New acid BisGMA analogs for dental adhesive applications with antimicrobial activity.
To achieve bisphenol A glycerolate dimethacrylate (BisGMA) analogs with reduced viscosity to be used in the formulation of dental adhesives containing biocidal components.



A series of low-viscosity BisGMA derivatives (η: 39-12Pas) modified with 30, 60 and, respectively 80mol% carboxylic acid units were synthesized and characterized. Hydrogen bonding interactions in our monomers, the photopolymerization behavior and implicitly the conversion degree (DC) for some experimental adhesive formulations containing acid-modified BisGMA, commercial BisGMA (only in F1-F3), triethyleneglycol dimethacrylate and 2-hydroxyethyl methacrylate were examined by FTIR spectroscopy. The water effects on the photocrosslinked networks together with the flexural strength/modulus were also investigated. The adhesive penetration into the dentin surface was surveyed by SEM analysis, and the antimicrobial activity triggered by the incorporation of 0.5wt% AgNO3, 10wt% zinc methacrylate or 1wt% triclosan methacrylate in selected adhesive formulations on the growth of Streptococcus mutans and Candida albicans strains was evidenced.



The contribution of the hydrogen bonding interactions was found to be lower in BisGMA derivatives than in non-modified BisGMA, and the DC varied between 56.5 (F6) and 83.7% (F1) compared with a control formulation based on BisGMA:TEGDMA (DC=58.2%). The flexural strength and flexural modulus varied in the range 33.7MPa (F6)-54.4MPa (F8)MPa and 0.64 (F6)-1.43 (F8)GPa, respectively. SEM observation of adhesive-dentin interface revealed the formation of resin tags for the carboxyl-containing adhesive, while for the control adhesive they are hardly formed. Also, the microorganism development was inhibited, the proposed materials displaying antimicrobial activity.



The experimental formulations based on carboxyl-functionalized BisGMA exhibit a similar or even improved behavior over control sample, suggesting their potential applicability as antimicrobial dental adhesives.
Polyaddition and Photochemistry Department, Petru Poni Institute of Macromolecular Chemistry, 41 A Gr. Ghica Voda Alley, 700487 Iasi, Romania.
Violeta
V
Melinte
Polyaddition and Photochemistry Department, Petru Poni Institute of Macromolecular Chemistry, 41 A Gr. Ghica Voda Alley, 700487 Iasi, Romania. Electronic address: tbur@icmpp.ro.
Tinca
T
Buruiana
Polyaddition and Photochemistry Department, Petru Poni Institute of Macromolecular Chemistry, 41 A Gr. Ghica Voda Alley, 700487 Iasi, Romania.
Andreea
A
Chibac
Laboratory of Antimicrobial Chemotherapy, "Ion Ionescu de la Brad" University, 8 Sadoveanu Alley, 700489 Iasi, Romania.
Mihai
M
Mares
Dental Office, 17 T. Vladimirescu Street, Iasi, Romania.
Horia
H
Aldea
Polyaddition and Photochemistry Department, Petru Poni Institute of Macromolecular Chemistry, 41 A Gr. Ghica Voda Alley, 700487 Iasi, Romania.
Emil C
EC
Buruiana
D000890:Anti-Infective Agents; D017438:Bisphenol A-Glycidyl Methacrylate; D003738:Dental Cements; D008422:Materials Testing; D008689:Methacrylates
D000890:Anti-Infective Agents; D003738:Dental Cements; D008689:Methacrylates; D017438:Bisphenol A-Glycidyl Methacrylate; C005044:hydroxyethyl methacrylate
Antimicrobial activity; Carboxyl-functionalized BisGMA; Dental adhesive; Photopolymerization