Cationic Hybrid Hydrogels from Amino‐Acid‐Based Poly(ester amide): Fabrication, Characterization, and Biological Properties

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.

Reduction of suture associated inflammation after 28 days using novel biocompatible pseudoprotein poly(ester amide) biomaterials

“…4,[9][10][11][12][13]17 In brief, the general scheme of AA-PEA synthesis could be divided into three major steps: the synthesis of di-p-nitrophenyl ester of dicarboxylic acids as monomer (I); the synthesis of tetra-p-toluenesulfonic acid salts of bis (L-amino acid) a,x-alkylene diesters as monomer (II); and the synthesis of AA-PEA via a solution polycondensation of monomers I and II. In the 8-Phe-4 PEA, sebacic acid (or sebacoyl chloride) was used as the dicarboxylic acid in the synthesis of monomer I and 1,4 butane-diol was used as the diol for the synthesis of monomer II.…”

“…[11][12][13][14][15][16] AA-PEA are synthesized from three naturally occurring and nontoxic building blocks: amino acids, diacids and dialcohol. 7,10,13,[17][18][19] Figure 1 demonstrates the generic chemical structure of the repeating unit of AA-PEA homopolymer. The AA-PEAs derive their amide (or peptide) linkage from amino acids.…”

“…[1][2][3][4] Suture materials are frequently coated to enhance their handling properties so as to reduce tissue drag when passing through tissue and ease with the downward sliding of knots during tying. Although nonabsorbable beeswax, paraffin, silicone, and polytetrafluoroethylene (Teflon TM ) were traditionally used as coating materials, new biodegradable coatings have been developed that degrade along with the absorbable sutures they coat, 1 [8][9][10] and as an efficient drug and gene delivery system. [11][12][13][14][15][16] AA-PEA are synthesized from three naturally occurring and nontoxic building blocks: amino acids, diacids and dialcohol.…”

“…Their composition includes unsaturated diols and/or diacids 4,19 used to synthesize unsaturated AA-PEA generations, using either polar amino acids like lysine (Lys), arginine (Arg), serine (Ser), or an unsaturated >C@C< moiety in the backbone or pendant groups to provide pendant functionalized AA-PEAs, 4,[9][10][11][12][13]17,20,21 and the different arrangement of these building blocks along the backbone. 4,9,10,22 In this study, two AA-PEA polymers (8-Phe-4 PEA and Arg-Phe-PEA) were selected as suture coatings. 8-Phe-4 PEA is a homopolymer and one of the simplest single AA-PEAs.…”

Polyethylene glycol modification decreases the cardiac toxicity of carbonaceous dots in mouse and zebrafish models

“…Novel nanomaterials are continually emerging to satisfy the requirements of use for various applications, and they have been used in multiple applications, including drug/protein/ nucleic acid delivery, contrast probe delivery, disease diagnosis and analysis [1][2][3] . However, although many nanomaterials have been developed with unique characteristics and functionalities, only a few of them have been approved for clinical use in humans, because of their potential toxicity [4] .…”