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At least 19 recordsLinked to original sources
PubMed1999

Application of bis-eugenol to a zinc oxide eugenol cement.

OBJECTIVES: To assess the usefulness of dimerized eugenol (bis-eugenol) in dentistry, the physical properties of zinc oxide eugenol cement (ZOE) with bis-eugenol and the cytotoxicity of bis-eugenol were studied. METHODS: Setting time, compressive strength, solubility and disintegration of ZOE cement with bis-eugenol according to the specifications of JDMAS315 were evaluated. The cytotoxicity of bis-eugenol and eugenol toward two different cell types, HGF (a primary culture of human gingival fibroblast) and HSG (a human epidermoid carcinoma cell line derived from a salivary gland) was evaluated by the MTT test and in terms of cell survival. RESULTS: Addition of bis-eugenol to ZOE did not decrease the physical properties when employed at the ratio of 9:1 or 6:1 (liquid ND:bis-eugenol, w/w). Bis-eugenol was less toxic than eugenol in the cell culture tests. CONCLUSIONS: The results of this assay demonstrated that bis-eugenol is useful in ZOE.

Adenocarcinoma↗
PubMed2003

Preventive effect of bis-eugenol, a eugenol ortho dimer, on lipopolysaccharide-stimulated nuclear factor kappa B activation and inflammatory cytokine expression in macrophages.

Eugenol exhibits antioxidant and anti-inflammatory activities, but at higher concentrations acts as an oxidant and potent allergen. It was earlier shown that bis-eugenol synthesized by the oxidation of eugenol was less cytotoxic and more highly antioxidative than eugenol. But its anti-inflammatory mechanism remains yet unclear. Since nuclear factor-kappa B (NF-kappa B) is a key transcriptional factor in the expression of inflammatory cytokines, we examined whether eugenol and bis-eugenol are inhibitors of NF-kappa B activation. We observed that bis-eugenol, but not eugenol, clearly inhibited the degradation of inhibitory kappa B-alpha in RAW264.7 murine macrophages stimulated with lipopolysaccharide and, consequently, the transcriptional activity of the stimulated NF-kappa B in the cells. In addition, bis-eugenol actually inhibited LPS-stimulated expression of inflammatory cytokines at both gene and protein levels. These findings suggest that bis-eugenol acts as a potent inhibitor of NF-kappa B.

Animals↗
PubMedDate not supplied

Efficacy of various eugenol and non-eugenol root canal sealers in the treatment of teeth with periapical radiolucent area--a clinical and radiological study.

A clinical and radiological study was conducted to compare the efficacy of various eugenol containing Viz. Zinc oxide eugenol, CRCS and Rosen's Cement and non eugenol containing sealers and N2 on forty eight non-vital anterior teeth, with a periapical radiolucent area of 1-7mm in diameter. The patients were recalled after 30,90,150 and 210 days On radiological examination after 210 days CRCS showed maximum decrease in periapical radiolucency from 4.39 mm. to 1.80mm. The teeth treated with N2 as root canal sealer showed minimum decrease in the periapical radiolucency from 3.0 mm. to 2.15mm. On clinical examination the results were 100% successful in both the eugenol and non-eugenol groups. The radiological findings indicate that the eugenol containing are better as compared to non-eugenol containing root canal sealer. Out of eugenol containing root canal sealers CRCS showed maximum decrease in radiolucency and from non-eugenol containing group N2.

Adolescent↗
PubMed1999

Concentration of eugenol apically released from zinc oxide-eugenol-based sealers.

This study investigated the amount of eugenol released from a zinc oxide-eugenol-based sealer at the apex of teeth filled according to two techniques: the single-cone and the Thermafil. The crown of 10 maxillary central incisors was removed, and the canal was prepared with ProFile to a size 30 under NaOCl irrigation. The patency of the apex was checked with a #8 K-file between each ProFile. Five roots were filled with a Thermafil #30 and 0.03 g of Sealite; five roots were filled using a Lentulo with 0.07 g of sealer and a gutta-percha cone #30. The powder/liquid ratio of the sealer was of 5/1. The concentration of eugenol released in phosphate-buffered saline was spectrofluorimetrically determined immediately after sealing, after 1 day, and after 1 month of storage. The roots filled with the single-cone technique released significantly more eugenol than these filled with Thermafil immediately after sealing (p = 0.002); but, after 1-day or 1-month storage, there was no difference. For both techniques, eugenol concentration decreased over time (p = 0.01): the immediate concentration was higher than the 1-day concentration (p = 0.04). Eugenol concentration after 1-month storage was undetectable. The results of this work show that the level of eugenol released from a zinc oxide-eugenol-based sealer beyond the apex is very low and decreases over time.

