Synthesis and characterization of novel biodegradable unsaturated poly(ester amide)s

Abstract

A series of novel biodegradable unsaturated poly(ester amide)s (UPEAs) were synthesized through the solution polycondensation of two unsaturated monomers, di-p-nitrophenyl fumarate and L-phenylalanine 2-butene-1,4-diol diester p-toluene sulfonate, and four other saturated monomers in different combinations. The UPEAs were obtained in fairly good yields with N,N-dimethylacetamide (DMA) as the solvent. The number-average and weight-average molecular weights of the UPEAs, measured by gel permeation chromatography, ranged from 10 to 30 kg/mol, they had a rather narrow molecular weight distribution of 1.40. The chemical structures of the novel biodegradable UPEAs were confirmed by both IR and NMR spectra. The UPEAs had higher glass-transition temperatures than saturated PEAs of similar structures, and their glass-transition temperatures were affected more by the CAC double bond located in the diamide part than by those in the diester part. The solubility of the polymers was poor in water but better in DMA and dimethyl sulfoxide. With the availability of these inherent CAC double bonds in the UPEA backbones, these UPEAs have the functionality of CAC bonds, such as photochemical reactivity or the ability to react with or be modified by other bioactive or other environmentally sensitive compounds, and this can easily extend their applications to biomedical and pharmaceutical areas.

Biological performance of biodegradable amino acid‐based poly(ester amide)s: Endothelial cell adhesion and inflammation in vitro

“…Recently, a new generation of PEAs, that are unsaturated PEAs (UPEA) have been reported 11–13. The most unique aspect of these UPEAs is that there are >CC< double bonds built into either the diamide or the diester segments of the polymer backbones.…”

Degradable Poly(ester amide)s for Biomedical Applications

“…Chu et al studied the polymerization of the p-toluenesulfonic acid salt of L-phenylalanine butane-1,4-diester with different mixtures of di-p-nitrophenyl esters of saturated (succinic, adipic or sebacic acids) and unsaturated (fumaric acid) dicarboxilic acids [59,64]. Copolymers could be obtained with rather high M n molecular weights which varied between 14,600 and 36,900 g/mol.…”

A comparison of covalent and noncovalent strategies for paclitaxel release using poly(ester amide) graft copolymer micelles

“…Flasks were oven dried and cooled in a desiccator prior to use. Starting monomers [56][57][58] and amine terminated PEO 59 (PEO-NH 2 ) with molar masses of 5000 g mol −1 were synthesized as previously reported. Unless noted otherwise, all chemicals were purchased from commercial suppliers and used as received.…”