Synthesis and biological activities of endo-3,6-epoxy-1,2,3,6-tetrahydrophthalimide and its polymers

✍ Scribed by Gi-Cheol Kim; Jin-Gon Jeong; Neung-Ju Lee; Chang-Sik Ha; Won-Jei Cho

• Publisher: John Wiley and Sons
• Year: 1997
• Tongue: English
• Weight: 143 KB
• Volume: 64
• Category: Article
• ISSN: 0021-8995
• DOI: 10.1002/(sici)1097-4628(19970627)64:13<2605::aid-app14>3.0.co;2-y

✦ Synopsis

Photocopolymerizations of endo-3,6-epoxy-1,2,3,6-tetrahydrophthalimide (ETPI)

with acrylic acid (AA), vinyl acetate (VAc), and maleic anhydride (MAH) were carried out in a mixed solvent of 2-butanone and acetone using 2,2-dimethoxy-2phenylacetophenone as an initiator at 25ЊC. Synthesized ETPI, poly(ETPI), poly(ETPIco-AA), poly(ETPI-co-VAc), and poly(ETPI-co-MAH) were characterized by IR and 1 H-NMR spectroscopies, elemental analysis, and gel permeation chromatography. The synthesized polymers have a number-average molecular weight ( M V n ) in the range of 3500-27,400. The in vitro cytotoxicities of poly(ETPI), poly(ETPI-co-AA), poly(ETPIco-VAc), and poly(ETPI-co-MAH) against fibroblast and K-562 human leukemia cells were lower than that of monomeric ETPI at a low concentration (0.02 mg/mL). The in vivo antitumor activities of the polymers were evaluated by the survival time with sarcoma 180 tumor-bearing mice. The polymers showed higher antitumor activity and lower toxicity than both monomeric ETPI and 5-fluorouracil at all doses tested.