Synthesis and characterization of functionalized water soluble cationic poly(ester amide)s

Journal of Polymer Science Part A Polymer Chemistry (Impact Factor: 3.54). 07/2010; 48(17):3758 - 3766. DOI: 10.1002/pola.24160

ABSTRACT A new family of positively charged, water soluble and functional amino acid-based poly(ester amide)s (Arg-AG PEA) consisting of four building blocks (L-Arginine, DL-2-Allylglycine, oligoethylene glycol, and aliphatic diacid) were synthesized by the solution copolycondensation. Functional pendant carbon–carbon double bonds located in the DL-2-allylglycine unit were incorporated into these Arg-AG PEAs, and the double bond contents could be adjusted by tuning the feed ratio of L-arginine to DL-2-allylglycine monomers. Chemical structures of this new functional Arg-AG PEA family were confirmed by Fourier transform infrared spectroscopy (FTIR) and nuclear magnetic resonance (NMR) spectra. The thermal property of these polymers was investigated; increasing the methylene chain in both the amino acid and diacid segments resulted in a reduction in the polymer glass-transition temperature. All these cationic Arg-AG PEAs had good solubility in water and polar organic solvents. The cytotoxity of Arg-AG PEAs was evaluated by 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. These preliminary MTT results indicated that Arg-AG PEAs were nontoxic to bovine aortic endothelial cells (BAECs). © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: 3758–3766, 2010

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    ABSTRACT: Poly(ester amide)s are an emerging group of biodegradable polymers that may cover both commodity and speciality applications. These polymers have ester and amide groups on their chemical structure which are of a degradable character and provide good thermal and mechanical properties. In this sense, the strong hydrogen‑bonding interactions between amide groups may counter some typical weaknesses of aliphatic polyesters like for example poly(e-caprolactone). Poly(ester amide)s can be prepared from different monomers and following different synthetic methodologies which lead to polymers with random, blocky and ordered microstructures. Properties like hydrophilic/hydrophobic ratio and biodegradability can easily be tuned. During the last decade a great effort has been made to get functionalized poly(ester amide)s by incorporation of a-amino acids with hydroxyl, carboxyl and amine pendant groups and also by incorporation of carbon-carbon double bonds in both the polymer main chain and the side groups. Specific applications of these materials in the biomedical field are just being developed and are reviewed in this work (e.g., controlled drug delivery systems, hydrogels, tissue engineering and other uses like adhesives and smart materials) together with the main families of functionalized poly(ester amide)s that have been developed to date.
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    ABSTRACT: A family of water soluble and positively charged L-arginine based poly(ester amide)s (Arg-PEAs) was synthesized and characterized. These biodegradable polymers consist of three nontoxic building blocks: L-arginine, diols, and dicarboxylic acids. The Arg-PEAs were prepared by solution polycondensation reaction of tetra-p-toluenesulfonic acids salts of bis-(L-arginine) α, ω-alkylene diesters and di-p-nitrophenyl esters of dicarboxylic acids. Optimal conditions of the monomers and polymers synthesis were investigated, and the monomers and Arg-PEAs were chemically characterized. Arg-PEAs were found to have good solubility in water and many other polar solvents. Structure-function relationship of the Arg-PEAs revealed that changing the number of methylene groups in the diol or/and diacid segment could finely tune the hydrophobic and cationic properties of the Arg-PEAs. MTT assay showed that all the prepared Arg-PEAs were non-toxic to the cell lines even at very large doses. Arg-PEAs with double bond functionality could be photo-crosslinked with polyethylene glycol diacrylate to form cationic hybrid hydrogels.
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