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1.
J Nat Prod ; 83(11): 3287-3297, 2020 Nov 25.
Artículo en Inglés | MEDLINE | ID: mdl-33151073

RESUMEN

The present study elucidated the structures of three A-type tri- and tetrameric proanthocyanidins (PACs) isolated from Cinnamomum verum bark to the level of absolute configuration and determined their dental bioactivity using two therapeutically relevant bioassays. After selecting a PAC oligomer fraction via a biologically diverse bioassay-guided process, in tandem with centrifugal partition chromatography, phytochemical studies led to the isolation of PAC oligomers that represent the main bioactive principles of C. verum: two A-type tetrameric PACs, epicatechin-(2ß→O→7,4ß→8)-epicatechin-(4ß→6)-epicatechin-(2ß→O→7,4ß→8)-catechin (1) and parameritannin A1 (2), together with a trimer, cinnamtannin B1 (3). Structure determination of the underivatized proanthocyanidins utilized a combination of HRESIMS, ECD, 1D/2D NMR, and 1H iterative full spin analysis data and led to NMR-based evidence for the deduction of absolute configuration in constituent catechin and epicatechin monomeric units.

2.
J Am Dent Assoc ; 151(10): 796-797.e2, 2020 Oct.
Artículo en Inglés | MEDLINE | ID: mdl-32979959

RESUMEN

BACKGROUND: Bonding crowns and bridges with resin cement can improve retention and reinforcement of the restoration. However, there is variation in the steps taken by different practitioners to achieve this goal. METHODS: The authors developed a survey on bonding dental crowns and bridges with resin cement and distributed it electronically to the American Dental Association Clinical Evaluators (ACE) Panel on May 22, 2020. The survey remained open for 2 weeks. Descriptive data analysis was conducted using SAS Version 9.4. RESULTS: A total of 326 panelists responded to the survey, and 86% of respondents who place crowns or bridges use resin cements for bonding. When placing a lithium disilicate restoration, an almost equal proportion of respondents etch it with hydrofluoric acid in their office or asked the laboratory to do it for them, and more than two-thirds use a silane primer before bonding. For zirconia restorations, 70% reported their restorations are sandblasted in the laboratory, and 39% use a primer containing 10-methacryloyloxydecyl dihydrogen phosphate. One-half of respondents clean their lithium disilicate or zirconia restorations with a cleaning solution. Resin cements used with a primer in the etch-and-rinse mode are the most widely used. The technique used to cure and clean excess resin cement varies among respondents. CONCLUSIONS: The types of resin cements used, tooth preparation, crown or bridge preparation, and bonding technique vary among this sample. PRACTICAL IMPLICATIONS: Although many dentists bond crowns and bridges on the basis of best practices, improvement in the process may be achieved by dentists communicating with their laboratory to confirm the steps performed there, ensuring an effective cleaning technique is used after try-in and verifying that the correct primer is used with their chosen restorative material.


Asunto(s)
Recubrimiento Dental Adhesivo , Cementos de Resina , American Dental Association , Coronas , Cementos Dentales , Materiales Dentales , Porcelana Dental , Análisis del Estrés Dental , Humanos , Ensayo de Materiales , Propiedades de Superficie , Encuestas y Cuestionarios , Estados Unidos
3.
Dent Mater ; 36(10): e302-e308, 2020 10.
Artículo en Inglés | MEDLINE | ID: mdl-32811665

