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1.
Biomolecules ; 14(3)2024 Feb 24.
Artigo em Inglês | MEDLINE | ID: mdl-38540694

RESUMO

Parkinson's disease (PD) is a neurodegenerative disorder characterized by the loss of dopaminergic neurons responsible for unintended or uncontrollable movements. Mutations in the leucine-rich repeat kinase 2 locus contribute to genetic forms of PD. The fruit fly Drosophila melanogaster carrying this mutation (LRRK2-Dm) is an in vivo model of PD that develops motor impairment and stands for an eligible non-mammalian paradigm to test novel therapeutic approaches. Dehydrozingerone (DHZ) is a natural phenolic compound isolated from ginger and presents anti-inflammatory, antioxidant and neuroprotective properties, making it a potential therapeutic target for PD. We administered DHZ and its C2-symmetric dimer (DHZ-DIM) at 0.5 and 1 mM for 14 and 21 days in the LRRK2-Dm, with the aim of assessing changes in rescuing motor behavior, brain dopaminergic neurons, mitochondria and synapses (T-bars). The shorter treatment with both molecules revealed efficacy at the higher dose, improving climbing behavior with a prevention of dopaminergic neuronal demise. After 21 days, a recovery of the motor disability, dopaminergic neuron loss, mitochondrial damage and T-bars failure was observed with the DHZ-DIM. Our data indicate that the DHZ-DIM exerts a more potent neuroprotective effect with respect to the monomer in LRRK2-Dm, prompting further investigation of these compounds in rodent models of PD.


Assuntos
Pessoas com Deficiência , Transtornos Motores , Fármacos Neuroprotetores , Doença de Parkinson , Estirenos , Animais , Humanos , Doença de Parkinson/tratamento farmacológico , Doença de Parkinson/genética , Drosophila , Fármacos Neuroprotetores/farmacologia , Fármacos Neuroprotetores/uso terapêutico , Drosophila melanogaster/genética , Neurônios Dopaminérgicos , Suplementos Nutricionais , Mutação
2.
Chemosphere ; 344: 140371, 2023 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-37820874

RESUMO

Unsaturated polyester resins (UPR) are composed of prepolymers and styrene diluents, while the former are produced by co-polycondensation between diol, unsaturated diacid and saturated diacid. In this work, bio-based UPR prepolymers were synthesized from bio-based oxalic acid, itaconic acid, and ethylene glycol, which were then diluted with bio-based isosorbide methacrylate (MI). Meanwhile, the phenylphosphonate were introduced into the molecular chains of prepolymers to achieve intrinsic flame retardancy of bio-based UPR. The potential of the reactive MI diluents as substitutes of volatile styrene, was also assessed through the volatility test, curing kinetics and gel contents analysis. For UPR materials with styrene diluents, the UPR materials can achieve UL-94 V0 level and the 28% of limiting oxygen index (LOI) with 2.63 wt% of phosphorus contents. By contrast, the UPR materials with MI diluents can reach UL-94 V0 level with only 2.14 wt% of phosphorus contents. As the phosphorus contents were further increased to 2.63 wt%, UPR materials can achieve highest 29%, while the peak of heat release rate (PHRR) and total heat release (THR) were decreased by 68.01% and 48.62%, respectively. The Flame Retardancy Index (FRI) was also used to comprehensively evaluate the flame retardant performance of UPR composites. Compared with neat UPR, the composites with MI diluents and phosphorus containing structures increased from 1.00 to 6.46. The mechanism for improved flame retardancy was analyzed from gaseous and condensed phase. Additionally, the tensile strengths of bio-based UPR materials with styrene and MI diluents were studied. This work provides an effective method to prepared high-performance and fully bio-based UPR materials with improved flame retardant properties and safety application of reactive diluents.


