Synthesis and characterization of novel biodegradable polymeric prodrugs containing 5‐fluorouracil and 4‐amino‐N‐(2‐pyrimidinyl) benzene sulfonamide terminal groups

To develop novel biodegradable polymeric prodrugs with target-directing and drug-active functional groups, a series of polymeric antitumor prodrugs containing sulfadiazine and 5-fluorouracil terminal groups were prepared via the two-step reaction of chlorinated poly(lactic acid) or chlorinated poly(lactic acid-co-glycolic acid) with potassium sulfadiazine (SF-K) and 1,3-dihydroxymethyl-5-fluorouracil. The synthesized polymers were characterized by means of infrared spectroscopy, proton nuclear magnetic resonance spectroscopy, gel permeation chromatography, viscosity measurements, differential scanning calorimetry, and ultraviolet (UV) spectroscopy. The GA/LA value was varied, so that the effects of the comonomer content on the solubility, thermal properties, and degradable behaviors were examined respectively. It was found that introducing the GA units could increase the melting temperature (Tm), the hydrolytic degradation, and the hydrophilicity, while it decreased the glass transition temperature (Tg). The drug content of 5-FU measured by UV spectra is 56.3 in maximum. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci, 2007