Enzyme-catalyzed hydrolysis of dentin adhesives containing a new urethane-based trimethacrylate monomer.
A new trimethacrylate monomer with urethane-linked groups, 1,1,1-tri-[4-(methacryloxyethylamino-carbonyloxy)-phenyl]ethane (MPE), was synthesized, characterized, and used as a comonomer in dentin adhesives. Dentin adhesives containing 2-hydroxyethyl methacrylate (HEMA, 45% w/w) and 2,2-bis[4(2-hydroxy-3-methacryloyloxy-propyloxy)-phenyl] propane (BisGMA, 30% w/w) in addition to MPE (25% w/w) were formulated with H(2)O at 0 (MPE0), 8 (MPE8), and 16 wt % water (MPE16) to simulate the wet demineralized dentin matrix and compared with controls [HEMA /BisGMA, 45/55 w/w, at 0 (C0), 8 (C8), and 16 wt % water (C16)]. The new adhesive showed a degree of double bond conversion and mechanical properties comparable with control, with good penetration into the dentin surface and a uniform adhesive/dentin interface. On exposure to porcine liver esterase, the net cumulative methacrylic acid (MAA) released from the new adhesives was dramatically (p < 0.05) decreased relative to the control, suggesting that the new monomer improves esterase resistance.
Park
Jong-Gu
JG
Bioengineering Research Center, School of Engineering, University of Kansas, Lawrence, Kansas 66045.
Ye
Qiang
Q
Bioengineering Research Center, School of Engineering, University of Kansas, Lawrence, Kansas 66045.
Topp
Elizabeth M
EM
Department of Pharmaceutical Chemistry, School of Pharmacy, University of Kansas, Lawrence, Kansas 66047.
Spencer
Paulette
P
Bioengineering Research Center, School of Engineering, University of Kansas, Lawrence, Kansas 66045.|Department of Mechanical Engineering, University of Kansas, Lawrence, Kansas 66045.
D020341:Absorbable Implants; D000180:Acrylic Resins / Q000737:chemistry; D000268:Adhesiveness; D000269:Adhesives / Q000737:chemistry*; D003764:Dental Materials / Q000737:chemistry*; D003804:Dentin / Q000737:chemistry*; D004798:Enzymes / Q000737:chemistry; D004950:Esterases / Q000737:chemistry; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D008422:Materials Testing; D008768:Methylmethacrylates / Q000737:chemistry*; D008855:Microscopy, Electron, Scanning; D013194:Staining and Labeling; D013314:Stress, Mechanical; D014520:Urethane / Q000737:chemistry*
D000180:Acrylic Resins; D000269:Adhesives; D003764:Dental Materials; D004798:Enzymes; D008768:Methylmethacrylates; D014520:Urethane; D004950:Esterases