Synthesis and biological activity of medium range molecular weight polymers containing exo-3,6-epoxy-1 2,3,6-tetrahydrophthalimidocaproic acid

A new monomer, exo-3,6-epoxy-1,2,3,6-tetrahydrophthalimidocaproic acid (ETC A), was prepared by reaction of maleimidocaproic acid and furan. The homopo lymer of ETCA and its copolymers with acrylic acid (AA) or with vinyl aceta te (VAc) were obtained by photopolymerizations using 2,2-dimethoxy-2-phenyl acetophenone as an initiator at 25 degreesC. The synthesized ETCA and its p olymers were identified by FTIR, H-1 NMR and C-13 NMR spectroscopies. The a pparent average molecular weights and polydispersity indices determined by gel permeation chromatography (GPC) were as follows: M-n =9600 g mol(-1), M -w=9800 g mol(-1), M-w/M-n = 1.1 for poly(ETCA); M-w = 14300gmol(-1)', M-w= 16200 gmol(-1) M-w/M-n= 1.2 for poly(ETCA-co-AA); M-n = 17900 gmol(-1), M- w = 18300 g mol(-1), M-w/M-n = 1.1 for poly(ETCA-co-VAc). The in vitro cyto toxicity of the synthesized compounds against mouse mammary carcinoma and h uman histiocytic lymphoma cancer cell lines decreased in the following orde r: 5-fluorouracil (5-FU) greater than or equal to ETCA > polymers. The in v ivo antitumour activity of the polymers against Balb/C mice bearing sarcoma 180 tumour cells was greater than that of 5-FU at all doses tested. (C) 20 01 Society of Chemical Industry.