New biocompatible polyesters derived from α-amino acids: Hydrolytic degradation behavior

Naomi Cohen-Arazi, Abraham J. Domb, Jeoshua Katzhendler

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

New polymers were synthesized from α-hydroxy acids derived from the natural amino acids Ile, Leu, Phe, and Val, combined with lactic acid, glycolic acid and 6-hydroxyhexanoic acid by direct condensation. The toxicity was determined and the degradation process of these polyesters was investigated under physiological conditions by analyzing the composition of the degraded polymers and the oligomers cleaved in the buffer medium. The polymers were found to be non toxic to two cell lines. Polymers displayed a biphasic degradation behavior. In most cases, a linear relationship was found between the weight loss constant and the hydrophobicity of the polymers, Log P. Regarding the second stage of weight loss, it is apparent that polymers derived from α-hydroxy(L)isoleucine ((L)HOIle) and α-hydroxy(L)Valine ((L)HOVal) degraded much faster than those derived from α-hydroxy(L)leucine ((L)HOLeu) and α-hydroxy(L)phenylalanine ((L)HOPhe), probably due to different spatial orientation of the side chains. Copolymers of 6-hydroxyhexanoic acid displayed slow degradation rates as expected, whereas the degradation profile of copolymers of lactic acid was similar to the other homopolymers. These new polyesters may serve as potential biocompatible materials for medical applications.

Original languageEnglish
Pages (from-to)418-439
Number of pages22
JournalPolymers
Volume2
Issue number4
DOIs
StatePublished - Dec 2010
Externally publishedYes

Keywords

  • Degradation
  • Drug delivery
  • Polyesters
  • Toxicity
  • α-hydroxy acids

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