Polymeric drug based on sulfanilamide: synthesis, antimicrobial and drug releasing studies

• Published in: Journal of pharmacy and pharmacology 2007-09, Vol.59 (9), p.1207-1213
• Main Authors: Reddy, C. Umamaheswara, Amalraj, A., Reddy, B. S. R., Arun, A.
• Format: Article
• Language: English
• Subjects: Acrylates - chemistry; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - pharmacology; Bacteria - drug effects; Benzoyl Peroxide - chemistry; Butanones - chemistry; Delayed-Action Preparations; Drug Carriers - chemistry; Escherichia coli; Gram-Positive Bacteria - drug effects; Hydrogen-Ion Concentration; Klebsiella; Magnetic Resonance Spectroscopy; Microbial Sensitivity Tests; Polymers - chemistry; Pseudomonas aeruginosa; Salmonella typhi; Solvents - chemistry; Spectrophotometry, Infrared; Spectrophotometry, Ultraviolet; Staphylococcus aureus; Sulfanilamides; Temperature
• ISSN: 0022-3573; 2042-7158
• DOI: 10.1211/jpp.59.9.0004

ABSTRACT N‐((4‐amino sulfonyl)phenyl)acrylamide (APA) was synthesized using sulfanilamide and acryloyl chloride in the presence of triethyl amine at 0–5°C. Homo‐ and co‐polymerization of 2‐hydroxyethyl acrylate (HEA) and acrylic acid (AA) were done by adopting a solution polymerization technique using methyl ethyl ketone (MEK) as a solvent and benzoyl peroxide (BPO) as a free radical initiator at 70+1°C. All the monomers and polymers were characterized by IR and NMR techniques. These monomers and polymers were tested for their antimicrobial activity against five different ATCC strain microorganisms (Escherichia coli (25922), Pseudomonas aeruginosa (27853), Klebsiella (70063), Salmonella typhi (6539) and Staphylococcus aureus (25923)). The effect of co‐monomer, other than the active drug moiety present in the polymeric drug, is discussed. The antimicrobial activity of APA on Gram‐positive bacteria was enhanced when copolymerized with AA and HEA. The polymer was made into a film form and that film was used for drug releasing study. The drug releasing rate was monitored by the absorption at 268 nm using a UV spectrophotometer. The effect of pH and the temperature on the drug releasing rate was monitored and found that the releasing rate was dependent on the co‐monomer, pH and temperature of the medium.