SYNTHESIS OF COPOLYMERS FROM 3,5-DIOXO-4,10-DIOXATRICYCLO-[5.2.0(2,6)]DEC-8-ENE AND VINYL MONOMERS BY PHOTOPOLYMERIZATION AND THEIR BIOLOGICAL-ACTIVITIES

Photocopolymerizations of 3,5-dioxo-4,10-dioxatricyclo [5.2.0(2,6)]dec -8-ene (DDTD) with methacrylic acid (MA) acrylamide (AAm) and vinyl py rrolidone (VP) were carried out in 2-butanone using dimethoxy benzoin (DMB) as an initiator at 25 degrees C. The structures of the polymers obtained from photopolymerizations of corresponding monomer pairs were confirmed to be poly(DDTD-co-MA), poly(DDTD-co-AAm) and poly(DDTD-co- VP) by H-1 NMR and C-13 NMR spectroscopies, and the average molecular weights were determined by gel permeation chromatography (GPC). The we ight average molecular weights ((M) over bar(w)) of the polymers were in the range 9500-17300. The polymers were soluble in water, dimethyl sulphoxide (DMSO) and dimethyl formamide (DMF). The contents of DDTD u nits in the copolymers were 19, 37 and 45%. The in vitro cytotoxicitie s of the polymers were evaluated using mouse mammary carcinoma (FM-3A) , mouse leukaemia (P-388) and human histiocytic lymphoma (U-937) cell lines. The in vivo antitumour activities of the polymers were estimate d by the survival time of sarcoma 180 tumour-bearing mice. The in vivo antitumour activities of the polymers were greater than those of 5-fl uorouracil (5-FU) and monomeric DDTD at a dose of 0.8 mg kg(-1). Poly( DDTD-co-AAm) and poly(DDTD-co-VP) showed higher antitumour activity th an 5-FU and monomeric DDTD at all doses tested. (C) 1998 SCI.