Assuntos
Retardadores de Chama , Poliésteres , Excipientes , Isossorbida , Ácido Oxálico , Fósforo , Estirenos
3.
Food Chem ; 409: 135335, 2023 May 30.
Artigo em Inglês | MEDLINE | ID: mdl-36599292

RESUMO

This study describes the development of 2-hydrazinobenzothiazole modified-amide/imide co-polymers for the extraction/pre-concentration of trace As(III), from edible vegetable oils. Their characterization was realized by help of instrumental techniques. The method is based on pH-dependent complexation between As(III) and co-polymeric chelators in presence of 35-fold excess As(V), their selective extraction into the mixed micellar phase, and detected at pH 2.0 and 6.0 by UV-vis spectrophotometer. The variables affecting extraction efficiency were optimized. From pre-concentration of 20-mL sample, the good linear relationships were obtained in range of 1-40 and 3-75 µg/L with DLs of 0.32 and 1.00 µg/L. The accuracy was verified by analysis of a certified sample without and with spiking. The method was applied into the analysis of iAs levels of samples. The results show that the functional co-polymers are efficient chelators, and exhibit great potential for the selective extraction of As(III) from edible vegetable oils.


Assuntos
Óleos de Plantas , Verduras , Óleos de Plantas/química , Polímeros , Quelantes , Estirenos/análise
4.
Ecotoxicol Environ Saf ; 227: 112903, 2021 Dec 20.
Artigo em Inglês | MEDLINE | ID: mdl-34673417

RESUMO

As a new pollutant, microplastics have increasingly drawn public attention to its toxic behavior in the environment. The aim was to investigate the effect of styrene-butadiene-rubber microplastics (mSBR) with different degrees of aging on petroleum hydrocarbon (PHC) degrading bacteria in an environment with simultaneously existing pollutants. A series of experiments were carried out to investigate the changes in the physical and chemical properties of mSBR with aging and to examine the influence of these changes on the inhibition of PHC-degrading bacteria by mSBR in the vicinity of coexisting pollutants. The results showed that in the early stage of ultraviolet aging (10d), the particle surface shows wrinkles, but the structure is intact. After reaching the late stage of aging (20d), nano-scale fragments were generated on the surface of mSBR, the average particle size decreased from 3.074 µm to 2.297 µm, and the zeta potential increased from - 25.1 mV to - 33.1 mV. The inhibitory effect of bacteria is greater. At the same time, these changes in the physicochemical properties increase the adsorption effect of Cd by 20%, and also improve the stability of mSBR in solution, whereby bacterial growth is inhibited by inhibiting the LPO activity and protein concentration of PHC degrading bacteria.


Assuntos
Poluição por Petróleo , Petróleo , Poluentes Químicos da Água , Bactérias , Biodegradação Ambiental , Butadienos/toxicidade , Elastômeros , Hidrocarbonetos , Microplásticos , Petróleo/toxicidade , Plásticos/toxicidade , Estirenos , Poluentes Químicos da Água/análise , Poluentes Químicos da Água/toxicidade
5.
Phytomedicine ; 92: 153729, 2021 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-34517257

RESUMO

BACKGROUND: Inflammation-mediated lung injury is a major cause of health problems in many countries and has been the leading cause of morbidity/mortality in intensive care units. In the current COVID-19 pandemic, the majority of the patients experienced serious pneumonia resulting from inflammation (Acute respiratory distress syndrome/ARDS). Pathogenic infections cause cytokine release syndrome (CRS) by hyperactivation of immune cells, which in turn release excessive cytokines causing ARDS. Currently, there are no standard therapies for viral, bacterial or pathogen-mediated CRS. PURPOSE: This study aimed to investigate and validate the protective effects of Dehydrozingerone (DHZ) against LPS induced lung cell injury by in-vitro and in-vivo models and to gain insights into the molecular mechanisms that mediate these therapeutic effects. METHODS: The therapeutic activity of DHZ was determined in in-vitro models by pre-treating the cells with DHZ and exposed to LPS to stimulate the inflammatory cascade of events. We analysed the effect of DHZ on LPS induced inflammatory cytokines, chemokines and cell damage markers expression/levels using various cell lines. We performed gene expression, ELISA, and western blot analysis to elucidate the effect of DHZ on inflammation and its modulation of MAPK and NF-κB pathways. Further, the prophylactic and therapeutic effect of DHZ was evaluated against the LPS induced ARDS model in rats. RESULTS: DHZ significantly (p < 0.01) attenuated the LPS induced ROS, inflammatory cytokine, chemokine gene expression and protein release in macrophages. Similarly, DHZ treatment protected the lung epithelial and endothelial cells by mitigating the LPS induced inflammatory events in a dose-dependent manner. In vivo analysis showed that DHZ treatment significantly (p < 0.001) mitigated the LPS induced ARDS pathophysiology of increase in the inflammatory cells in BALF, inflammatory cytokine and chemokines in lung tissues. LPS stimulated neutrophil-mediated events, apoptosis, alveolar wall thickening and alveolar inflammation were profoundly reduced by DHZ treatment in a rat model. CONCLUSION: This study demonstrates for the first time that DHZ has the potential to ameliorate LPS induced ARDS by inhibiting cytokine storm and oxidative through modulating the MAPK and NF-κB pathways. This data provides pre-clinical support to develop DHZ as a potential therapeutic agent against ARDS.


