title: Synthesis and Characterization of Poly(glyceric Acid Carbonate): A Degradable Analogue of Poly(acrylic Acid).
abstract: The synthesis and characterization of a degradable version of poly(acrylic acid), poly(glyceric acid carbonate), are reported. Specifically, atactic and isotactic poly(benzyl glycidate carbonate)s are obtained via the ring-opening copolymerization of rac-/(R)-benzyl glycidate with CO2 using a bifunctional rac-/(S,S)-cobalt salen catalyst in high carbonate linkage selectivity (>99%) and polymer/cyclic carbonate selectivity (∼90%). Atactic poly(benzyl glycidate carbonate) is an amorphous material with a T(g) (glass transition temperature) of 44 °C, while its isotactic counterpart synthesized from enantiopure epoxide and catalyst is semicrystalline with a T(m) (melting temperature) = 87 °C. Hydrogenolysis of the resultant polymers affords the poly(glyceric acid carbonate). Poly(glyceric acid carbonate) exhibits an improved cell cytotoxicity profile compared to poly(acrylic acid). Poly(glyceric acid carbonate)s also degrade remarkably fast (t(1/2) ≈ 2 weeks) compared to poly(acrylic acid). Cross-linked hydrogels prepared from poly(glyceric acid carbonate) and poly(ethylene glycol) diaziridine show significant degradation in pH 8.4 aqueous buffer solution compared to similarly prepared hydrogels from poly(acrylic acid) and poly(ethylene glycol) diaziridine.
authors.affiliation: Departments of Chemistry and Biomedical Engineering, Boston University , Boston, Massachusetts 02215, United States.
authors.forename: Heng
authors.initials: H
authors.lastname: Zhang
authors.affiliation: Departments of Chemistry and Biomedical Engineering, Boston University , Boston, Massachusetts 02215, United States.
authors.forename: Xinrong
authors.initials: X
authors.lastname: Lin
authors.affiliation: Departments of Chemistry and Biomedical Engineering, Boston University , Boston, Massachusetts 02215, United States.
authors.forename: Stacy
authors.initials: S
authors.lastname: Chin
authors.affiliation: Departments of Chemistry and Biomedical Engineering, Boston University , Boston, Massachusetts 02215, United States.
authors.forename: Mark W
authors.initials: MW
authors.lastname: Grinstaff
mesh_terms: D000179:Acrylates / Q000737:chemistry*; D017209:Apoptosis / Q000187:drug effects; D002254:Carbonates / Q000138:chemical synthesis / Q000737:chemistry*; D002478:Cells, Cultured; D005347:Fibroblasts / Q000187:drug effects; D005988:Glyceric Acids / Q000737:chemistry*; D006801:Humans; D020100:Hydrogels / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011108:Polymers / Q000737:chemistry* / Q000494:pharmacology
chemical_list: D000179:Acrylates; D002254:Carbonates; D005988:Glyceric Acids; D020100:Hydrogels; D011108:Polymers; C042971:glyceric acid; C036658:acrylic acid