CU1+Assisted Nucleophilic Exchange Radiohalogenation: Application and Mechanistic Approach

  • J. Mertens
  • M. Gysemans
Chapter

Abstract

During the last ten years the development of radiopharmaceuticals for SPECT was a continuous struggle between radioiodinated compounds and 99mTc labeled radiopharmaceuticals. If 99mTc labeled compounds won as far as pure “routine radiopharmaceuticals” for blood flow, kidneys and heart were concerned, the development of 123I labeled receptor and metabolic tracers gained more interest. The major part of the radioiodinated pharmaceuticals belong to the iodoarylcompounds.

Keywords

High Performance Liquid Chromatography Isotopic Exchange High Specific Activity Halogen Bond Aryl Halide 
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References

  1. 1.
    L. Carlsen, K. Andresen, I-131-Labelled N-Isopropyl-p-Iodoamphetamine, Eur. J. Nucl. Med., 7: 280–281 (1982).PubMedCrossRefGoogle Scholar
  2. 2.
    L. Hawkins, A. Elliott, R. Shields et al, A Rapid Quantitative Method for the Preparation of 1–123-lodohippuric Acid, Eur. J. Nucl. Med., 7: 58–61 (1982).PubMedCrossRefGoogle Scholar
  3. 3.
    P. Wanek, Notes on the Radioiodination of Hippuric Acid, Radiochem. Radioanal. Lett.; 46: 401–404 (1981).Google Scholar
  4. 4.
    G.H. Hinkle, G.P. Basmadjan, A.S. Kirschener et al, Kit Preparation of Radioiodinated lodohippuran, J. Pharm. Sciences, 70: 312–316 (1981).CrossRefGoogle Scholar
  5. 5.
    S. Mills, Rapid Synthesis of I-123-Labelled Iodinated Contrast Media by Kittype Labeling Procedure, Int. J. Appl. Radiat. Isot., 33: 467–468 (1982).PubMedCrossRefGoogle Scholar
  6. 6.
    P. Angelberger, M. Wagner-Loffler, E. Hruby et al, Radiochemical and Analytical Aspects in Optimized Preparation of I-123-N-Isopropyl-p-Iodoamphetamine, J. Lab. Comp. Radiopharm., 21: 1110–1112 (1984).Google Scholar
  7. 7.
    T. Horne, L. Hawkins, M. CarolI et al, m-I-123-Benzylguanidine, Synthesis and Imaging the Adrenal and Pheochromocytoma. Presented at the European Nuclear Medicine Congress, Helsinki (1984).Google Scholar
  8. 8.
    D. Fortman, P. Robbins, V. Sodd, A Study on the Labeling of o-lodohippuric Acid with 1–123, Int. J. Appl. Radiat. Isot., 29: 449–451 (1978).PubMedCrossRefGoogle Scholar
  9. 9.
    D. Kuhl, J. Barrio, S. Huang et al, Quantifying Local Cerebral Blood Flow by NIsopropyl-p-I-123-Amphetamine Tomography, J. Nucl. Med., 23: 196–203 (1982).PubMedGoogle Scholar
  10. 10.
    M. Eisenhut, B. Kimmig, B. Bubeck et al, Labelling of I-131-Metaiodobenzylguanidine with High Specific Activity for Radiotherapeutic Purposes, J. Lab. Comp. Radiopharm., 21: 1130–1132 (1984).Google Scholar
  11. 11.
    D. Wieland, J. Wu, L. Brown et al, Radiolabelled Adrenergic Neuron Blocking Agents: Adrenomedullary Imaging with 1–141-lodobenzylguanidine, J. Nucl. Med., 21: 349–353 (1980).PubMedGoogle Scholar
  12. 12.
    S. M. Moerlein, D-R. Hwang, M.J. Welch,No-Carrier-Added Radiobromination via Cuprous Chloride-Assisted Nucleophilic Aromatic Bromodeiodination, Int. J. Appl. Radiat. Isot., 39: 369–372 (1988).CrossRefGoogle Scholar