Assuntos
COVID-19 , Síndrome do Desconforto Respiratório , Animais , Síndrome da Liberação de Citocina , Células Endoteliais/metabolismo , Humanos , Lipopolissacarídeos , Pulmão/metabolismo , NF-kappa B/metabolismo , Estresse Oxidativo , Pandemias , Ratos , Síndrome do Desconforto Respiratório/tratamento farmacológico , SARS-CoV-2 , Estirenos
6.
J Oleo Sci ; 69(4): 277-295, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-32249258

RESUMO

Fatty acid and monoglyceride are examples of lipid compounds that can be founded in vegetable oils. The fatty acid has an important role in the human diet, lubricants, detergents, cosmetics, plastics, coatings, and resin. Monoglyceride has a wide function in the food industry in particular as natural emulsifier, pharmaceuticals, cosmetics, antioxidant, and antibacterial. Therefore, isolation and preparation of fatty acid and monoglyceride are the crucial step. This article focuses on providing the chemical reaction paths of isolation fatty acid and synthesis of monoglyceride from vegetable oils. Fatty acids could be isolated by Colgate-Emery steam hydrolysis, hydrolysis of vegetable oils using inorganic base catalyst or lipase, and base-catalyzed hydrolysis of pure fatty acid methyl ester. There are three steps in the synthesis of pure fatty acid methyl ester which are neutralization, transesterification, and fractional distillation. There are four reactions paths in preparing monoglyceride from vegetable oils. They are glycerolysis, ethanolysis using lipase enzyme (sn-1,3), esterification of fatty acid with glycerol in the presence of inorganic acid catalyst or lipase, transesterification of fatty acid methyl ester with glycerol, transesterification of fatty acid methyl ester with protected glycerol (1,2-O-isopropylidene glycerol), and deprotection using an acid resin (Amberlyst-15).


Assuntos
Ácidos Graxos/isolamento & purificação , Monoglicerídeos/síntese química , Óleos de Plantas/química , Catálise , Esterificação , Ésteres , Ácidos Graxos/química , Glicerol/química , Hidrólise , Lipase , Estirenos
7.
Molecules ; 25(7)2020 Mar 27.
Artigo em Inglês | MEDLINE | ID: mdl-32230972

RESUMO

Alkene cleavage is a possibility to generate aldehydes with olfactory properties for the fragrance and flavor industry. A dye-decolorizing peroxidase (DyP) of the basidiomycete Pleurotus sapidus (PsaPOX) cleaved the aryl alkene trans-anethole. The PsaPOX was semi-purified from the mycelium via FPLC, and the corresponding gene was identified. The amino acid sequence as well as the predicted tertiary structure showed typical characteristics of DyPs as well as a non-canonical Mn2+-oxidation site on its surface. The gene was expressed in Komagataella pfaffii GS115 yielding activities up to 142 U/L using 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid) as substrate. PsaPOX exhibited optima at pH 3.5 and 40 °C and showed highest peroxidase activity in the presence of 100 µM H2O2 and 25 mM Mn2+. PsaPOX lacked the typical activity of DyPs towards anthraquinone dyes, but oxidized Mn2+ to Mn3+. In addition, bleaching of ß-carotene and annatto was observed. Biotransformation experiments verified the alkene cleavage activity towards the aryl alkenes (E)-methyl isoeugenol, α-methylstyrene, and trans-anethole, which was increased almost twofold in the presence of Mn2+. The resultant aldehydes are olfactants used in the fragrance and flavor industry. PsaPOX is the first described DyP with alkene cleavage activity towards aryl alkenes and showed potential as biocatalyst for flavor production.


