NDLI: Comparison of the Synthesis and Bioerodible Properties of N-Linked Versus O-Linked Amino Acid Substituted Polyphosphazenes

Content Provider	Springer Nature Link
Author	Morozowich, Nicole L. Mondschein, Ryan J. Allcock, Harry R.
Copyright Year	2013
Abstract	Phosphazene polymers with N-linked and O-linked amino acid side groups are of biomedical interest, especially for their ability to bioerode under physiological conditions. Polyphosphazenes containing serine and threonine substituents, which contain two different functional sites for attachment to a polyphosphazene backbone (N- and O-terminus), were synthesized using an improved technique, and their hydrolysis behavior was investigated. In aqueous media the solid polymers yield hydrolysis products phosphate, ammonia, the amino acid, and ethanol and have the potential to be used in several different biomedical applications ultimately determined by their hydrolysis behavior. A hydrolysis study in deionized water revealed that all the polymers are hydrolytically sensitive, regardless of the type of linkage to the polyphosphazene backbone, although the hydrolysis rates may be different. Polymers with amino acid ester side groups linked through the N-terminus underwent solid phase hydrolysis between 16 and 60 % within a 6-week period. This is the fastest reported solid state hydrolysis of any amino acid ester substituted polyphosphazene. The mechanism of hydrolysis is by bulk erosion as monitored by environmental scanning electron microscopy. Polymers with the amino acid units linked through the O-terminus are soluble in water; thus their solid state erosion profile in aqueous media could not be determined. However, $^{31}$P NMR spectroscopy confirmed their hydrolytic sensitivity in aqueous solution and the formation of phosphorus-containing oligomeric species, the concentrations of which increased during the 6-week hydrolysis period. Complete hydrolysis did not occur within 6 weeks. The O-linked species are possible starting points for bioerodible hydrogel formation.
Starting Page	164
Ending Page	172
Page Count	9
File Format	PDF
ISSN	15741443
Journal	Journal of Inorganic and Organometallic Polymers and Materials
Volume Number	24
Issue Number	1
e-ISSN	15741451
Language	English
Publisher	Springer US
Publisher Date	2013-11-07
Publisher Place	Boston
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Phosphazenes Polyphosphazenes Bioerodible Amino acid esters Inorganic Chemistry Organic Chemistry Polymer Sciences
Content Type	Text
Resource Type	Article
Subject	Materials Chemistry Polymers and Plastics

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