Eugenol↗
PubMed1981

A comparison of the inflammatory response produced by commercial eugenol and purified eugenol.

Eugenol "purified" by HPLC20 was compared to commercial USP eugenol to determine if any difference exists between the inflammatory response caused by each. Mixtures of each eugenol with zinc oxide were also compared. Each material was injected subcutaneously beneath the abdominal skin of 40 Walter Reed white rats. Ten animals were sacrificed at four different dates, and the degree of necrosis and inflammation was compared. The purified eugenol caused less necrosis and inflammation at all times than did the commercial eugenol. The purified ZOE mixture produced less necrosis and inflammation than the commercial ZOE mixture at each sacrifice date. The two mixtures of ZOE and the two samples of eugenol produced roughly parallel amounts of inflammation, suggesting that the degree of inflammation of ZOE mixtures is strongly influenced by the amounts of free eugenol in the mixtures. This study suggests that the impurities in commercial eugenol do cause an increase in the inflammatory response in the rat system studied. This increase is most evident at day two and after day ten.

Animals↗
PubMed2003

Effect of eugenol and non-eugenol containing temporary cement on permanent cement retention and microhardness of cured composite resin.

This present study had three aims: 1) to evaluate the bond strengths of carboxylate and resin cements in cementing cast Co-Cr crowns to pretreatment of composite resin cores with eugenol and non-eugenol containing temporary cements, 2) to determine the microhardness of composite resin treated with temporary cement, 3) to view the surface differences of composite resin with SEM. The composite cores were divided into three experimental groups for the following pretreatments: Group 1, No treatment was provided, Group 2, The external walls of the composite cores were covered with eugenol-containing temporary cement, Group 3, The external walls of the composite cores were covered with non-eugenol containing temporary cement. Analysis of variance results showed that there was a significant difference between all three groups. Temporary cement with eugenol was significantly reduced the bond strength of full crown casting with resin cement compared with non-eugenol. The resin specimens treated with the eugenol-containing temporary cement showed the lowest microhardness values, the non-eugenol-containing temporary cement was not significantly different from those of the control groups.

Analysis of Variance↗
PubMed2001

Characterization of the eugenol hydroxylase genes (ehyA/ehyB) from the new eugenol-degrading Pseudomonas sp. strain OPS1.

During the screening for bacteria capable of converting eugenol to vanillin, strain OPS1 was isolated, which was identified as a new Pseudomonas species by 16 s rDNA sequence analysis. When this bacterium was grown on eugenol, the intermediates, coniferyl alcohol, ferulic acid, vanillic acid, and protocatechuic acid, were identified in the culture supernatant. The genes encoding the eugenol hydroxylase (ehyA, ehyB), which catalyzes the first step of this biotransformation, were identified in a genomic library of Pseudomonas sp. strain OPS1 by complementation of the eugenol-negative mutant SK6165 of Pseudomonas sp. strain HR199. EhyA and EhyB exhibited 57% and 85% amino acid identity to the eugenol hydroxylase subunits of Pseudomonas sp. strain HR199 and up to 34% and 54% identity to the corresponding subunits of p-cresol methylhydroxylase from P. putida. Moreover, the amino-terminal sequences of the alpha- and beta-subunits reported recently for an eugenol dehydrogenase of P fluorescens E118 corresponded well with the appropriate regions of EhyA and EhyB. Downstream of ehyB, an open reading frame was identified, whose deduced amino acid sequence exhibited up to 71% identity to azurins, representing most probably the gene (azu) of the physiological electron acceptor of the eugenol hydroxylase. The eugenol hydroxylase genes were amplified by PCR, cloned, and functionally expressed in Escherichia coli.

Bacterial Proteins↗
PubMed1996

Antiplatelet and calcium inhibitory properties of eugenol and sodium eugenol acetate.

