The aim of this in vitro study was to synthesize three new methacrylate monomers based on the modification of saccharides structures (glucose-Gluc, sucrose-Sucr and chitosan-Chit) with glycidyl methacrylate, and to use them in the composition of dental adhesives. Three methacrylate saccharide monomers were synthesized and characterized by mid-IR, 1H and 13C NMR, antioxidant activity and cytotoxic effect. Monomers included: one monosaccharide - Gluc-MA; one disaccharide - Sucr-MA; and one polysaccharide - Chit-MA. Primers containing HEMA, methacrylate saccharide monomers at concentrations of 0 (control), 1, 2 or 4 wt%, 60 wt% ethanol aqueous solution (pH3.0) and initiator system were formulated. Primers were used in conjunction with a bond step and composite paste to restore caries-free third molars, and dentin bond strength (24 hours and 6 month of storage in water), and antimicrobial activity (Alamar Blue test) were tested. Degree of conversion (DC) and maximum rate of polymerization (Rpmax) of the primers themselves were also analyzed. The mid-IR, 1H and 13C spectrum confirmed the presence of vinyl group on the structure of saccharides. Chit-MA showed low antioxidant activity and did not present a cytotoxic effect. Gluc-MA and Sucr-MA possess antioxidant and cytotoxic activity, concentration dependent. In the presence of methacrylate saccharide monomers, the primers showed DC comparable to the control group, except Gluc-MA4%, Sucr-MA4% and Chit-MA1%, which showed a range of 64.6 from 58.5 %DC. Rpmax was not statistically different for all the groups (p = 0.01). The bond strength of Sucr-MA1% increased from 25.7 (±2.8) to 40.6 (±5.3) MPa after 6 months of storage. All the synthesized monomers showed some antimicrobial activity after polymerization. Gluc-MA and Chit-MA 4% and Sucr-MA 1, 2 and 4% led to decrease bacterial metabolism. Sucr-MA 1% showed better results regarding the decrease in bacterial metabolism and increasing the bond strength after 6 months of storage.

中文翻译：

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用于牙科粘合剂系统的甲基丙烯酸酯糖基单体

这项体外研究的目的是合成三种基于用甲基丙烯酸缩水甘油酯修饰糖类结构（葡萄糖-Gluc、蔗糖-Sucr 和壳聚糖-Chit）的新型甲基丙烯酸酯单体，并将它们用于牙科粘合剂的组合物中。合成了三种甲基丙烯酸酯糖单体，并通过中红外、1H 和 13C NMR、抗氧化活性和细胞毒作用对其进行了表征。单体包括：一种单糖 - Glu-MA；一种双糖 - Sucr-MA；和一种多糖 - Chit-MA。配制含有HEMA、浓度为0（对照）、1、2或4wt%、60wt%乙醇水溶液（pH3.0）的甲基丙烯酸酯糖单体和引发剂体系的引物。底漆与粘合步骤和复合糊剂结合使用，以修复无龋的第三磨牙，和牙本质粘合强度（在水中储存 24 小时和 6 个月）和抗菌活性（Alamar Blue 测试）进行了测试。还分析了引物本身的转化度 (DC) 和最大聚合速率 (Rpmax)。中红外、1H 和 13C 光谱证实了糖类结构上存在乙烯基。Chit-MA 显示出低抗氧化活性并且不呈现细胞毒性作用。Glu-MA 和 Sucr-MA 具有抗氧化和细胞毒活性，浓度依赖。在甲基丙烯酸酯糖单体的存在下，引物显示出与对照组相当的 DC，除了 Gluc-MA4%、Sucr-MA4% 和 Chit-MA1%，其显示范围为 58.5%DC 的 64.6。所有组的 Rpmax 没有统计学差异（p = 0.01）。Sucr-MA1% 的结合强度从 25.7 (±2.8) 增加到 40.6 (±5. 3) 储存 6 个月后 MPa。所有合成的单体在聚合后都显示出一定的抗菌活性。Gluc-MA 和 Chit-MA 4% 以及 Sucr-MA 1、2 和 4% 导致细菌代谢减少。储存 6 个月后，Sucr-MA 1% 在细菌代谢减少和粘合强度增加方面显示出更好的结果。