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Aim: The design, synthesis, docking studies and evaluation of the in vitro antifungal and cytotoxic properties of eugenol (EUG) containing 1,2,3-triazole derivatives are reported. Most of the derivatives have not been reported.Materials & methods: The EUG derivatives were synthesized, molecular docked and tested for their antifungal activity.Results: The compounds showed potent antifungal activity against Trichophyton rubrum, associated with dermatophytosis. Compounds 2a and 2i exhibited promising results, with 2a being four-times more potent than EUG. The binding mode prediction was similar to itraconazole in the lanosterol-14-α-demethylase wild-type and G73E mutant binding sites. Additionally, the pharmacokinetic profile prediction suggests good gastrointestinal absorption and potential oral administration.Conclusion: Compound 2a is a promising antifungal agent against dermatophytosis caused by T. rubrum.
[Box: see text].
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Antifúngicos , Diseño de Fármacos , Eugenol , Pruebas de Sensibilidad Microbiana , Simulación del Acoplamiento Molecular , Triazoles , Eugenol/farmacología , Eugenol/química , Eugenol/síntesis química , Eugenol/análogos & derivados , Triazoles/química , Triazoles/farmacología , Triazoles/síntesis química , Antifúngicos/farmacología , Antifúngicos/síntesis química , Antifúngicos/química , Humanos , Trichophyton/efectos de los fármacos , Relación Estructura-Actividad , Estructura MolecularRESUMEN
Alginate encapsulates loaded with clove essential oil (CEO) were prepared by ionic gelation, with subsequent freeze-drying. The objective of the present work was to develop a product with the ability to protect CEO against its easy volatility and oxidation. The following techniques were used to characterize the formulations: eugenol release, degree of swelling, GC/MS, TGA/DSC, and SEM. The alginate solution (1.0%) containing different concentrations of CEO (LF1: 1.0%; LF2: 0.5%; LF3: 0.1%) was dropped into a 3.0% CaCl2 solution. After lyophilization, the encapsulated samples were wrinkled and rigid, with high encapsulation power (LF3: 76.9% ± 0.5). Three chemical components were identified: eugenol (the major one), caryophyllene, and humulene. The antioxidant power (LF1: DPPH IC50 18.1 µg mL-1) was consistent with the phenol content (LF1: 172.2 mg GAE g-1). The encapsulated ones were thermally stable, as shown by analysis of FTIR peaks, eugenol molecular structure was kept unaltered. The degree of swelling was 19.2% (PBS). The release of eugenol (92.5%) in the PBS solution was faster than in the acidic medium. It was concluded that the low-cost technology used allows the maintenance of the content and characteristics of CEO in the three concentrations tested, offering a basis for further research with essential oil encapsulates.
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A series of 19 novel eugenol derivatives containing a 1,2,3-triazole moiety was synthesized via a two-step process, with the key step being a copper(I)-catalyzed azide-alkyne cycloaddition reaction. The compounds were assessed for their antifungal activities against Colletotrichum gloeosporioides, the causative agent of papaya anthracnose. Triazoles 2k, 2m, 2l, and 2n, at 100 ppm, were the most effective, reducing mycelial growth by 88.3, 85.5, 82.4, and 81.4%, respectively. Molecular docking calculations allowed us to elucidate the binding mode of these derivatives in the catalytic pocket of C. gloeosporioides CYP51. The best-docked compounds bind closely to the heme cofactor and within the channel access of the lanosterol (LAN) substrate, with crucial interactions involving residues Tyr102, Ile355, Met485, and Phe486. From such studies, the antifungal activity is likely attributed to the prevention of substrate LAN entry by the 1,2,3-triazole derivatives. The triazoles derived from natural eugenol represent a novel lead in the search for environmentally safe agents for controlling C. gloeosporioides.
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Carica , Colletotrichum , Eugenol , Fungicidas Industriales , Simulación del Acoplamiento Molecular , Enfermedades de las Plantas , Triazoles , Colletotrichum/efectos de los fármacos , Eugenol/farmacología , Eugenol/química , Carica/química , Fungicidas Industriales/farmacología , Fungicidas Industriales/química , Fungicidas Industriales/síntesis química , Triazoles/química , Triazoles/farmacología , Triazoles/síntesis química , Enfermedades de las Plantas/microbiología , Enfermedades de las Plantas/prevención & control , Relación Estructura-Actividad , Diseño de Fármacos , Proteínas Fúngicas/química , Estructura MolecularRESUMEN
Nitroimidazole compounds are well-known bioactive substances, and the structural activity relationship has been reported whereby the position of the nitro group within the imidazole ring has a large influence on the activity. This study focuses on synthesising new trypanocidal agents from the hybridisation of metronidazole with different natural phenols (eugenol, dihydroeugenol and guaiacol). Two different coupling methodologies have been explored in order to analyse the influence of the connector on bioactivity: i) classic direct esterification (AD compounds) and ii) "click" chemistry using a triazole connector (AC compounds). The in vitro trypanocidal tests show good results for both AC and AD hybrid compounds against both epimastigote and trypomastigote forms of T. cruzi. In silico studies showed positive data for most of the synthesised compounds and, in general present low toxicological risks. The AC compounds present lower ClogP (lipophilicity) values than those found for the AD series and higher TPSA (topological polar surface area) values, suggesting lower lipophilicity may be related to the presence of the triazole connector. The AD series compounds have higher Drug Score values than the AC series derivatives, suggesting better general properties for a pharmacological action.
