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A facile direct nucleophilic synthesis of O-(2-[18F]fluoroethyl)-l-tyrosine ([18F]FET) without HPLC purification

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Abstract

Due to favourable in vivo characteristics, its high specificity and the longer half-life of 18F (109.8 min) allowing for remote-site delivery, O-(2-[18F]fluoroethyl)-l-tyrosine ([18F]FET) has gained increased importance for molecular imaging of cerebral tumors. Consequently, the development of simple and efficient production strategies for [18F]FET could be an important step to further improve the cost-effective availability of [18F]FET in the clinical environment. In the present study [18F]FET was synthesized via direct nucleophilic synthesis using an earlier developed chiral precursor, the NiII complex of an alkylated (S)-tyrosine Schiff base, Ni-(S)-BPB-(S)-Tyr-OCH2CH2OTs. The purification method has been developed via solid phase extraction thereby omitting cumbersome HPLC purification. The suggested SPE purification using combination of reverse phase and strong cation exchange cartridges provided [18F]FET in high chemical, radiochemical and enantiomeric purity and 35 % radiochemical yield (decay-corrected, 45 min synthesis time). The method was successfully automated using a commercially available synthesis module, Scintomics Hotboxone. Based on the current results, the proposed production route appears to be well suited for transfer into an automated cassette-type radiosynthesizers without using HPLC.

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Acknowledgments

This work was performed within the CRP program of the International Atomic Energy Agency (IAEA), contract No. 15436.

Conflict of interest

We wish to thank Scintomics GmbH, Germany, for the support of this study. The authors declare that they have no conflict of interest.

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Authors and Affiliations

  1. N.P. Bechtereva Institute of the Human Brain of the Russian Academy of Science (IHB RAS), 9, Pavlova str., 197376, Saint-Petersburg, Russian Federation

    Olga Fedorova, Olga Kuznetsova, Maria Stepanova & Raisa Krasikova

  2. A.N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Science (INEOS RAS), B-334, Vavilova str. 28, 119991, Moscow, Russian Federation

    Victor Maleev & Yuri Belokon

  3. Pharmaceutical Radiochemistry, Technische Universität München, Garching, Germany

    Hans-Juergen Wester

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

    Raisa Krasikova

Authors
  1. Olga Fedorova
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  2. Olga Kuznetsova
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  3. Maria Stepanova
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  4. Victor Maleev
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  5. Yuri Belokon
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  6. Hans-Juergen Wester
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  7. Raisa Krasikova
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Correspondence to Raisa Krasikova.

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Fedorova, O., Kuznetsova, O., Stepanova, M. et al. A facile direct nucleophilic synthesis of O-(2-[18F]fluoroethyl)-l-tyrosine ([18F]FET) without HPLC purification. J Radioanal Nucl Chem 301, 505–512 (2014). https://doi.org/10.1007/s10967-014-3121-2

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  • DOI: https://doi.org/10.1007/s10967-014-3121-2

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