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1.
Clin Oral Investig ; 28(9): 500, 2024 Aug 26.
Artigo em Inglês | MEDLINE | ID: mdl-39186077

RESUMO

OBJECTIVES: To investigate urushiol's potential as a dentin cross-linking agent, promoting remineralization of etched dentin and preventing activation of endogenous proteases causing collagen degradation within the hybrid layer. The goal is to improve bond strength and durability at the resin-dentin interface. METHODS: Urushiol primers with varying concentrations were prepared using ethanol and dimethyl sulfoxide (DMSO) as solvents. Dentin from healthy molars underwent grinding and acid etching for 15 s, followed by a 1min application of urushiol primer. After 14 and 28 days of remineralization incubation and remineralization were used to assess by Attenuated Total Reflection Fourier Transform Infrared spectroscopy (ATR-FTIR), Micro-Raman spectroscopy, X-ray Diffraction (XRD), Atomic Force Microscopy (AFM), Vickers Hardness, Scanning Electron Microscopy (SEM), and Energy X-ray dispersive spectroscopy (EDS). The overall performance of urushiol primers as dentin adhesives was observed by microtensile bond strength (µTBS) testing and nanoleakage assessment. Investigated the inhibitory properties of the urushiol primers on endogenous metalloproteinases (MMPs) utilizing in situ zymography, and the cytotoxicity of the primers was tested. RESULTS: Based on ATR-FTIR, Raman, XRD, EM-EDS and Vickers hardness analyses, the 0.7%-Ethanol group significantly enhanced dentin mineral content and improved mechanical properties the most. Pretreatment notably increased the µTBS of restorations, promoted the stability of the mixed layer, and reduced nanoleakage and MMPs activity after 28 days. SIGNIFICANCE: The urushiol primer facilitates remineralization in demineralized dentin, enhancing remineralization in etched dentin, effectively improving the bonding interface stability, with optimal performance observed at a 0.7 wt% concentration of the urushiol primer.


Assuntos
Dentina , Teste de Materiais , Microscopia Eletrônica de Varredura , Solventes , Resistência à Tração , Remineralização Dentária , Humanos , Espectroscopia de Infravermelho com Transformada de Fourier , Dentina/efeitos dos fármacos , Remineralização Dentária/métodos , Solventes/química , Difração de Raios X , Adesivos Dentinários/química , Análise Espectral Raman , Propriedades de Superfície , Colagem Dentária/métodos , Microscopia de Força Atômica , Técnicas In Vitro , Condicionamento Ácido do Dente , Espectrometria por Raios X , Dente Molar , Reagentes de Ligações Cruzadas/química , Dureza
2.
Chembiochem ; 24(18): e202300238, 2023 09 15.
Artigo em Inglês | MEDLINE | ID: mdl-37366008

RESUMO

In the present study, a novel series of 11 urushiol-based hydroxamic acid histone deacetylase (HDAC) inhibitors was designed, synthesized, and biologically evaluated. Compounds 1-11 exhibited good to excellent inhibitory activities against HDAC1/2/3 (IC50 : 42.09-240.17 nM) and HDAC8 (IC50 : 16.11-41.15 nM) in vitro, with negligible activity against HDAC6 (>1409.59 nM). Considering HDAC8, docking experiments revealed some important features contributing to inhibitory activity. According to Western blot analysis, select compounds could notably enhance the acetylation of histone H3 and SMC3 but not-tubulin, indicating their privileged structure is appropriate for targeting class I HDACs. Furthermore, antiproliferation assays revealed that six compounds exerted greater in vitro antiproliferative activity against four human cancer cell lines (A2780, HT-29, MDA-MB-231, and HepG2, with IC50 values ranging from 2.31-5.13 µM) than suberoylanilide hydroxamic acid; administration of these compounds induced marked apoptosis in MDA-MB-231 cells, with cell cycle arrest in the G2/M phase. Collectively, specific synthesized compounds could be further optimized and biologically explored as antitumor agents.