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Enfermedad de Chagas , Tripanocidas , Trypanosoma cruzi , Humanos , Enfermedad de Chagas/tratamiento farmacológico , Eugenol , Metronidazol/farmacología , Metronidazol/uso terapéutico , Relación Estructura-Actividad , Triazoles/uso terapéutico , Tripanocidas/química , Guayacol/síntesis química , Guayacol/química , Guayacol/farmacologíaRESUMEN
Eugenol-ß-cyclodextrin complex has been widely used because of the enhanced stability and conservation of the properties of eugenol. Applications in food and health sciences have been shown previously, which makes this complex an excellent model to understand and develop methodologies for the analysis and prediction of physical properties. In this work, the dynamics of eugenol incorporated into ß-cyclodextrin are presented, using NMR relaxation rates, and the predictive capabilities of molecular dynamics simulations are discussed. Results show a hindered rotation of eugenol around the principal inertial axes when located inside ß-cyclodextrin. Moreover, a translational movement of the whole complex is demonstrated.
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Among the different handling techniques in aquaculture, the use of anesthetics has had a growing interest focused on guaranteeing animal welfare, and reducing possible stress situations during general handling. The aim of this study was to present the use of eugenol and lidocaine with non-invasive anesthesia procedures in Dormitator latifrons, in which the different stages of anesthesia (induction and recovery) were determined. One hundred and twenty healthy fish of average weight of 73.59 ± 13.53 g and standard length of 17 ± 1.36 cm were used. The experimental fish were subjected to fasting for 24 h prior to the tests. Five fish were subjected to eugenol (25, 50, 100, and 200 µL/L), and lidocaine (100, 200, 300, and 400 mg/L), in triplicate. The time to reach deep and recovery anesthesia were recorded and the data analyzed using ANOVA (α= 0.05). Organisms exposed to anesthetics evidenced early episodes of fast, short-distance swimming (initial hyperactivity) for short periods of time. Survival was 100% with both compounds and concentrations. Fish exposed to a eugenol concentration of 200 µL/L had longer anesthesia times and took longer time to recover (P<0.05). The most effective concentrations for eugenol and lidocaine were of 200 µL/L and 400 µL/L in juvenile fish, promoting rapid inductions, without compromising the conditions for the recovery of the fish. This work provides practical information for handling and transportation D. latiforns with the least possible stress and ensuring animal welfare.
Dentre as diferentes técnicas de manejo na aquicultura, o uso de anestésicos tem despertado interesse crescente voltado para a garantia do bem-estar animal, reduzindo possíveis situações de estresse durante o manejo geral. O objetivo deste estudo foi apresentar o uso de eugenol e lidocaína com procedimentos anestésicos não invasivos em Dormitator latifrons, nos quais foram determinadas as diferentes etapas da anestesia (indução e recuperação). Foram utilizados 120 peixes saudáveis, com peso médio de 73,59 ± 13,53 g e 17 ± 1,36 cm de comprimento, em jejum de 24 horas antes dos testes. Cinco peixes foram submetidos a eugenol (25, 50, 100 e 200 µL/L) e lidocaína (100, 200, 300 e 400 mg/L), em triplicata. O tempo para atingir a anestesia profunda e de recuperação foi registrado, os dados foram analisados com ANOVA (α= 0,05). Organismos expostos a anestésicos evidenciaram episódios precoces de nado rápido de curta distância (hiperatividade inicial) por curtos períodos de tempo. A sobrevivência atinge 100% com ambos compostos e concentrações. Peixes expostos a uma concentração de eugenol de 200 µL/L tiveram tempos de anestesia mais longos e demoraram mais para se recuperar (P<0,05). As concentrações mais efetivas para eugenol e lidocaína foram de 200 µL/L e 400 µL/L em peixes juvenis, promovendo induções rápidas, sem comprometer as condições de recuperação dos peixes. Este trabalho fornece informações práticas para o manejo e transporte de D. latifrons com o mínimo de estresse possível e garantindo o bem-estar animal.
