A1 Refereed original research article in a scientific journal

Synthesis of antibacterial and radio-opaque dimethacrylate monomers and their potential application in dental resin




AuthorsJingwei He, Eva Söderling , Lippo V.J. Lassila, Pekka K. Vallittu

PublisherELSEVIER SCI LTD

Publication year2014

JournalDental Materials

Journal name in sourceDENTAL MATERIALS

Journal acronymDENT MATER

Volume30

Issue9

First page 968

Last page976

Number of pages9

ISSN0109-5641

DOIhttps://doi.org/10.1016/j.dental.2014.05.013(external)


Abstract

Objective. In this study, three dimethacrylate quaternary ammonium compounds N,N-bis[2-(3-(methacryloyloxy)propanamido)ethyl]-N-methyldodecyl ammonium iodide (QADMAI-12), N,N-bis[2-(3-(methacryloyloxy)propanamido)ethyl]-N-methylhexadecyl-ammoniumiodide (QADMAI-16), and N,N-bis[2-(3-(methacryloyloxy)propanamido)ethyl]-N-methyl-octadectyl ammonium iodide (QADMAI-18) were synthesized and proposed to be used asantibacterial and radio-opaque agents in dental resin.Methods. All QADMAIs were synthesized through a 2-steps reaction route, and theirstructures were confirmed by FT-IR and1H NMR spectra. Antibacterial activities againstStreptococcus mutans (S. mutans) of QADMAIs were measured by agar diffusion test. EachQADMAI was mixed with TEGDMA (50/50, w/w) and photoinitiation system (0.7 wt% of CQand 0.7 wt% of DMAEMA) to form resin system. Degree of monomer conversion (DC) wasdetermined by FT-IR analysis. The flexural strength (FS) and modulus (FM) of the polymerwere measured using a three-point bending set up. Radiograph was taken to determine theradio-opacity of the polymer, and aluminum step-wedge (0.5–4 mm) was used as calibrationstandard. Surface charge density was measured using fluorescein binding. A single-speciesbiofilm model with S. mutans as the tests organism was used to evaluate the antibacterialproperty of the polymer. Bis-GMA/TEGDMA resin system was used as control material in allof the tests.Results. FT-IR and1H NMR spectra showed that the structures of QADMAIs were the sameas designed. ANOVA analysis revealed that antibacterial activity of QADMAI decreased withthe increasing of alkyl chain length (p < 0.05). QADMAI containing polymers had higher DC(p < 0.05) but lower FS and FM (p < 0.05) than control polymer. Alkyl chain length had no influ-ence on DC (p > 0.05), but FS and FM of QADMAI-12 containing polymer were better than thoseof QADMAI-16 and QADMAI-18 containing polymers (p < 0.05). QADMAI containing poly-mers had much better radio-opacity than control polymer (p < 0.05), and the radio-opacity




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