Assuntos
Antineoplásicos , Neoplasias Ovarianas , Humanos , Feminino , Inibidores de Histona Desacetilases/química , Linhagem Celular Tumoral , Relação Estrutura-Atividade , Proliferação de Células , Ensaios de Seleção de Medicamentos Antitumorais , Histona Desacetilases/metabolismo , Simulação de Acoplamento Molecular , Antineoplásicos/química , Ácidos Hidroxâmicos/farmacologia , Ácidos Hidroxâmicos/química , Proteínas Repressoras/metabolismo
3.
Proc Jpn Acad Ser B Phys Biol Sci ; 99(9): 335-351, 2023 Nov 10.
Artigo em Inglês | MEDLINE | ID: mdl-37648504

RESUMO

Riko Majima published seven papers in this journal, and seeing these papers and their surrounding contexts allows us to glance at the birth of a galaxy of scientists.

4.
Molecules ; 29(1)2023 Dec 26.
Artigo em Inglês | MEDLINE | ID: mdl-38202732

RESUMO

Lacquer sap has been traditionally used in coatings and artwork. Suitable types of lacquer are required to preserve and restore artifacts. Recently, unsuitable cashew nut shell liquid (CNSL) has often been mixed with lacquer sap, so it is necessary to identify the characteristics of lacquer sap by the production area. However, research is still focused on urushiol and laccol. In this study, Myanmarese lacquer sap collected from Gluta usitata, which contains thitsiol as the main component, was analyzed by HPLC to quantify thitsiol using the standards 3-(10-phenyldecyl) benzene-1,2-diol (thitsiol 16) and 3-(8Z,11Z-pentadecadienyl)-benzenediol (urushiol 15:2) as markers, and calibration curves were plotted. The coefficients of determination (R2) for thitsiol 16 and urushiol 15:2 were 0.9985 and 0.9983, respectively. In addition, a blind test was conducted to confirm that accurate quantitative analysis was possible even when Myanmarese lacquer was mixed with lacquer from another production area, which contained urushiol as the main component, and CNSL, which contained cardol, a completely different catechol. Quantitative analysis of thitsiol 16 and urushiol 15:2 in Myanmarese lacquer using HPLC can be used to evaluate the quality of lacquer sap and for more sophisticated activities such as restoration by classifying differences in lacquer sap by the production area.

5.
Molecules ; 28(24)2023 Dec 11.
Artigo em Inglês | MEDLINE | ID: mdl-38138530

RESUMO

Zwitterionic polymer coatings facilitate the formation of hydration layers via electrostatic interactions on their surfaces and have demonstrated efficacy in preventing biofouling. They have emerged as a promising class of marine antifouling materials. However, designing multifunctional, environmentally friendly, and natural products-derived zwitterionic polymer coatings that simultaneously resist biofouling, inhibit protein adhesion, exhibit strong antibacterial properties, and reduce algal adhesion is a significant challenge. This study employed two diisocyanates as crosslinkers and natural urushiol and ethanolamine as raw materials. The coupling reaction of diisocyanates with hydroxyl groups was employed to synthesize urushiol-based precursors. Subsequently, sulfobetaine moieties were introduced into the urushiol-based precursors, developing two environmentally friendly and high-performance zwitterionic-functionalized polyurushiol antifouling coatings, denoted as HUDM-SB and IPUDM-SB. The sulfobetaine-functionalized polyurushiol coating exhibited significantly enhanced hydrophilicity, with the static water contact angle reduced to less than 60°, and demonstrated excellent resistance to protein adhesion. IPUDM-SB exhibited antibacterial efficacy up to 99.9% against common Gram-negative bacteria (E. coli and V. alginolyticus) and Gram-positive bacteria (S. aureus and Bacillus. sp.). HUDM-SB achieved antibacterial efficacy exceeding 95.0% against four bacterial species. Furthermore, the sulfobetaine moieties on the surfaces of the IPUDM-SB and HUDM-SB coatings effectively inhibited the growth and reproduction of algal cells by preventing microalgae adhesion. This zwitterionic-functionalized polyurushiol coating does not contain antifouling agents, making it a green, environmentally friendly, and high-performance biomaterial-based solution for marine antifouling.


