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Synthesis and biological activity of medium molecular weight polymers containing 3,6‐ endo ‐methylene‐1,2,3,6‐tetrahydrophthalimidobutanoyl‐5‐fluorouracil
Author(s) -
Lee NeungJu,
Kim KwangHyuk,
Rhew HyunYul,
Choi WonMoon,
Chung IlDoo,
Cho WonJei
Publication year - 2000
Publication title -
polymer international
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.592
H-Index - 105
eISSN - 1097-0126
pISSN - 0959-8103
DOI - 10.1002/1097-0126(200012)49:12<1702::aid-pi599>3.0.co;2-z
Subject(s) - methylene , fluorouracil , methylene blue , polymer , chemistry , polymer chemistry , materials science , organic chemistry , biology , genetics , catalysis , cancer , photocatalysis
Abstract A new monomer, 3,6‐ endo ‐methylene‐1,2,3,6‐tetrahydrophthalimidobutanoyl‐5‐fluorouracil (ETBFU), was synthesized by reaction of 3,6‐ endo ‐methylene‐1,2,3,6‐tetrahydrophthalimidobutanoyl chloride and 5‐fluorouracil. The homopolymer of ETBFU and its copolymers with acrylic acid (AA) or vinyl acetate (VAc) were prepared by photopolymerization using 2,2‐dimethoxy‐2‐phenylacetophenone as an initiator at 25 °C. The synthesized ETBFU and its polymers were identified by FTIR, 1 H NMR and 13 C NMR spectroscopies. The ETBFU content in poly(ETBFU‐ co ‐AA) and poly(ETBFU‐ co ‐VAc) was 43 and 14 mol%, respectively. The apparent number‐average molecular weight ( M n ) of the polymers determined by GPC ranged from 8400 to 11 300. The in vitro cytotoxicity of the samples against mouse mammary carcinoma (FM3A), mouse leukaemia (P388), and human histiocytic lymphoma (U937) cancer cell lines decreased in the order 5‐FU ≥ ETBFU > poly(ETBFU) > poly(ETBFU‐ co ‐AA) > poly(ETBFU‐ co ‐VAc). The in vivo antitumour activity of the polymers against Balb/C mice bearing sarcoma 180 tumour cells was greater than that of 5‐fluorouracil at all doses tested. © 2000 Society of Chemical Industry