Methacrylate saccharide-based monomers for dental adhesive systems

Andressa dos Santos, Carolina B. André, Gedalias C. Martim, Ivania T.A. Schuquel, Carmem Pfeifer, Jack Ferracane, Tania T. Tominaga, Najeh M. Khalil, Eduardo Radovanovic, Emerson M. Girotto

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

The aim of this in vitro study was to synthesize three new methacrylate monomers based on the modification of saccharides structures (glucose-Gluc, sucrose-Sucr and chitosan-Chit) with glycidyl methacrylate, and to use them in the composition of dental adhesives. Three methacrylate saccharide monomers were synthesized and characterized by mid-IR, 1H and 13C NMR, antioxidant activity and cytotoxic effect. Monomers included: one monosaccharide – Gluc-MA; one disaccharide – Sucr-MA; and one polysaccharide – Chit-MA. Primers containing HEMA, methacrylate saccharide monomers at concentrations of 0 (control), 1, 2 or 4 wt%, 60 wt% ethanol aqueous solution (pH3.0) and initiator system were formulated. Primers were used in conjunction with a bond step and composite paste to restore caries-free third molars, and dentin bond strength (24 h and 6 month of storage in water), and antimicrobial activity (Alamar Blue test) were tested. Degree of conversion (DC) and maximum rate of polymerization (Rpmax) of the primers themselves were also analyzed. The mid-IR, 1H and 13C spectrum confirmed the presence of vinyl group on the structure of saccharides. Chit-MA showed low antioxidant activity and did not present a cytotoxic effect. Gluc-MA and Sucr-MA possess antioxidant and cytotoxic activity, concentration dependent. In the presence of methacrylate saccharide monomers, the primers showed DC comparable to the control group, except Gluc-MA4%, Sucr-MA4% and Chit-MA1%, which showed a range of 64.6 from 58.5%DC. Rpmax was not statistically different for all the groups (p = 0.01). The bond strength of Sucr-MA1% increased from 25.7 (± 2.8) to 40.6 (± 5.3) MPa after 6 months of storage. All the synthesized monomers showed some antimicrobial activity after polymerization. Gluc-MA and Chit-MA 4% and Sucr-MA 1, 2 and 4% led to decrease bacterial metabolism. Sucr-MA 1% showed better results regarding the decrease in bacterial metabolism and increasing the bond strength after 6 months of storage.

Original languageEnglish (US)
Pages (from-to)1-11
Number of pages11
JournalInternational Journal of Adhesion and Adhesives
Volume87
DOIs
StatePublished - Dec 1 2018

Fingerprint

Dental Cements
Methacrylates
Adhesives
Monomers
Antioxidants
Metabolism
Polymerization
Adhesive pastes
Monosaccharides
Disaccharides
Chitosan
Sugar (sucrose)
Polysaccharides
Ointments
Glucose
Sucrose
Ethanol
Nuclear magnetic resonance
Water
Composite materials

Keywords

  • Antibacterial adhesives
  • Dentine
  • Mechanical properties of adhesives
  • Nuclear magnetic resonance spectroscopy

ASJC Scopus subject areas

  • Biomaterials
  • Chemical Engineering(all)
  • Polymers and Plastics

Cite this

Methacrylate saccharide-based monomers for dental adhesive systems. / dos Santos, Andressa; André, Carolina B.; Martim, Gedalias C.; Schuquel, Ivania T.A.; Pfeifer, Carmem; Ferracane, Jack; Tominaga, Tania T.; Khalil, Najeh M.; Radovanovic, Eduardo; Girotto, Emerson M.

In: International Journal of Adhesion and Adhesives, Vol. 87, 01.12.2018, p. 1-11.

Research output: Contribution to journalArticle

dos Santos, A, André, CB, Martim, GC, Schuquel, ITA, Pfeifer, C, Ferracane, J, Tominaga, TT, Khalil, NM, Radovanovic, E & Girotto, EM 2018, 'Methacrylate saccharide-based monomers for dental adhesive systems', International Journal of Adhesion and Adhesives, vol. 87, pp. 1-11. https://doi.org/10.1016/j.ijadhadh.2018.09.009
dos Santos, Andressa ; André, Carolina B. ; Martim, Gedalias C. ; Schuquel, Ivania T.A. ; Pfeifer, Carmem ; Ferracane, Jack ; Tominaga, Tania T. ; Khalil, Najeh M. ; Radovanovic, Eduardo ; Girotto, Emerson M. / Methacrylate saccharide-based monomers for dental adhesive systems. In: International Journal of Adhesion and Adhesives. 2018 ; Vol. 87. pp. 1-11.
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AU - Martim, Gedalias C.

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AU - Pfeifer, Carmem

AU - Ferracane, Jack

AU - Tominaga, Tania T.

AU - Khalil, Najeh M.

AU - Radovanovic, Eduardo

AU - Girotto, Emerson M.

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N2 - The aim of this in vitro study was to synthesize three new methacrylate monomers based on the modification of saccharides structures (glucose-Gluc, sucrose-Sucr and chitosan-Chit) with glycidyl methacrylate, and to use them in the composition of dental adhesives. Three methacrylate saccharide monomers were synthesized and characterized by mid-IR, 1H and 13C NMR, antioxidant activity and cytotoxic effect. Monomers included: one monosaccharide – Gluc-MA; one disaccharide – Sucr-MA; and one polysaccharide – Chit-MA. Primers containing HEMA, methacrylate saccharide monomers at concentrations of 0 (control), 1, 2 or 4 wt%, 60 wt% ethanol aqueous solution (pH3.0) and initiator system were formulated. Primers were used in conjunction with a bond step and composite paste to restore caries-free third molars, and dentin bond strength (24 h and 6 month of storage in water), and antimicrobial activity (Alamar Blue test) were tested. Degree of conversion (DC) and maximum rate of polymerization (Rpmax) of the primers themselves were also analyzed. The mid-IR, 1H and 13C spectrum confirmed the presence of vinyl group on the structure of saccharides. Chit-MA showed low antioxidant activity and did not present a cytotoxic effect. Gluc-MA and Sucr-MA possess antioxidant and cytotoxic activity, concentration dependent. In the presence of methacrylate saccharide monomers, the primers showed DC comparable to the control group, except Gluc-MA4%, Sucr-MA4% and Chit-MA1%, which showed a range of 64.6 from 58.5%DC. Rpmax was not statistically different for all the groups (p = 0.01). The bond strength of Sucr-MA1% increased from 25.7 (± 2.8) to 40.6 (± 5.3) MPa after 6 months of storage. All the synthesized monomers showed some antimicrobial activity after polymerization. Gluc-MA and Chit-MA 4% and Sucr-MA 1, 2 and 4% led to decrease bacterial metabolism. Sucr-MA 1% showed better results regarding the decrease in bacterial metabolism and increasing the bond strength after 6 months of storage.

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