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Synthesis and labelling of Df-DUPA-Pep with gallium-68 and zirconium-89 as new PSMA ligands

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Abstract

Prostate-specific membrane antigen (PSMA) is a cell surface protein that is overexpressed in prostate cancer. Due to the specificity of expression of PSMA, numerous urea-based ligands have been synthesized until now. In the current study, we describe the coupling of the chelator desferrioxamine to DUPA-Pep and the subsequent labelling with Ga-68 and Zr-89 as new PSMA ligands. The labelling step is performed at room temperature and pH 7.5. In both radiosyntheses, the RCYs were higher than 95 % within 10 min, making dispensable any further purification and providing the radiotracers directly applicable for further utilization.

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References

  1. David A, Silver DA, Pellicer I, Fair WR, Heston WDW, Cordon-Cardo C (1997) Prostate-specific membrane antigen expression in normal and malignant human tissues. Clin Cancer Res 3(1):81–85

    Google Scholar 

  2. Dangshe MA, Hopf CE, Malewicz AD, Donovan GP, Senter PD, Goeckeler WF, Maddon PJ, Olson WC (2006) Potent antitumor activity of an auristatin-conjugated, fully human monoclonal antibody to prostate-specific membrane antigen. Clin Cancer Res 12(8):2591–2596

    Article  Google Scholar 

  3. Olson WC, Heston WDW, Rajasekaran AK (2007) Clinical trials of cancer therapies targeting prostate-specific membrane antigen. Rev Recent Clin Trial 2(3):182–190

    Article  CAS  Google Scholar 

  4. Hao G, Zhou J, Guo Y, Long MA, Anthony T, Stanfield J, Hsieh J-T, Sun X (2011) A cell permeable peptide analog as a potential-specific PET imaging probe for prostate cancer detection. Amino Acids 41:1093–1101

    Article  CAS  Google Scholar 

  5. Foss CA, Mease RC, Fan H, Wang Y, Ravert HT, Dannals RF, Olszewski RT, Heston WD, Kozikowski AP, Pomper MG (2005) Radiolabeled small-molecule ligands for prostate-specific membrane antigen: in vivo imaging in experimental models of prostate cancer. Clin Cancer Res 11:4022–4028

    Article  CAS  Google Scholar 

  6. 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(3):780–789

    Article  CAS  Google Scholar 

  7. Kularatne SA, Venkatesh C, Santhapuram H-KR, Wang K, Vaitilingam B, Henne WA, Low PS (2010) Synthesis and biological analysis of prostate-specific membrane antigen-targeted anticancer prodrugs. J Med Chem 53(21):7767–7777

    Article  CAS  Google Scholar 

  8. Chen Y, Pullambhatla M, Foss CA, Byun Y, Nimmagadda S, Senthamizhchelvan S, Sgouros G, Mease RC, Pomper MG (2011) 2-(3-{1-Carboxy-5-[(6-[18F]fluoro-pyridine-3-carbonyl)-amino]-pentyl}-ureido)-pentanedioic acid, [18F]DCFPyL, a PSMA-based PET imaging agent for prostate cancer. Clin Cancer Res 17:7645–7653

    Article  CAS  Google Scholar 

  9. Malik N, Machulla H-J, Solbach C, Winter G, Reske SN, Zlatopolskiy B (2011) Radiosynthesis of a new PSMA targeting ligand ([18F]FPy-DUPA-Pep). Appl Radiat Isot 69(7):1014–1018

    Article  CAS  Google Scholar 

  10. Malik N, Zlatopolskiy B, Machulla H-J, Reske SN, Solbach C (2012) One pot radiofluorination of a new potential PSMA ligand [Al18F]NOTA-DUPA-Pep. J Label Compd Radiopharm 55:320–325

    Article  CAS  Google Scholar 

  11. Al-Momani E, Malik N, Machulla H-J, Reske SN, Solbach C (2013) Radiosynthesis of [18F]FEt-Tyr-urea-Glu ([18F]FEtTUG) as a new PSMA ligand. J Radioanal Nucl Chem 295(3):2289–2294

