Studies on the biodegradation and biocompatibility of a new poly(ester amide) derived fromL-alanine

Abstract

ABSTRACT:A new poly(ester amide) derived from L-alanine has been synthesized and characterized. The polymer has good fiber-and film-forming properties, as well as other characteristics like thermal stability and solubility in chloroform, which enhance its processing facilities. Degradation studies show that both pH and temperature influence in the hydrolisis rate that takes mainly place through the ester linkages. Degradation was also studied by using different enzymes. Results indicated that papain was the most efficient of these, and that the hydrolysis to water-soluble products could be attained in a few days. Basal cytotoxicity was assayed using a mouse L929 fibroblast permanent cell line. The MTT viability test was performed with liquid extract of the material (50 days, 37ЊC). An attachment and proliferation screening study with intact material was also carried out. No cytotoxic responses were detected, in either assay, after a 24-and 48-h incubation period with the cells. After 72 h a slight cytotoxicity was detected in the polymer material, while a more significant one was detected in the material extract.

Degradable Poly(ester amide)s for Biomedical Applications

“…Typically poly(ester amide)s containing -amino acid units can be, in this case, prepared by reaction of a diacid chloride with a diester-diamine obtained by previous condensation of a diol with two -amino acid units [27][28][29][30]. Since the diester-diamine is unstable as free base and tends to produce undesirable side reactions, the monomer is prepared as a stable salt of di-p-toluenesulfonic acid ( Figure 4).…”

Advances in synthetic optically active condensation polymers - A review

“…Degradable polymers may still be obtained when oxaloyl or terephthaloyl units were incorporated. In another study by Paredes et al [200], a new kind of PEA derived from Lalanine was synthesized and the biodegradation and biocompatibility of the resulted polymer were investigated by them. The obtained polymer had good fiber and film-forming properties, as well as other characteristics like thermal stability and solubility in chloroform, which enhanced its processing facilities.…”

Concept and Synthesis of Poly(ester amide)s with One Isolated, Two or Three Consecutive Amide Bonds Randomly Distributed Along the Polyester Backbone

“…Other types of preformed monomers were condensed with activated esters in solution [37,[42][43][44][45][46][47][48] or with dicarboxylic acid dichlorides or activated esters by interfacial polymerisation [49][50][51][52][53][54][55][56][57]. Polymerization of diamide-diesters with diols yields alternating PEAs which have a higher degree of crystallinity than the corresponding random PEAs [58][59][60].…”

“…The incorporation of amino acids makes the polymer biocompatible. Preformed monomers can be synthesized by condensing amino acids such as alanine or glycine with diols to form diester-diamine salts which are then reacted with dicarboxylic acids or their dichlorides to form alternating PEAs [41,43,47,48,[51][52][53][54][55][61][62][63]. α,ω-Amino-alcohols-based alternating PEAs can also be obtained by condensing dicarboxylic acids with linear aliphatic amino alcohols with varying numbers of methylene groups [41,64].…”