1. Eugenol (3-methoxy-4-hydroxy-propenylbenzene) or sodium eugenol acetate (4-O-acetic acid sodium-3-methoxy-1-propenylbenzene) (0.25, 0.5, 1 mM) concentration-dependently inhibited arachidonic acid (AA)-, collagen-, epinephrine- and ADP-induced platelet aggregation. 2. Eugenol or sodium eugenol acetate inhibited collagen-induced aggregation of washed rabbit platelets synergistically with creatine phosphate/creatine phosphokinase (CP/CPK, 5 mM/10 U/ml) or p-bromophenacyl bromide (p-BPB, 10 microM), and they also potentiated the inhibitory action of imidazole (0.5 mM) on AA-induced aggregation. 3. Eugenol or sodium eugenol acetate (0.25, 0.5, 1 mM) concentration-dependently inhibited AA-induced thromboxane B2 and prostaglandin E2 formation. 4. The rise of intracellular Ca2+ caused by collagen, epinephrine, ADP, and AA were inhibited by eugenol or sodium eugenol acetate (1 mM).

Animals↗
PubMed2001

Comparative effects of eugenol to bis-eugenol on oral mucous membranes.

The purpose of this study was to evaluate the histopathological effect of eugenol and bis-eugenol on oral mucous membranes at the tissue organ level. Oral mucous membranes of mice were applied with three reagents, eugenol, bis-eugenol, and acetone (as the control). The control group showed a normal architecture. The eugenol group showed severe hyperkeratosis, parakeratosis, cellular edema, patchy chronic inflammation, pleomorphism and hyperchromatism of basal layer cells, indicating high mitotic activity. Comparatively, the bis-eugenol group showed mild hyperkeratosis, parakeratosis, however, the shape or arrangement of basal layer cells were normal. Bis-eugenol was considerably less toxic than eugenol.

Acetone↗
PubMed1992

Biologic properties of eugenol and zinc oxide-eugenol. A clinically oriented review.

Eugenol-containing dental materials are frequently used in clinical dentistry. When zinc oxide-eugenol (ZOE) is applied to a dentinal cavity, small quantities of eugenol diffuse through the dentin to the pulp. Low concentrations of eugenol exert anti-inflammatory and local anesthetic effects on the dental pulp. Thus use of ZOE temporary filling may facilitate pulpal healing; on the other hand, high eugenol concentrations are cytotoxic. Direct application of eugenol to pulp tissue may result in extensive tissue damage. The ability of ZOE-based endodontic sealers to influence periapical tissue healing is considered in view of eugenol's anti-inflammatory and toxic properties.

Biocompatible Materials↗
PubMedDate not supplied

The effect of eugenol-containing and eugenol-free temporary cements on microleakage in resin bonded restorations.

Eugenol is known to have a detrimental effect on both composite resin and dentin bonding agents. The purpose of this in vitro investigation was to compare the microleakage among groups of resin-luted inlays when the cavity preparations were pretreated with a eugenol-containing temporary cement, a eugenol-free temporary cement, or no temporary cement. Class 5 inlay preparations (20 per group) were completed in extracted human molars. Following the fabrication of composite resin inlays, the preparations were filled with either a eugenol-based temporary cement, a eugenol-free temporary cement, or no cement. After removal of the cement from the cavity preparations and application of a dentin bonding agent, the composite inlays were luted with a resin cement, thermocycled, stained, sectioned, and evaluated for microleakage under a stereomicroscope. None of the groups exhibited significant leakage at the enamel margins. Both of the groups treated with temporary cement leaked at the nonenamel margins significantly more than the control (no cement) group. No significant difference in leakage was demonstrated between the groups treated with the eugenol-containing and the eugenol-free temporary cements.

Analysis of Variance↗
PubMed1984

An analysis of the release and the diffusion through dentin of eugenol from zinc oxide-eugenol mixtures.

Tritium-labeled eugenol was released from mixtures of zinc oxide eugenol (ZOE) into aqueous solution at rates which declined exponentially with time, and which were directly proportional to the liquid-powder ratio. The release pattern was consistent with a model of progressive hydrolysis of zinc eugenolate in a limited-thickness ZOE surface layer. Intervening dentin had a profound effect on this pattern of release. In human teeth in vitro containing ZOE as a base or temporary filling, peak eugenol release at the pulpal surface of dentin was of the order of a thousand-fold less than that at the salivary surface. In such teeth, eugenol reached concentrations in excess of 10(-2) M in dentin just beneath ZOE, and 10(-4) M or less adjacent to the pulp space. Both pulpal outflow and dentin concentrations of eugenol remained relatively constant for more than a week, unlike release into aqueous solution. While these data were derived from studies on human teeth in vitro, they give a strong indication of probable events in vivo, and appear to provide a basis for the explanation of the paradox of the therapeutic and toxic actions of ZOE.

Adolescent↗
PubMed1994

The effect of eugenol containing and non-eugenol temporary cements on the resin-enamel bond.

