Synthesis of polymerizable betulin maleic diester derivative for dental restorative resins with antibacterial activity.
Dent Mater
; 40(6): 941-950, 2024 Jun.
Article
en En
| MEDLINE
| ID: mdl-38719709
ABSTRACT
OBJECTIVE:
Bisphenol A glycidyl methacrylate (Bis-GMA) is of great importance for dental materials as the preferred monomer. However, the presence of bisphenol-A (BPA) core in Bis-GMA structure causes potential concerns since it is associated with endocrine diseases, developmental abnormalities, and cancer lesions. Therefore, it is desirable to develop an alternative replacement for Bis-GMA and explore the intrinsic relationship between monomer structure and resin properties.METHODS:
Here, the betulin maleic diester derivative (MABet) was synthesized by a facile esterification reaction using plant-derived betulin and maleic anhydride as raw materials. Its chemical structure was confirmed by 1H and 13C NMR spectra, FT-IR spectra, and HR-MS, respectively. The as-synthesized MABet was then used as polymerizable comonomer to partially or completely substitute Bis-GMA in a 5050 Bis-GMA TEGDMA resin (5B5T) to formulate dental restorative resins. These were then determined for the viscosity behavior, light transmittance, real-time degree of conversion, residual monomers, mechanical performance, cytotoxicity, and antibacterial activity against Streptococcus mutans (S. mutans) in detail.RESULTS:
Among all experimental resins, increasing the MABet concentration to 50 wt% made the resultant 5MABet5T resin have a maximum in viscosity and appear dark yellowish after polymerization. In contrast, the 1MABet4B5T resin with 10 wt% MABet possessed comparable shear viscosity and polymerization conversion (46.6 ± 1.0% in 60 s), higher flexural and compressive strength (89.7 ± 7.8 MPa; 345.5 ± 14.4 MPa) to those of the 5B5T control (48.5 ± 0.6%; 65.7 ± 6.7 MPa; 223.8 ± 57.1 MPa). This optimal resin also had significantly lower S. mutans colony counts (0.35 ×108 CFU/mL) than 5B5T (7.6 ×108 CFU/mL) without affecting cytocompatibility.SIGNIFICANCE:
Introducing plant-derived polymerizable MABet monomer into dental restorative resins is an effective strategy for producing antibacterial dental materials with superior physicochemical property.Palabras clave
Texto completo:
1
Base de datos:
MEDLINE
Asunto principal:
Streptococcus mutans
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Triterpenos
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Ensayo de Materiales
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Bisfenol A Glicidil Metacrilato
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Antibacterianos
Idioma:
En
Revista:
Dent Mater
Asunto de la revista:
ODONTOLOGIA
Año:
2024
Tipo del documento:
Article
País de afiliación:
China