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Synthesis and biological activities of polymers containing exo ‐3,6‐epoxy‐1,2,3,6‐tetrahydrophthalic glycinyl imide
Author(s) -
Lee DongYeol,
Jeong JinGon,
Lee NeungJu,
Kang HoSung,
Ha ChangSik,
Cho WonJei
Publication year - 1996
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(19961017)62:3<557::aid-app13>3.0.co;2-w
Subject(s) - polymer chemistry , monomer , hela , gel permeation chromatography , copolymer , polymer , nuclear chemistry , imide , chemistry , materials science , in vitro , organic chemistry , biochemistry
The monomer, exo ‐3,6‐epoxy‐1,2,3,6‐tetrahydrophthalic glycinyl imide(ETGI), was prepared by the Diels‐Alder reaction of N ‐glycinylmaleimide and furan. Poly(ETGI), poly(ETGI‐ co ‐methacrylic acid)[poly(ETGI‐ co ‐MA)] and poly(ETGI‐ co ‐vinylacetate)[poly(ETGI‐ co ‐VAc)] were synthesized by photoinitiated homopolymerization of ETGI or copolymerizations of ETGI with MA and VAc. Synthesized ETGI, poly(ETGI), poly(ETGI‐ co ‐MA), and poly(ETGI‐ co ‐VAc) were characterized by IR and 1 H‐NMR spectroscopies, elemental analysis, and gel permeation chromatography. The in vitro cytotoxicities of ETGI, poly(ETGI), poly(ETGI‐ co ‐MA), and poly(ETGI‐ co ‐VAc) were evaluated using K‐562 human leukemia cells and HeLa cells. In vitro cytotoxicity of monomer and polymers at a concentration of 1.0 mg/mL against K‐562 human leukemia cells increased in the following order:poly(ETGI‐ co ‐MA) > poly(ETGI‐ co ‐VAc) > poly(ETGI) > Etgi. The cytotoxicities of copolymers against HeLa cells are less cytotoxic than ETGI at a dosage of 0.02, 1.0, and 5.0 mg/mL. The copolymers were very effective at any dosage tested. The in vivo antitumor activities of ETGI, poly(ETGI), poly(ETGI‐ co ‐MA), and poly(ETGI‐ co ‐VAc) were also evaluated against mice bearing sarcoma 180. In vivo antitumor activity of monomer and polymers at a dosage of 80 mg/kg increased in the following order: ETGI > poly(ETGI‐ co ‐VAc) > poly(ETGI‐ co ‐MA) > poly(ETGI) > 5‐fluorouracil (5‐FU).ETGI and polymers containing ETGI showed higher antitumor activity than 5‐FU at any dosage tested. © 1996 John Wiley & Sons, Inc.