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Animales , Bienestar del Animal , Aceite de Clavo/administración & dosificación , Peces , Anestésicos/administración & dosificación , Lidocaína/administración & dosificaciónRESUMEN
Cancer still represents a serious public health problem and one of the main problems related to the worsening of this disease is the ability of some tumors to develop metastasis. In this work, we synthesized a new series of chalcones and isoxazoles derived from eugenol and analogues as molecular hybrids and these compounds were evaluated against different tumor cell lines. This structural pattern was designed considering the cytotoxic potential already known for eugenol, chalcones and isoxazoles. Notably, chalcones 7, 9, 10, and 11 displayed significant activity (4.2-14.5 µM) against two cancer cell lines, surpassing the potency of the control drug doxorubicin. The reaction of chalcones with hydroxylamine hydrochloride provided the corresponding isoxazoles that were inactive against these cancer cells. The dihydroeugenol chalcone 7 showed the most promising results, demonstrating higher potency against HepG2 (CC50: 4.2 µM) and TOV-21G (CC50: 7.2 µM). Chalcone 7 was also three times less toxic than doxorubicin considering HepG2 cells, with a selectivity index greater than 11. Further investigations including clonogenic survival, cell cycle progression and cell migration assays confirmed the compelling antitumoral potential of chalcone 7, as it reduced long-term survival due to DNA fragmentation, inducing cell death and inhibiting HepG2 cells migration. Moreover, in silico studies involving docking and molecular dynamics revealed a consistent binding mode of chalcone 7 with metalloproteinases, particularly MMP-9, shedding light on its potential mechanism of action related to anti-migratory effects. These significant findings suggest the inclusion of compound 7 as a promising candidate for future studies in the field of cancer therapeutics.
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Antineoplásicos , Chalcona , Chalconas , Neoplasias , Chalcona/farmacología , Chalcona/química , Chalconas/farmacología , Chalconas/química , Eugenol/farmacología , Antineoplásicos/química , Línea Celular Tumoral , Doxorrubicina/farmacología , Isoxazoles/farmacología , Proliferación Celular , Estructura Molecular , Ensayos de Selección de Medicamentos Antitumorales , Simulación del Acoplamiento Molecular , Relación Estructura-ActividadRESUMEN
Aims: To investigate whether bioceramicsealers induce a lower incidence and intensity of postoperative pain compared to other sealers. Materials and Methods: Six electronic databases were searched for studies published up to April 2022, following the PICOS strategy: (P) adult patients undergoing root canal treatment or retreatment; (I) root canal filling using bioceramic sealer; (C) root canal filling using other types of sealers; (O) Primary: postoperative pain incidence and/or intensity; Secondary: number of medication intake; (S) randomizedclinical trials. Risk of bias assessment was performed with the revised Cochrane risk of bias tools for randomized trials (RoB 2). Overall certainty of evidence was assessed through the Grading of Recommendations Assessment, Development, and Evaluation (GRADE) tool. Results: Ten studies were included. Eight studies had a low risk of bias, and two had some concerns risk. Meta-analyses showed no differences regarding postoperative pain intensity and incidence between bioceramic sealers and AH Plus. Number of medication intake seemed to be associated to the preoperative diagnosis. Zinc oxide-eugenol sealer demonstrated an intense postoperative pain compared to bioceramic sealers and AH Plus. GRADE analysis showed a low certainty of evidence for all outcomes. Conclusions: There seem to be no differences between bioceramic sealers and AH Plus regarding postoperative pain intensity and incidence. Number of medication intake seem to be associated to the preoperative diagnosis. Zinc oxide-eugenol evoked a more pronounced postoperative pain.
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Eugenol is an aromatic compound used in the manufacture of medicines, perfumes, cosmetics and as an anaesthetic due to the ability of the drug to block the neuronal isoform of voltage-gated Na+ channels (NaV ). Some arrhythmias are associated with gain of function in the sodium current (INa ) found in cardiomyocytes, and antiarrhythmic sodium channel blockers are commonly used in the clinical practice. This study sought to elucidate the potential mechanisms of eugenol's protection in the arrhythmic model of ouabain-induced arrhythmias in guinea pig heart. Ex vivo arrhythmias were induced using 50 µM of ouabain. The antiarrhythmic properties of eugenol were evaluated in the ex vivo heart preparation and isolated ventricular cardiomyocytes. The compound's effects on cardiac sodium current and action potential using the patch-clamp technique were evaluated. In all, eugenol decreased the ex vivo cardiac arrhythmias induced by ouabain. Furthermore, eugenol showed concentration dependent effect upon peak INa , left-shifted the stationary inactivation curve and delayed the recovery from inactivation of the INa . All these aspects are considered to be antiarrhythmic. Our findings demonstrate that eugenol has antiarrhythmic activity, which may be partially explained by the ability of eugenol to change de biophysical properties of INa of cardiomyocytes.