Assuntos
Alcenos/química , Peroxidase/química , Pleurotus/enzimologia , beta Caroteno/metabolismo , Aldeídos/química , Derivados de Alilbenzenos , Anisóis/química , Antraquinonas/química , Biocatálise , Bixaceae/metabolismo , Clareadores/química , Clareadores/metabolismo , Carotenoides/metabolismo , Corantes/química , Expressão Gênica , Peróxido de Hidrogênio/química , Peróxido de Hidrogênio/metabolismo , Concentração de Íons de Hidrogênio , Manganês/química , Oxirredução , Peroxidase/isolamento & purificação , Peroxidase/metabolismo , Extratos Vegetais/metabolismo , Pleurotus/metabolismo , Saccharomycetales/metabolismo , Estirenos/química
8.
Int Immunopharmacol ; 83: 106469, 2020 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-32251963

RESUMO

Despite various advances in the arena of the current system of medicine, there are numerous side effects associated with the therapeutics which essentially demand research on the development of safer therapeutics. One way is to explore the bioactive plant secondary metabolites and their semisynthetic derivatives. In context to this, we analyzed OA-DHZ, a dehydrozingerone derivative as the later has been reported to show anti-inflammatory and analgesic properties. OA-DHZ was found to be having promising anti-inflammatory and analgesic potential. OA-DHZ was found to inhibit the carrageenan-induced edema and leukocyte migration, acetic acid-induced increase in vascular permeability and lipopolysaccharide-induced pro-inflammatory cytokines like TNF-α, IL-6, and IL-1ß. Meanwhile, it was also found to potentially inhibit thermally as well as chemically induced pain signifying its analgesic/nociceptive potential. Further, safety pharmacology studies using in vivo animal models for the central nervous system, gastrointestinal tract, the cardio-respiratory system suggest that optimum functioning of vital organ systems does not get altered after single oral administration. Also, the acute toxicity study revealed its nontoxic nature up to 2000 mg/kg. This study paves the way for future exploration and development of OA-DHZ based on its potent activity and nontoxic nature.


Assuntos
Anti-Inflamatórios/uso terapêutico , Edema/tratamento farmacológico , Estirenos/uso terapêutico , Triazóis/uso terapêutico , Administração Oral , Animais , Carragenina , Citocinas/metabolismo , Edema/induzido quimicamente , Feminino , Zingiber officinale , Humanos , Mediadores da Inflamação/metabolismo , Extratos Vegetais , Ratos , Ratos Wistar , Estirenos/síntese química , Triazóis/síntese química
9.
Org Biomol Chem ; 18(13): 2468-2474, 2020 04 01.
Artigo em Inglês | MEDLINE | ID: mdl-32167516

RESUMO

A new N2O-type BODIPY probe (LF-Bop) has been proposed for the selective and sensitive detection of biologically relevant small molecular thiols. This detection is based on the Michael addition reaction between the thiol and nitrostyrene groups in the probe, which decreases the quenching effect from the nitro group, thus resulting in the recovery of the deep-red fluorescence from the BODIPY structure. The results show that LF-Bop is able to detect all tested free thiols through a fluorescence turn-on assay. The lowest limit of detection (LOD) for glutathione was found to be down to nanomolar levels (220 nM). Based on this probe, we have developed a new fluorescence assay for the screening of acetylcholinesterase inhibitors. In total, 11 natural and synthetic alkaloids have been evaluated. Both experimental measurements and theoretical molecular docking results reveal that both natural berberine and its synthetic derivative dihydroberberine are potential inhibitors of acetylcholinesterase.


