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Poly(Butanediol Spermate): A Hydrolytically Labile Polyester-Based Nitric Oxide Carrier

Departments of Chemistry and Biomedical Engineering, The University of Akron, Akron, Ohio 44325-3601

Daniel J. Smith

Departments of Chemistry and Biomedical Engineering, The University of Akron, Akron, Ohio 44325-3601

A polyester composed of spermic acid and 1,4-butanediol was synthesized via a Michael-type reaction, using 1,4-diaminobutane and 1,4-butanediol diacrylate. A linear polymer, poly(butanediol spermate), with Mw of 3,000 and a molecular weight distribution of 1.95, was insoluble in organic solvents, but slowly dissolved in water. After dissolving in water poly(butanediol spermate) hydrolyzed to produce spermic acid and 1,4-butanediol. The rate of hydrolysis was pH-dependent. At 20°C in buffers of pH 9.7, 7.4, and 4.8, 50% decomposition occurred in 2.5, 1.5, and 3.5 hours, respectively. Secondary amines in the polymer were chemically modified (34-45%) with nitric oxide to form 1-substituted diazen-1-ium-1,2-diolates which spontaneously released nitric oxide in neutral or acidic aqueous solutions. The poly(butanediol spermate) diazeniumdiolate, in pH 7.4 buffer at 37°C, slowly dissolved and hydrolyzed with a 50% hydrolysis in 190 hours. Nitric oxide release from the polymer was delayed for approximately 100 hours then given a first order release of nitric oxide with a half-life of 110 hours. In contrast, at pH 5.0 and 37°C, the poly(butanediol spermate) diazeniumdiolate slowly dissolved but immediately released nitric oxide with a half-life of 180 hours, and 50% hydrolysis time for polymer of 520 hours. Poly(butanediol spermate) diazeniumdiolate is potentially useful for site-specific nitric oxide delivery with subsequent hydrolysis of polymer to natural products when used in mildly acidic to neutral conditions.

Journal of Bioactive and Compatible Polymers, Vol. 14, No. 1, 54-63 (1999)
DOI: 10.1177/088391159901400106


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