Diverse approaches dealing with the reinforcement of dental composite resins with quaternary ammonium compounds (QAC) have been previously reported. This work aims to investigate the physicochemical and mechanical performance of dental resins containing silica nanofillers with novel QAC. Different types of quaternary ammonium silane compounds (QASiC) were initially synthesized and characterized with proton nuclear magnetic resonance (1H-NMR) and Fourier transform infrared (FTIR) spectroscopy. Silica nanoparticles were surface modified with the above QASiC and the structure of silanized products (S.QASiC) was confirmed by means of FTIR and thermogravimetric analysis. The obtained S.QASiC were then incorporated into methacrylate based dental resins. Scanning electron microscopy images revealed a satisfactory dispersion of silica nanoclusters for most of the synthesized nanocomposites. Curing kinetics disclosed a rise in both the autoacceleration effect and degree of conversion mainly induced by shorter QASiC molecules. Polymerization shrinkage was found to be influenced by the particular type of S.QASiC. The flexural modulus and strength of composites were increased by 74% and 19%, while their compressive strength enhancement reached up to 19% by adding 22 wt% S.QASiC nanoparticles. These findings might contribute to the proper design of multifunctional dental materials able to meet the contemporary challenges in clinical practice.

In this study, chitooligosaccharide-niacin acid conjugate was designed and synthesized through the reaction of chitooligosaccharide and nicotinic acid with the aid of N,N'-carbonyldiimidazole. Its cationic derivatives were prepared by the further nucleophilic substitution reaction between the chitooligosaccharide-niacin acid conjugate and bromopropyl trialkyl ammonium bromide with different alkyl chain lengths. The specific structural characterization of all derivatives was identified using Fourier Transform Infrared Spectroscopy (FTIR) and Nuclear Magnetic Resonance (NMR), and the degree of substitution was obtained using the integral area ratio of the hydrogen signals. Specifically, the antibacterial activities against Escherichia coli, Staphylococcus aureus, Pseudoalteromonas citrea and Vibrio harveyi were evaluated using broth dilution methods. In addition, their antifungal activities, including Botrytis cinerea, Glomerella cingulate and Fusarium oxysporum f. sp. cubense were assayed in vitro using the mycelium growth rate method. Experimental data proved that the samples showed antibacterial activity against four pathogenic bacteria (MIC = 1-0.125 mg/mL, MBC = 8-0.5 mg/mL) and enhanced antifungal activity (50.30-68.48% at 1.0 mg/mL) against Botrytis cinerea. In particular, of all chitooligosaccharide derivatives, the chitooligosaccharide derivative containing pyridinium and tri-n-butylamine showed the strongest antibacterial capacity against all of the test pathogenic bacteria; the MIC against Vibrio harveyi was 0.125 mg/mL and the MBC was 1 mg/mL. The experimental results above showed that the introduction of pyridinium salt and quaternary ammonium salt bearing trialkyl enhanced the antimicrobial activity. In addition, the cytotoxicity against L929 cells of the chitooligosaccharide derivatives was evaluated, and the compounds exhibited slight cytotoxicity. Specifically, the cell viability was greater than 91.80% at all test concentrations. The results suggested that the cationic chitooligosaccharide derivatives bearing pyridinium and trialkyl ammonium possessed better antimicrobial activity than pure chitooligosaccharide, indicating their potential as antimicrobial agents in food, medicine, cosmetics and other fields.

Recently, much effort has been expended on the development of non-viral gene delivery systems based on polyplexes of nucleic acids with various cationic polymers. Natural polysaccharide derivatives are promising carriers due to their low toxicity. In this work, chitosan was chemically modified by a reaction with 4-formyl-n,n,n-trimethylanilinium iodide and pyridoxal hydrochloride and subsequent reduction of the imine bond with NaBH4. This reaction yielded three novel derivatives, n-[4-(n',n',n'-trimethylammonium)benzyl]chitosan chloride (TMAB-CS), n-[(3-hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridine)methyl]chitosan chloride (Pyr-CS), and n-[4-(n',n',n''-trimethylammonium)benzyl]-n-[(3-hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridine)methyl]chitosan chloride (PyrTMAB-CS). Their structures and degrees of substitution were established by 1H NMR spectroscopy as DS1 = 0.22 for TMAB-CS, DS2 = 0.28 for Pyr-CS, and DS1 = 0.21, DS2 = 0.22 for PyrTMAB-CS. Dynamic light scattering measurements revealed that the new polymers formed stable polyplexes with plasmid DNA encoding the green fluorescent protein (pEGFP-N3) and that the particles had the smallest size (110-165 nm) when the polymer:DNA mass ratio was higher than 5:1. Transfection experiments carried out in the HEK293 cell line using the polymer:DNA polyplexes demonstrated that Pyr-CS was a rather poor transfection agent at polymer:DNA mass ratios less than 10:1, but it was still more effective than the TMAB-CS and PyrTMAB-CS derivatives that contained a quaternary ammonium group. By contrast, TMAB-CS and PyrTMAB-CS were substantially more effective than Pyr-CS at higher polymer:DNA mass ratios and showed a maximum efficiency at 200:1 (50%-70% transfected cells). Overall, the results show the possibility of combining substituent effects in a single carrier, thereby increasing its efficacy.

: Quaternary ammonium compounds and calcium phosphates have been incorporated into dental materials to enhance their biointeractivity and preventive effects. This study aimed at evaluating the physical and chemical properties and effects against Streptococcus mutans of a dental sealant containing 1,3,5-tri acryloyl hexahydro-1,3,5-triazine (TAT) and α-tricalcium phosphate (α-TCP). A methacrylate-based dental sealant was initially formulated. α-TCP and TAT (Gα-TCPTAT) were added to the experimental sealant at 2 wt.% each. One group was formulated without α-TCP and TAT and used as control (GCTRL). All tested resins were analyzed for polymerization kinetics and degree of conversion (DC %), Knoop hardness (KHN), softening in solvent (∆KHN%), ultimate tensile strength (UTS), the contact angle with water or with α-bromonaphthalene, surface free energy (SFE) and antibacterial activity against Streptococcus mutans in biofilm and in planktonic cells. The polymerization kinetic was different between groups, but without statistical differences in the DC % (p<0.05). KHN and ΔKHN% did not change between groups (p>0.05), but Gα-TCPTAT presented greater UTS compared to GCTRL (p<0.05). No differences were found for contact angle (p>0.05) or SFE (p>0.05). Gα-TCPTAT showed greater antibacterial activity in comparison to GCTRL (p<0.05). The formulation of dental sealants containing TAT and α-TCP can be characterized by improved mechanical and antibacterial properties.