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BACKGROUND: Clove volatile oil (CVO) and its major compound, eugenol (EUG), have anxiolytic effects, but their clinical use has been impaired due to their low bioavailability. Thus, their encapsulation in nanosystems can be an alternative to overcome these limitations. OBJECTIVES: This work aims to prepare, characterize and study the anxiolytic potential of CVO loaded-nanoemulsions (CVO-NE) against anxious-like behavior in adult zebrafish (Danio rerio). METHODS: The CVO-NE was prepared using Agaricus blazei Murill polysaccharides as stabilizing agent. The drug-excipient interactions were performed, as well as colloidal characterization of CVO-NE and empty nanoemulsion (B-NE). The acute toxicity and potential anxiolytic activity of CVO, EUG, CVO-NE and B-NE against adult zebrafish models were determined. RESULTS: CVO, EUG, CVO-NE and B-NE presented low acute toxicity, reduced the locomotor activity and anxious-like behavior of the zebrafish at 4 - 20 mg kg-1. CVO-NE reduced the anxious-like behavior of adult zebrafish without affecting their locomotor activity. In addition, it was demonstrated that anxiolytic activity of CVO, EUG and CVO-NE is linked to the involvement of GABAergic pathway. CONCLUSION: Therefore, this study demonstrates the anxiolytic effect of CVO, in addition to providing a new nanoformulation for its administration.
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Ansiolíticos , Aceites Volátiles , Syzygium , Animales , Aceite de Clavo/farmacología , Aceite de Clavo/metabolismo , Aceites Volátiles/farmacología , Pez Cebra , Syzygium/metabolismo , Ansiolíticos/farmacología , Ansiolíticos/metabolismo , Eugenol/farmacología , Eugenol/metabolismoRESUMEN
Chagas disease (CD) is a neglected tropical disease endemic in 21 countries and affects about 8 million people around the world. The pharmacotherapy for this disease is limited to two drugs (Benznidazole and Nifurtimox) and both are associated with important limitations, as low cure rate in the chronic phase of the disease, high toxicity and increasing resistance by Trypanosoma cruzi. Recently, we reported a bioactive 1,2,3-triazole (compound 35) active in vitro (IC50 42.8 µM) and in vivo (100 mg/kg) against T. cruzi Y strains and preliminary in silico studies suggested the cysteine protease cruzain as a possible target. Considering these initial findings, we describe here the design and synthesis of new 1,2,3-triazoles derivatives of our hit compound (35). The triazoles were initially evaluated against healthy cells derived from neonatal rat cardiomyoblasts (H9c2 cells) to determine their cytotoxicity and against epimastigotes forms of T. cruzi Y strain. The most active triazoles were compounds 26 (IC50 19.7 µM) and 27 (IC50 7.3 µM), while benznidazole was active at 21.6 µM. Derivative 27 showed an interesting selectivity index considering healthy H9c2 cells (>77). Promising activities against trypomastigotes forms of the parasite were also observed for triazoles 26 (IC50 20.74 µM) and 27 (IC50 8.41 µM), mainly 27 which showed activity once again higher than that observed for benznidazole (IC50 12.72 µM). While docking results suggested cruzain as a potential target for these compounds, no significant enzyme inhibition was observed in vitro, indicating that their trypanocidal activity is related to another mode of action. Considering the promising in vitro results of triazoles 26 and 27, the in vivo toxicity was initially verified based on the evaluation of behavioral and physiological parameters, mortality, effect in body weight gain, and through the measurement of AST/ALT enzymes, which are markers of liver toxicity. All these evaluations pointed to a good tolerability of the animals, especially considering triazole 27. A reduction in parasitemia was observed among animals treated with triazole 27, but not among those treated with derivative 26. Regarding the dosage, derivative 27 (100 mg/kg) was the most active sample against T. cruzi infection, showing a 99.4% reduction in parasitemia peak. Triazole 27 at a dosage of 100 mg/kg influenced the humoral immune response and reduced myocarditis in the animals, bringing antibody levels closer to those observed among healthy mice. Altogether, our results indicate compound 27 as a new lead for the development of drug candidates to treat Chagas disease.