Assuntos
Incrustação Biológica , Incrustação Biológica/prevenção & controle , Escherichia coli , Staphylococcus aureus , Polímeros/farmacologia , Antibacterianos/farmacologia
6.
Wilderness Environ Med ; 34(3): 388-392, 2023 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-37120383

RESUMO

Toxicodendron dermatitis is an underappreciated disease seen in the emergency department. Although self-limiting, symptoms can be distressing and can last for weeks if untreated, particularly with re-exposure. Continuing research has improved our understanding of specific inflammatory markers that are associated with exposure to urushiol-the compound responsible for Toxicodendron dermatitis-although consensus for treatment remains varied and poorly supported. Owing to the lack of recent primary literature on the topic, many providers rely on historical precedent, expert opinion, and personal experience when treating this disease. This article provides a narrative review of the literature currently available on the effects of urushiol on key molecular and cellular functions and the prevention and treatment of Toxicodendron dermatitis.


Assuntos
Dermatite por Toxicodendron , Toxicodendron , Dermatite por Toxicodendron/prevenção & controle , Catecóis , Serviço Hospitalar de Emergência
7.
Wilderness Environ Med ; 33(3): 351-354, 2022 09.
Artigo em Inglês | MEDLINE | ID: mdl-35718643

RESUMO

This article describes the clinical presentation, differential diagnosis, and treatment of 2 unrelated cases with different presentations of black-spot Toxicodendron dermatitis. In the first case, a healthy 7-y-old male presented with a rash consisting of black dots with localized surrounding erythema on the left arm. The rash then progressed to a vesicular, pinpoint, raised rash spreading to the face, arms, and neck. In the second case, a 4-y-old male presented with non-pruritic, black, flat, non-erythematous lesions that did not progress. This patient's older sibling had been diagnosed with poison ivy 1 wk prior, and they attended the same child care where the poison ivy was thought to be acquired. In both cases, diagnosis of black-spot Toxicodendron dermatitis was made. The black spot of Toxicodendron dermatitis is caused by urushiol oxidation on exposure to air. The subject may or may not go on to develop allergic contact dermatitis after the exposure. Diagnosis of this dermatitis is made on clinical presentation, with careful consideration of history, distribution, and lesion morphology. When allergic dermatitis does develop as in the first case, systemic treatment with oral steroids is recommended. In both of these cases the black dots completely resolved in 2 to 3 wk. Dermatologic referral for dermoscopy and biopsy may be necessary if the dermatosis does not resolve as anticipated.


Assuntos
Dermatite por Toxicodendron , Exantema , Toxicodendron , Administração Cutânea , Dermatite por Toxicodendron/diagnóstico , Dermatite por Toxicodendron/tratamento farmacológico , Dermatite por Toxicodendron/patologia , Humanos , Masculino
8.
Molecules ; 26(2)2021 Jan 15.
Artigo em Inglês | MEDLINE | ID: mdl-33467697

RESUMO

Lacquer sap has been used by humans from antiquitywhen it was treated as a luxury item because of its desirable physical properties. In modern times, although access barriers are lower, lacquer is still considered to be rare and valuable. Thus, low quality, inexpensive Vietnamese and Myanmarese lacquers and cashew nutshell liquid are frequently added to the costly Toxicodendron vernicifluum lacquer sap from Korea, China, and Japan. However, these blended lacquers can diminish the quality of artisan works. The Toxicodendron vernicifluum lacquer saps mixed with other natural lacquers were characterized using time-of-flight secondary-ion mass spectrometry (ToF-SIMS) and high-performance liquid chromatography (HPLC). ToF-SIMS provided the chemical structure of the lacquer monomer, copolymerized dimers, trimers, etc. HPLC provided quantitative analysis of the components of a randomly mixed lacquer. These techniques can be used to control the quality of commercial lacquer sap for the Asian lacquer industry and the traditional conservation of ancient objects.