RESUMEN

OBJECTIVES: To investigate the role of proteoglycans (PGs) on the physical properties of the dentin matrix and the bond strength of methacrylate resins with varying hydrophilicities. METHODS: Dentin were obtained from crowns of human molars. Enzymatic removal of PGs followed a standard protocol using 1 mg/mL trypsin (Try) for 24 h. Controls were incubated in ammonium bicarbonate buffer. Removal of PGs was assessed by visualization of glycosaminoglycan chains (GAGs) in dentin under transmission electron microscopy (TEM). The dentin matrix swelling ratio was estimated using fully demineralized dentin. Dentin wettability was assessed on wet, dry and re-wetted dentin surfaces through water contact angle measurements. Microtensile bond strength test (TBS) was performed with experimental adhesives containing 6% HEMA (H6) and 18% HEMA (H18) and a commercial dental adhesive. Data were statistically analyzed using ANOVA and post-hoc tests (α = 0.05). RESULTS: The enzymatic removal of PGs was confirmed by the absence and fragmentation of GAGs. There was statistically significant difference between the swelling ratio of Try-treated and control dentin (p < 0.001). Significantly lower contact angle was found for Try-treated on wet and dry dentin (p < 0.002). The contact angle on re-wet dentin was not recovered in Try-treated group (p = 0.9). Removal of PGs significantly improved the TBS of H6 (109% higher, p < 0.001) and H18 (29% higher, p = 0.002) when compared to control. The TBS of commercial adhesive was not affected by trypsin treatment (p = 0.9). SIGNIFICANCE: Changing the surface energy of dentin by PGs removal improved resin adhesion, likely due to more efficient water displacement, aiding to improved resin infiltration and polymerization.

4.
J Adhes Dent ; 22(3): 285-296, 2020.
Artículo en Inglés | MEDLINE | ID: mdl-32435769

RESUMEN

PURPOSE: To investigate the long-term effect of 0.05% or 0.1% caffeic acid phenethyl ester (CAPE) on dentin matrix stability and hybrid layer stability, using an etch-and-rinse (Adper Scotchbond Multipurpose/ASB) or a self-etch adhesive (Clearfil SE Bond/CSE). MATERIALS AND METHODS: Dentin matrix specimens were assigned to five groups: 0.05% or 0.1% CAPE, green tea (GT), and the controls distilled water (DW) and dimethyl sulfoxide (DMSO). Following immersion of specimens for 1 h, modulus of elasticity (ME) and dentin mass change (MG) were determined at 3 post-treatment time points: immediately afterwards and at 3 and 6 months. Collagen solubilization (CS) was estimated by hydroxyproline (HYP) quantification. Resin-dentin interfaces with both adhesives were assessed with in situ zymography tests to evaluate gelatinolytic activity (GA). The dentin pretreatments were actively applied for 60 s. The sealing ability of aged resin-bonded slices was assessed by nanoleakage tests. RESULTS: GT increased immediate ME, which decreased significantly after 3 months (p < 0.0001). The CAPE groups did not differ from the control groups. GT provided a significant increase in dentin matrix mass after treatment (p < 0.0001). No significant differences regarding MG were observed for CAPE 0.1%, CAPE 0.05%, DW, and DMSO groups after 3 and 6 months. Cumulative HYP release revealed that CAPE groups and GT were statistically similar to DW and DMSO; the GT group exhibited statistically significantly less HYP release than did CAPE groups (p = 0.0073). Treatment with 0.05% or 0.1% CAPE presented lower GA when applied to ASB before acid conditioning (p < 0.05), but no differences were detected when the CAPE groups were applied to CSE. CAPE at 0.1% significantly reduced nanoleakage for CSE, and 0.05% CAPE with CSE presented levels of nanoleakage similar to those of the CSE control group. CONCLUSION: CAPE at 0.05% or 0.01% did not influence ME, MG, or CS, but reduced GA when applied to ASB before acid conditioning. CAPE at 0.1% with CSE promoted adhesive layer integrity.


Asunto(s)
Recubrimiento Dental Adhesivo , Recubrimientos Dentinarios , Ácidos Cafeicos , Cementos Dentales , Dentina , Ensayo de Materiales , Alcohol Feniletílico/análogos & derivados , Resistencia a la Tracción
5.
J Nat Prod ; 82(9): 2387-2399, 2019 09 27.
Artículo en Inglés | MEDLINE | ID: mdl-31433178