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Enfermedad de Chagas , Tripanocidas , Trypanosoma cruzi , Ratones , Ratas , Animales , Eugenol/farmacología , Triazoles/farmacología , Triazoles/uso terapéutico , Parasitemia/tratamiento farmacológico , Tripanocidas/toxicidad , Enfermedad de Chagas/tratamiento farmacológicoRESUMEN
This study investigates the role of eugenol (EUG) on CS-induced acute lung injury (ALI) and how this compound is able to modulate macrophage activity. C57BL/6 mice were exposed to 12 cigarettes/day/5days and treated 15 min/day/5days with EUG. Rat alveolar macrophages (RAMs) were exposed to CSE (5%) and treated with EUG. In vivo, EUG reduced morphological changes inflammatory cells, oxidative stress markers, while, in vitro, it induced balance in the oxidative stress and reduced the pro-inflammatory cytokine release while increasing the anti-inflammatory one. These results suggest that eugenol reduced CS-induced ALI and acted as a modulator of macrophage activity.
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This work describes the design, synthesis and antifungal activity of new imidazoles and 1,2,4-triazoles derived from eugenol and dihydroeugenol. These new compounds were fully characterized by spectroscopy/spectrometric analyses and the imidazoles 9, 10, 13 e 14 showed relevant antifungal activity against Candida sp. and Cryptococcus gattii in the range of 4.6-75.3 µM. Although no compound has shown a broad spectrum of antifungal activity against all evaluated strains, some azoles were more active than either reference drugs employed against specific strains. Eugenol-imidazole 13 was the most promising azole (MIC: 4.6 µM) against Candida albicans being 32 times more potent than miconazole (MIC: 150.2 µM) with no relevant cytotoxicity (selectivity index >28). Notably, dihydroeugenol-imidazole 14 was twice as potent (MIC: 36.4 µM) as miconazole (MIC: 74.9 µM) and more than 5 times more active than fluconazole (MIC: 209.0 µM) against alarming multi-resistant Candida auris. Furthermore, in vitro assays showed that most active compounds 10 and 13 altered the fungal ergosterol biosynthesis, reducing its content as fluconazole does, suggesting the enzyme lanosterol 14α-demethylase (CYP51) as a possible target for these new compounds. Docking studies with CYP51 revealed an interaction between the imidazole ring of the active substances with the heme group, as well as insertion of the chlorinated ring into a hydrophobic cavity at the binding site, consistent with the behavior observed with control drugs miconazole and fluconazole. The increase of azoles-resistant isolates of Candida species and the impact that C. auris has had on hospitals around the world reinforces the importance of discovery of azoles 9, 10, 13 e 14 as new bioactive compounds for further chemical optimization to afford new clinically antifungal agents.
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Antifúngicos , Cryptococcus gattii , Antifúngicos/farmacología , Antifúngicos/química , Azoles/farmacología , Azoles/química , Miconazol/farmacología , Candida , Fluconazol , Eugenol/farmacología , Eugenol/química , Pruebas de Sensibilidad Microbiana , Candida albicans , Imidazoles/farmacología , ErgosterolRESUMEN
In the constant search for new pharmacological compounds, molecular hybridisation is a well-known technique whereby two or more known pharmacophoric subunits are combined to create a new "hybrid" compound. This hybrid is expected to maintain the characteristics of the original compounds whilst demonstrating improvements to their pharmacological action. Accordingly, we report here a series of molecular hybrid compounds based upon eugenol and chloramphenicol pharmacophores. The hybrid compounds were screened for their in vitro antimicrobial potential against Gram-negative and Gram-positive bacteria and also rapidly growing mycobacteria (RGM). The results highlight that the antimicrobial profiles of the hybrid compounds improve in a very clear fashion when moving through the series. The most prominent results were found when comparing the activity of the hybrid compounds against some of the multidrug-resistant clinical isolates of Pseudomonas aeruginosa, methicillin-resistant clinical isolates of Staphylococcus aureus (MRSA) and clinical isolates of rapidly growing mycobacteria.
