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An approach to the asymmetric synthesis of 18F-labeled analog of l-threo-3,4-dihydroxyphenylserine (6-l-threo-[18F]FDOPS) — a new radiotracer for visualization of norepinephrine transporters by positron emission tomography

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Abstract

An asymmetric synthesis method has been suggested as a feasible approach for the preparation of fluorine-18-labeled (T 1/2 110 min) analog of l-threo-3,4-dihydroxyphenylserine, i.e., 6-l-threo-[18F]FDOPS ((2S,3R)-2-amino-3-(2-[18F]fluoro-4,5-dihydroxyphenyl)-3-hydroxypropionic acid), a new radiotracer for the evluation of norepinephrine transporters by positron emission tomography (PET). The approach is based on the condensation reaction of 2-[18F]fluoro-4,5-bis(methoxymethoxy)benzaldehyde with a chiral nickel(II) complex and glycine (Ni-(R)-BPB-Gly) with subsequent removal of protection from hydroxy groups by acid hydrolysis. The radiochemical synthesis includes three steps and can be easily implemented into modern automated modules for the synthesis of radiopharmaceutical agents for PET.

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References

  1. K. Hamacher, H. H. Coenen, G. Stocklin, J. Nucl. Med., 1986, 27, 235.

    CAS  Google Scholar 

  2. A. F. Shields, Mol. Imag. Biol. 2006, 8, 141.

    Article  Google Scholar 

  3. S. Vallabhajosula, L. Solnes, B. Vallabhajosula, Sevenn. Nucl. Med., 2011, 41, 246.

    Article  Google Scholar 

  4. K. Nagren, C. Halldin, O. Rinne, Eur. J. Nucl. Med. Mol. Imaging, 2010, 37, 1575.

    Article  CAS  Google Scholar 

  5. D. M. Wieland, J. Wu, L. Brown, T. J. Mangner, D. P. Swanson, W. H. Beierwaltes, J. Nucl. Med., 1980, 21, 349.

    CAS  Google Scholar 

  6. A. Naranjo, M. T. Parisi, B. L. Shulkin, W. B. London, K. K. Matthay, S. G. Kreissman, G. A. Yanik, Pediatr. Blood Cancer, 2011, 56, 1041.

    Article  Google Scholar 

  7. D. M. Raffel, D. M. Wieland, Nucl. Med. Biol., 2001, 28, 541.

    Article  CAS  Google Scholar 

  8. P. K. Garg, S. Garg, M. R. Zalutsky, Nucl. Med. Biol., 1994, 21, 97.

    Article  CAS  Google Scholar 

  9. K. S. Jang, Y. W. Jung, P. S. Sherman, C. A. Quesada, G. Gu, D. M. Raffel, Bioorg. Med. Chem. Lett., 2013, 23, 1612.

    Article  CAS  Google Scholar 

  10. M. Yu, J. Bozek, M. Lamoy, M. Guaraldi, P. Silva, M. Kagan, P. Yalamanchili, D. Onthank, M. Mistry, J. Lazewatsky, M. Broekema, H. Radeke, A. Purohit, M. Cdebaca, M. Azure, R. Cesati, D. Casebier, S. P. Robinson, Circ. Cardiovasc. Imaging, 2011, 4, 435.

    Article  Google Scholar 

  11. M. Yu, J. Bozek, M. Lamoy, M. Kagan, P. Benites, D. Onthank, S. P. Robinson, Eur. J. Nucl. Med. Mol. Imaging, 2012, 39, 1910.

    Article  CAS  Google Scholar 

  12. F. C. Gaertner, T. Wiedemann, B. H. Yousefi, M. Lee, I. Repokis, T. Higuchi, S. G. Nekolla, M. Yu, S. Robinson, M. Schwaiger, N.S. Pellegata, J. Nucl. Med., 2013, 54, 1.

    Article  Google Scholar 

  13. D. S. Goldstein, Cardiovascular Drug Reviews, 2006, 24, 189.

    Article  CAS  Google Scholar 

  14. B.-H. Chen, J.-Y. Nie, M. Singh, V. W. Pike, K. L. Kirk, J. Fluorine Chem., 1995, 75, 93.

    Article  CAS  Google Scholar 

  15. R. Ashique, N. Vasdev, S. Kish, S. Houle, R. Chirakal, J. Label. Compds. Radiopharm., 2009, 52,Suppl. 1, 195.

    Google Scholar 

  16. C. B. Voltattorni, M. Bertoldi, S. Bianconi, W. Deng, K. Wong, I. Kim, B. Herbert, K. L. Kirk, Biochem. Biophys. Res. Commun., 2002, 295, 107.

    Article  Google Scholar 

  17. R. N. Krasikova, O. F. Kuznetsova, O. S. Fedorova, I. K. Mosevich, V. I. Maleev, Yu. N. Belokon’, T. F. Savel’eva, A. S. Sagiyan, S. A. Dadayan, A. A. Petrosyan, Radiochemistry, 2007, 49, 512 [Radiokhimiya, 2007, 49, 449].

    Article  CAS  Google Scholar 

  18. R. N. Krasikova, V. V. Zaitsev, S. M. Ametamey, O. F. Kuznetsova, O. S. Fedorova, I. K. Mosevich, Yu. N. Belokon, Š. Vyskočil, S. V. Shatik, M. Nader, P. A. Schubiger, Nucl. Med. Biol., 2004, 31, 597.

