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

R. Alkattan; G. Koller; S. Banerji; S. Deb

doi:10.1177/00220345211023477

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

R. Alkattan, G. Koller, S. Banerji, S. Deb^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

5 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1081-1089
Number of pages	9
Journal	Journal of Dental Research
Volume	100
Issue number	10
DOIs	https://doi.org/10.1177/00220345211023477
Publication status	Published - Sept 2021

Keywords

adhesives
dental bonding
dental etching
matrix metalloproteinases
phosphoric acid esters
polymerization

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10.1177/00220345211023477

Cite this

@article{cc0049b6715a49b7bb23272f92080479,

title = "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{\textquoteright}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.",

keywords = "adhesives, dental bonding, dental etching, matrix metalloproteinases, phosphoric acid esters, polymerization",

author = "R. Alkattan and G. Koller and S. Banerji and S. Deb",

note = "Funding Information: The authors thank the Nikon Imaging Centre at King?s College London for help with light microscopy. The authors disclosed receipt of the following financial support for the research, authorship, and/or publication of this article: This study was supported by the Saudi Arabian Cultural Bureau in the United Kingdom. Funding Information: The authors disclosed receipt of the following financial support for the research, authorship, and/or publication of this article: This study was supported by the Saudi Arabian Cultural Bureau in the United Kingdom. Publisher Copyright: {\textcopyright} International & American Associations for Dental Research 2021. Copyright: Copyright 2021 Elsevier B.V., All rights reserved.",

year = "2021",

month = sep,

doi = "10.1177/00220345211023477",

language = "English",

volume = "100",

pages = "1081--1089",

journal = "Journal of Dental Research",

issn = "0022-0345",

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T1 - Bis[2-(Methacryloyloxy) Ethyl] Phosphate as a Primer for Enamel and Dentine

AU - Alkattan, R.

AU - Koller, G.

AU - Banerji, S.

AU - Deb, S.

N1 - Funding Information: The authors thank the Nikon Imaging Centre at King?s College London for help with light microscopy. The authors disclosed receipt of the following financial support for the research, authorship, and/or publication of this article: This study was supported by the Saudi Arabian Cultural Bureau in the United Kingdom. Funding Information: The authors disclosed receipt of the following financial support for the research, authorship, and/or publication of this article: This study was supported by the Saudi Arabian Cultural Bureau in the United Kingdom. Publisher Copyright: © International & American Associations for Dental Research 2021. Copyright: Copyright 2021 Elsevier B.V., All rights reserved.

PY - 2021/9

Y1 - 2021/9

N2 - 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.

AB - 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.

KW - adhesives

KW - dental bonding

KW - dental etching

KW - matrix metalloproteinases

KW - phosphoric acid esters

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

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