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Antiinfecciosos , Staphylococcus aureus Resistente a Meticilina , Cloranfenicol/farmacología , Eugenol/farmacología , Farmacóforo , Antiinfecciosos/farmacología , Staphylococcus aureus , Antibacterianos/uso terapéutico , Pruebas de Sensibilidad MicrobianaRESUMEN
Pimenta dioica L. is one the most recognized species with diverse biological activities. In this study, in vitro activity and in vivo efficacy of essential oil from P. dioica (EO-Pd) was evaluated. The main compound was also included in the animal studies and its in silico prediction related to biological activities, molecular ligands, drug likeness, and ADME (absorption, distribution, metabolism, and excretion) properties are listed. The chemical composition analyzed by GC-MS retrieved 45 components, which the most abundant compound was the eugenol (80.1%). The EO-Pd was able to inhibit the growth of L. amazonensis (IC50 = 9.7 ± 0.7 and 11.3 ± 2.1 µg/mL, promastigotes and amastigotes, respectively). The cytotoxicity assay showed a CC50 of 104.5 ± 0.9 µg/mL and a selectivity index of 9. In the model of cutaneous leishmaniasis in BALB/c mice, the effect of EO-Pd and eugenol was observed after treatment at 30 mg/kg by intralesional route with 5 administrations every 4 days. In the in silico predictions, some targets that justified the antileishmanial activity of eugenol and good drug like properties for this compound, were obtained. This study showed for first time the potential of EO-Pd to inhibit L. amazonensis, which could be linked to the activity of major compound eugenol.
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The determination of eugenol in clove essential oil was performed using a smartphone-operated device, which was used for image capture and processing. The colorimetric reaction with the Folin-Ciocalteu reagent was used, and the lighting conditions were evaluated to capture images directly in 2 mL disposable vessels. The free application PhotoMetrix UVC was used for partial least squares regression calibration with suitable values (R² greater than 0.99). The accuracy of the proposed method was compared with traditional methods, such as gas chromatography (GC) and spectrophotometry, and it can be observed that there were no significant differences (Student's t-test (P > 0.05), with agreements from 97% to 101%. The smartphone method allowed the evaluation of several samples in a few minutes, with simple analysis steps and easy interpretation of the results. The miniaturized scale allowed the use of small amounts of reagents with minimal waste generation. Therefore, the proposed method can be easily operated in the field and allows the evaluation of the quality of clove essential oil in places of restricted access without the need for a laboratory structure and specialized analysts.
A determinação de eugenol em óleo essencial de cravo-da-índia foi realizada utilizando um dispositivo operado com smartphone para captura e processamento de imagens. Para tal desenvolvimento foi utilizada a reação colorimétrica com o reagente de Folin-Ciocalteu. Foram avaliadas diferentes condições de iluminação para a captura das imagens diretamente em frascos descartáveis de 2 mL. O aplicativo livre PhotoMetrix UVC foi usado para a calibração por regressão de mínimos quadrados parciais com valores adequados (R2 maior que 0.99). A exatidão do método proposto foi comparada com métodos tradicionais, tais como cromatografia gasosa (CG) e espectrofotometria, sem diferenças significativas (teste t de Student (P > 0,05) e com concordâncias entre 97% e 101%. O método com smartphone permitiu a avaliação de várias amostras em poucos minutos, com etapas de análise simples e com fácil interpretação dos resultados. A escala miniaturizada permitiu o uso de pequenas quantidades de reagentes e mínima geração de resíduos. Portanto, o método proposto pode ser facilmente operado em campo e permite avaliar a qualidade de óleo essencial de cravo- da- índia em locais de acesso restrito, sem a necessidade de estrutura laboratorial e analistas especializados.
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Eugenol , Aceites Volátiles , Syzygium , Teléfono InteligenteRESUMEN
ABSTRACT: The determination of eugenol in clove essential oil was performed using a smartphone-operated device, which was used for image capture and processing. The colorimetric reaction with the Folin-Ciocalteu reagent was used, and the lighting conditions were evaluated to capture images directly in 2 mL disposable vessels. The free application PhotoMetrix UVC was used for partial least squares regression calibration with suitable values (R² greater than 0.99). The accuracy of the proposed method was compared with traditional methods, such as gas chromatography (GC) and spectrophotometry, and it can be observed that there were no significant differences (Student's t-test (P > 0.05), with agreements from 97% to 101%. The smartphone method allowed the evaluation of several samples in a few minutes, with simple analysis steps and easy interpretation of the results. The miniaturized scale allowed the use of small amounts of reagents with minimal waste generation. Therefore, the proposed method can be easily operated in the field and allows the evaluation of the quality of clove essential oil in places of restricted access without the need for a laboratory structure and specialized analysts.
RESUMO: A determinação de eugenol em óleo essencial de cravo-da-índia foi realizada utilizando um dispositivo operado com smartphone para captura e processamento de imagens. Para tal desenvolvimento foi utilizada a reação colorimétrica com o reagente de Folin-Ciocalteu. Foram avaliadas diferentes condições de iluminação para a captura das imagens diretamente em frascos descartáveis de 2 mL. O aplicativo livre PhotoMetrix UVC foi usado para a calibração por regressão de mínimos quadrados parciais com valores adequados (R2 maior que 0.99). A exatidão do método proposto foi comparada com métodos tradicionais, tais como cromatografia gasosa (CG) e espectrofotometria, sem diferenças significativas (teste t de Student (P > 0,05) e com concordâncias entre 97% e 101%. O método com smartphone permitiu a avaliação de várias amostras em poucos minutos, com etapas de análise simples e com fácil interpretação dos resultados. A escala miniaturizada permitiu o uso de pequenas quantidades de reagentes e mínima geração de resíduos. Portanto, o método proposto pode ser facilmente operado em campo e permite avaliar a qualidade de óleo essencial de cravo- da- índia em locais de acesso restrito, sem a necessidade de estrutura laboratorial e analistas especializados.