Assuntos
Compostos de Boro/química , Inibidores da Colinesterase/química , Corantes Fluorescentes/química , Glutationa/análise , Estirenos/química , Acetilcolinesterase/química , Acetilcolinesterase/metabolismo , Animais , Berberina/análogos & derivados , Berberina/química , Berberina/metabolismo , Compostos de Boro/síntese química , Inibidores da Colinesterase/metabolismo , Avaliação Pré-Clínica de Medicamentos , Elasmobrânquios , Peixe Elétrico , Corantes Fluorescentes/síntese química , Glutationa/química , Limite de Detecção , Simulação de Acoplamento Molecular , Ligação Proteica , Estirenos/síntese química , Tacrina/química , Tacrina/metabolismo
10.
Phytochemistry ; 171: 112248, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-31918304

RESUMO

The phytochemical investigation of the twig and leaf extracts of Goniothalamus tamirensis led to the isolation and identification of 15 compounds including three rare previously undescribed styryllactones, goniotamirenones A-C, together with 12 known compounds. (Z)-6-Styryl-5,6-dihydro-2-pyranone and 5-(1-hydroxy-3-phenyl-allyl)-dihydro-furan-2-one are reported here for the first time as previously undescribed natural products. Their structures were elucidated by spectroscopic methods. Goniotamirenone A was synthesized via a [2 + 2] cycloaddition reaction of 6-styrrylpyran-2-one in quantitative yield. The absolute configurations of goniotamirenones B and C were identified from experimental and calculated ECD data, while the absolute configurations of (-)-5-acetoxygoniothalamin, (-)-isoaltholactone, parvistone E, and 5-(1-hydroxy-3-phenyl-allyl)-dihydro-furan-2-one were identified by single-crystal X-ray diffraction analysis using Cu Kα radiation. The absolute configurations of the other related compounds were determined from comparisons of their ECD spectra with relevant compounds reported in the literature. (-)-5-Acetoxygoniothalamin exhibited potent cytotoxicity against the colon cancer cell line (HCT116) with an IC50 value of 8.6 µM which was better than the standard control (doxorubicin, IC50 = 9.7 µM), while (Z)-6-styryl-5,6-dihydro-2-pyranone was less active with an IC50 value of 22.1 µM.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Goniothalamus/química , Lactonas/farmacologia , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/farmacologia , Estirenos/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Proliferação de Células/efeitos dos fármacos , Cristalografia por Raios X , Teoria da Densidade Funcional , Ensaios de Seleção de Medicamentos Antitumorais , Células HCT116 , Humanos , Lactonas/química , Lactonas/isolamento & purificação , Modelos Moleculares , Estrutura Molecular , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Estirenos/química , Estirenos/isolamento & purificação
11.
Colloids Surf B Biointerfaces ; 180: 298-305, 2019 Aug 01.
Artigo em Inglês | MEDLINE | ID: mdl-31071569

RESUMO

Formulation of new liposoma-based systems can always be in the spotlight for their unique utilization as carriers. Some changes in the composition of lipids may give rise to new mixed liposomes exhibiting modified size and physico-chemical characteristics. Consequently, these display different encapsulating properties toward various molecules. In this work, we have explored the variations in the model lecithin liposomes with casein additive from their size, shape, microenvironment and dynamics in solution. It is observed that with introduction of casein, the size of the liposome is substantially reduced due to incorporation of the additive in its bilayer. Strong interaction between the hydrophobic side chains of casein and lipid bilayer, and electrostatic repulsion of head groups of lipid are responsible to result small casein-mixed liposomes. Spectral properties of coumarin-153 disclose that the microenvironment of the bi-layer of mixed system is predominantly hydrophobic in nature and much rigid too. Fluorescence-lifetime-imaging-microscopy indicates that casein mixed systems exhibit wider lifetime distribution than pure liposomes with predominance of longer lifetimes, entirely arising from the outer bilayer. This indicates that casein gets incorporated in the bilayer of the vesicle to cater rigid and more hydrophobic microenvironment with an effective decrease in size. It is found that such mixed system is very efficient to stabilize the hydrophobic drugs (curcumin and ß-carotene) for prolonged period than the pure liposome or casein-only. The findings are indeed important from the perspective of drug stabilization by liposomes, and is suggestive of possible utilization in oral drug delivery applications involving such size-reduced nano-encapsulates.


