Novel hydrolytic resistant antibacterial monomers for dental resin adhesive.

Piangkwan Saiprasert, Chittreeya Tansakul, Arthit Pikulngam, Prompat Promphet, Supawadee Naorungroj, Somjin Ratanasathien, Juthatip Aksornmuang, Supitcha Talungchit

Journal: Journal of dentistry 2023;135():104597

PMID: 37348643

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Abstract

OBJECTIVES

To evaluate the properties of novel hydrolytic resistant antibacterial monomers and to determine the properties of resin adhesives containing these monomers.

METHODS

Methacrylamide-based QAC (Quaternary Ammonium Compound) monomers, 1-(11-Methacryla-midoundecyl)pyridine-1-ium bromide (MAUPB) and 1-(12-Methacryl-amidododecyl)pyridine-1-ium bromide (MADPB), and their methacrylate-derivatives, N-(1-Methacryloylundecanyl)pyridinium bromide (MUPB) and N-(1-Methacryloyldodecanyl)pyridinium bromide (MDPB), were synthesized and characterized. The minimum inhibitory (MIC) and bactericidal (MBC) concentrations were determined against S.mutans and E.faecalis. Cytotoxicity of unpolymerized monomers were evaluated using L-929 and MDPC-23. Each monomer was incorporated into experimental resins (BisGMA/TEGDMA/CQ/EDMAB or BisGMA/HEMA/CQ/EDMAB) at 10wt%. FTIR Spectra were collected for degree of conversion (DC%) measurement. Bacterial attachment on resin disks were determined by fluorescent microscope. Mechanical properties of experimental resins were evaluated by flexural strength & modulus and shear bond strength testing.

RESULTS

The antibacterial activity of MDPB≥MUPB>MADPB>MAUPB. The TC of MAUPB> MADPB>MUPB >MDPB. Incorporation of MAUPB in BisGMA/TEGDMA-based resin, had no significant effect on DC%, while significantly increase DC% in BisGMA/HEMA-based Resin. MUPB and MAUPB containing resins showed less viable bacterial attachment than pure resins. After 3-month storage, resins containing MAUPB illustrated higher flexural strength than their corresponding resins containing MUPB. BisGMA/HEMA-based resin containing MAUPB illustrated significantly higher resin-dentin shear bond strength than that of MUPB and pure resin.

CONCLUSIONS

Methacrylamide monomer containing QAC, MAUPB, possessed antibacterial properties and superior physical and mechanical properties when incorporated in resin adhesives as compared to their corresponding methacrylate monomer, MUPB.

CLINICAL SIGNIFICANCE

Methacrylamide-based QAC monomers are potentially used to formulate antibacterial hydrolytic resistant resin adhesives and enhance resin-dentin bond strength.

Address: Department of Prosthetic Dentistry, Faculty of Dentistry, Prince of Songkla University, Songkhla, Thailand, 90112. Electronic address: [email protected].; Division of Physical Science and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Songkhla, Thailand, 90112. Electronic address: [email protected].; Division of Physical Science and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Songkhla, Thailand, 90112. Electronic address: [email protected].; Division of Physical Science and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Songkhla, Thailand, 90112. Electronic address: [email protected].; Department of Conservative Dentistry, Faculty of Dentistry, Prince of Songkla University, Songkhla, Thailand, 90112. Electronic address: [email protected].; Department of Conservative Dentistry, Faculty of Dentistry, Prince of Songkla University, Songkhla, Thailand, 90112. Electronic address: [email protected].; Department of Prosthetic Dentistry, Faculty of Dentistry, Prince of Songkla University, Songkhla, Thailand, 90112. Electronic address: [email protected].; Department of Conservative Dentistry, Faculty of Dentistry, Prince of Songkla University, Songkhla, Thailand, 90112. Electronic address: [email protected].

DOI: 10.1016/j.jdent.2023.104597

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MeSH Terms: Dental Cements, Bromides, Methacrylates, Polymethacrylic Acids, Anti-Bacterial Agents, Pyridines, Materials Testing, Composite Resins