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Automated synthesis of symmetric integrin αvβ3-targeted radiotracer [18F]FP-PEG3-β-Glu-RGD2

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Abstract

A automated synthesis of symmetric integrin αvβ3-targeted radiotracer [18F]FP-PEG3-β-Glu-RGD2 was carried out by multi-step procedure on the modified PET-MF-2V-IT-I synthesizer. Firstly, the prosthetic group of 4-nitrophenyl 2-[18F]fluoropropionate ([18F]NFP) was automated synthesized by a convenient three-step, one-pot procedure. Secondly, [18F]FP-PEG3-β-Glu-RGD2 was synthesized by coupling [18F]NFP with the symmetric RGD-peptide (PEG3-β-Glu-RGD2) and purified by a solid-phase extraction cartridge. The radiochemical yields of [18F]NFP were 35 ± 5 % (n = 10, decay-corrected) based on [18F]fluoride in 80 min. [18F]FP-PEG3-β-Glu-RGD2 was obtained with yield 40 ± 10 % (n = 5, decay-corrected) from [18F]NFP within 20 min. The radiochemical purity of [18F]FP-PEG3-β-Glu-RGD2 was greater than 98 %.

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References

  1. Stupack DG, Cheresh DA (2004) Integrins and angiogenesis. Curr Top Dev Biol 64:207–238

    CAS  Google Scholar 

  2. Haubner R, Decristoforo C (2009) Radiolabelled RGD peptides and peptidomimetics for tumour targeting. Front Biosci 14:872–886

    Article  CAS  Google Scholar 

  3. Liu S (2006) Radiolabeled multimeric cyclic RGD peptides as integrin αvβ3 targeted radiotracers for tumor imaging. Mol Pharm 3:472–487

    Article  CAS  Google Scholar 

  4. Chin FT, Shen B, Liu S, Berganos RA, Chang E, Mittra E, Chen X, Gambhir SS (2012) First experience with clinical-grade [18F]FPP(RGD)2: an automated multi-step radiosynthesis for clinical PET studies. Mol Imaging Biol 14:88–95

    Article  Google Scholar 

  5. Hu K, Wang H, Tang G (2012) Progress of the methods for [18F]labeled peptides. J Isot 25:243–252

    Google Scholar 

  6. Tang G, Zen W, Yu M, Kabalka G (2008) Facile synthesis of N-succinimidyl 4-[18F]fluorobenzoate ([18F]SFB) for protein labeling. J Label Compd Radiopharm 51:68–71

    Article  CAS  Google Scholar 

  7. Tang G, Tang X, Wang X (2010) A facile automated synthesis of N-succinimidyl 4-[18F]fluorobenzoate ([18F]SFB) for [18F]labeled cell-penetrating peptide as PET tracer. J Label Compd Radiopharm 53:543–547

    Article  CAS  Google Scholar 

  8. Wester HJ, Schottelius M, Scheidhauer K, Meisetschläger G, Herz M, Rau FC, Reubi JC, Schwaiger M (2003) PET imaging of somatostatin receptors: design, synthesis and preclinical evaluation of a novel 18F-labelled, carbohydrated analogue of octreotide. Eur J Nucl Med Mol Imaging 30:117–122

    Article  CAS  Google Scholar 

  9. Haubner R, Kuhnast B, Mang C, Weber WA, Kessler H, Wester HJ, Schwaiger M (2004) [18F]Galacto-RGD: synthesis, radiolabeling, metabolic stability, and radiation dose estimates. Bioconjug Chem 15:61–69

    Article  CAS  Google Scholar 

  10. Liu S, Liu H, Ren G, Kimura RH, Cochran JC, Cheng Z (2011) PET imaging of integrin positive tumors using [18F]labeled Knottin peptides. Theranostics 1:403–412

    Article  CAS  Google Scholar 

  11. Lang L, Li W, Guo N, Ma Y, Zhu L, Kiesewetter DO, Shen B, Niu G, Chen X (2011) Comparison study of [18F]FAl-NOTA-PRGD2, [18F]FPPRGD2, and [68Ga]Ga-NOTA-PRGD2 for PET imaging of U87MG tumors in mice. Bioconjugate Chem 22:2415–2422

    Article  CAS  Google Scholar 

  12. Yang M, Gao H, Zhou Y, Ma Y, Quan Q, Lang L, Chen K, Niu G, Yan Y, Chen X (2011) [18F]Labeled GRPR agonists and antagonists: a comparative study in prostate cancer imaging. Theranostics 1:220–229

    Article  CAS  Google Scholar 

  13. Liu S, Liu Z, Chen K, Yan Y, Watzlowik P, Wester HJ, Chin FT, Chen X (2010) [18F]Labeled Galacto and PEGylated RGD dimers for PET imaging of αvβ3 integrin expression. Mol Imaging Biol 12:530–538

    Article  Google Scholar 

  14. Guhlke S, Coenen HH, Stocklin G (1994) Fluoroacylation agents based on small n.c.a. [18F]fluorocarboxylic acids. Appl Radiat Isot 45:715–727

    Article  CAS  Google Scholar 

  15. Lemaire C, Damhaut P, Lauricella B, Mosdzianowski C, Morelle JL, Monclus M, Naemen JV, Mulleneers E, Aerts J, Plenevaux A, Brihaye C, Luxen A (2002) Fast [18F]FDG synthesis by alkaline hydrolysis on a low polarity solid phase support. J Label Compd Radiopharm 45:435–447

    Article  CAS  Google Scholar 

  16. Wang H, Hu K, Tang G, Huang T, Liang X (2012) Simple and efficient automated radiosynthesis of 2-[18F]fluoropropionic acid using solid-phase extraction cartridges purification. J Label Compd Radiopharm 55:366–370

    Article  Google Scholar 

Download references

Acknowledgments

We thank Zhaobao Ye and Kening Wu for assistance with this work. This work was partly supported by the National High Technology Research and Development Program of China (863 Program, No. 2008AA02Z430), the National Natural Science Foundation (No. 30970856, No. 81371584, No. 81101076), the International Atomic Energy Agency (IAEA) Research Contract (No. 15245), the Science Technology Foundation of Guangdong Province (No. 2010B031600054), and Sun Yat-Sen University (No. 80000-3126132).

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Correspondence to Ganghua Tang.

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Hu, KZ., Wang, H., Tang, G. et al. Automated synthesis of symmetric integrin αvβ3-targeted radiotracer [18F]FP-PEG3-β-Glu-RGD2 . J Radioanal Nucl Chem 299, 271–276 (2014). https://doi.org/10.1007/s10967-013-2736-z

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  • DOI: https://doi.org/10.1007/s10967-013-2736-z

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