Assuntos
Produtos Biológicos/análise , Laca/análise , Toxicodendron/química , Árvores/química , Cromatografia Líquida de Alta Pressão/métodos , Humanos , Espectrometria de Massa de Íon Secundário/métodos
9.
Medicina (Kaunas) ; 57(11)2021 Nov 13.
Artigo em Inglês | MEDLINE | ID: mdl-34833457

RESUMO

INTRODUCTION: The most common clinical manifestation of mango allergy is contact dermatitis, which can be localized or systemic. The sensitising substances that have long been suspected are alk(en)yl catechols and/or alk(en)yl resorcinols. METHODS: We reviewed the original articles published on Pubmed, Embase and Cochrane Library before 15 September 2021, on the topic of contact allergy induced by mango and we synthesized the key data. RESULTS: We found 12 case reports and four case series, with a total of 37 patients. Only seven of these cases were reported in patients from mango-cultivating countries, the other 30 were from countries where mango cultivation does not occur, and 26 were also from countries where poison ivy/oak are commonly found. We found that contact dermatitis may occur on the first exposure to mango due to previous sensitisation to urushiol-containing plants. The diagnosis was confirmed by patch testing in some of the cases. There was great heterogeneity between the reagents used. CONCLUSION: Mango fruit is frequently consumed, but mango induced contact dermatitis, the main hypersensitivity reaction induced by mango, is rare. Further data is necessary for a better understanding of sensitising substances and, consecutively, standardization of patch test reagents.


Assuntos
Dermatite Alérgica de Contato , Mangifera , Toxicodendron , Alérgenos , Dermatite Alérgica de Contato/diagnóstico , Dermatite Alérgica de Contato/etiologia , Humanos , Testes do Emplastro
11.
Molecules ; 24(23)2019 Nov 20.
Artigo em Inglês | MEDLINE | ID: mdl-31757036

RESUMO

Poison ivy (Toxicodendron radicans (L.) Kuntze) shows accession-level differentiation in a variety of morphometric traits, suggesting local adaptation. To investigate whether the presumed defense compound urushiol also demonstrates accession-level accumulation differences, in vitro nascent germinated poison ivy seedlings from geographically isolated populations were germinated in vitro and then assayed for known urushiol congener accumulation levels. Significant accession-level differences in the accumulation levels of total C15- and C17-, total C15-, total C17-, specific C15 congeners, and specific C17 congeners of urushiol were identified. In addition, hereto novel C15- and C17-urushiol isomers were identified as well. Cardanols are assumed to be the penultimate metabolites giving rise to urushiols, but this assumption was not previously empirically validated. C15-cardanol congeners and isomers corresponding to expected substrates needed to produce the observed C15-urushiol congeners and isomers were identified in the same poison ivy seedling extracts. Total C15-cardanol and C15-cardanol congeners also showed significant accession-level differences. Based on the observed C15-cardanol congeners in poison ivy, the penultimate step in urushiol biosynthesis was proposed to be a cardanol-specific hydroxylase activity.


