| Abstract: | The new monomer α-ethoxy-3,6-endo-methylene-1,2,3,6-tetrahydrophthaloyl-5-fluorouracil (EMTFU) was synthesized from 5-fluorouracil (5-FU) and α-ethoxy-3,6-endo-methylene-1,2,3,6-tetrahydrophthaloyl chloride (EMTC). Poly(α-ethoxy-3,6-endomethylene-1,2,3,6-tetrahydrophthaloyl-5-fluorouracil) poly(EMTFU)], poly(α-ethoxy-3,6-endo-methylene-1,2,3,6-tetrahydrophthaloyl-5-fluorouracil-co-acrylic acid) poly(EMTFU-co-AA)], and poly(α-ethoxy-3,6-endomethylene-1,2,3,6-tetrahydrophthaloyl-5-fluorouracil-co-vinyl acetate) poly(EMTFU-co-VAc)] were synthesized by photopolymerizations using 2,2-dimethoxy-2-phenylacetophenone (DMP) as the photoinitiator. The synthesized EMTFU and its polymers were identified by Fourier transfer infrared (FT-IR), 1H nuclear magnetic resonance (NMR), and 13C-NMR spectroscopies. The contents of EMTFU in poly(EMTFU-co-AA) and poly(EMTFU-co-VAc) determined by elemental analysis were 46 and 70 mol %, respectively. The number average molecular weights of the synthesized polymers determined by gel permeation chromatography (GPC) were in range of 17,200–20,900. The in vitro cytotoxicities of samples were evaluated with mouse mammary carcinoma (FM3A), mouse leukemia (P388), and human histiocytic lymphoma (U937) as cancer cell lines and AC2F as a normal cell line. The cytotoxicities of 5-FU and synthesized samples against cancer cell lines increased in following orders: 5-FU ≈ EMTFU > poly(EMTFU-co-AA) > poly(EMTFU) > poly(EMTFU-co-VAc). The in vivo antitumor activities of the synthesized samples against mice bearing the sarcoma 180 tumor cell line were evaluated. The in vivo antitumor activities of EMTFU and its polymers were greater than those of 5-FU at a dosage of 80 mg/kg. © 1998 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 36: 2985–2992, 1998 |
