Department of Biological Sciences, Bauru School of Dentistry, University of São Paulo, 17012-901, Brazil.
Department of Clinical Sciences, Orthodontics Discipline, Faculty of Dentistry, University of Toronto, Toronto, Ontario M5G1G6, Canada; Dental Research Institute, Restorative Discipline, Faculty of Dentistry, University of Toronto, Toronto, Ontario M5G1G6, Canada.
Dent Mater. 2021 Dec;37(12):1751-1760. doi: 10.1016/j.dental.2021.09.005. Epub 2021 Sep 24.
Synthesize novel epigallocatechin-gallate (EGCG) methacrylate monomers with the ability to copolymerize with dental methacrylate resins.
EGCG was reacted with 1/3 (E33), 2/3 (E67) and 1 (E100) molar equivalents of methacyloyl chloride introducing three degrees of polymerizablility. EGCG-methacrylates were characterized by Fourier Transform Infrared Spectroscopy (FTIR) and Nuclear Magnetic Resonance (NMR). E33, E67, E100 and neat EGCG were incorporated into TEGDMA at 0.5-20% ratios (m/m). Copolymers were tested for degree of conversion (%DC), EGCG release, gel content (%GC), degree of swelling (%DS), flexural properties and bacterial viability (Streptococcus mutans, baseline/30-days). Neat TEGDMA and TEGDMA passively loaded with EGCG (E0) were used as controls. Data were analysed by one-way ANOVA, Tukey, and Dunnett's method (α=5%). Two-way ANOVA and Bonferroni were used to investigate factor interaction.
FTIR/NMR confirmed synthesis of desired compounds. All of E100 incorporated ratios had %DC similar to TEGDMA. Remaining groups had reduction in %DC at 2% in E0, 10% in E33 and 20% in E67 ratios. EGCG was stable within ECGC-methacrylate copolymers. Release of EGCG from E0 significantly increased with higher EGCG ratios. Except for E100, higher EGCG or EGCG-methacrylate ratios led to decreased %CG and %DS. At baseline, E0 had the lowest bacterial survival rates (1-10% survival) at all ratios compared to E33, E67, E100, and neat TEGDMA. However, E33, E67 and E100 still had statistically lower survival rates (7-53%) compared with neat TEGDMA. After 30-days, all compounds had similar survival rates for all ratios, which were lower than that of neat TEGDMA.
Demonstration of methacrylate functionalized EGCG- with inherited antibacterial activity for improved restoration longevity.
合成具有与牙科甲基丙烯酸酯树脂共聚能力的新型表没食子儿茶素没食子酸酯（EGCG）甲基丙烯酯单体。
用 1/3（E33）、2/3（E67）和 1（E100）摩尔当量的甲酰氯与 EGCG 反应，引入三个聚合度。通过傅里叶变换红外光谱（FTIR）和核磁共振（NMR）对 EGCG-甲基丙烯酯进行了表征。将 E33、E67、E100 和纯 EGCG 以 0.5-20%（m/m）的比例掺入 TEGDMA 中。测试共聚物的转化率（%DC）、EGCG 释放量、凝胶含量（%GC）、溶胀度（%DS）、弯曲性能和细菌活力（变形链球菌，基线/30 天）。纯 TEGDMA 和 TEGDMA 被动负载 EGCG（E0）用作对照。采用单因素方差分析、Tukey 和 Dunnett 法（α=5%）对数据进行分析。采用双因素方差分析和 Bonferroni 法研究因素间的相互作用。
FTIR/NMR 证实了所需化合物的合成。所有 E100 掺入比例的%DC 与 TEGDMA 相似。其余各组在 E0 中 2%、E33 中 10%和 E67 中 20%的比例下，%DC 降低。EGCG 在 ECGC-甲基丙烯酯共聚物中稳定。E0 中 EGCG 释放量随 EGCG 比例的增加而显著增加。除 E100 外，较高的 EGCG 或 EGCG-甲基丙烯酯比例会导致较低的%CG 和%DS。在基线时，与 E33、E67、E100 和纯 TEGDMA 相比，E0 以所有比例的细菌存活率最低（1-10%存活）。然而，E33、E67 和 E100 与纯 TEGDMA 相比，其存活率仍有统计学上的降低（7-53%）。30 天后，所有化合物在所有比例下的存活速率相似，均低于纯 TEGDMA。
证明了具有内在抗菌活性的甲基丙烯酰化 EGCG-，可提高修复体的耐久性。
