Hadi Bakhshi

Synthesis and characterization of antibacterial polyurethane coatings from quaternary ammonium salts functionalized soybean oil based polyols.

In this study, a simple and versatile synthetic approach was developed to prepare bactericidal polyurethane coatings. For this purpose, introduction of both quaternary ammonium salts (QASs), with well-known antibacterial activity, and reactive hydroxyl groups on to the backbone of soybean oil was considered. Epoxidized soybean oil was reacted with diethylamine and the intermediate tertiary amine containing polyol was reacted with two different alkylating agents, methyl iodide and benzyl chloride, to produce MQAP and BQAP, respectively. These functional polyols were reacted with different diisocyanate monomers to prepare polyurethane coatings. Depending on the structure of monomers used for the preparation of polyurethane coatings, initial modulus, tensile strength and elongation at break of samples were in the ranges of 122-339 MPa, 4.6-12.4 MPa and 8.4-46%, respectively. Polyurethane coatings based on isophorone diisocyanate showed proper mechanical properties and adhesion strength (0.41 MPa) for coating application. Study of fibroblast cells interaction with prepared polyurethanes showed promising cells viability in the range of 78-108%. Meanwhile, MQAP based samples with higher concentration of QASs showed better adhesion strength, surface hydrophilicity and antibacterial activity (about 95% bacterial reduction). Therefore, these materials can find applications as bactericidal coating for biomedical devices and implants.

Preparation and characterization of novel antibacterial castor oil‐based polyurethane membranes for wound dressing application

Preparation of novel antibacterial and cytocompatible polyurethane membranes as occlusive dressing, which can provide moist and sterile environment over mild exudative wounds is considered in this work. In this regard, an epoxy-terminated polyurethane (EPU) prepolymer based on castor oil and glycidyltriethylammonium chloride (GTEAC) as a reactive bactericidal agent were synthesized. Polyurethane membranes were prepared through cocuring of EPU and different content of GTEAC with 1,4-butane diamine. The physical and mechanical properties, as well as cytocompatibility and antibacterial performance of prepared membranes were studied. Depending on their chemical formulations, the equilibrium water absorption and water vapor transmission rate values of the membranes were in ranges of 3-85% and 53-154g m(-2) day(-1), respectively. Therefore, these transparent membranes can maintain for a long period the moist environment over the wounds with low exudates. Detailed cytotoxicity analysis of samples against mouse L929 fibroblast and MCA-3D keratinocyte cells showed good level of cytocompatibility of membranes after purification via extraction of residual unreacted GTEAC moieties. The antibacterial activity of the membranes against Escherichia coli and Staphylococcus aureus bacteria was also studied. The membrane containing 50% GTEAC exhibited an effective antibacterial activity, while showed acceptable cytocompatibility and therefore, can be applied as an antibacterial occlusive wound dressing.

Synthesis and evaluation of antibacterial polyurethane coatings made from soybean oil functionalized with dimethylphenylammonium iodide and hydroxyl groups

Preparation of antibacterial polyurethane coatings from novel functional soybean oil was considered in this work. First, epoxidized soybean oil (ESBO) as a low price and widely available renewable resource raw material was subjected to the reaction with aniline using an ionic liquid as a green catalyst. The intermediate phenylamine containing polyol (SAP) was then methylated by reaction with methyl iodide to produce a polyol (QAP) with pendant dimethylphenylammonium iodide groups. To regulate the physical and mechanical properties as well as biological characteristics of final coatings, QAP was mixed with different portions of a similar soybean oil-based polyol (MSP) without quaternary ammonium groups. The mixtures were reacted with isophorone diisocyanate to produce crosslinked polyurethane coatings. Evaluation of viscoelastic properties by DMA method revealed single phase structure with Tg in the range of 50-82°C. Stress-strain analysis of the prepared polyurethanes showed initial modulus, tensile strength, and elongation at break in the ranges of 13-299 MPa, 4.5-13.8 MPa, and 16-109%, respectively. Additionally, the coatings showed good adherence to aluminum and PVC substrates. The solvent extracted samples showed excellent biocompatibility as determined by monitoring L929 fibroblast cells morphology and MTT assay. Meanwhile, very promising antibacterial properties against both Gram-positive (S. aureus) and Gram-negative (E. coli) bacteria with bacterial reduction in the range of 83-100% was observed.

Castor oil-based polyurethane coatings containing benzyl triethanol ammonium chloride: synthesis, characterization, and biological properties

In the present work, benzyl triethanol ammonium chloride (BTEAC) was employed as a reactive bactericidal additive for preparing of polyurethane coatings. In this regard, castor oil as a renewable resource-based polyol, polyethylene glycol (PEG1000), and BTEAC were reacted with toluene diisocyanate. Physical, mechanical, and thermal characteristics as well as biocompatibility and antibacterial properties of polyurethanes were evaluated. The prepared polyurethanes showed two-phase structure with soft and hard segments glass transition temperature transitions in the range of 18–70 and 85–153xa0°C, respectively. Initial modulus and tensile strength were improved for coatings with higher BTEAC content, while elongation at break and thermal stability were decreased. Hydrophilicity of coatings was increased for polyurethanes based on higher content of BTEAC and PEG1000. Polyurethanes with higher BTEAC content showed better cytocompatibility for mouse L929 fibroblast cells. Moreover, coatings with higher hydrophilicity and BTEAC content displayed superior antibacterial activity against both Escherichia coli and Staphylococcus aureus bacteria.