RESUMEN

Aimed at exploring the dentin biomodification potential of proanthocyanidins (PACs) for the development of dental biomaterials, this study reports the phytochemical and dental evaluation of nine B-type PACs from grape seed extract (GSE). Out of seven isolated dimers (1-7), four new compounds (2, 3, 5, and 6) involved relatively rare ent-catechin or ent-epicatechin monomeric flavan-3-ol units. Low-temperature NMR analyses conducted along with phloroglucinolysis and electronic circular dichroism enabled unequivocal structural characterization and stereochemical assignment. Additionally, one known (8) and one new (9) B-type trimer were characterized. Differential 13C NMR chemical shifts (Δδ) were used to determine the absolute configuration of 9, relative to the dimers 1 and 2 as the possible constituent subunits. Compared to the dimers, the trimers showed superior dentin biomodification properties. The dimers, 1-7, exhibited pronounced differences in their collagenase inhibitory activity, while enhancing dentin stiffness comparably. This suggests that PAC structural features such as the degree of polymerization, relative and absolute configuration have a differential influence on enhancement of dentin biomechanical and biostability. As mechanical enhancement to dentin and resistance to proteolytic biodegradation are both essential properties functional and stable dentin substrate, the structurally closely related PACs suggest a new metric, the dentin biomodification potential (DBMP) that may rationalize both properties.


Asunto(s)
Biopolímeros/química , Biotina/química , Proantocianidinas/química
6.
Dent Mater ; 35(10): 1471-1478, 2019 10.
Artículo en Inglés | MEDLINE | ID: mdl-31405618

RESUMEN

OBJECTIVE: This study investigated the effects of dentin pretreatment with 2.5% titanium tetrafluoride (TiF4) on nanomechanical properties, and the in situ gelatinolytic activity of the dentin-resin interface, for up to 6 months. METHODS: Twenty-four human teeth were prepared by exposing occlusal flat dentin surfaces, and were randomly assigned to experimental groups, according to application or non-application of a TiF4 pretreatment, and to the adhesive systems (Clearfil SE Bond or Scotchbond Universal). Resin composite (Filtek Supreme Ultra) was built up incrementally on the teeth in all the groups. Then, the specimens were sectioned and randomly selected for evaluation at 24h, 3 months and 6 months of storage time. The reduced modulus of elasticity (Er) and the nanohardness of the underlying dentin, as well as the hybrid layer and the adhesive layer were measured using a nanoindenter. Gelatinolytic activity at the dentin-resin interfaces was assessed by in situ zymography using quenched fluorescein-conjugated gelatin at 24h and 6 months. Statistical analyses were performed with ANOVA and Tukey's tests. RESULTS: There were no differences in Er and nanohardness values between adhesives systems and pretreatment (p=0.1250). In situ zymography showed significantly higher gelatinolytic activity after 6 months for all the experimental groups (p=0.0004), but no differences between the adhesive systems (p=0.7708) and the surface pretreatment (p=0.4877). SIGNIFICANCE: Dentin pretreatment with 2.5% TiF4 followed by self-etching adhesive systems did not influence nanomechanical properties or gelatinolytic activity of the adhesive-dentin interface layers, over time.


Asunto(s)
Recubrimiento Dental Adhesivo , Recubrimientos Dentinarios , Resinas Compuestas , Cementos Dentales , Dentina , Fluoruros , Humanos , Ensayo de Materiales , Cementos de Resina , Propiedades de Superficie , Resistencia a la Tracción , Titanio
7.
Dent Mater ; 35(2): 328-334, 2019 02.
Artículo en Inglés | MEDLINE | ID: mdl-30580969

RESUMEN

OBJECTIVES: The interactivity of proanthocyanidins (PACs) with collagen modulates dentin matrix biomechanics and biostability. Herein, PAC extracts selected based on structural diversity were investigated to determine key PAC features driving sustained effects on dentin matrices over a period of 18months. METHODS: The chemical profiles of PAC-rich plant sources, Pinus massoniana (PM), Cinnamomum verum (CV) and Hamamelis virginiana (HV) barks, as well as Vitis vinifera (VV) seeds, were obtained by diol HPLC analysis after partitioning of the extracts between methyl acetate and water. Dentin matrices (n=15) were prepared from human molars to determine the apparent modulus of elasticity over 18months of aging. Susceptibility of the dentin matrix to degradation by endogenous and exogenous proteases was determined by presence of solubilized collagen in supernatant, and resistance to degradation by bacterial collagenase, respectively. Data were analyzed using ANOVA and Games-Howell post hoc tests (α=0.05). RESULTS: After 18months, dentin matrices modified by PM and CV extracts, containing only non-galloylated PACs, were highly stable mechanically (p<0.05). Dentin matrices treated with CV exhibited the lowest degradation by bacterial collagenase after 1h and 18months of aging (p<0.05), while dentin matrices treated with PM showed the least mass loss and collagen solubilization by endogenous enzymes over time (p<0.05). SIGNIFICANCE: Resistance against long-term degradation was observed for all experimental groups; however, the most potent and long-lasting dentin biomodification resulted from non-galloylated PACs.


