Article

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

0 Bookmarks
 · 
77 Views
  • [Show abstract] [Hide abstract]
    ABSTRACT: An advanced family of biodegradable cationic hybrid hydrogels was designed and fabricated from two precursors via a UV photocrosslinking in an aqueous medium: unsaturated arginine (Arg) based functional poly(ester amide) (Arg-UPEA) and glycidyl methacrylate chitosan (GMA-chitosan). These Arg-UPEA/GMA-chitosan hybrid hydrogels were characterized in terms of their chemical structure, equilibrium swelling ratio (Qeq), compressive modulus, interior morphology, and biodegradation properties. Lysozyme effectively accelerated the biodegradation of the hybrid hydrogels. The mixture of both precursors in an aqueous solution showed virtually non-cytotoxicity toward porcine aortic valve smooth muscle cells at total concentrations up to 6 mg/mL. The live/dead assay data showed that 3T3 fibroblasts were able to attach and grow on the hybrid hydrogel and pure GMA-chitosan hydrogel well. Arg-UPEA/GMA-chitosan hybrid hydrogels activated both TNF-α and NO production by RAW 264.7 macrophages, and the arginase activity was elevated as well. The integration of the biodegradable Arg-UPEA into the GMA-chitosan can provide the advantages in terms of elevated and balanced NO production and arginase activity that free Arg supplement could not achieve. The hybrid hydrogels may have the potential applications as a wound healing accelerator.
    Acta biomaterialia 02/2014; · 5.68 Impact Factor
  • [Show abstract] [Hide abstract]
    ABSTRACT: AbstractA new family of biodegradable amino acid‐based poly(ether ester amide)s (AA‐PEEAs) consisting of three building blocks [poly(ε‐caprolactone) (PCL), L‐phenylalanine (Phe), and aliphatic acid dichloride] were synthesized by a solution polycondensation. Using DMA as the solvent, these PCL‐containing Phe‐PEEA polymers were obtained with fair to very good yields with weight average molecular weight (M w ) ranging from 6.9 kg/mol to 31.0 kg/mol, depending on the original molecular weight of PCL. The chemical structures of the PCL‐containing Phe‐PEEA polymers were confirmed by IR and NMR spectra. These PCL‐containing Phe‐PEEAs had lower T g than most of the oligoethylene glycol (OEG) based AA‐PEEAs due to the more molecular flexibility of the PCL block in the backbones, but had higher T g than non‐amino acid based PEEA. The solubility of the PCL‐containing Phe‐PEEA polymers in a wide range of common organic solvents, such as THF and chloroform, was significantly improved when comparing with aliphatic diol based poly(ester amide)s and OEG based AA‐PEEAs. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2012
    Journal of Applied Polymer Science 07/2012; 125(1). · 1.64 Impact Factor
  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: A family of biodegradable, biocompatible, water soluble cationic polymer precursor, arginine-based unsaturated poly (ester amide) (Arg-UPEA), is reported. Its incorporation into conventional Pluronic diacrylate (Pluronic-DA) to form hybrid hydrogels for a significant improvement of the biological performance of current synthetic hydrogels is shown. The gel fraction (Gf), equilibrium swelling ratio (Qeq), compressive modulus, and interior morphology of the hybrid hydrogels as well as their interactions with human fibroblasts and bovine endothelial cells are fully investigated. It is found that the incorporation of Arg-UPEA into Pluronic-DA hydrogels significantly changes their Qeq, mechanical strength, and interior morphology. The structure–property relationship of the newly fabricated hybrid hydrogels is studied in terms of the chemical structure of the Arg-UPEA precursor, i.e., the number of methylene groups in the Arg-UPEA repeating unit. The results indicate that increasing methylene groups in the Arg-UPEA repeating unit increases Qeq and decreases the compressive modulus of hydrogels. When compared with a pure Pluronic hydrogel, the cationic Arg-UPEAs/Pluronic hybrid hydrogels greatly improve the attachment and proliferation of human fibroblasts on hydrogel surfaces. A bovine aortic endothelial cells (BAEC) viability test in the interior of the hydrogels shows that the positively charged hybrid hydrogels can significantly improve the viability of the encapsulated endothelial cell over a 2 week study period when compared with a pure Pluronic hydrogel.
    Advanced Functional Materials 09/2012; 22(18). · 10.44 Impact Factor