ABSTRACT
Skin wound dressing materials, which can accelerate wound healing and have the synthetic advantages of simplicity, environmental safety, and resource abundance, are becoming a hot topic of research now. Following such a research trend, we prepared novel decanoic acid functionalized chitosan (CSDA) with good solubility by acylation via a facile one-step method. FTIR, 1H NMR, and UV-Vis results demonstrated that alkyl chains were successfully grafted onto C2 positions of chitosan (CS) skeleton through acylation. XRD patterns implied that the crystallinity of CSDA greatly declined due to the introduction of alkyl moieties, favorable for improving water solubility. Conductometric titration results showed that the degrees of substitution of CSDA, CSDA1, and CSDA2 were 41.42, 26.12, and 23.17%, respectively. MTT assay and hemolysis experiments illustrated that all the CSDA samples tested in this work possessed good hemocompatibility (hemolysis rateâ¯<â¯2%) and excellent cytocompatibility (relative cell viability >75%) toward L929 cells. Moreover, CSDA-soaked gauze dressings and full-thickness excisional wound models were employed to estimate the feasibility of CSDA as wound dressing material, and the results displayed that CSDA with the degree of substitution of 41.42% could enhance the wound healing rate to 100% on day 16. Altogether, CSDA might be potential material used as wound dressing.
Subject(s)
Bandages , Biocompatible Materials/chemical synthesis , Biocompatible Materials/pharmacology , Chitosan/chemical synthesis , Chitosan/pharmacology , Decanoic Acids/chemistry , Wound Healing/drug effects , Acylation , Animals , Biocompatible Materials/chemistry , Biocompatible Materials/toxicity , Chemistry Techniques, Synthetic , Chitosan/chemistry , Chitosan/toxicity , Hemolysis/drug effects , Male , Rats , SolubilityABSTRACT
This work aims to prepare 3,6-O-N-acetylethylenediamine modified chitosan (AEDMCS) and evaluate its potential use as an antimicrobial wound dressing material. UV, FTIR, and 1H NMR results demonstrated N-acetylethylenediamine groups were successfully grafted to C3OH and C6OH on polysaccharide skeletons. TGA, XRD, and solubility tests indicated that as compared with chitosan, AEDMCS had diminished thermostability, decreased crystallinity, and greatly improved solubility. AEDMCS, with degrees of deacetylation and substitution being respectively 90.3% and 0.72, exhibited higher antibacterial activity than chitosan against six bacteria generally causing wound infections. Meanwhile, AEDMCS had permissible hemolysis and cytotoxicity and low BSA adsorption even at a AEDMCS concentration of 25mg/mL. Acute toxicity tests showed AEDMCS was nontoxic. Moreover, the wound healing property was preliminarily evaluated, illustrating that AEDMCS enhanced wound healing rates as expected and had no significant differences as compared with chitosan. These results suggested AEDMCS might be a potential material used as antibacterial wound dressings.
Subject(s)
Anti-Bacterial Agents/pharmacology , Biocompatible Materials/pharmacology , Chitosan/analogs & derivatives , Chitosan/pharmacology , Ethylenediamines/pharmacology , Occlusive Dressings , Adsorption , Animals , Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/toxicity , Biocompatible Materials/chemical synthesis , Biocompatible Materials/chemistry , Biocompatible Materials/toxicity , Cattle , Chitosan/chemical synthesis , Chitosan/toxicity , Ethylenediamines/chemical synthesis , Ethylenediamines/chemistry , Ethylenediamines/toxicity , Female , Fibroblasts/cytology , Fibroblasts/drug effects , Gram-Negative Bacteria/drug effects , Hemolysis/drug effects , Male , Mice , Rabbits , Serum Albumin, Bovine/chemistry , Solubility , Staphylococcus aureus/drug effects , Staphylococcus epidermidis/drug effects , Water/chemistry , Wound Healing/drug effectsABSTRACT
This work aims to synthesize a novel itaconic acid (IA) grafted carboxymethyl chitosan (PICMCS), and further fabricate its nanoparticles for potential biomedical applications. First, PICMCS was prepared via free-radical polymerization of IA monomer, in the presence of ammonium persulfate as an initiator and nitrogen as a protector. Its chemical structure was confirmed by FTIR and 1H NMR. The IA substitution degree calculated by elemental analysis data was 1.85, implying that IA was successfully grafted to carboxymethyl chitosan (CMCS). XRD and TGA patterns illustrated its well-defined crystallinity and thermostability. Second, PICMCS nanoparticles were fabricated by electrostatic attraction between carboxyl and amino groups in the absence of any additional agent, which were of obvious core-shell structures with an average particle size of 144nm and a polydispersity index of 0.11. PICMCS nanoparticles exhibited excellent physical stability after storage at 25°C for 30days, without any aggregation. PICMCS nanoparticles with high negative surface charge also indicated the good stability, especially in neutral or alkaline media. Additionally, the cytotoxicity experiments showed that either PICMCS or its nanoparticles had better cytocompatibility toward L929 cells than CMCS. These findings above suggested that PICMCS was a kind of promising material for preparing nanoparticles used in biomedical field.