Asunto(s)
Proantocianidinas , Cromatografía Líquida de Alta Presión , Colágeno , Colagenasas , Dentina , Humanos
8.
Dent Clin North Am ; 61(4): 713-731, 2017 10.
Artículo en Inglés | MEDLINE | ID: mdl-28886765

RESUMEN

From the conception of resin-enamel adhesion to today's contemporary dental adhesive systems, clinicians are no longer afraid of exploring the many advantages brought by adhesive restorative concepts. To maximize the performance of adhesive-based restorative procedures, practitioners must be familiar with the mechanism of adhesion, clinical indications, proper handling, the inherent limitations of the materials and the biological challenges. This review provides an overview of the current status of restorative dental adhesives, their mechanism of adhesion, mechanisms of degradation of dental adhesive interfaces, how to maximize performance, and future trends in adhesive dentistry.


Asunto(s)
Recubrimiento Dental Adhesivo/métodos , Cementos Dentales/uso terapéutico , Biopelículas , Dentina/metabolismo , Recubrimientos Dentinarios/uso terapéutico , Humanos , Propiedades de Superficie
9.
Arch Oral Biol ; 82: 203-208, 2017 Oct.
Artículo en Inglés | MEDLINE | ID: mdl-28651092

RESUMEN

OBJECTIVE: Proteoglycans (PGs) are multifunctional biomacromolecules of the extracellular matrix of collagen-based tissues. In teeth, besides a pivotal regulatory role on dentin biomineralization, PGs provide mechanical support to the mineralized tissue and compressive strength to the biosystem. This study assessed enzymatic protocols for selective PGs removal from demineralized dentin to determine the roles of these biomacromolecules in the bulk mechanical properties and biostability of type I collagen. METHODS: Selective removal of glycosaminoglycans chains (GAGs) and PGs from demineralized dentin was carried out by enzymatic digestion protocols using chondroitinase ABC (c-ABC) and trypsin (Try). A comprehensive study design included assessment of dentin matrix mass loss, biodegradability of the PGs/GAGs-depleted dentin matrix, ultimate tensile strength (UTS) and energy to fracture tests. Quantitative data was statistically analyzed by two-way and one-way ANOVA followed by the appropriate post hoc tests (α=0.05). RESULTS: Transmission electron microscopy images show effective GAGs removal by c-ABC and Try and both enzymatic methods released statistically similar amounts of GAGs from the demineralized dentin. Try digestion resulted in about 25% dentin matrix mass loss and increased susceptibility to collagenolytic digestion when compared to c-ABC (p=0.0224) and control (p=0.0901). Moreover, PGs digestion by Try decreased the tensile strengths of dentin. Statistically lower energy to fracture was observed in c-ABC-treated dentin matrix. CONCLUSIONS: GAGs plays a pivotal role on tissue mechanics and anisotropy, while the core protein of PGs have a protective role on matrix biostability.


Asunto(s)
Dentina/química , Proteoglicanos/fisiología , Anisotropía , Fenómenos Biomecánicos , Colágeno Tipo I/metabolismo , Fuerza Compresiva , Matriz Extracelular/metabolismo , Glicosaminoglicanos/fisiología , Humanos , Técnicas In Vitro , Microscopía Electrónica de Transmisión , Diente Molar , Resistencia a la Tracción , Desmineralización Dental
10.
Acta Biomater ; 55: 262-270, 2017 06.
Artículo en Inglés | MEDLINE | ID: mdl-28365481