    Article  CAS  Google Scholar 

  19. C. Lemaire, P. Damhaut, A. Plenevaux, D. Comar, J. Nucl. Med., 1994, 35, 1996.

    CAS  Google Scholar 

  20. L. C. Libert, X. Franci, A. R. Plenevaux, T. Ooi, K. Maruoka, A. J. Luxen, C. F. Lemaire, J. Nucl. Med., 2013, 54, 1.

    Article  Google Scholar 

  21. R. Krasikova, O. Fedorova, T. Savel’eva, Y. Belokon’, V. Maleev, J. Label. Compds. Radiopharm., 2011, 54,Suppl. 1, 489.

    Google Scholar 

  22. L. Cai, S. Lu, V. W. Pike, Eur. J. Org. Chem., 2008, 2853.

    Google Scholar 

  23. R. Krasikova, Curr. Org. Chem., 2013, 17, 2097.

    Article  CAS  Google Scholar 

  24. R. N. Krasikova, O. F. Kuznetsova, O. S. Fedorova, Yu. N. Belokon, V. I. Maleev, L. Mu, S. Ametamey, P. A. Schubiger, M. Friebe, M. Berndt, N. Koglin, A. Mueller, K. Graham, L. Lehmann, L. M. Dinkelborg, J. Med. Chem., 2011, 54, 406.

    Article  CAS  Google Scholar 

  25. K. Hamacher, H. H. Coenen, Appl. Radiat. Isot., 2002, 57, 853.

    Article  CAS  Google Scholar 

  26. R. N. Krasikova, O. F. Kuznetsova, O. S. Fedorova, V. I. Maleev, T. F. Savel’eva, Yu. N. Belokon, Bioorg. Med. Chem., 2008, 16, 4994.

    Article  CAS  Google Scholar 

  27. Y.-S. Ding, C.-Y. Shiue, J. S. Fowler, A. P. Wolf, A. Plenevaux, J. Fluorine Chem., 1990, 48, 189.

    Article  CAS  Google Scholar 

  28. Y.-S. Ding, J. S. Fowler, S. J. Gatley, S. L. Dewey, A. P. Wolf, J. Med. Chem., 1991, 34, 767.

    Article  CAS  Google Scholar 

  29. B. Shen, D. Loffler, K.-P. Zeller, M. Ubele, G. Reischl, H.-J. Machulla, J. Fluorine Chem., 2007, 128, 1461.

    Article  CAS  Google Scholar 

  30. V. A. Soloshonok, D. V. Avilov, V. P. Kukhar’, V. I. Tararov, T. F. Savel’eva, T. D. Churkina, N. S. Ikonnikov, K. A. Kochetkov, S. A. Orlova, A. P. Pysarevsky, Y. T. Struchkov, N. I. Raevsky, Y. N. Belokon’, Tetrahedron: Asymmetry, 1995, 6, 1741–1756.

    Article  CAS  Google Scholar 

  31. Yu. N. Belokon, V. I. Tararov, V. I. Maleev, T. F. Savel’eva, M. G. Ryzhov, Tetrahedron Asymmetry, 1998, 9, 4249.

    Article  CAS  Google Scholar 

  32. K. M. Markovich, H. A. Tantishaiyakul, D. D. Miller, K. J. Romstedt, G. Shams, Y. Shin, P. F. Fraundorfer, K. Doyle, D. R. Feller, J. Med. Chem. 1992, 35, 466.

    Article  CAS  Google Scholar 

  33. A. Gordon, R. Ford, The Chemist’s Companion, Wiley, New York, 1972.

    Google Scholar 

  34. J. Harley-Mason, J. Chem. Soc., 1948, 1244.

    Google Scholar 

  35. K. L. Kirk, D. Cantacuzene, Y. Nimitkitpaisan, D. McCulloh, W. L. Padgett, J. W. Daly, C. R. Creveling, J. Med. Chem., 1979, 22, 1493.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. N. P. Bechtereva Institute of Human Brain, Russian Academy of Sciences, 9 ul. Akad. Pavlova, 197376, St.-Petersburg, Russian Federation

    O. S. Fedorova, V. V. Orlovskaya & R. N. Krasikova

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    V. I. Maleev, Yu. N. Belokon’ & T. F. Savel’eva

  3. Veterans General Hospital, National Yang-Ming University and National PET/Cyclotron Center, Sec. 2, 201 Shih-Pai Road, 11217, Taipei, Taiwan

    Ch. V. Chang, Ch. L. Chen & R. Sh. Liu

  4. Department of Chemistry, St.-Petersburg State University, 7-9 Universitetskaya nab., 199034, St.-Petersburg, Russian Federation

    R. N. Krasikova

Authors
  1. O. S. Fedorova
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  2. V. V. Orlovskaya
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  3. V. I. Maleev
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  4. Yu. N. Belokon’
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  5. T. F. Savel’eva
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  6. Ch. V. Chang
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  7. Ch. L. Chen
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  8. R. Sh. Liu
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  9. R. N. Krasikova
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Corresponding author

Correspondence to R. N. Krasikova.

Additional information

Based on the materials of the First Russian Conference on Medicinal Chemistry (“MedChem Russia-2013”) with International Participation (September 8–12, 2013, Moscow).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1169–1177, May, 2014.

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Fedorova, O.S., Orlovskaya, V.V., Maleev, V.I. et al. An approach to the asymmetric synthesis of 18F-labeled analog of l-threo-3,4-dihydroxyphenylserine (6-l-threo-[18F]FDOPS) — a new radiotracer for visualization of norepinephrine transporters by positron emission tomography. Russ Chem Bull 63, 1169–1177 (2014). https://doi.org/10.1007/s11172-014-0567-x

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  • DOI: https://doi.org/10.1007/s11172-014-0567-x

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