title: Poly(ester amide)s based on (L)-lactic acid oligomers and α-amino acids: influence of the α-amino acid side chain in the poly(ester amide)s properties.
abstract: Novel biodegradable and low cytotoxic poly(ester amide)s (PEAs) based on α-amino acids and (L)-lactic acid (L-LA) oligomers were successfully synthesized by interfacial polymerization. The chemical structure of the new polymers was confirmed by spectroscopic analyses. Further characterization suggests that the α-amino acid plays a critical role on the final properties of the PEA. L-phenylalanine provides PEAs with higher glass transition temperature, whereas glycine enhances the crystallinity. The hydrolytic degradation in PBS (pH = 7.4) at 37 °C also depends on the α-amino acid, being faster for glycine-based PEAs. The cytotoxic profiles using fibroblast human cells indicate that the PEAs did not elicit an acute cytotoxic effect. The strategy presented in this work opens the possibility of synthesizing biodegradable PEAs with low citotoxicity by an easy and fast method. It is worth to mention also that the properties of these materials can be fine-tuned only by changing the α-amino acid.
authors.affiliation: Department of Chemical Engineering, University of Coimbra, Polo II, Rua Sílvio Lima, Coimbra 3030-790, Portugal. anafs@eq.uc.pt
authors.forename: Ana C
authors.initials: AC
authors.lastname: Fonseca
authors.forename: Jorge F J
authors.initials: JF
authors.lastname: Coelho
authors.forename: Joana F A
authors.initials: JF
authors.lastname: Valente
authors.forename: Tiago R
authors.initials: TR
authors.lastname: Correia
authors.forename: Ilídio J
authors.initials: IJ
authors.lastname: Correia
authors.forename: Maria H
authors.initials: MH
authors.lastname: Gil
authors.forename: Pedro N
authors.initials: PN
authors.lastname: Simões
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D005347:Fibroblasts / Q000187:drug effects / Q000378:metabolism; D005998:Glycine / Q000737:chemistry; D006801:Humans; D006863:Hydrogen-Ion Concentration; D019344:Lactic Acid / Q000031:analogs & derivatives* / Q000737:chemistry*; D015394:Molecular Structure; D009757:Nylons / Q000737:chemistry* / Q000633:toxicity; D010649:Phenylalanine / Q000737:chemistry; D011091:Polyesters / Q000737:chemistry* / Q000633:toxicity; D058105:Polymerization; D013696:Temperature
chemical_list: D000596:Amino Acids; D009757:Nylons; D011091:Polyesters; D019344:Lactic Acid; D010649:Phenylalanine; D005998:Glycine