Assuntos
Fenóis , Extratos Vegetais/química , Plântula , Toxicodendron , Fenóis/química , Fenóis/metabolismo , Plântula/química , Plântula/metabolismo , Toxicodendron/química , Toxicodendron/metabolismo
12.
Int J Mol Sci ; 19(10)2018 Oct 16.
Artigo em Inglês | MEDLINE | ID: mdl-30332739

RESUMO

A series of novel C15 urushiol derivatives were designed by introducing a pechmann structure and F-, Cl-, and Br-nitro substituents with different electronic properties into its alkyl side chain, as well as a triazolyl functional group in its aromatic oxide. Their chemical structures were determined based on the analysis of the NMR (nuclear magnetic resonance) spectroscopic and mass spectrometric data. The results showed that compound 4 exhibited a strong inhibition of the HepG2 cell proliferation (half maximal inhibitory concentration (IC50): 2.833 µM to human hepatocellular carcinoma (HepG2), and 80.905 µM to human normal hepatocytes (LO2)). Furthermore, it had an excellent synergistic effect with levopimaric acid. The nitrogen atom of the triazole ring formed a hydrogen-bonding interaction with Gly103, Gly154, and Tyr308, which made compound 4 bind to histone deacetylase (HDAC)2 more tightly. One triazole ring and His33 formed a π⁻π stacking effect; the other, whose branches were deep into the pocket, further enhanced the interaction with HDAC2. Meanwhile, compound 4 involved a hydrophobic interaction with the residues Phe210 and Leu276. The hydrophobic interaction and π⁻π stacking provided powerful van der Waals forces for the compounds.


Assuntos
Inibidores de Histona Desacetilases/farmacologia , Triazóis/farmacologia , Antineoplásicos/farmacologia , Apoptose/efeitos dos fármacos , Cálcio/análise , Catecóis/farmacologia , Sinergismo Farmacológico , Células Hep G2 , Humanos , Concentração Inibidora 50 , Íons , Ligantes , Potencial da Membrana Mitocondrial/efeitos dos fármacos , Simulação de Acoplamento Molecular , Triazóis/síntese química , Triazóis/química
13.
Molecules ; 23(5)2018 05 03.
Artigo em Inglês | MEDLINE | ID: mdl-29751548

RESUMO

A series of C15 triene urushiol derivatives were synthesized and evaluated for their anti-HepG2 aggregation in vitro. The results indicated that all compounds had an effective anti-HepG2 vitality. Compound 1 was a potent inhibitor of HepG2 with IC50 of 7.886 µM and 150 µM against LO2. Moreover, compound 1 increased the apoptosis of HepG2. Compound 1's thiol sulfur formed hydrogen bonding interactions with Gly154 and Tyr308, respectively, and made it bound more closely to HDAC2. In addition, it also formed hydrophobic interactions with the residues His33, Pro106, Val107, Gly154, Phe155, and His183, and was provided with a strong van der Waals force by the hydrophobic action.


Assuntos
Antineoplásicos/síntese química , Antineoplásicos/farmacologia , Catecóis/síntese química , Catecóis/farmacologia , Inibidores de Histona Desacetilases/síntese química , Inibidores de Histona Desacetilases/farmacologia , Apoptose/efeitos dos fármacos , Sítios de Ligação , Linhagem Celular Tumoral , Movimento Celular , Proliferação de Células/efeitos dos fármacos , Técnicas de Química Sintética , Células Hep G2 , Histona Desacetilase 2/antagonistas & inibidores , Humanos , Ligação de Hidrogênio , Potencial da Membrana Mitocondrial/efeitos dos fármacos , Conformação Molecular , Simulação de Acoplamento Molecular , Simulação de Dinâmica Molecular , Relação Estrutura-Atividade
15.
17.
Biosci Biotechnol Biochem ; 79(11): 1915-8, 2015.
Artigo em Inglês | MEDLINE | ID: mdl-26125525

RESUMO

Synthesized urushiol derivatives possessing different carbon atomic length in the alkyl side chain inhibited the growth of food spoilage and pathogenic microorganisms. Particularly, non-allergenic 3-pentylcatechol showed a broad antimicrobial spectrum on an agar plate. Most food spoilage and pathogenic microorganisms were sensitive to urushiol derivatives in the liquid culture. The morphologies of the microorganisms were changed after treatment of 3-pentylcatechol.