RESUMEN
The most common form of psycho-social dysfunction is anxiety with depression being related closely without any age bar. They are present with combined state of sadness, confusion, stress, fear etc. Glyoxalase system contains enzyme named glyoxalase 1 (GLO1).It is a metabolic pathway which detoxifies alpha-oxo-aldehydes, particularly methylglyoxal (MG). Methylglyoxal is mainly made by the breakdown of the glycolytic intermediates, glyceraldehyde-3-phosphates and dihydroxyacetone phosphate. Glyoxylase-1 expression is also related with anxiety behavior. A casual role or GLO-1 in anxiety behavior by using viral vectors for over expression in the anterior cingulate cortex was found and it was found that local GLO-1 over expression increased anxiety behavior. The present study deals with the molecular mechanism of protective activity of eugenol against anxiolytic disorder. A pre-clinical animal study was performed on 42 BALB/c mice. Animals were given stress through conventional restrain model. The mRNA expression of GLO-1 was analyzed by real time RT-PCR. Moreover, the GLO-1 protein expression was also examined by immunohistochemistry in whole brain and mean density was calculated. The mRNA and protein expressions were found to be increased in animals given anxiety as compared to the normal control. Whereas, the expressions were decreased in the animals treated with eugenol and its liposome-based nanocarriers in a dose dependent manner. However, the results were better in animals treated with nanocarriers as compared to the compound alone. It is concluded that the eugenol and its liposome-based nanocarriers exert anxiolytic activity by down-regulating GLO-1 protein expression in mice.(AU)
A forma mais comum de disfunção psicossocial é a ansiedade intimamente relacionada com a depressão, sem qualquer barreira de idade. Elas estão presentes em um estado combinado de tristeza, confusão, estresse, medo etc. O sistema de glioxalase contém uma enzima chamada glioxalase 1 (GLO1). É uma via metabólica que desintoxica alfa-oxo-aldeídos, particularmente metilglioxal (MG). O metilglioxal é produzido principalmente pela quebra dos intermediários glicolíticos, gliceraldeído-3-fosfatos e fosfato de diidroxiacetona. A expressão da glioxalase 1 também está relacionada ao comportamento de ansiedade. Um papel casual ou GLO1 no comportamento de ansiedade usando vetores virais para superexpressão no córtex cingulado anterior foi encontrado e descobriu-se que a superexpressão local de GLO1 aumentava o comportamento de ansiedade. O presente estudo trata do mecanismo molecular da atividade protetora do eugenol contra o transtorno ansiolítico. Um estudo pré-clínico em animais foi realizado em 42 camundongos BALB / c. Os animais foram submetidos ao estresse por meio do modelo de contenção convencional. A expressão de mRNA de GLO1 foi analisada por RT-PCR em tempo real. Além disso, a expressão da proteína GLO1 também foi examinada por imuno-histoquímica em todo o cérebro e a densidade média foi calculada. Verificou-se que as expressões de mRNA e proteínas estavam aumentadas em animais que receberam ansiedade em comparação com o controle normal. Considerando que as expressões foram diminuídas nos animais tratados com eugenol e seus nanocarreadores baseados em lipossomas de forma dependente da dose. No entanto, os resultados foram melhores em animais tratados com nanocarreadores em comparação com o composto sozinho. Conclui-se que o eugenol e seus nanocarreadores baseados em lipossomas exercem atividade ansiolítica por regulação negativa da expressão da proteína GLO1 em camundongos.(AU)
Asunto(s)
Animales , Masculino , Ratones , Ansiedad/tratamiento farmacológico , Eugenol/administración & dosificación , Lactoilglutatión LiasaRESUMEN
Abstract The most common form of psycho-social dysfunction is anxiety with depression being related closely without any age bar. They are present with combined state of sadness, confusion, stress, fear etc. Glyoxalase system contains enzyme named glyoxalase 1 (GLO1).It is a metabolic pathway which detoxifies alpha-oxo-aldehydes, particularly methylglyoxal (MG). Methylglyoxal is mainly made by the breakdown of the glycolytic intermediates, glyceraldehyde-3-phosphates and dihydroxyacetone phosphate. Glyoxylase-1 expression is also related with anxiety behavior. A casual role or GLO-1 in anxiety behavior by using viral vectors for over expression in the anterior cingulate cortex was found and it was found that local GLO-1 over expression increased anxiety behavior. The present study deals with the molecular mechanism of protective activity of eugenol against anxiolytic disorder. A pre-clinical animal study was performed on 42 BALB/c mice. Animals were given stress through conventional restrain model. The mRNA expression of GLO-1 was analyzed by real time RT-PCR. Moreover, the GLO-1 protein expression was also examined by immunohistochemistry in whole brain and mean density was calculated. The mRNA and protein expressions were found to be increased in animals given anxiety as compared to the normal control. Whereas, the expressions were decreased in the animals treated with eugenol and its liposome-based nanocarriers in a dose dependent manner. However, the results were better in animals treated with nanocarriers as compared to the compound alone. It is concluded that the eugenol and its liposome-based nanocarriers exert anxiolytic activity by down-regulating GLO-1 protein expression in mice.
