Bis[2-(Methacryloyloxy) Ethyl] Phosphate as a Primer for Enamel and Dentine

Abstract

Dental resin composites are commonly used in the restorative management of teeth via adhesive bonding, which has evolved significantly over the past few decades. Although current self-etch bonding systems decrease the number of clinical steps, the acidic functional monomers employed exhibit a limited extent of demineralization of enamel in comparison to phosphoric acid etchants, and the resultant superficial ionic interactions are prone to hydrolysis. This study evaluates the etching of primers constituted with bis[2-(methacryloyloxy) ethyl] phosphate (BMEP) of dental hard tissue, interfacial characteristics, and inhibition of endogenous enzymes. We examine the incorporation of 2 concentrations of BMEP in the formulation of experimental primers used with a hydrophobic adhesive to constitute a 2-step self-etching bonding system and compare to a commercial 10–methacryloyloxydecyl dihydrogen phosphate (10-MDP)–containing system. The interaction of the primer with enamel and dentine was characterized using scanning electron, confocal laser scanning, and Raman microscopy while the polymerization reaction between the BMEP primers and hydroxyapatite was evaluated by Fourier-transform infrared spectroscopy. The inhibitory effect against matrix metalloproteinase (MMP) enzymes of these primers was studied and percentage of inhibition analyzed using 1-way analysis of variance and Tukey’s post hoc test ( P < 0.05). Results of the scanning electron microscopy micrographs demonstrated potent etching of both enamel and dentine with the formation of longer resin tags with BMEP primers compared to the 10-MDP–based system. The BMEP polymerized on interaction with pure hydroxyapatite in the dark, while the 10-MDP primer exhibited the formation of salts. Furthermore, BMEP primers were able to inhibit MMP activity in a dose-dependent manner. BMEP could be used as a self-etching primer on enamel and dentine, and the high degree of polymerization in the presence of hydroxyapatite can contribute to an increased quality of the resin polymer network, prompting resistance to gelatinolytic and collagenolytic degradation.

In Search of Novel Degradation-Resistant Monomers for Adhesive Dentistry: A Systematic Review and Meta-Analysis

“…In the study by Alkattan et al in 2022, they reported the use of a multi-functional adhesive system with an experimental primer incorporating BMEP [ 44 ] and an adhesive containing EgMA in the formulation of a two-step self-etch system in order to provide an adhesive with long-lasting antibacterial activity that is chemically stable [ 31 ].…”

Interface between Materials and Oral Biology

“…Several articles investigate bacterial adhesion to material surfaces and novel compositions and surface preparation techniques designed to modulate oral biofilm formation (Balhaddad et al, 2021; Lehnfeld et al, 2021; Thongthai et al, 2021). Securing durable adhesion to tooth surfaces using strategies that modify and/or chemically interact with components in the dentin surface is discussed in 3 articles (Alkattan et al, 2021; Cai et al, 2021; Maravic et al, 2021). Biomineralization mechanisms and arrest of carious lesions are explained (Sulyanto et al, 2021).…”