    Article  CAS  Google Scholar 

  12. Wängler C, Wängler B, Lehner S, Elsner A, Todica A, Bartenstein P, Hacker M, Schirrmacher R (2011) A universally applicable 68Ga-labeling technique for proteins. J Nucl Med 52:586–591

    Article  Google Scholar 

  13. Perk LR, Vosjan MJ, Visser GW, Budde M, Jurek P, van Kiefer GE, Dongen GA (2010) p-Isothiocyanatobenzyl-desferrioxamine: a new bifunctional chelate for facile radiolabeling of monoclonal antibodies with zirconium-89 for immuno-PET imaging. Eur J Nucl Med Mol Imaging 37:250–259

    Article  CAS  Google Scholar 

  14. Ramogida CF, Orvig C (2013) Tumour targeting with radiometals for diagnosis and therapy. Chem Commun 49:4720–4739

    Article  CAS  Google Scholar 

  15. Brechbiel MW (2008) Bifunctional chelates for metal nuclides. Q J Nucl Med Mol Imaging 52(2):166–173

    CAS  Google Scholar 

  16. Wadas TJ, Wong EH, Weisman GR, Anderson CJ (2010) Coordinating radiometals of copper, gallium, indium, yttrium and zirconium for PET and SPECT imaging of disease. Chem Rev 110(5):2858–2902

    Article  CAS  Google Scholar 

  17. Solbach C, Bertram J, Scheel W, Baur B, Machulla H-J, Reske SN (2013) Production of Zr-89 on a PETtrace cyclotron. J Nucl Med 54(Suppl 2):1098

    Google Scholar 

  18. Holland JP, Phil D, Sheh Y, Lewis JS (2009) Standardized methods for the production of high specific-activity zirconium-89. Nucl Med Biol 36(7):729–739

    Article  CAS  Google Scholar 

  19. Meyer GJ, Mäcke H, Schuhmacher J, Knapp WH, Hofmann M (2004) 68Ga-labelled DOTA-derivatised peptide ligands. Eur J Nucl Med Mol Imaging 31:1097–1104

    Article  CAS  Google Scholar 

  20. Jackson GE, Byrne MJ (1996) Metal ion speciation in blood plasma: gallium-67-citrate and MRJ contrast agents. J Nucl Med 37:379–386

    CAS  Google Scholar 

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Acknowledgments

The project was supported by funding of the German Ministry of Economy and Technology (ZIM, Zentrales Innovationsprogramm Mittelstand) with a research grant. In addition we like gratefully to acknowledge the funding of the University of Milano-Bicocca (Milan, Italy) through a PhD fellowship in Biomedical Technology.

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Authors and Affiliations

  1. Clinic for Nuclear Medicine, University of Ulm, Albert-Einstein Allee 23, 89081, Ulm, Germany

    Benjamin Baur, Elena Andreolli, Ehab Al-Momani, Noeen Malik, Hans-Jürgen Machulla, Sven N. Reske & Christoph Solbach

  2. Department of Health Sciences, University of Milano-Bicocca, Milan, Italy

    Elena Andreolli

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  1. Benjamin Baur
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  2. Elena Andreolli
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  3. Ehab Al-Momani
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  4. Noeen Malik
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  5. Hans-Jürgen Machulla
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  6. Sven N. Reske
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  7. Christoph Solbach
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Corresponding author

Correspondence to Hans-Jürgen Machulla.

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Benjamin Baur and Elena Andreolli contributed equally to this work.

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Baur, B., Andreolli, E., Al-Momani, E. et al. Synthesis and labelling of Df-DUPA-Pep with gallium-68 and zirconium-89 as new PSMA ligands. J Radioanal Nucl Chem 299, 1715–1721 (2014). https://doi.org/10.1007/s10967-013-2876-1

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  • DOI: https://doi.org/10.1007/s10967-013-2876-1

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