RESUMEN

Proanthocyanidins (PACs) are plant-derived, multifunctional compounds that possess high interactivity with extracellular matrix (ECM) components. The documented affinity of PACs for type-I collagen is directly correlated with their structural features and degree of polymerization. In this investigation, centrifugal partition chromatography (CPC) was used to sequentially deplete less active monomeric and polymeric PACs from a crude Pinus massoniana bark extract to create refined mixtures enriched in oligomeric PACs. The ability of these oligomeric PACs to modify the mechanical properties of the dentin collagen matrix and their biocompatibility with dental pulp cells (DPCs) was evaluated in an innovative biomimetic environment. The refined mixtures displayed high interactivity with dentin collagen as demonstrated by a significant increase (>5-fold) in the modulus of elasticity of the dentin matrix. In a simplified model of the dentin-DPC complex, DPCs embedded within their native ECM in the presence of PAC-treated dentin exhibited increased proliferation. Quantitative gene expression analyses indicated that exposure to PAC-treated dentin increased the expression of key biomineralization and odontogenic differentiation regulators, including RUNX2, BMP2, OCN, and DSPP. LC-MS/MS analysis revealed that PACs two to four units long (dimers, trimers, and tetramers) were being released from dentin into media, influencing cell behavior. Overall, the results suggested that PAC dimers, trimers, and tetramers are not only biocompatible, but enhance the differentiation of DPCs towards a phenotype that favors biomineralization. PAC-enriched refined mixtures can influence the field of biomaterials and regeneration by serving as renewable, non-cytotoxic agents that can increase the mechanical properties of biomaterials. STATEMENT OF SIGNIFICANCE: Pine bark extract is a renewable source of structurally diverse proanthocyanidins (PACs), multifunctional compounds whose interaction with collagen can be tailored to specific purposes by enrichment of selected PACs from the complex mixture. Oligomeric PACs were enriched from the extract and were shown here to sustain desired tissue modification and were thus assessed for cellular response in a model of the dentin-pulp interface. This model was developed to mimic leaching of potentially reactive compounds into pulp tissue. Dental pulp cells exposed to PAC-treated dentin showed increased proliferation and expression of genes necessary for extracellular matrix deposition and biomineralization, processes crucial for forming new dentin. Thus, collagen-interactive PACs may also enhance tissue regeneration and have broad impact in tissue engineering.


Asunto(s)
Calcificación Fisiológica/efectos de los fármacos , Pulpa Dental/metabolismo , Dentina/química , Pinus/química , Proantocianidinas , Regeneración/efectos de los fármacos , Células Cultivadas , Preparaciones de Acción Retardada/química , Preparaciones de Acción Retardada/farmacocinética , Preparaciones de Acción Retardada/farmacología , Pulpa Dental/citología , Humanos , Proantocianidinas/química , Proantocianidinas/farmacocinética , Proantocianidinas/farmacología
11.
Dent Mater ; 33(6): 630-636, 2017 06.
Artículo en Inglés | MEDLINE | ID: mdl-28392021

RESUMEN

OBJECTIVE: To sustain the bioactivity of proanthocyanidins-rich plant-derived extracts via encapsulation within biodegradable polymer microcapsules. METHODS: Polylactide microcapsules containing grape seed extract (GSE) were manufactured using a combination of double emulsion and solvent evaporation techniques. Microcapsule morphology, size distribution, and cross-section were examined via scanning electron microscopy. UV-vis measurements were carried out to evaluate the core loading and encapsulation efficiency of microcapsules. The bioactivity of extracts was evaluated after extraction from capsules via solvent partitioning one week or one year post-encapsulation process. Fifteen human molars were cut into 7mm×1.7mm×0.5mm thick mid-coronal dentin beams, demineralized, and treated with either encapsulated GSE, pristine GSE, or left untreated. The elastic modulus of dentin specimens was measured based on three-point bending experiments as an indirect assessment of the bioactivity of grape seed extracts. The effects of the encapsulation process and storage time on the bioactivity of extracts were analyzed. RESULTS: Polynuclear microcapsules with average diameter of 1.38µm and core loading of up to 38wt% were successfully manufactured. There were no statistically significant differences in the mean fold increase of elastic modulus values among the samples treated with encapsulated or pristine GSE (p=0.333), or the storage time (one week versus one year storage at room temperature, p=0.967). SIGNIFICANCE: Polynuclear microcapsules containing proanthocyanidins-rich plant-derived extracts were prepared. The bioactivity of extracts was preserved after microencapsulation.


