Methacrylation of epigallocatechin-gallate for covalent attachment with a dental polymer

Autor(es)

Bortolatto, Janaina Freitas ^[1] ; Buzalaf, Marilia Rabelo Afonso ^[1] ; Ebrahimi, Jessica ^[2] ; Floros, Michael Christopher ^[3] ; Ho, Mayhay ^[3] ; Prakki, Anuradha ^[3]

Afiliação do(s) autor(es)

^[1] Univ Sao Paulo, Bauru Sch Dent, Dept Biol Sci, BR-17012901 Sao Paulo - Brazil

^[2] Univ Toronto, Fac Dent, Dept Clin Sci Orthodont Discipline, Toronto, ON M5G 1G6 - Canada

^[3] Univ Toronto, Fac Dent, Dent Res Inst Restorat Discipline, Toronto, ON M5G 1G6 - Canada

• Tipo de documento: Artigo Científico
• Fonte: Dental Materials; v. 37, n. 12, p. 1751-1760, DEC 2021.
• Citações Web of Science: 0

Resumo

Objective. Synthesize novel epigallocatechin-gallate (EGCG) methacrylate monomers with the ability to copolymerize with dental methacrylate resins. Methods. 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 ( = 5%). Two-way ANOVA and Bonferroni were used to investigate factor interaction. Results. 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. Significance. Demonstration of methacrylate functionalized EGCG- with inherited antibacterial activity for improved restoration longevity. (c) 2021 The Academy of Dental Materials. Published by Elsevier Inc. All rights reserved. (AU)

• Processo FAPESP: 17/09827-6 - Síntese de adesivos dentários bioativos para o aumento da longevidade de restaurações
• Beneficiário: Janaína Freitas Bortolatto
• Modalidade de apoio: Bolsas no Brasil - Pós-Doutorado