Abstract
Heavy radiohalogenated derivatives of methylene blue of potential value as possible diagnostic and endoradiotherapeutic agents for malignant melanoma, have been synthesized by both electrophilic and nucleophilic reaction routes. Thermal halogen isotope exchange in molten crown ether catalyst facilitated the rapid preparation of high specific activity radioiodinated and [211At]-astatinated derivatives; radiochemical yields were in the order of 60–79%. Radiohalogenation mediated by chloramine-T or via diazonium intermediary proved more laborious, far less efficient and inappropriately is only suited to the preparation of low specific activity product.
Similar content being viewed by others
References
G.W. Milton, Malignant Melanoma of the Skin and Mucous Membrane, Churchill Livingstone, Edinburgh, London and New York, 1977, p. 174.
L. Dencker, B. Larsson, K. Olander, S. Ullberg, M. Yokota,Br. J. Cancer, 39 /1979/ 449.
ChM. Boyd, W.H. Bierwaltes, V.M. Varma,J. Nucl. Med., 11 /1970/ 303.
G. Kloss, M. Leven,Europ. J. Nucl. Med., 4 /1979/ 179.
H. Bockslaff, M. Spitznas, I. Hahn, G. Kloster,Archiv. Klin. Exp. Ophthalmol., 217 /1981/ 255.
H. Bockslaff, G. Kloster, D. Dausch, K. Schad, H. Hundeshagen,Archiv. Klin. Exp. Ophthalmol., 219 /1982/ 149.
V.V. Shishkina, E.D. Chebotareva, V.N. Bobrova, V.I. Korolev, S.M. Idlis, N.P. Voskoboinik, D.S. Mechev, A.D. Shestakov, L.N. Rumiantseva, E.D. Gaponenko, V.V. Arungazyeva,Vrach. Delo., 6 /1978/ 96.
I.I. Ivanov, V.M. Vdovenko, V.N. Bobrova, I.S. Gavrilenko,Vopr. Onkol., 18 /1972/ 76.
A.M. Potts,Trans. Am. Ophthalmol. Soc., 60 /1962/ 517; A.M. Potts,Invest. Ophthalmol. Vis. Science, 3 /1964/ 400.
C.N.M. Bakker, F.M. Kaspersen,J. Lab. Comp. Radiopharm., 15 /1978/ 681.
ChM. Boyd, W.H. Beierwaltes, L.M. Lieberman, I.J. Bergstrom,J. Nucl. Med., 11 /1970/ 303.
M.H. Van Woert, S.H. Palmer,Cancer Res., 29 /1969/ 1952.
J. Panasiewicz, Z. Rybakow, M. Kaskiewicz, J. Wiza,Radiochem. Radioanal. Lett., 33 /1979/ 397.
E. Link, S. Lukiewicz,Europ. J. Nucl. Med., 7 /1982/ 469.
B. Fertil, E.P. Malaise,Int. J. Radiat. Oncol. Biol. Phys., 11 /1985/ 1689.
I. Brown, M.D. Thesis, University of Cambridge, U.K., 1986, p. 437.
I. Brown,Appl. Radiation Isotope /Part A/, 36 /1986/ 489.
I. Brown, R.N. Carpenter, J.S. Mitchell, E. Link,J. Lab. Comp. Radiopharm., /in press, 1986/.
B.-L. Liu, Y.-T. Jin, M. Maeda, M. Kojima,Radioisotopes, 30 /1981/ 391.
B.-L. Liu, Y.-T. Jin, Z.-H. Liu, C. Luo, M. Kojima, M. Maeda,Int. J. Appl. Radiation Isotopes, 36 /1985/ 561.
R. Gnehm,J. Prakt. Chemie, 76 /1907/ 401.
G.-J. Meyer, K. Rössler, G. Stöcklin,J. Lab. Comp. Radiopharm., 12 /1975/ 449.
G.N.B. DeSalas, C.E.A. Mitta, Comisión Nacional de Energia Atómica, Argentina,CNEA 371 /1974/, p. 8.
M. Argentini, Labelling with Iodine, Federal Institute for Reactor Research, Würenlingen, Switzerland, 1982, p. 152.
G.-J. Meyer, PhD Thesis, Universität Köln, Report Jülich-1418, 1977, p. 107.
S. Patai /Ed./. The Chemistry of Diazonium and Diazo Groups, Part II. J. Wiley and Sons, New York, 1978, p. 558.
I. Szele, H. Zollinger,J. Am. Chem. Soc., 100 /1978/ 2811.
Y. Hashida, R.G.M. Landells, G.E. Lewis, I. Szele, H. Zollinger,J. Am. Chem. Soc. 100 /1978/ 2816.
H. Zollinger,Acc. Chem. Res., 6 /1973/ 335.
G.W.M. Visser, E.L. Diemer,Radiochem. Radioanal. Lett., 51 /1982/ 135.
E. Link, I. Brown, R.N. Carpenter, J.S. Mitchell,Br. J. Radiol., /in press, 1986/.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Brown, I., Carpenter, R.N., Link, E. et al. Potential diagnostic and therapeutic agents for malignant melanoma: Synthesis of heavy radiohalogenated derivatives of methylene blue by electrophilic and nucleophilic methods. Journal of Radioanalytical and Nuclear Chemistry Letters 107, 337–351 (1986). https://doi.org/10.1007/BF02164199
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF02164199