Asunto(s)
Materiales Dentales , Extracto de Semillas de Uva , Poliésteres , Cápsulas , Diente Molar
12.
J Org Chem ; 82(3): 1316-1329, 2017 02 03.
Artículo en Inglés | MEDLINE | ID: mdl-28098463

RESUMEN

The structurally complex oligomeric proanthocyanidins (OPACs) are promising biomimetic agents, capable of strengthening the macromolecular backbone of teeth via intermolecular and intermicrofibrillar cross-linking. This study establishes analytical methods capable of determining the absolute configuration of the catechin-type monomeric units of underivatized OPACs. This preserves the capacity of their biological evaluation, aimed at understanding the inevitably stereospecific interactions between the OPACs and dentin collagen. Guided by dental bioassays (modulus of elasticity, long-term stability), two new trimeric and tetrameric A-type OPACs were discovered as dentin biomodifiers from pine (Pinus massoniana) bark: epicatechin-(2ß→O→7,4ß→8)-epicatechin-(2ß→O→7,4ß→8)-catechin (5) and epicatechin-(2ß→O→7,4ß→8)-epicatechin-(2ß→O→7,4ß→6)-epicatechin-(2ß→O→7,4ß→8)-catechin (6), respectively. Combining 1D/2D NMR, HRESIMS, ECD, 1H iterative full spin analysis (HiFSA), and gauge-invariant atomic orbital (GIAO) δ calculations, we demonstrate how 13C NMR chemical shifts (diastereomeric building blocks (A-type dimers)) empower the determination of the absolute configuration of monomeric units in the higher oligomers 5 and 6. Collectively, NMR with ECD reference data elevates the level of structural information achievable for these structurally demanding molecules when degradation analysis is to be avoided. Considering their numerous and deceptively subtle, but 3D impactful, structural variations, this advances the probing of OPAC chemical spaces for species that bind selectively to collagenous and potentially other biologically important biomacromolecules.


Asunto(s)
Dentina/química , Pinus/química , Proantocianidinas/química , Dentina/metabolismo , Humanos , Conformación Molecular
13.
Dent Mater ; 32(10): 1248-1255, 2016 10.
Artículo en Inglés | MEDLINE | ID: mdl-27524231

RESUMEN

OBJECTIVE: To evaluate the effect of experimental primers (chlorhexidine, enriched mixture of proanthocyanidins, and doxycycline) on the adhesive properties and gelatinolytic activity at dentin-resin interfaces of occlusal Class I restorations. METHODS: The inactivation of enzymes by the experimental primers was assessed by fluorescence assay and gelatin zymography. To assess the adhesive properties, occlusal Class I cavities were prepared in sound human molars, etched with phosphoric acid and restored with one of the primers and an etch-and-rinse adhesive system (Adper Single Bond Plus-3M ESPE). After the restorative procedures, specimens were divided into two subgroups (n=6) consisting of storage in incubation buffer or axial cyclic loading at 50N and 1,000,000 cycles. Then, the specimens were sectioned and slices were assigned to in situ zymography assay and microtensile bond strength (TBS) test. RESULTS: Fluorescence assay and gelatin zymography revealed that the experimental primers inactivated rMMPs. In situ zymography (2-way ANOVA, Tukey, p<0.05) showed that cyclic loading increased the gelatinolytic activity at the resin-dentin interface and the experimental primers decreased the gelatinolytic activity at the adhesive interface. The experimental primers had no significant effects on dentin-adhesive bond strengths with or without cyclic loading (2-way ANOVA, p>0.05). SIGNIFICANCE: The use of experimental primers impaired the enzymatic activity at the dentin-adhesive interface after cyclic loading and the activity of rMMPs. Cyclic loading did not have a significant effect on the bond strength.


Asunto(s)
Recubrimiento Dental Adhesivo , Cementos Dentales , Recubrimientos Dentinarios , Grabado Ácido Dental , Resinas Compuestas , Dentina , Humanos , Ensayo de Materiales , Cementos de Resina , Resistencia a la Tracción
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