Resumo A forma mais comum de disfunção psicossocial é a ansiedade intimamente relacionada com a depressão, sem qualquer barreira de idade. Elas estão presentes em um estado combinado de tristeza, confusão, estresse, medo etc. O sistema de glioxalase contém uma enzima chamada glioxalase 1 (GLO1). É uma via metabólica que desintoxica alfa-oxo-aldeídos, particularmente metilglioxal (MG). O metilglioxal é produzido principalmente pela quebra dos intermediários glicolíticos, gliceraldeído-3-fosfatos e fosfato de diidroxiacetona. A expressão da glioxalase 1 também está relacionada ao comportamento de ansiedade. Um papel casual ou GLO1 no comportamento de ansiedade usando vetores virais para superexpressão no córtex cingulado anterior foi encontrado e descobriu-se que a superexpressão local de GLO1 aumentava o comportamento de ansiedade. O presente estudo trata do mecanismo molecular da atividade protetora do eugenol contra o transtorno ansiolítico. Um estudo pré-clínico em animais foi realizado em 42 camundongos BALB / c. Os animais foram submetidos ao estresse por meio do modelo de contenção convencional. A expressão de mRNA de GLO1 foi analisada por RT-PCR em tempo real. Além disso, a expressão da proteína GLO1 também foi examinada por imuno-histoquímica em todo o cérebro e a densidade média foi calculada. Verificou-se que as expressões de mRNA e proteínas estavam aumentadas em animais que receberam ansiedade em comparação com o controle normal. Considerando que as expressões foram diminuídas nos animais tratados com eugenol e seus nanocarreadores baseados em lipossomas de forma dependente da dose. No entanto, os resultados foram melhores em animais tratados com nanocarreadores em comparação com o composto sozinho. Conclui-se que o eugenol e seus nanocarreadores baseados em lipossomas exercem atividade ansiolítica por regulação negativa da expressão da proteína GLO1 em camundongos.
Asunto(s)
Animales , Conejos , Eugenol/uso terapéutico , Eugenol/farmacología , Lactoilglutatión Liasa/antagonistas & inhibidores , Ansiedad/tratamiento farmacológico , Liposomas , Ratones Endogámicos BALB CRESUMEN
Aim: To evaluate the resistance of the union between a glass fiber post and radicular dentine after cleaning the root with 17% EDTA and filling with different endodontic cements. Methods: Forty uniradicular bovine incisors were removed to obtain root lengths of 18 mm. Endodontic treatment was performed on all roots using different filling cements (zinc oxide and eugenol-based, OZE; cement based on epoxy resin, AH) and cleaning solutions (saline, SA or EDTA), which made it possible to obtain four groups: OZESA, OZEEDTA, AHSA and AHEDTA. Subsequently, 12 mm of filling material was removed from the roots, and they were prepared to receive fiber posts luted with resin cement. To execute the mechanical cycles (2x106 cycles, 90 N, 4 Hz), coronal reconstruction was performed with a silicon matrix. The roots were then sliced (2-mm thick) to perform the push-out test. The results were analyzed using analysis of variance (one factor and two factors) and Tukey's test (α=0,05). Results: Bond strength (Mpa) was significantly higher for OZEEDTA (9,18) and AHEDTA (8,70) than for OZESA (6,06) AHSA (8,7). OZEEDTA also presented the highest values in the cervical region (15,18) but was significantly lower in the apical region (2,99). However, AHEDTA had a homogeneous bond strength in all thirds. Conclusion: Regardless of the endodontic cement used, EDTA was used as an irrigating solution, culminating in a higher bond strength between the glass fiber post and dentin