WO2024112285A1 - Adhésif dentaire - Google Patents

Adhésif dentaire Download PDF

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WO2024112285A1
WO2024112285A1 PCT/TR2023/050784 TR2023050784W WO2024112285A1 WO 2024112285 A1 WO2024112285 A1 WO 2024112285A1 TR 2023050784 W TR2023050784 W TR 2023050784W WO 2024112285 A1 WO2024112285 A1 WO 2024112285A1
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ngo
group
dental
synthesis
bond
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PCT/TR2023/050784
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English (en)
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Soley ARSLAN
İsmail ÖÇSOY
Nilay ILDIZ
Semiha EKRİKAYA
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T.C. Erciyes Üniversitesi
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Publication of WO2024112285A1 publication Critical patent/WO2024112285A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/30—Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00—Medicinal preparations containing inorganic active ingredients
    • A61K33/24—Heavy metals; Compounds thereof
    • A61K33/38—Silver; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/70—Preparations for dentistry comprising inorganic additives
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery

Definitions

  • the present invention discloses green synthesis silver nanoparticle and silver nanographene oxide nanocomposite added dental adhesives and their antibacterial activity and bond strengths.
  • Nanoparticles are bioactive materials that can be used in many areas with their superior properties.
  • Current nanotechnological studies are carried out in all branches of dentistry. Materials developed with nanotechnological approaches are successfully used in preventive dentistry and restorative dentistry.
  • the remineralization and antibacterial capacities of various nanoparticles are shown.
  • the introduction of these nanoparticles into dental composites, cements, base materials, and adhesives is promising and has the potential to significantly improve the protective -re storing dentistry of nanotechnology.
  • information about the possible toxicity and disadvantages of nanotechnology products is limited. Long-term antimicrobial, toxic, physical, and clinical effects of nanoparticles on dental materials should be investigated in further studies.
  • Green synthesis nanoparticles obtained as an alternative to nanoparticles obtained by chemical methods have advantages such as being simple to prepare, having an affordable price, having no risk of contamination and being biocompatible.
  • Nanoparticles exhibit superior antibacterial, biological, physical, and chemical properties due to their nanoscale size. Today, they attract attention to these aspects and can be used in many areas.
  • Nanomaterials are used in many disciplines due to their superior properties. Nanomaterials also enable the development of new products in dentistry. Studies have developed dental materials with antimicrobial effects such as composite resins, cements, fissure sealants, temporary restorations, and adhesive resins. Since metal nanoparticles have a large surface area/mass ratio, their antimicrobial properties are good. They can be used as growth inhibitors of various microorganisms. Although nanoparticles are used in many fields of dentistry such as caries control and remineralization, prevention of biofilm formation, drug release, root canal disinfection, removal of dentin sensitivity, some nanoparticles may be toxic to oral and other tissues. Therefore, it may be advantageous to use non-toxic synthesis methods. Green approach is an alternative to chemical methods based on the use of various biomolecules such as DNA, enzymes, proteins, amino acids. Advantages of green synthesis are simple preparation, affordable price, no risk of contamination and biocompatibility.
  • Dental caries is a bacterial disease modified by dietary carbohydrate and is one of the most common bacterial infections in humans. It is a threat to oral and systemic health and represents a heavy financial burden worldwide.
  • the main mechanism of dental caries is demineralization by acids produced by bacteria in dental plaque biofilms. Acidogenic bacterial growth and exposure to fermentable carbohydrates are the main factors in the development of caries.
  • Microbial communities within the oral cavity exist as biofilms on various surfaces, including teeth, dental materials, and mucosa.
  • Oral biofilms consist of bacterial components, microbial species embedded in the peptide matrix, salivary proteins, and food residues. Oral biofilms are one of the primary causes of dental caries. /Van Meerbeck et al., 2011).
  • the treatment procedure involves removing decayed dental tissues and filling the cavity with a restorative material.
  • the first step in the restoration of caries-related losses in dental tissues is cavity preparation.
