Amino alcohol-based degradable poly(ester amide) elastomers

Abstract

Currently available synthetic biodegradable elastomers are primarily composed of crosslinked aliphatic polyesters, which suffer from deficiencies including (1) high crosslink densities, which results in exceedingly high stiffness, (2) rapid degradation upon implantation, or (3) limited chemical moieties for chemical modification. Herein, we have developed poly(1,3-diamino-2-hydroxypropane-co-polyol sebacate)s, a new class of synthetic, biodegradable elastomeric poly(ester amide)s composed of crosslinked networks based on an amino alcohol. These crosslinked networks feature tensile Young's modulus on the order of 1MPa and reversable elongations up to 92%. These polymers exhibit in vitro and in vivo biocompatibility. These polymers have projected degradation half-lives up to 20 months in vivo.

Degradable Poly(ester amide)s for Biomedical Applications

“…Functionalized PEAs can be obtained by ring opening polymerization of morpholine-2,5-diones derived from -amino acids like L-aspartic acid, L-glutamic acid, L-lysine, L-serine (or L-tyrosine) and L-cysteine (Figure 8), which provide pendant carboxylic acid, amine, hydroxyl and thiol groups, respectively [38][39][40][41][42][43]. The synthesis of the six-membered ring required a previous protection of functional groups, which should be stable under the polymerization conditions [8].…”

“…New biodegradable elastomeric PEAs have also been synthesized for tissue engineering applications [102]. These new materials allow overcoming some limitations of conventional crosslinked aliphatic polyesters: (a) High crosslink densities, which result in exceedingly high stiffness; (b) rapid degradation upon implantation; or (c) limited chemical moieties for chemical modification.…”

Erratum: In vivo and in vitro tracking of erosion in biodegradable materials using non-invasive fluorescence imaging

“…Collagen in vivo erosion was used to infer physiologic in vitro conditions that mimic erosive in vivo environments. This approach enables rapid in vitro screening of materials, and can be extended to simultaneously determine drug release and material erosion from a drug-eluting scaffold, or cell viability and material fate in tissue-engineering formulations.Users may view, print, copy, download and text and data-mine the content in such documents, for the purposes of academic research, subject always to the full Conditions of use: http://www.nature.com/authors/editorial_policies/license.html#terms 3,10,11,12,13 . Chromatography tracks molecular weight changes 2,12 but cannot be applied to eliminable materials that do not undergo chain scission.…”

“…Users may view, print, copy, download and text and data-mine the content in such documents, for the purposes of academic research, subject always to the full Conditions of use: http://www.nature.com/authors/editorial_policies/license.html#terms 3,10,11,12,13 . Chromatography tracks molecular weight changes 2,12 but cannot be applied to eliminable materials that do not undergo chain scission.…”

“…Gravimetric determinations from periodic sampling of explant weight cannot follow the same formulation over time, necessitate large number of animals to follow small number of samples and have excessive variability. 3,10,11,12,13 . Chromatography tracks molecular weight changes 2,12 but cannot be applied to eliminable materials that do not undergo chain scission.…”