Assuntos
Anti-Infecciosos/química , Bactérias/efeitos dos fármacos , Catecóis/química , Extratos Vegetais/administração & dosagem , Anti-Infecciosos/administração & dosagem , Anti-Infecciosos/síntese química , Carbono/química , Catecóis/administração & dosagem , Catecóis/síntese química , Microbiologia de Alimentos , Humanos , Extratos Vegetais/química
19.
Arch Dermatol Res ; 316(8): 596, 2024 Sep 03.
Artigo em Inglês | MEDLINE | ID: mdl-39225822

RESUMO

Poison oak-induced contact dermatitis poses a significant challenge due to its urushiol oil-induced allergic reactions. Conventional preventive measures like avoidance and post-exposure cleansing are often impractical, necessitating innovative strategies. This comprehensive review explores emerging technologies and formulations for preventing poison oak dermatitis. Literature search via PubMed and Covidence identified 13 relevant studies, with six discussing preventive measures. Barrier methods, including occlusive creams and protective clothing, showed promise in reducing dermatitis risk. Immunotherapy, although investigated, requires further development. Complete avoidance, while effective, is often impractical. The complexity of poison oak management underscores the need for ongoing research to develop more effective preventive measures. This review highlights the current landscape, identifies gaps in knowledge, and emphasizes the importance of continued research for improved prevention and management of poison oak-induced dermatitis.


Assuntos
Dermatite Alérgica de Contato , Humanos , Dermatite Alérgica de Contato/prevenção & controle , Dermatite Alérgica de Contato/imunologia , Dermatite Alérgica de Contato/etiologia , Dermatite por Toxicodendron/prevenção & controle , Quercus , Alérgenos/imunologia , Alérgenos/efeitos adversos , Toxicodendron/efeitos adversos , Toxicodendron/imunologia , Catecóis
20.
Adv Healthc Mater ; 13(13): e2303802, 2024 05.
Artigo em Inglês | MEDLINE | ID: mdl-38341630

RESUMO

Hydrogel is a very promising dressing for hemostasis and wound healing due to its good adhesion and long-term moist environment. However, secondary injury caused by tissue adhesion due to homogeneous hydrogel cannot be ignored. The obvious interface existing in Janus hydrogel will weaken its asymmetric function. Here, a hierarchical adhesive polyacrylic acid-polyurushiol water-oil Janus hydrogel (JPs@PAA-PU) without adhesive layer is fabricated by one-pot method in the stabilization of polystyrene@silica-siliver Janus particles (JPs). The morphological structure, mechanical properties, anisotropic chemical composition, and adhesion performance, in vivo, and in vitro hemostatic properties of Janus hydrogel are investigated. Result shows that the obtained Janus hydrogel possesses obvious compartmentalization in microstructure, functional groups, and chemical elements. Janus hydrogel is provided with asymmetric interfacial toughness with top 52.45 ± 2.29 Kpa and bottom 7.04 ± 0.88 Kpa on porcine liver. The adhesion properties of PAA side to tissue, red blood cells and platelets, promoting effect of PU side on coagulation cascade reaction and its physical battier endow Janus hydrogel with shorter hemostatic time and less blood loss than control group. It also exhibits excellent antibacterial effects against Escherichia coli and Staphylococcus aureus (>90%). Janus hydrogel possesses biosafety, providing safety guarantee for clinical applications in the future.


Assuntos
Resinas Acrílicas , Hidrogéis , Animais , Hidrogéis/química , Hidrogéis/farmacologia , Resinas Acrílicas/química , Escherichia coli/efeitos dos fármacos , Hemostasia/efeitos dos fármacos , Suínos , Hemostáticos/química , Hemostáticos/farmacologia , Staphylococcus aureus/efeitos dos fármacos , Camundongos , Antibacterianos/química , Antibacterianos/farmacologia
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