  • residual bacteria may remain in the cavity and cause secondary caries (Mjor et al., 2000).
  • cavity disinfectants it is recommended to use cavity disinfectants to eliminate residual bacteria (Duarte et al., 2005; Fruits et al., 2006).
  • Chlorhexidine gluconate, sodium hypochlorite, hydrogen peroxide, iodine, benzalkonium chloride, ozone gas and lasers are used for cavity disinfection.
  • monomers such as MDPB, DMAE-CB, DMADDM, QADM, fluorine, and metal ions such as Ti, Cu, Zn, Ag are added to dental adhesives for antibacterial effect (Tavassoli et al., 2013).
  • Ag NP silver nanoparticles
  • the antimicrobial effect occurs with cell death, where Ag + ions inactivate the enzymes of bacteria and cause them to lose their ability to replicate DNA.
  • Ag NP has a high surface area-mass ratio (Choi et al. 2008). For this reason, a small amount of Ag NP is sufficient for strong antibacterial activity.
  • Ag NPs have a strong antibacterial activity that greatly reduces biofilm growth and lactic acid production, without adversely affecting the physical and mechanical properties of dental resins (Duarte et al., 2005; Lynch et al., 2011; Imazato et al., 2006).
  • the chamomile (matricaria chamomilla) plant also has the advantage of not causing color change. It also has antibacterial and antioxidant activity (Duman et al., 2016).
  • Graphene oxide which is a current material, is used as a platform to fix the nanoparticles and prevent their aggregation. Studies have shown that Ag NPs fixed to the graphene oxide surface have more antibacterial activity (Jingwen et al., 2020; Tang et al., 2013; Wu et al., 2018).
  • nanotechnology with its superior properties such as inhibition of biofilm formation, regulation of demineralization and remineralization balance is a promising method for the prevention and treatment of dental caries.
  • new nanostructured adhesives with an effective caries prevention feature can be promising for a wide range of dental applications.
  • Figure 1 A) SEM image of chemical synthesis Ag NP B) SEM image of nGO C) SEM image of chemical synthesis Ag@nGO NK
  • Figure 2 A) UV-Vis spectrophotometer of chemical synthesis Ag NP B) Zeta potential of chemical synthesis Ag NP C) UV-Vis spectrophotometer of chemical synthesis Ag@nGONK D) Zeta potential of chemical synthesis Ag@nGO NK
  • Figure 3 A) SEM image of green synthesis Ag NP B) SEM image of nGO C) SEM image of green synthesis Ag@nGONK
  • Figure 4 A) UV-Vis spectrophotometer of green synthesis Ag NP B) Zeta potential of Green synthesis Ag NP C) UV-Vis spectrophotometer of Green synthesis Ag@nGONK D) Zeta potential of Green synthesis Ag@nGONK Ag NP doped primer, bond, and primer+bond produced by chemical synthesis method EDX spectrum and mapping and demonstration of Ag metal presence.
  • Figure 5 A) EDX spectrum of Ag NP-primer, B) EDX map of Ag NP-primer, C) EDX spectrum of Ag NP-bond, D) EDX map of Ag NP-bond, E) EDX spectrum of Ag NP- primer + bond, F) EDX map of Ag NP-primer + bond.
  • FIG. 6 Ag NP doped primary, bond and primer+bond EDX spectrum and mapping and Ag metal presence produced with the green synthesis method.
  • Figure 7 EDX spectrum, F) Chemical synthesis method of Ag@GO NK-doped primer, bond and primer + bond EDX spectrum and mapping of Ag NP-primer +bond and demonstration of Ag metal presence
  • FIG. 8 Ag@GO NK doped primary, bond and primary-bond EDX spectrum and mapping produced with the green synthesis method and demonstration of Ag metal presence.
