We investigated the enamel demineralization-prevention ability and shear bond strength (SBS) properties of 4-methacryloxyethyl trimellitic anhydride/methyl methacrylate-tri-n-butyl borane (4-META/MMA-TBB)-based resin containing various amounts (0-50%) of bioactive glass (BG). Disk-shaped specimens were immersed in distilled water and ions released were analysed by inductively coupled plasma atomic-emission spectroscopy. Samples were also immersed in lactic acid solution (pH 4.6) to estimate acid-neutralizing ability. Brackets were bonded to human premolars with BG-containing resins and the bonded teeth were alternately immersed in demineralizing (pH 4.55) and remineralizing (pH 6.8) solutions for 14d. The enamel hardness was determined by nanoindentation testing at twenty equidistant distances from the external surface. The SBS for each sample was examined. The amounts of ions released [calcium (Ca), sodium (Na), silicon (Si), and boron (B)] and the acid-neutralizing ability increased with increasing BG content. After alternating immersion, the specimens bonded with the BG-containing resin with high BG content were harder than those in the other groups in some locations 1-18.5m from the enamel surface. Bioactive glass-containing (10-40%) resin had bond strength equivalent to the control specimen. Thus, the SBS obtained for BG-containing resin (6.5-9.2MPa) was clinically acceptable, suggesting that this material has the ability to prevent enamel demineralization.