Synthesis and biological activities of polymers containing exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic glycinyl imide

✍ Scribed by Dong-Yeol Lee; Jin-Gon Jeong; Neung-Ju Lee; Ho-Sung Kang; Chang-Sik Ha; Won-Jei Cho

• Publisher: John Wiley and Sons
• Year: 1996
• Tongue: English
• Weight: 513 KB
• Volume: 62
• Category: Article
• ISSN: 0021-8995
• DOI: 10.1002/(sici)1097-4628(19961017)62:3<557::aid-app13>3.0.co;2-w

✦ Synopsis

SYNOPSIS

The monomer, exo-3,6-epoxy-l,2,3,6-tetrahydrophthalic glycinyl imide(ETGI), was prepared by the Diels-Alder reaction of N-glycinylmaleimide and furan. Poly(ETGI), poly(ETG1co-methacrylic acid) [poly(ETGI-co-MA)] and poly(ETG1-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(ETG1-co-MA), and poly(ETG1-co-VAc) were characterized by IR and 'H-NMR spectroscopies, elemental analysis, and gel permeation chromatography. T h e in vitro cytotoxicities of ETGI, poly(ETGI), poly(ETG1-co-MA), and poly(ETG1-co-VAc) were evaluated using K-562 human leukemia cells and HeLa cells. I n vitro cytotoxicity of monomer and polymers a t a concentration of 1.0 mg/mL against K-562 human leukemia cells increased in the following order: poly(ETG1co-MA) > poly(ETG1-co-VAc) > poly(ETG1) > ETGI. The cytotoxicities of copolymers against HeLa cells are less cytotoxic than ETGI a t a dosage of 0.02, 1.0, and 5.0 mg/mL.

T h e copolymers were very eff'ective a t any dosage tested. The in vivo antitumor activities of ETGI, poly(ETGI), poly(ETG1-co-MA), and poly(ETG1-co-VAc) were also evaluated against mice bearing sarcoma 180. I n vivo antitumor activity of monomer and polymers a t a dosage of 80 mg/kg increased in the following order: ETGI > poly(ETG1-co-VAc) > poly(ETG1-co-MA) > poly(ETG1) > 5-fluorouracil(5-FU). ETGI and polymers containing ETGI showed higher antitumor activity than 5-FU a t any dosage tested.