Syntheses and antitumor activities of monomer and medium molecular weight polymers. III. 3,6-endo-methylene-1,2,3,6-tetrahydrophthalimidopropanoyl-5-fluorouracil and its polymers

✍ Scribed by Jong-Gu Park; Chang-Sik Ha; Won-Jei Cho

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 134 KB
• Volume: 37
• Category: Article
• ISSN: 0887-624X
• DOI: 10.1002/(sici)1099-0518(19990701)37:13<2113::aid-pola26>3.0.co;2-c

✦ Synopsis

The new monomer, 3,6-endo-methylene-1,2,3,6-tetrahydrophthalimidopropanoyl-5-fluorouracil (ETPFU), was synthesized by the reaction of 5-fluorouracil (5-FU) and 3,6-endo-methylene-1,2,3,6-tetrahydrophthalimidopropanoyl chloride (ETPC). The homopolymer of ETPFU and its copolymers with acrylic acid (AA) and vinyl acetate (VAc) were prepared by photopolymerizations. The synthesized ETPFU and polymers were identified by Fourier transfer infrared (FTIR), 1 H nuclear magnetic resonance (NMR), and 13 C-NMR spectroscopies. The contents of ETPFU units in poly(ETPFU-co-AA) and poly(ETPFU-co-VAc) were 26 and 32 mol %, respectively. The number average molecular weights of the synthesized polymers determined by gel permeation chromatography (GPC) were in range from 8,800 to 10,700. The in vitro cytotoxicities of the samples were evaluated with mouse mammary carcinoma (FM3A), mouse leukemia (P388), and human histiocytic lymphoma (U937) as a cancer cell line and mouse liver cells (AC2F) as a normal cell line. The in vivo antitumor activities of polymers against Balb/c mice bearing the sarcoma 180 tumor cells were greater than those of 5-FU at all doses tested.