  13. 13.
    J. Mertens, W. Vanryckeghem, L. Carlsen, 1986, Cu(I) Supported Isotopic Exchange of Arylbound Iodide, New Future for Fast High Yield Labeling, in: Progress in Radiopharmacy, 101–109, P.H. Cox et al, ed., M. Nijhoff, pubi., Dordrecht, The Netherlands.Google Scholar
  14. 14.
    J. Mertens, M. Gysemans, C. Piron et al, High Yield Preparation of Pure 2Radioiodo-Ketanserin of High Specific Activity, A Serotonin S2 Receptor Tracer for SPECT, J. Lab. Comp. Radiopharm., 28: 732–738 (1990).CrossRefGoogle Scholar
  15. 15.
    J. Mertens, W. Vanryckeghem, M. Gysemans et al, New Fast Preparation of I-123 Labeled Radiopharmaceuticals, Eur. J. Nucl. Med., 13: 380–381 (1987)PubMedGoogle Scholar
  16. 16.
    J. Mertens, W. Vanryckeghem, 1985, Fast Quantitative Labelling of N-Isopropylp-Iodoamphetamine with I-123 in Presence of Cu(I) and Ascorbic Acid, Allowing Kit-Form Preparation, in: Radiopharmaceuticals and Labelled Compounds, 303–310, IAEA, ed., Vienna.Google Scholar
  17. 17.
    W. Vanryckeghem, J. Mertens, Fast Quality Control of I-123-Labelled Radiopharmaceuticals by means of Small Size Columns, Proceedings 2nd European Symposium on Radiopharmacy and Radiopharmaceuticals, Cambridge (1985).Google Scholar
  18. 18.
    W. Vanryckeghem, J. Mertens, Determination of the Quality of I-123 and 1–131 Solution by means of Ion-Pair Radiochromatography, J. Lab. Comp. Radiopharm., 27: 137–139 (1989).CrossRefGoogle Scholar
  19. 19.
    J. Mertens, M. Gysemans, W. Vanryckeghem et al, New high Yield Cu(I) Assisted Nucleophilic Radiobromination, J. Lab. Comp. Radiopharm., 23: 12731275 (1986).Google Scholar
  20. 20.
    J. Mertens, A. Callaerts, W. Vanryckeghem, New Realistic Approach of the Kinetics in Fast Labeling Procedures, J. Lab. Comp. Radiopharm., 24: 607–612 (1986).CrossRefGoogle Scholar
  21. 21.
    V. Stanko, N. Iroshinikova, A. Volkov et al, Int. J. Appl. Radiat. Isot., 35: 11291132 (1984).Google Scholar
  22. 22.
    M. Tarie, R. Padovan, S. Spaventi, Radioiodination of Iodinated Estradiol-17Diphosphates, J. Lab. Comp. Radiopharm., 20: 7–21 (1978).Google Scholar
  23. 23.
    T. Cohen, J. Wood, A. G. Dietz, Organocopper Intermediates in the Exchange Reaction of Aryl Halides with Salts of Copper(I), Tetrahedron Lett., 40: 35553558 (1974).Google Scholar
  24. 24.
    J. Lindley, Copper Assisted Nucleophilic Substitution of Aryl Halogen, Tetrahedron, 40: 1433–1456 (1984).CrossRefGoogle Scholar
  25. 25.
    B. Liedholm, Copper(I) Catalyzed Replacement of Iodine by Chloride Ion in Halonitrobenzenes, Acta Chem. Scand., 25: 113–117 (1971).CrossRefGoogle Scholar
  26. 26.
    B. Liedholm, Copper(I) Catalyzed Replacement of Iodine by Chloride Ion in Halonitrobenzenes. Part II, Acta Chem. Scand., 30: 141–149 (1979).Google Scholar

Copyright information

© Springer Science+Business Media New York 1991

Authors and Affiliations

  • J. Mertens
    • 1
  • M. Gysemans
    • 1
  1. 1.VUB-CyclotronVrije Universiteit BrusselBelgium

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