  • Figure 9 Number of viable bacteria (%) Group 1: Control, Group 2: nGO, Group 3: Green synthesis Ag NP, Group 4: Green synthesis Ag@nGO NK, Group 5: Chemical synthesis Ag NP, Group 6: Chemical synthesis Ag@nGO NK
  • Figure 10 A) Control B) nGO C) Green synthesis Ag NP D) Green synthesis Ag@nGO NK E) Chemical synthesis Ag NP F) Confocal microscope images of chemical synthesis Ag@nGO NK groups
  • Figure 11 .S'. mutans MTT metabolic activity
  • Group 1 Control
  • Group 2 nGO
  • Group 3 Green synthesis Ag NP
  • Group 4 Green synthesis Ag@nGO NK
  • Group 5 Chemical synthesis Ag NP
  • Group 6 Chemical synthesis Ag@nGO NK
  • Figure 12 Inhibition zone (mm) Group 1: Control, Group 2: nGO, Group 3: Green synthesis Ag NP, Group 4: Green synthesis Ag@nGO NK, Group 5: Chemical synthesis Ag NP, Group 6: Chemical synthesis Ag@nGO NK
  • Figure 13 Lactic acid production Group 1: Control, Group 2: nGO, Group 3: Green synthesis Ag NP, Group 4: Green synthesis Ag@nGO NK, Group 5: Chemical synthesis Ag NP, Group 6: Chemical synthesis Ag@nGO NK
  • Figure 14 .S'. mutans colony-forming unit (CFUs)
  • Group 1 Control
  • Group 2 nGO
  • Group 3 Green synthesis Ag NP
  • Group 4 Green synthesis Ag@nGO NK
  • Group 5 Chemical synthesis Ag NP
  • Group 6 Chemical synthesis Ag@nGO NK
  • Figure 15 Group 1 rupture of a) cohesive and b) mixed type
  • Figure 16 Group 2 rupture of a) adhesive, b) cohesive, and c) mixed type
  • Figure 17 Group 3 rupture of a) adhesive, b) cohesive, and c) mixed type
  • Figure 18 Group 4 rupture of a) adhesive, b) cohesive, and c) mixed type
  • Figure 19 Group 5 rupture of a) adhesive, b) cohesive, and c) mixed type
  • Figure 20 Group 6 rupture of a) adhesive, b) cohesive, and c) mixed type
  • the disadvantages of the chemical method were eliminated by using green synthesis instead of the chemical method in Ag NP synthesis.
  • nGO nanosized GO
  • GO graphene oxide
  • the chamomile was first cleaned and weighed at a certain rate, mixed with 100 m of deionized water, and boiled for 5 minutes. After boiling, the mixture was cooled to room temperature (20°C) and filtered with Whatman filter paper. The extract obtained was stored at +4°C in a refrigerator in a sealed container for use in both total phenol determination and Ag NP synthesis. The extract was used as a reducing and stabilizing agent in Ag NP synthesis.
  • the morphology of Ag NPs was imaged with scanning electron microscopy (SEM) (Leo-440, Zeiss, Cambridge, UK). Energy dissipating X-ray (EDX) spectroscopy was used for the elemental analysis of Ag NPs. The presence of plant extracts on the surface of Ag NPs has been verified by FT-IR spectrometry.
  • SEM scanning electron microscopy
  • EDX Energy dissipating X-ray
  • GO synthesis was performed using the modified form of the Hummers method (Duman et al., 2016). NaCl solution was added to the nGO surface in two stages at different concentrations to bind Ag NPs. While the nGO (0.1 mg/mL) aqueous solution was mixed, the previously synthesized Ag NP (2 mg/ml) solution was added. During the mixing process, first the first NaCl solution (2.4 mL, 0.09 M) and then the second NaCl solution (5 mL, 0.29 M) were added dropwise. The mixture was centrifuged at 3000 rpm for 5 minutes. The resulting Ag NP@GO NKs were separated by centrifugation. Ag@nGO NKs were distributed in 5 mL of deionized water and the centrifugation process was repeated (Song et al., 2016).
