Tumor uptake of radiolabelled pyrimidine bases and pyrimidine nucleosides in animal models--VIII. Synthesis and tissue distribution of N-[2-(hydroxyethoxy) methyl]-5-[3H]methyluracil.
The tritium-labelled acyclonucleoside, N-[2-(hydroxyethoxy)methyl]-5-[3H]methyluracil (3H-3), was synthesized for evaluation as a tumor diagnostic agent. 5-[3H]-Methyluracil, 3H-1, was converted to the 2,4-bis-trimethylsilyl intermediate which was coupled with 2-acetoxyethoxymethyl bromide to afford 1-[(2-acetoxyethoxy)methyl-5-[3H]methyluracil (3H-2). Treatment of 3H-2 with sodium methoxide in methanol afforded 3H-3 (specific activity 188 MBq mmol-1. The tissue distribution of 3H-3 was examined in male BDF1 mice bearing Lewis Lung (LL) carcinomas. Long bone exhibited the highest tumor: tissue ratios. The kidney contained the highest radioactivity level relative to the tumor. This suggested a major urinary route of excretion. The major radioactive blood component (89.21%) was found to have a biological half-life of 0.19 min. The title compound is unsuitable for use as a diagnostic agent for LL carcinoma because of low tumor uptake and rapid urinary elimination of injected radioactivity from the body.
D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D006207:Half-Life; D008297:Male; D051379:Mice; D008815:Mice, Inbred Strains; D009374:Neoplasms, Experimental / Q000000981:diagnostic imaging / Q000378:metabolism*; D011877:Radionuclide Imaging; D014018:Tissue Distribution; D014498:Uracil / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism
D014498:Uracil; C046151:N-(2-(hydroxyethoxy)methyl)-5-methyluracil