Utilizing a degradation prediction pathway system to understand how a novel methacrylate derivative polymer with flipped external ester groups retains physico-mechanical properties following esterase exposure

Kumar, Dhiraj; Ghose, Debarati; Mutreja, Isha; Bolskar, Robert D.; Aparicio, Conrado; Jones, Robert S.

doi:10.1016/j.dental.2021.12.008

Cited by 3 publications

(11 citation statements)

References 43 publications

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“…Recent studies demonstrated that EGEMA and EGDMA can photo-polymerized with similar degrees of conversion after 40 second exposure to 385-515 nm high intensity (1000 mW/cm 2 ) light (28,30,31). The two macromers used the same photoinitiator/co-initiators system of CQ/EDMAB/DPIHP.…”

Section: Novel Methacrylate Design and Initial Propertiesmentioning

confidence: 99%

“…Degradation assays examined EGDMA and EGEMA under various aqueous storage conditions. Materials (28,30,31).…”

Section: Degradation Assay Comparisonmentioning

confidence: 99%

“…(EC 3.1.1.13) at 0.5 units/ml concentration in 1x PBS can be used. This CEase has reproducible esterase activity that is measurable with a colorimetric p-nitrophenol acetate assay (31). The CEase model is more severe for materials that contain ester bonds than the temperature accelerated model that examines effects of accelerated water hydrolysis of ester bonds.…”

Section: Degradation Assay Comparisonmentioning

confidence: 99%

“…These measurements supported the hypothesis that polymer backbone preservation occurred in EGEMA polymerization. To test the degradation chemical reactions in EGDMA and EGEMA, the 37 • C buffer and CEase assay storage solutions were analyzed for degradation by-products with liquid/gas chromatography (LC/GC)/mass spectroscopy (MS) (31).…”

Section: Degradation Pathwaysmentioning

confidence: 99%

“…The molar mass of predicted degradation by-products could be compared to LC/GC-MS experimental results. Further details into the methodology of this approach are found elsewhere (31).…”

Section: Degradation Pathwaysmentioning

confidence: 99%

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Methacrylate Polymers With “Flipped External” Ester Groups: A Review

et al. 2022

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Current resin composites have favorable handling and upon polymerization initial physical properties that allow for efficient material replacement of removed carious tooth structure. Dental resin composites have long term durability limitations due to the hydrolysis of ester bonds within the methacrylate based polymer matrix. This article outlines the importance of ester bonds positioned internal to the carbon-carbon double bond in current methacrylate monomers. Water and promiscuous salivary/bacterial esterase activity can initiate ester bond hydrolysis that can sever the polymer backbone throughout the material. Recent studies have custom synthesized, with the latest advances in modern organic chemical synthesis, a novel molecule named ethylene glycol bis (ethyl methacrylate) (EGEMA). EGEMA was designed to retain the reactive acrylate units. Upon intermolecular polymerization of vinyl groups, EGEMA ester groups are positioned outside the backbone of the polymer chain. This review highlights investigation into the degradation resistance of EGEMA using buffer, esterase, and microbial storage assays. Material samples of EGEMA had superior final physical and mechanical properties than traditional ethylene glycol dimethacrylate (EGDMA) in all degradation assays. Integrating bioinformatics-based biodegradation predictions to the experimental results of storage media analyzed by LC/GC-MS revealed that hydrolysis of EGEMA generated small amounts of ethanol while preserving the strength bearing polymer backbone. Prior studies support investigation into additional custom synthesized methacrylate polymers with “flipped external” ester groups. The long term goal is to improve clinical durability compared to current methacrylates while retaining inherent advantages of acrylic based chemistry, which may ease implementation of these novel methacrylates into clinical practice.

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Section: Novel Methacrylate Design and Initial Propertiesmentioning

confidence: 99%

“…Degradation assays examined EGDMA and EGEMA under various aqueous storage conditions. Materials (28,30,31).…”

Section: Degradation Assay Comparisonmentioning

confidence: 99%

Section: Degradation Assay Comparisonmentioning

confidence: 99%

Section: Degradation Pathwaysmentioning

confidence: 99%

“…The molar mass of predicted degradation by-products could be compared to LC/GC-MS experimental results. Further details into the methodology of this approach are found elsewhere (31).…”

Section: Degradation Pathwaysmentioning

confidence: 99%

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Methacrylate Polymers With “Flipped External” Ester Groups: A Review

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Lipid nanoparticle-based formulations for high-performance dentistry applications

et al. 2023

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Comparative Assessment of Different Pre-Treatment Bonding Strategies to Improve the Adhesion of Self-Adhesive Composites to Dentin

et al. 2022

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The aim of this study is to compare the adhesive interface formed in dentin, using self-adhesive composites applied with different bonding strategies, by testing the microtensile bond strength (μTBS) and ultramorphology through the use of light microscopy. Permanent, sound human molars were randomly allocated to six experimental groups. The groups included a negative control group, where only etching was performed via EtchOnly; a positive control group where an adhesive was applied, OptiBondFL (OBFL); and an experimental group where a primer was applied using a co-curing strategy together with a composite (Primer_CoCuring). The samples were sectioned into microspecimens for μTBS (n = 8) and into 1-mm thick slabs for light microscopy using Masson’s trichrome staining protocol (n = 3). The statistical analysis included a two-way ANOVA for μTBS data and Tukey’s HSD was used as a post-hoc test (significance level of 5%; SPSS v. 26.0). The results of the μTBS revealed that the self-adhesive composite (F = 6.0, p < 0.018) and the bonding strategy (F = 444.1, p < 0.001) significantly affected the bond strength to dentin. However, their interactions were not significant (F = 1.2, p = 0.29). Etching dentin with no additional treatment revealed the lowest μTBS (VF_EtchOnly = 2.4 ± 0.8 MPa; CC_EtchOnly = 2.0 ± 0.4 MPa), which was significantly different from using a primer (VF_CoCu = 8.8 ± 0.8 MPa; CC_CoCu = 6.3 ± 1.0 MPa) or using the full adhesive (VF_OptiBondFL = 22.4 ± 0.3 MPa; CC_OptibondFL = 21.2 ± 0.4 MPa). Microscopy images revealed that the experimental Primer_CoCuring was the only group with no collagen fibers exposed to the dentin–composite interface. Overall, the use of a primer, within the limitations of this study, increased the bonding of the self-adhesive composite and provided sufficient infiltration of the collagen based on light-microscopic imaging.

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Utilizing a degradation prediction pathway system to understand how a novel methacrylate derivative polymer with flipped external ester groups retains physico-mechanical properties following esterase exposure

Cited by 3 publications

References 43 publications

Methacrylate Polymers With “Flipped External” Ester Groups: A Review

Methacrylate Polymers With “Flipped External” Ester Groups: A Review

Lipid nanoparticle-based formulations for high-performance dentistry applications

Comparative Assessment of Different Pre-Treatment Bonding Strategies to Improve the Adhesion of Self-Adhesive Composites to Dentin

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