Dendrons as active clicking tool for generating non-leaching antibacterial materials

We show a novel concept of using dendrons as a tool for making non-active materials antibacterial in a simple way. A dendron is a part of a dendrimer with the advantage of having many peripheral functional groups and a focal point. We used this structural advantage in making an antibacterial polymeric tool for clicking to other non-active polymers and surfaces. We show the success of the concept by making new antibacterial poly(urethane-biuret) dendrons containing quaternary ammonium salts (QASs) on the periphery and a primary hydroxyl group as the focal point in one pot. The chemical structure and thermal properties of the dendrons were fully studied. All quaternized dendrons were stable until above 200 °C. The newly synthesized dendrons show high activity against Escherichia coli (E. coli) and Bacillus subtilis (B. subtilis) as tested by the determination of MIC, MBC values and the Kirby–Bauer assay. The hydroxyl group enabled the attachment of the dendrons to a cotton mat and PU foam, as a reactive additive, bringing them non-leaching fast bactericidal activity. The interaction of urethane and biuret bonds in the dendrons’ backbone led to a transparent non-leaching bactericidal coating on the treated glass slides.

Hyperbranched polyesters as biodegradable and antibacterial additives

Herein, we present novel hyperbranched poly(amino-ester)s functionalized with quaternary ammonium salts (QAS-HPAEs). These materials can be used as antibacterial and biodegradable additives for mixing with non-active polymers. The chemical structure and thermal properties of the HPAEs were studied. All QAS-HPAEs were stable until 192 °C, which makes their thermal blending with other polymers possible. Blending polycaprolactone (PCL) as a biodegradable polymer with QAS-HPAEs improved its surface and bulk hydrophilicity, while partially decreasing its elastic modulus and tensile strength. Mixing 10 wt% of QAS-HPAEs in PCL resulted in a film with high contact-killing activity against E. coli and B. subtilis and faster degradability in the presence and absence of esterase. The activity of esterase was inhibited in the presence of a higher content of QAS-HPAEs (20 wt%).

β-Carotene: a natural osteogen to fabricate osteoinductive electrospun scaffolds

β-Carotene (βC) as a natural osteogenic material was incorporated in PCL electrospun mats to fabricate scaffolds for bone tissue engineering. These scaffolds successfully supported the attachment and proliferation of mesenchymal stem cells (MSCs). Seeded scaffolds were calcinated during 21 days of cell culture in a non-differential medium, which showed the osteodifferentiation of MSCs. Expression of RUNX2, SOX9, and osteonectin proved the osteoinductive effect of incorporated β-carotene on the differentiation of MSCs to osteoblasts without using any external osteogenic differential agent. However, the cells did not pass the early phase of osteogenesis and were still osteochondro-progenitor after 21 days of incubation. Thus, the fabricated fibrous scaffolds are potential candidates for direct bone tissue engineering.

Polycaprolactone/carboxymethyl chitosan nanofibrous scaffolds for bone tissue engineering application

This research focused on the physical properties and cell compatibility of nanofibrous scaffolds based on polycaprolactone/chitosan (PCL/CTS) and PCL/carboxymethyl chitosan (PCL/CMC) blends for bone tissue engineering application. Scaffolds were fabricated by electrospinning technique. SEM images showed that the undesirable ultrafine and splitting fibers in PCL/CTS scaffolds are eliminated by replacing CTS with CMC. PCL/CMC scaffolds exposed significantly improved surface hydrophilicity improvement comparing to PCL/CTS ones. The water contact angle of PCL scaffold was reduced on the addition of 15% CMC from 123u202f±u202f1° to 51u202f±u202f3° in high concentration of CMC scaffold. The average diameter of fibers in PCL/CTS 15% and PCL/CMC 15% were 439 and 356u202fnm, respectively, which demonstrated higher concentrations of CMC resulted in decrease fibers diameter than other blended scaffolds. FTIR spectroscopy confirmed the composition of PCL/CTS and PCL/CMC scaffolds. The culturing of human osteoblast cells (MG63) on the scaffolds showed that all scaffolds are biocompatible. The PCL/CMC nanofibers exhibited promoting proliferation trend, compared to the PCL and PCL/CTS ones, especially at maximum concentrations of CMC. The results demonstrate that the PCL/CMC electrospun scaffolds can be an excellent candidate for bone tissue engineering application.

Correction: β-Carotene: a natural osteogen to fabricate osteoinductive electrospun scaffolds

Correction for ‘β-Carotene: a natural osteogen to fabricate osteoinductive electrospun scaffolds’ by Atiyeh Dabouian et al., RSC Adv., 2018, 8, 9941–9945.

Biodegradable bead-on-spring nanofibers releasing β-carotene for bone tissue engineering

Bead-on-string mats based on poly(lactide-co-glycolide) (PLGA) releasing β-carotene (βC) as a natural osteogen were fabricated and used for bone tissue engineering. Mesenchymal stem cells (MSCs) seeded on the scaffolds successfully differentiated to osteoblasts without using any a differential medium. The mats showed a small burst of β-carotene (24-27%) during the first day and a sustained slow release up to 21u202fdays. The MTT and SEM results indicated good attachment and proliferation of MSCs on the scaffolds. Calcination of scaffolds and expression of RUNX2, SOX9, and osteonectin genes approved the differentiation of seeded MSCs to osteoblasts without using any external osteogenic differential agent. The scaffold loaded with 4% β-carotene not only induced the early phase of osteogenesis but also advanced the differentiation to the osteoblast maturation phase. Thus, these bead-on-string scaffolds can be used as a substrate for direct bone tissue engineering.