Synthesis and Physiological Genetic Effects of 1-(Methacryloyloxyethyl)- 5-Fluorouracil and Its Polymers

Abstract

The monomer 1-(methacryloyloxyethyl)-5-fluorouracil (MAO EFU) was synthesized from 2,4-bis(trimethylsilyloxy)-5-fluoropyrimidine. Poly- (MAOEFU) and poly(MAOEFU-co-methyl methacrylate) were obtained by radical polymerization at 60°C. The monomer reactivity ratios, r ₁ and r ₂ were determined by the Kelen-Tüdös method; r, (MAOEFU) = 0.77 and r ₂(MMA) = 1.13. The physiological genetic effect of MAOEFU and its polymers in Dro sophila melanogaster was investigated and found that MAOEFU, poly- (MAOEFU) and poly(MAOEFU-co-MMA) are considerably less effective than 5- fluorouracil.

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References

Pato, J. , M. Azori , K. Ulbrich and J. Kopecek. 1984. Makromol. Chem., 185:231.

Ouchi, T. , Y. Sakamoto , S. Jokei and H. Chikashita. 1984. Makromol. Chem., 185:255.

Matsuzaki, K. , I. Yamamoto , T. Sato and R. Oshima. 1984. Makromol. Chem., 186:49.

Hung, R.Y. , J. Kopecek , J.D. Andrade. 1987. Makromol. Chem., 190:69.

Breslow, D.S. 1976. Pure Appl. Chem., 46:103.

Bounous, G. , R. Pageau and D. Regoli. 1978. J. Chem. Pharmacol. Biopharm., 16:51.

Bosch, L. , E. Harbers and C. Heidelberger . 1958. Cancer Rev., 18:335.

Umrigar, P.P. , S. Ohashi and G.B. Butler. 1979. J. Polym. Sci., Polym. Chem. Ed., 17:351.

Gebelein, C.G. and R.M. Morgan. 1977. Polymer Preprints , 18(1):811.

10.

Akashi, M. , K. Beppu , I. Kikuchi and N. Miyauchi. 1986. J. Macromol. Sci.-Chem., A23:1233.

11.

Akashi, M. , Y. Tanaka , T. Miyazaki and N. Miyauchi. 1987. J. Bioactive and Compat. Polym., 2:120.

12.

Levine, L. and N.M. Schwartz. 1973. Laboratory Exercises in Genetics. St. Louis: C. V. Mosby Co., p. 3.

13.

Lewis, E.B. and F. Bacher. 1968. Drosophila Inform. Ser., 43:193.

14.

Demerec, M. and B.P. Kaufmann. 1967. Drosophila Guide , 8th Ed., Washington, D.C.: Carnegie Inst. of Washington, p. 10.

15.

Inoue, Y. and T.K. Watanabe. 1978. Japan J. Genetics, 53(3):183.

16.

Duschinsky, R. and T.F. Gabriel. U.S. Pat., No. 3,354,160, 1967 .

17.

Sankaranarayan, K. and F.H. Sobels. 1976. Radiation Genetics . New York: Academic Press , p. 1089.