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Poly(anhydrides)

Catalog number Type Package size Price, USD
19661-100 poly(SA) 10 g 1,200.00
19661-101 poly(SA-CPP) [80:20] 5 g 1,500.00

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Product Details

Handling

Handle with normal care, but minimize exposure to moisture to avoid degradation.

Storage

Protect against moisture. Store at -20°C.

Molecular Weight

5-30 kDa (size exclusion chromatography, polystyrene standards)

Description

Polyanhydrides are a class of polymers first synthesized and reported by Bucher and Slade in 1909. Around 20 years later, Hill and Carothers synthesized polyanhydrides for textile applications, but found these materials unsuitable due to their hydrolytic instability. The polyanhydride research was renewed in the 1950s and 1960s by Conix and Yoda, who synthesized more than a hundred new polymers. However, it was not until 1980 when Langer proposed the use of polyanhydrides as biodegradable carriers for drugs that polyanhydrides had their breakthrough and have seen extensive research since then.

Polyanhydrides have a backbone with hydrolytically labile anhydride linkages, and the rate of hydrolytic degradation can be controlled by modifying the polymer composition. The degradation products are non-toxic diacid monomers, which can be eliminated from the body as metabolites.

Materials prepared from hydrophobic diacids degrade through surface erosion, as water is only able to hydrolyze anhydride bonds at the polymer-water interface but cannot enter into the bulk due to hydrophobicity of the polymer. The layer-by-layer erosion is an attractive feature for controlled drug delivery applications, allowing a constant release of payload over a period of time.

The most well-studied polyanhydrides are probably those based on sebacic acid (SA) and 1,3-bis(p-carboxyphenoxy)propane (CPP). The structures of SA and CPP are shown below.

Copolymer materials prepared from SA and CPP have relatively low melting points (around 60-240°C, depending on copolymer composition) and are soluble in common organic solvents such as dichloromethane and chloroform. These properties allows for dispersion of drugs into the polymer matrix by various techniques such as solvent casting and compression or melt molding processes. The degradation rates of these materials range from approximately 10 days for a SA homopolymer to around 3 years for a CPP homopolymer.

The most recognized example and FDA-approved drug delivery system based on polyanhydrides is the GLIADEL® Wafer for the treatment of glioblastoma, which is a type of brain tumor. The implant consists of a polyanhydride copolymer of sebacic acid (SA) and 1,3-bis(p-carboxyphenoxy)propane (CPP), and an anticancer agent, carmustine.

Product Literature

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