Assuntos
Caseínas/química , Interações Hidrofóbicas e Hidrofílicas , Lecitinas/química , Lipossomos/química , Substâncias Macromoleculares/química , Tamanho da Partícula , Piranos/análise , Espectrometria de Fluorescência , Estirenos/análise
12.
J Oleo Sci ; 67(10): 1265-1269, 2018.
Artigo em Inglês | MEDLINE | ID: mdl-30305559

RESUMO

The volatile components of the Tahitian liverwort Cyathodium foetidissimum was analyzed using headspace solid phase micro-extraction (SPME) and GC-MS. Three volatile components, 4-methoxystyrene (24.4%), 3,4-dimethoxystyrene (28.7%), and skatole (15.9%) were identified as the major components from the fresh C. foetidissimum, along with several aliphatic aldehydes, n-octanal, n-nonanal, and n-decanal. However, (E)-2-nonenal recognized as aged malodor was not identified. In GC-O analysis, 2-aminoacetophenone was detected as one of the minor components with a strong aging note. In fact, C. foetidissimum showed the characteristic aging odor reminiscent the damp smell from old chest of drawers, or the civet like note with very strong feces and urine odor. The mixture consisted of 4-methoxystyrene, 3,4-dimethoxystyrene, and skatole in the detected ratio showed the sedative effect on CNV (contingent negative variation) measurement.


Assuntos
Acetofenonas/isolamento & purificação , Hepatófitas/química , Odorantes/análise , Extratos Vegetais/isolamento & purificação , Escatol/isolamento & purificação , Estirenos/isolamento & purificação , Compostos Orgânicos Voláteis/isolamento & purificação , Acetofenonas/farmacologia , Antibacterianos , Variação Contingente Negativa/efeitos dos fármacos , Eletroencefalografia/efeitos dos fármacos , Cromatografia Gasosa-Espectrometria de Massas , Humanos , Hipnóticos e Sedativos , Extratos Vegetais/farmacologia , Escatol/farmacologia , Extração em Fase Sólida/métodos , Estirenos/farmacologia , Compostos Orgânicos Voláteis/farmacologia
13.
Int J Med Mushrooms ; 20(7): 637-645, 2018.
Artigo em Inglês | MEDLINE | ID: mdl-30055555

RESUMO

The phenolic compounds of Inonotus rheades (Pers.) Bondartsev and Singer (Hymenochaetaceae), a typical xylotrophic basidiomycete, and accumulation of styrylpyrones in mycelium under the influence of light of different wavelengths were investigated. Six styrylpyrones (cis- and trans-hispidin, cis- and trans-bisnoryangonin, and phellinins A1 and A2) and 5 bis(styrylpyrones) (3,14'-bishispidinyl, hypholomin B, 3-bisnoryangonyl-14'-hispidin, 1,1-distyrylpyrylethane, and rheadinin) were detected in the extract of I. rheades mycelium using reversed phase ultra-performance liquid chromatography with diode array detection and electrospray ionization mass spectrometry (RP-UPLC-DAD-ESI/MS). The results showed that the maximal content of styrylpyrones was observed under the influence of blue light (8.10 mg/g of dry mycelium weight). Moreover, hispidin was the dominant compound in all experimental groups. Pigmentation intensity gradually decreased after shifting the light spectrum into darkness. It can be concluded that cultivation of I. rheades mycelium under the blue part of the light spectrum leads to the accumulation of styrylpyrones that have nutraceutical and medicinal significance.


Assuntos
Basidiomycota/química , Basidiomycota/efeitos da radiação , Fenóis/química , Extratos Vegetais/química , Basidiomycota/crescimento & desenvolvimento , Cromatografia Líquida de Alta Pressão , Micélio/química , Micélio/crescimento & desenvolvimento , Micélio/efeitos da radiação , Fenóis/isolamento & purificação , Extratos Vegetais/isolamento & purificação , Pironas/química , Pironas/isolamento & purificação , Espectrometria de Massas por Ionização por Electrospray , Estirenos/química , Estirenos/isolamento & purificação
14.
Luminescence ; 33(3): 582-587, 2018 May.
Artigo em Inglês | MEDLINE | ID: mdl-29405584

