Abstract
[18F]-5-fluorocytosine-arabinoside (2) and [18F]-5-fluorocyclocytidine (4) were prepared by reaction of [18F]-acetylhypofluorite with cytosine-arabinoside (1) or cyclocytidine (3) in acetic acid and were isolated in an overall radiochemical yield of 20% and 9%, respectively. The biodistribution of both radiopharmaceuticals was determined in melanoma bearing Syrian golden hamsters. It was found that 2 is a good tumour-localizing agent for pigmented and non-pigmented Greene melanoma.
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Chou T-C, Hutchison DJ, Schmid FA, Phillips FS (1975) Metabolism and selective effect of 1-β-d-arabinofuranosylcytosine in L1210 and host tissues in vivo. Cancer Res 35:225–236
Creasy WA (1975) Arabinosylcytosine. In: Sartorelli AC, Johns DG (eds) Antineoplastic and immunosuppressive agents Handbook of experimental pharmacology, vol 38, part 2. Springer, New York, pp 232–256
Franken NAP, van Langevelde A, Journée-de Korver JG, Bakker CNM, Feitsma RIJ, van Delft JL, Oosterhuis JA, Pauwels EKJ (1985) Uptake of 123I-5-iodo-2-thiouracil, a possible radiopharmaceutical for noninvasive detection of ocular melanoma, in melanotic and amelanotic melanomas in hamsters. Nucl Med Comm 6:657–663
Frei E, Bickers J, Hewllet J, Lane M, Leary W, Tally R (1969) Dose schedule and antitumour studies of arabinosylcytosine. Cancer Res 29:1325–1332
Ho DHW, Rodriguez V, Loo TL (1975) Clinical pharmacology of O2-2′-cyclocytidine. Clin Pharmacol Ther 17:66–70
Kessel D, Hall TC, Wodinsky I (1967) Transport and phosphorylation as factors in the anticancer action of cytosine arabinoside. Science (Washington, DC) 156:1240–1241
Kreis W, Watanabe KA, Fox JJ (1978) Structural requirements for the enzymatic deamination of cytosine nucleosides. Helv Chim Acta 61:1011–1016
Pallavicini MG (1984) Cytosine arabinoside: molecular, pharmacokinetic and cytokinetic considerations. Pharmacol Ther 25:207–238
Pinedo HM (1979) Cancer chemotherapy. Exerpta Medica, Amsterdam Oxford [and references cited therein]
Robins MJ, MacGoss M, Naik SR, Ramani G (1976) Nucleic acid related compounds 21. Direct fluorination of uracil and cytosine bases and nucleosides using trifluoromethyl hypofluorite. Mechanism, stereochemistry and synthetic applications. J Am Chem Soc 98:7381–7390
Rustum YM (1975) Metabilism and intracellular retention of 1-β-d-arabinofuranosylcytosine as predictors of response of animal tumours. Cancer Res 38:543–549
Rustum YM, Preisler HD (1979) Correlation between leukemic cell retention of 1-β-d-arabinofuranosylcytosine 5′-triphosphate and response to therapy. Cancer Res 39:42–49
Talley RW, Vaitkevicius VK (1963) Megaloblastosis produced by cytosine antagonist, 1-β-d-arabinofuranosylcytosine. Blood 21:352
Turner JH, Maziere M, Comar D (1985) Localization of 11C-radio-pharmaceuticals in the Greene melanoma of hamsters. Eur J Nucl Med 10:392–397
Visser GWM, Boele S, Knops GHJN, Herscheid JDM, Hoekstra A (1985) Synthesis and biodistribution of [18F]-5-fluorocytosine. Nucl Med Commun 6:455–459
Wodinsky I, Kensler CJ (1965) Activity of cytosine arabinoside (NSC-63878) in a spectrum of rodent tumours. Cancer Chemother Rep 47:65–68
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Visser, G.W.M., Zwaagstra, O., Gorree, G.C.M. et al. Synthesis and tumour-localizing properties of [18F]-5-fluorocytosine-arabinoside and [18F]-5-fluorocyclocytidine. Eur J Nucl Med 12, 137–140 (1986). https://doi.org/10.1007/BF00276706
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DOI: https://doi.org/10.1007/BF00276706