  • a two-component dental adhesive (Clearfil SE Bond, Kuraray, Okayama, Japan) consisting of self-etch primer and bonding agent.
  • the primary agent is applied first and then the bond is applied.
  • the hybrid layer formed in the tooth tissue provides the adhesion of the filling materials to the tooth surface.
  • the synthesized NPs were preferably incorporated into both the primary and bond components of the dental adhesive in equal proportions (0.05% by weight).
  • nanoparticles were added at different rates by weight, referring to similar studies, and antimicrobial activities were evaluated. As a result of these experiments, the ideal antimicrobial activity was obtained by adding 0.05 wt% of nanoparticles to the primer and bond.
  • Group 2 Primary + 0.05 wt% nGO, Bond + 0.05 wt% nGO
  • Group 3 Primary + 0.05 wt% Green synthesis Ag NP, Bond+ 0.05 wt% Green synthesis Ag NP
  • Group 4 Primary + 0.05 wt% Green synthesis Ag@nGO NK, Bond + 0.05 wt% Ag@nGO NK
  • Group 5 Primary + 0.05 wt% Chemical synthesis Ag NP, Bond+ 0.05 wt% Chemical synthesis Ag NP
  • a 10 mm diameter and 2mm high silicone mold was used to prepare the sample. After 10 microliters of primer were air dried by placing them at the bottom of the mold, 10 microliters of primer/bond were added and photo polymerized (VALO led, Ultradent, USA) for 20 seconds. Then, the composite was placed and photopolymerized by pressing on the silicone mold with a glass plate for 60 seconds. A three-layer primary/bond/composite disc with a diameter of approximately 10 mm and a thickness of 2 mm was obtained by this method. The discs were then sterilized with ethylene oxide. In order to determine .S', mutans live/dead assay analysis, MTT metabolic activity test, agar disc diffusion test, lactic acid production and CFUs values, 3 discs were used for each test from each group.
  • the biofilm-forming .S', mutans ATCC 25175 strain was used in our antimicrobial studies. A subculture was obtained by anaerobically incubating 1% sucrose-containing tryptic soybean liquid medium from the bacterial strain at 37°C for 24 hours.
  • Discs containing a 24-hour biofilm were transferred in a 24-compartment play with 1 mU MTT dye in each compartment. All samples were incubated for Ih in 5% CO2 at 37°C. After 1 hour, the biofilm samples were transferred to a new 24-compartment plate. The planktonic bacteria were collected by centrifugation. 1 mU of dimethyl sulfoxide could not be added to dissolve the formazan crystals. After 20 minutes of incubation in the dark, the absorbance at 540 nm of 200 L DMSO solution was measured with a microplate reader. 3 samples were tested for each group.
  • Mueller hinton agar was used as medium.
  • a corkborer was used to create a hole in the desired diameter (6 mm) in the agar, which was sterilized in the autoclave and poured into the petri dishes. The wells of the desired sizes were drilled with a sterilized corkborer.
  • the suspension method was used to prepare the bacterial solution.
  • 0.5 McFarland bacterial solution was prepared from 18-24-hour culture and spread to agar petri dishes by swarming (EUCAST, 2019). Inhibition zones were measured as a result of 24 hours of incubation under anaerobic conditions. Study 3 was performed repeatedly, and the experiments resulted in negative/positive controls.
  • BPW buffered peptone water
  • the surfaces of the samples were coated with gold and examined with SEM (Leo-440, Zeiss, Cambridge, England) to determine the types of rupture (adhesive, cohesive, mixed). If the rupture occurs between different materials (e.g., between tooth tissue and composite resin), the adhesive type, if the material occurs within itself, the cohesive type, adhesive and cohesive types are seen together, and the type of rupture is called mixed type rupture (Perdigao et al., 2014).
  • the morphology of the synthesized Ag NP, nGO and Ag@nGO NKs was characterized using scanning electron microscopy (SEM). Characteristic absorbance points of Ag NP, nGO and Ag@nGO NKs were determined with UV-Vis spectrophotometer. In addition, the synthesized nanoparticles were characterized by zeta potential ( Figure 1-4).
