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Synthesis and biological activities of endo‐3,6‐epoxy‐1,2,3,6‐tetrahydrophthalimide and its polymers
Author(s) -
Kim GiCheol,
Jeong JinGon,
Lee NeungJu,
Ha ChangSik,
Cho WonJei
Publication year - 1997
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/(sici)1097-4628(19970627)64:13<2605::aid-app14>3.0.co;2-y
Subject(s) - polymer chemistry , gel permeation chromatography , monomer , polymer , chemistry , nuclear chemistry , solvent , vinyl acetate , acetone , acrylic acid , copolymer , organic chemistry
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‐2‐phenylacetophenone as an initiator at 25°C. Synthesized ETPI, poly(ETPI), poly(ETPI‐co‐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 n ) in the range of 3500‐27,400. The in vitro cytotoxicities of poly(ETPI), poly(ETPI‐co‐AA), poly(ETPI‐co‐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. © 1997 John Wiley & Sons, Inc. J Appl Polym Sci 64: 2605–2612, 1997