This study was undertaken to compare the effect of eugenol containing and non-eugenol temporary cements on the bond strength of three brands of luting cements to enamel. Flat enamel surfaces were prepared on 90 surgically removed, unerupted, human third molar teeth. The teeth were randomly divided into three groups of thirty. The flat enamel surfaces in two of the groups were treated with either a eugenol containing or non-eugenol temporary cement and the third group was left untreated. The teeth were stored in water for 7 days and the cements then removed and all surfaces etched. The teeth were divided into 9 sub-groups of 10 each and one of the three resin cements was then bonded to each sub-group. The relevant shear bond strengths were determined after 7 days. The results indicated that prior use of a eugenol containing temporary cement reduced the resin cement-enamel bond strengths. No differences were found between the bonds achieved by the three brands. It was concluded that eugenol containing temporary cements should not be used prior to bonding with resin luting cements.

Analysis of Variance↗
PubMedDate not supplied

Diffusion behavior of eugenol from zinc oxide-eugenol mixtures through human and bovine dentin in vitro.

The objective of this in vitro study was to evaluate the long-term diffusion behavior of eugenol from different zinc oxide-eugenol mixtures through thin dentin layers. In 24 freshly extracted, caries-free human teeth standardized cavities were prepared exhibiting a dentin surface area of 7 mm2. The remaining thickness of the dentin close to the pulp chamber amounted to at least 0.2 mm. In a second experiment standardized dentin disks (0.2 mm thick) were prepared from 24 bovine incisors. The disks were embedded in epoxy resin, thus exposing a resin-free, standardized area of 7 mm2. Specimens from both experiments were inserted into a screw cap of a vial. Cp-Cap, Temp Bond, and two zinc oxide-eugenol mixtures (P/L ratios of 10:1 and 2:1) were applied to each of six specimens from both experiments. The opposing surface was in contact with 1 ml of Ringer solution. After 1 day, 7 days, and 21 days respectively, the amount of penetrated eugenol was determined with High-Performance Liquid Chromatography (HPLC). In both experiments we found a persistent release and diffusion of eugenol, irrespective of the applied material. However, for the second experiment, we saw more pronounced diffusion rates. Furthermore, the materials showed significant differences, particularly for low versus high P/L ratios.

Adolescent↗
PubMed1991

Lack of correlation between the amount of eugenol released from zinc oxide-eugenol sealer and cytotoxicity of the sealer.

The purpose of this study was to examine a possible correlation between the eugenol released from a zinc oxide-eugenol sealer (Canals) and the degree of cytotoxicity. The cytotoxicity and eugenol release from root canal filling material containing eugenol was examined for test solutions at several experimental periods. No positive correlation was found between eugenol release and cytotoxicity of the root canal filling material.

Animals↗
PubMed1980

The pulpal response to ZOE with stock eugenol versus ZOE with purified eugenol.

Sixty-nine rat mandibular molars were exposed surgically, and the pulpal response to ZOE with a purified form of eugenol versus ZOE with stock eugenol was investigated. Evaluation and analysis of the control and experimental specimens at 1, 3, 7 and 21 days indicated that there were no differences in the amount of inflammation observed between the two groups. Thus, it may be inferred from the results of this study that the impurities found in stock eugenol are not of clinical significance.

Animals↗
PubMed1990

Effect of non-eugenol- and eugenol-containing periodontal dressings on the incidence and severity of pain after periodontal soft tissue surgery.

This study examines the incidence and severity of postoperative pain after gingivectomy using one non-eugenol-containing periodontal dressing, Coe-pak (n = 76) and 2 eugenol-containing periodontal dressings, Wondrpak (n = 64) and Nobetec (n = 86). All patients were subjected to gingivectomy using 1 type of local anaesthesia (lidocaine + adrenalin) only and covering the surgical areas with either of the 3 different dressings in a randomized study. Postoperative pain was assessed on 100 mm visual analogue scales over 5 days starting immediately after surgery. No pain was reported by 22.0% of the patients after Coe-pak, 23.4% after Wondrpak and 30.2% after Nobetec. 13.2% of the patients took analgesics after Coe-pak treatment, 3.1% after Wondrpak and 1.2% after Nobetec. Mean pain score after Coe-pak was higher (P less than 0.05) than after Nobetec 2 h after operation until the morning on the 3rd postoperative day. Mean pain score after Coe-pak was higher (P less than 0.05) than after Wondrpak 3 h to 9 h after operation. No statistically significant difference was found between Wondrpak and Nobetec regarding mean pain score.

Adult↗