific membrane antigen. J Nucl Med 50:606–611
3. 68Ga]gallium-labelled PSMA ligand for the diagnosis of prostate cancer: biodistribution in humans and first evaluation of tumour lesions. Eur J Nucl Med Mol Imaging 40:969–970
4. Goodman OB Jr, Barwe SP, Ritter B et al (2007) Interaction of prostate specific membrane antigen with a highly specific antibody against the clathrin and the adaptor protein complex-2. Int J Oncol 31:1199–1203
5. Ikeda M, Ochi R, Wada A et al (2010) Supramolecular hydrogel capsule showing prostate specific antigen-responsive function for sensing and targeting prostate cancer cells. Chem Sci 1:491–498
6. Blank BR, Alayoglu P, Engen W et al (2011) N-substituted glutamyl sulfonamides as inhibitors of glutamate carboxypeptidase II (GCP2). Chem Biol Drug Des 77:241–247
7. Olson WC, Heston WD, Rajasekaran AK (2007) Clinical trials of cancer therapies targeting prostate-specific membrane antigen. Rev Recent Clin Trials 2:182–190
8. 99mTc-radioimaging agents. Mol Pharm 6:790–800
9. Kularatne SA, Wang K, Santhapuram H-KR, Low PS (2009) Prostate-specific membrane antigen targeted imaging and therapy of prostate cancer using a PSMA inhibitor as a homing ligand. Mol Pharm 6:780–789
10. 18F-labeling of peptides via nucleophilic aromatic substitution. Bioconjug Chem 20:2254–2261
11. Zhang AX, Murelli RP, Barinka C et al (2010) A remote arene-binding site on prostate specific membrane antigen revealed by antibody-recruiting small molecules. J Am Chem Soc 132:12711–12716
12. 18F-fluorine. J Nucl Med 51:454–461
13. Kularatne SA, Venkatesh C, Santhapuram H-KR et al (2010) Synthesis and biological analysis of prostate-specific membrane antigen-targeted anticancer prodrugs. J Med Chem 53:7767–7777
14. 18F]DCFPyL, a PSMA-based PET imaging agent for prostate cancer. Clin Cancer Res 17:7645–7653
15. 18F]FEtTUG) as a new PSMA ligand. J Radioanal Nucl Chem 295:2289–2294
16. 18F]F-Py-TFP): a new prosthetic group for efficient labelling of biomolecules with fluorine-18. J Med Chem 53:1732–1740
17. 18F]FPy-DUPA-Pep). Appl Radiat Isot 69:1014–1018
18. 18F-labeling of peptides with a fluoride-aluminum-chelate complex. Bioconjug Chem 21:1331–1340
19. 18F chelation. Bioconjug Chem 22:1793–1803
20. 18F]AlF method. Appl Radiat Isot 70:200–204
21. McBride WJ, D’Souza CA, Karacay H et al (2013) New lyophilized kit for rapid radiofluorination of peptides. Bioconjug Chem 23:538–547
22. 18F). EJNMMI Res 3:36
23. 18F]NOTA-DUPA-Pep. J Label Compd Radiopharm 55:320–325
24. Wan W, Guo N, Pan D et al (2013) First experience of 18F-Alfatide in lung cancer patients using a new lyophilized kit for rapid radiofluorination. J Nucl Med 54:691–698
25. 68Ga-labeled small recombinant antibodies. Eur J Nucl Med Mol Imaging 35:1878–1886
26. 68Ga]gallium-labelled PSMA ligand for the diagnosis of prostate cancer: biodistribution in humans and first evaluation of tumour lesions. Eur J Nucl Med Mol Imaging 40:486–495
27. Rajasekaran AK, Anilkumar G, Christiansen JJ (2005) Is prostate-specific membrane antigen a multifunctional protein? Am J Physiol Cell Physiol 288:975–981
28. −. Biochem Biophys Res Commun 155:1194–1200
29. Delgado R, Sun Y, Motekaitis RJ, Martel AE (1993) Stabilities of divalent and trivalent metal ion complexes of macrocyclic triazatriacetic acids. Inorg Chem 32:3320–3326
30. Kodama K, Kimura E (1995) Complexation reactions of aluminum ions with polyamino polycarboxylic macrocycles in an aqueous solution. Bull Chem Soc Jpn 68:852–857