Methacrylate saccharide-based monomers for dental adhesive systems. (December 2018)

• Record Type: Journal Article
• Authors: dos Santos, Andressa; André, Carolina B.; Martim, Gedalias C.; Schuquel, Ivania T.A.; Pfeifer, Carmem S.; Ferracane, Jack L.; Tominaga, Tania T.; Khalil, Najeh M.; Radovanovic, Eduardo; Girotto, Emerson M.
• Is Part Of: International journal of adhesion & adhesives. Volume 87(2018)
• Page Start: 1
• Page End: 11
• Publication Date: 2018-12
• Subjects: Antibacterial adhesives -- Dentine -- Nuclear magnetic resonance spectroscopy -- Mechanical properties of adhesives; Adhesion -- Periodicals; Adhesives -- Periodicals; Adhésion (Physique) -- Périodiques; Adhésifs -- Périodiques; Adhesie; Kleefstoffen; Adhesion; Adhesives; Periodicals; 668.3
• DOI: 10.1016/j.ijadhadh.2018.09.009
• Languages: English
• ISSNs: 0143-7496

Abstract

Abstract: 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, 1 H and 13 C NMR, antioxidant activity and cytotoxic effect. Monomers included: one monosaccharide – Gluc-MA; one disaccharide – Sucr-MA; and one polysaccharide – Chit-MA. Primer s 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 h 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, 1 H and 13 C 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.