Methacrylation of epigallocatechin-gallate for covalent attachment with a dental polymer.
Dent Mater
; 37(12): 1751-1760, 2021 12.
Article
em En
| MEDLINE
| ID: mdl-34565584
ABSTRACT
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 (α=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.Palavras-chave
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Polímeros
/
Streptococcus mutans
Idioma:
En
Revista:
Dent Mater
Assunto da revista:
ODONTOLOGIA
Ano de publicação:
2021
Tipo de documento:
Article
País de afiliação:
Brasil