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Journal of Bioactive and Compatible Polymers
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Synthesis and Degradation Characteristics of Polyurethanes Containing AZO Derivatives of 5-Amino Salicylic Acid

Soodabeh Davaran

Drug Applied Research Centre, Tabriz University of Medical Sciences, Tabriz, Iran davaran{at}tbzmed.ac.ir

Mohammad R. Rashidi

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

Jalal Hanaee

Abbas Khani

Faculty of Pharmacy, Tabriz University of Medical Sciences, Tabriz, Iran

Mehrdad Mahkam

Faculty of Science, Azarbaijan Tarbyat Moallem University

Mahdi Hashemi

Hakim Kashef Co., R&D Dept., 22 Masjed Jameh, Motahari Ave., Tabriz, Iran mhashemi{at}dr.com

New types of biodegradable and pH sensitive polyurethanes containing azo derivatives of 5-aminosalicylic acid (5-ASA) were synthesized by condensation of hexamethylene diisocyanate (HDI) with 4, 4-dihydroxy azobenzene-3, 3-dicarboxylic acid (AZO I) or 4, 4-dihydroxy 3-formyl azobenzene-3-carboxylic acid (AZO II). They contained both hydrolysable urethane bonds and enzymatically degradable azo-aromatic links. Degradation of polyurethanes (PU-AZO I and PU-AZO II) in phosphate buffer solutions was pH dependant. In basic conditions AZO I or AZO II was rapidly released over 48h. Incubation of PU-AZO I and PU-AZO II with rat cecal contents at 37°C gradually released 5-ASA, and the amount of drug released was 85% and 78% in 48h respectively. These polyurethane derivatives are being investigated for colon-specific drug delivery systems for treating inflammatory bowel disease based on the pH-dependant degradation of the polymer.

Key Words: 5-ASA • AZO • polyurethane • inflammatory bowel disease • colon-specific drug delivery • prodrug • degradation

Journal of Bioactive and Compatible Polymers, Vol. 21, No. 4, 315-326 (2006)
DOI: 10.1177/0883911506066933
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