Syntheses and antitumor activities of medium molecular weight polymers containing ?-ethoxy-exo-3,6-epoxy-1,2,3,6-tetrahydrophthaloyl-5-fluorouracil

A series of novel copolymers, poly(methacryloyl-2-oxy-1,2,3-propanetricarboxylic acid-co-exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic acid) [poly(MTCA-co-ETAc)], poly(methacryloyl-2-oxy-1,2,3-propanetricarboxylic acid-cohydrogenethyl-exo-3,6-epoxy-1,2,3,6-tetrahydrophthalate) [poly(MTCA-co-HEET)], and poly(methacryloyl-2-oxy-1,2,3-propanetricarboxylic acid-co-␣-ethoxy-exo-3,6-epoxy-1,2,3,6-tetrahydrophthaloyl-5-fluorouracil) [poly(MTCA-co-EETFU)], were prepared from corresponding monomers by photopolymerizations at 25°C for 48 h. The polymers were identified by FTIR, 1 H-NMR, and 13 C-NMR spectroscopies. The number-average molecular weights of the fractionated polymers determined by GPC were in the range from 9400 to 14,900 and polydispersity indices were 1.2-1.4. The in vitro IC 50 values of polymers against mouse mammary carcinoma (FM3A), mouse leukemia (P388), and human histiocytic lymphoma (U937) as cancer cell lines and mouse liver cells (AC2F) as a normal cell line were much higher compared to that of 5-fluorouracil (5-FU). The in vivo antitumor activities of monomers and polymers against mice bearing sarcoma 180 tumor cell line were better than those of 5-FU. The inhibition of DNA replication and antiangiogenesis activities of MTCA and copolymers were better compared to those of 5-FU.

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Synthesis, antitumour and DNA replication activities of polymers containing vinyl‐(5‐fluorouracil)‐ethanoate

Kang

Lee

Maeda

et al. 2002

Polymer International

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A new monomer, vinyl‐(5‐fluorouracil)‐ethanoate (VFUE), was synthesized by reaction of 5‐fluorouracil (5‐FU) and vinyl iodoacetate. The homopolymer of VFUE and its copolymers with acrylic acid (A, A) and maleic anhydride (MAH) were prepared by photopolymerization. The synthesized VFUE and polymers were identified by FTIR, 1H NMR and 13C NMR spectroscopies. The contents of VFUE unit in poly(VFUE‐co‐AA) and poly(VFUE‐co‐MAH) were 21 mol% and 16 mol%, respectively. The number average molecular weights of the polymers determined by gel permeation chromatography were in the range 9600–17900 g mol−1. The in vitro cytotoxicities of the samples against a normal cell line decreased as follows: 5‐FU > VFUE > poly(VFUE) > poly(VFUE‐co‐AA) > poly(VFUE‐co‐MAH). The in vivo antitumour activities of the polymers against Balb/C mice bearing the sarcoma 180 tumour cells were greater than those of 5‐FU at all concentrations. The inhibition of simian virus 40 DNA replication by the samples was much greater than that of the control.© 2002 Society of Chemical Industry

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Syntheses and antitumor activities of medium molecular weight polymers containing ?-ethoxy-exo-3,6-epoxy-1,2,3,6-tetrahydrophthaloyl-5-fluorouracil

Cited by 6 publications

References 33 publications

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Synthesis and antitumour and antiangiogenesis activity of polymers containing methacryloyl-2-oxy-1,2,3-propane tricarboxylic acid

Syntheses and biological activities of polymers containing methacryloyl‐2‐oxy‐1,2,3‐propanetricarboxylic acid or 5‐fluorouracil

Synthesis, antitumour and DNA replication activities of polymers containing vinyl‐(5‐fluorouracil)‐ethanoate

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