  • the presence and ratio of Ag in Ag@nGO NKs were determined using the Energy Dispersive X-ray (EDX) spectrometer.
  • EDX Energy Dispersive X-ray
  • the Live bacteria, .S', mutans MTT metabolic activity, Agar disc diffusion, Lactic acid production and CFUs values of all groups are given in Table 1.
  • Group 1 Control
  • Group 2 nGO
  • Group 3 Green synthesis Ag NP
  • Group 4 Green synthesis Ag@nGO NK
  • Group 5 Chemical synthesis Ag NP
  • Group 6 Chemical synthesis Ag@nGO.
  • Different superscript Hafs (a,b,...,f) show statistical differences
  • Table 2 shows the mean and standard deviations of the bond strength values of the groups in megapascals (Mpa) and their fracture types.
  • Group 1 Control
  • Group 2 nGO
  • Group 3 Green synthesis Ag NP
  • Group 4 Green synthesis Ag@nGO NK
  • Group 5 Chemical synthesis Ag NP
  • Group 6 Chemical synthesis Ag@nGO.
  • the superscript letters show the statistical differences.
  • Ag NPs are frequently used in various areas and dentistry due to their antibacterial properties.
  • the antimicrobial mechanism of Ag NPs is that Ag ions cause cell death by inactivating the vital enzymes of bacteria (Rai et al., 2009).
  • Antimicrobial activity has been proven by adding Ag NPs to many dental materials such as dental composites, dental adhesives, and glass ionomer cements (Fan et al., 2011; Lu et al., 2013; Jandt et al., 2020; Porter et al., 2020).
  • Ag NPs give dental resins antibacterial, antifungal, and antiviral properties (Monterio et al., 2009). Therefore, Ag NP was preferred as an antibacterial nanoparticle in our study.
  • a small amount of Ag NP should be used in order not to adversely affect the color, aesthetics, and mechanical properties of dental materials (Fan et al., 2011).
  • the results of the studies showed that properly used Ag NP provides a strong antibacterial activity that greatly reduces biofilm growth and lactic acid production without adversely affecting the other physical and mechanical properties of resins (Ahn et al., 2009; Besinis et al., 2014; Cheng et al., 2012 a- 2012 b; Fan et al., 2011).
  • the amount of Ag NP in the dental adhesive is generally 0.05% and 0.1% by weight (Melo et al., 2013; Zhang et al., 2013).
  • NPs synthesized with the green synthesis method attract more attention than chemically synthesized NPs in recent studies (Duman et al., 2016; Ocsoy et al., 2013; Strayer et al., 2016).
  • chemical methods toxic reduction and stabilizing agents are generally used for the synthesis of NPs. Toxicity is the main disadvantage in biological applications. Therefore, there is a need for non-toxic methods of synthesis.
  • the green synthesis method provides a significant advantage in this regard (Dcmirbas et al., 2016; Wei et al., 2011).
  • Many different types of plant extracts have been used to obtain green synthesis NPs (Nartop, 2019). Since chamomile plant does not cause color change and has antibacterial and antioxidant activity (Duman et al., 2016), it was preferred as a reducing agent for Ag NPs synthesized by the green synthesis method in our study.
  • Ag NPs can be used alone in the resin for antibacterial activity or in combination with other bioactive substances to achieve the desired properties.
  • researchers combined Ag NP with amorphous calcium phosphate nanoparticles (NACP) in dental composite to benefit from the antibacterial and remineralization effect of two different nanoparticles (Cheng et al., 2012 b).
  • NACP amorphous calcium phosphate nanoparticles
  • the antibacterial and remineralization properties desired in the experimental composite obtained were obtained without adversely affecting the mechanical properties of the composite.
  • the flexural strength and elastic modulus of NACP nanocomposite containing Ag nanoparticles were found to be the same as that of a commercial dental composite (Cheng et al., 2012 a).
