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Journal of Bioactive and Compatible Polymers
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Linear Type Azo-Containing Polyurethanes for Colon-Specific Drug Delivery

M. Mahkam

Faculty of Science, Chemistry Department, Azarbaijan University of Tarbiat Moallem, Tabriz, Iranmmahkam{at}yahoo.com

M. G. Assadi

R. Zahedifar

M. Ramesh

Faculty of Science, Chemistry Department, Azarbaijan University of Tarbiat Moallem, Tabriz, Iran

S. Davaran

Drug Applied Research Center, Tabriz University of Medical Sciences, Tabriz, Iran

New biodegradable polyurethanes containing azo-linked polymeric prodrugs of 5-aminosalicylic acid (5-ASA) in the main chain were prepared by reacting 1,6-Hexamethylenediisocyanate (HDI) with 3,30-azobis(6-hydroxy benzoic acid) (ABHB) and 5-[4-(hydroxyl phenyl) azo] salicylic acid (HPAS) as azo derivatives of 5-ASA. The polymers were characterized by FTIR and 1H-NMR spectroscopy. The hydrolysis of polyurethane containing azoderivatives of 5-ASA was carried out in cellophane membrane dialysis bags containing aqueous buffer solution (pH 1/4 8.5 and pH 1/4 1) at 37 C. Detection of the hydrolysis product by UV spectroscopy showed that ABHB and HPAS were released by the hydrolysis of the urethane bond in the polymer chain.

Key Words: biodegradable • polymeric prodrug • 5-aminosalicylic acid • hydrolysis • pH sensitive

Journal of Bioactive and Compatible Polymers, Vol. 19, No. 1, 45-53 (2004)
DOI: 10.1177/0883911504041602
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