☆ 4.6 Article

Synthesis and characterization of dimethacrylates containing quaternary ammonium functionalities for dental applications

DENTAL MATERIALS (2012)

期刊

DENTAL MATERIALS

卷 28, 期 2, 页码 219-228

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ELSEVIER SCI LTD

DOI: 10.1016/j.dental.2011.10.004

关键词

Bacterial adhesion; Cytotoxicity; Dental restorative material; Degree of conversion; Dimethacrylate monomer; Menschutkin reaction; MTT assay; Quaternary ammonium salts; Streptococcus mutans; Surface charge density

类别

Dentistry, Oral Surgery & Medicine Materials Science, Biomaterials

资金

National Institute of Dental and Craniofacial Research (NIDCR) [YI-DE-7005-01]
National Institute of Standards and Technology (NIST) [YI-DE-7005-01]

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摘要

Objectives. The widespread incidence of recurrent caries highlights the need for improved dental restorative materials. The objective of this study was to synthesize low viscosity ionic dimethacrylate monomers (IDMAs) that contain quaternary ammoniums groups (antimicrobial functionalities) and are compatible with existing dental dimethacrylate-based monomers. Such monomers have the potential to copolymerize with other methacrylate monomers and produce antibacterial polymers. Methods. Two monomers (IDMA-1 and IDMA-2) were synthesized using the Menschutkin reaction and incorporated at 0-30% (by mass) into a 1:1 (by mass) bisphenol A glycerolate dimethacrylate (BisGMA): triethylene glycol dimethacrylate (TEGDMA) resin. Resin viscosity was quantified using rheology, and polymer degree of conversion (DC) and surface charge density were measured using Fourier transform infrared spectroscopy (FTIR) and fluorescein binding, respectively. Effects of IDMA-1 on initial attachment of Streptococcus mutans and on viability and metabolic activity (via reductase enzymes) of RAW 264.7 macrophage-like cells were quantified. Results. IDMA-1 and IDMA-2 were prepared and characterized. IDMA-1 was miscible with BisGMA: TEGDMA and slightly increased the resin viscosity and DC. As expected, polymeric surface charge density increased with increasing IDMA-1. Incorporation of 10% IDMA-1 into BisGMA: TEGDMA reduced bacterial colonization without affecting viability or metabolic activity of mammalian cells. Increasing IDMA-1 up to 30% had no additional effect on bacterial coverage, but >= 20% IDMA-1 significantly reduced macrophage density, viability, and metabolic activity. Leachables from polymers containing IDMA-1 were not cytotoxic. Significance. The Menschutkin reaction provides a facile, convenient means to synthesize new monomers with quaternary ammonium groups for dental and medical applications. Published by Elsevier Ltd on behalf of Academy of Dental Materials.

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Bis-quaternary ammonium betulin-based dimethacrylate: synthesis, characterization, and application in dental restorative resins

Lusi Zhang, Zhiyuan Ma, Ruili Wang, Weiwei Zuo, Meifang Zhu

Summary: Secondary caries resulting from tooth-adherent cariogenic bacteria is a common cause of restoration failures in dental practices. The use of polymerizable quaternary ammonium monomers (QAMs) to immobilize antimicrobials in dental materials is seen as a promising strategy for caries prevention. This study synthesized three types of quaternary ammonium betulin-based dimethacrylate derivatives and investigated their antibacterial activity, physicochemical properties, and cytotoxicity when incorporated into dental resins. The results showed that the derivative with an alkyl chain length of 8 carbons exhibited the most effective inhibition of S. mutans growth, while maintaining good flowability and low cytotoxicity.

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