Pharmacologically active polymers, 11. Polymeric sulfonamides as potential antibacterials and carriers for antitumor agents

A number of acryl and methacryl derivatives of different sulfanilamides ( 1a—I ) were prepared and polymerized. The fixation of the sulfonamide to the polymerizable group was carried out directly, using the acryl- and methacrylamides, and by means of spacer groups, to favour the enzymatic or hydrolytic release of the drug moiety. Selected sulfonamide types of different pK_A values were used, and the pH-dependant solubility of the corresponding polymers was studied. The monomeric acryloyl and methacryloyl sulfonamides were homopolymerized radically by AIBN. For distribution studies polysulfadiazineacrylamide, ¹⁴C-labelled in the main chain ( 2e' ), was synthesized. Copolymerization with 2-methylsulfinylethyl methacrylate ( 5a ) yielded water soluble polymers of lower toxicity. Eventually biodegradable polymers containing sulfonamide units in the backbone were obtained by anionic polymerization of acryloyl and methacryloyl sulfanilamide. The new monomers and polymers were characterized by elemental analysis, IR- and NMR-spectroscopy, pyrolysis mass spectrometry, and hydrolytic degradation.