  • GO is used as a platform to fix the nanoparticles and prevent aggregation.
  • GO application has been successfully used in antimicrobial effect, regenerative dentistry, bone tissue engineering, drug distribution, increasing the physicomechanical properties of dental biomaterials, implant surface modification and oral cancer treatment. Due to the biocompatibility of graphene oxide and nanocomposites, it can be used successfully in bone regeneration, osseointegration and cell proliferation.
  • the adhesive groups containing Ag NP/Ag@nGO NK synthesized by the green synthesis method provided sufficient antibacterial efficacy compared to the control group.
  • Kulshrestha et al. (2007) conducted a study on Legistromia speciosa (L.) They synthesized Ag@nGO NK by green synthesis method using Persian flower extract and evaluated its antibacterial efficacy.
  • Ag@nGO NK reduced biofilm formation in both gram-negative (E. cloacae) and gram-positive (.S', muians) bacterial models.
  • the antibacterial activity of Ag@nGO NK obtained by the green synthesis method was found to be successful.
  • Ag@GO which was added to glass ionomer cement at a concentration of about 2% by weight, provided antibacterial properties without compromising the mechanical performances of glass ionomer cements (Jingwen et al., 2020).
  • Wu et al. (2018) investigated the inhibitory effect of Ag@GO NK on initial caries. According to the results of the study, when compared with the control groups, Ag@GO NK groups caused a decrease in enamel surface roughness, shallow lesion depth and reduced mineral loss.
  • Ag@GO NK was used as an endodontic irrigation solution and it was reported to have sufficient antimicrobial and anti-biophilic capacity compared to the control group (loannidis et al., 2019). The results of our study are also consistent with these studies.
  • Binding strength tests are used in order to assess the ability of restorative materials to bind to enamel and dentin. Shear and tensile test methods are the most preferred bond strength tests for this purpose. These test methods are divided into two subgroups: macro and micro tests according to the binding surface area. In studies, it has been reported that the microstretch test method is one of the appropriate and safe test methods in testing the bond strength of dentinadhesive materials (Dutra-Correa et al., 2018; Li et al., 2013; Saiz and Bock, 2010).

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Abstract

L'invention divulgue des nanoparticules d'argent de synthèse verte et des adhésifs dentaires nanocomposites à base d'oxyde de nanographène d'argent, ainsi que leur activité antibactérienne et leurs résistances de liaison.
PCT/TR2023/050784 2022-11-23 2023-08-05 Adhésif dentaire WO2024112285A1 (fr)

Applications Claiming Priority (4)

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TR2022017761 2022-11-23
TR2022/017761 2022-11-23
TR2023/005860 2023-05-23
TR2023005860 2023-05-23

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020031481A1 (en) * 1998-02-27 2002-03-14 Jin Xu Stable herbal dentrifice
EP2641583A2 (fr) * 2012-03-21 2013-09-25 Christos Kotsokolos Crème adhésive pour prothèses dentaires à base de composants naturels
CN107753317A (zh) * 2016-08-22 2018-03-06 上海利康消毒高科技有限公司 一种芍药和洋甘菊混合精油牙科术后护理牙膏
CN110856702A (zh) * 2018-08-23 2020-03-03 上海利康消毒高科技有限公司 种植牙口腔护理凝胶及其制备方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020031481A1 (en) * 1998-02-27 2002-03-14 Jin Xu Stable herbal dentrifice
EP2641583A2 (fr) * 2012-03-21 2013-09-25 Christos Kotsokolos Crème adhésive pour prothèses dentaires à base de composants naturels
CN107753317A (zh) * 2016-08-22 2018-03-06 上海利康消毒高科技有限公司 一种芍药和洋甘菊混合精油牙科术后护理牙膏
CN110856702A (zh) * 2018-08-23 2020-03-03 上海利康消毒高科技有限公司 种植牙口腔护理凝胶及其制备方法

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