RESUMO

The red-emitting indolium derivative compound (E)-2-(4-(diphenylamino)styryl)-1,3,3-trimethyl-3H-indol-1-ium iodide (H3) was demonstrated as a sensitive membrane fluorescence probe. The probe located at the interface of liposomes when mixed showed much fluorescence enhancement by inhibiting the twisted intramolecular charge transfer state. After ultrasonic treatment, it penetrated into lipid bilayers with the emissions leveling off and a rather large encapsulation efficiency (71.4%) in liposomes. The ζ-potential and particle size measurement confirmed that the charged indolium group was embedded deeply into lipid bilayers. The probe was then used to monitor the affinities of antioxidant flavonoids for membranes. It was verified that quercetin easily interacted with liposomes and dissociated the probe from the internal lipid within 60 s under the condition of simply mixing. The assessment of binding affinities of six flavonoids and the coincident results with their antioxidation activities indicated that it was a promising membrane probe for the study of drug bio-affinities.


Assuntos
Membrana Celular/química , Flavonoides/metabolismo , Corantes Fluorescentes/química , Indóis/química , Estirenos/química , Antioxidantes/análise , Antioxidantes/química , Membrana Celular/efeitos dos fármacos , Membrana Celular/metabolismo , Colesterol/química , Cor , Avaliação Pré-Clínica de Medicamentos/métodos , Flavonoides/análise , Flavonoides/química , Corantes Fluorescentes/metabolismo , Indóis/metabolismo , Bicamadas Lipídicas/química , Lipossomos/química , Tamanho da Partícula , Fosfatidilcolinas/química , Quercetina/análise , Quercetina/química , Quercetina/metabolismo , Espectrometria de Fluorescência , Estereoisomerismo , Estirenos/metabolismo
15.
Zhongguo Zhong Yao Za Zhi ; 42(5): 912-914, 2017 Mar.
Artigo em Chinês | MEDLINE | ID: mdl-28994534

RESUMO

A new styrene dimer derivative has been isolated from the branch of Litsea greenmaniana by column chromatography over silica gel and Sephadex LH-20, as well as semi-preparative HPLC. Its structure was identified by spectroscopic data analysis (MS, UV, IR, 1D and 2D NMR) as (E)-2,4-bis(p-hydroxyphenyl)-2-butenol, named as listeanol. At a concentration of 1×10-5 mol•L⁻¹, compound 1 was inactive in the assays, including cytotoxicity against human tumor cell lines (HCT-8, Bel-7402, BGC-823, A549 and A2780), antioxidant activity in Fe²âº-cystine-induced rat liver microsomal lipid peroxidation, neuroprotective activity against serum deprivation or glutamate induced neurotoxicity in cultures of PC12 cells, and the inhibitory activity against protein tyrosine phosphatase 1B (PTP1B).


Assuntos
Litsea/química , Estirenos/isolamento & purificação , Animais , Antineoplásicos Fitogênicos , Antioxidantes , Linhagem Celular Tumoral , Cromatografia Líquida de Alta Pressão , Humanos , Peroxidação de Lipídeos , Microssomos Hepáticos/efeitos dos fármacos , Estrutura Molecular , Fármacos Neuroprotetores , Células PC12 , Proteína Tirosina Fosfatase não Receptora Tipo 1/antagonistas & inibidores , Ratos
16.
Hear Res ; 346: 25-33, 2017 03.
Artigo em Inglês | MEDLINE | ID: mdl-28115229

RESUMO

While multimodal interactions have been known to exist in the early sensory cortices, the response properties and spatiotemporal organization of these interactions are poorly understood. To elucidate the characteristics of multimodal sensory interactions in the cerebral cortex, neuronal responses to visual stimuli with or without auditory stimuli were investigated in core and belt fields of guinea pig auditory cortex using real-time optical imaging with a voltage-sensitive dye. On average, visual responses consisted of short excitation followed by long inhibition. Although visual responses were observed in core and belt fields, there were regional and temporal differences in responses. The most salient visual responses were observed in the caudal belt fields, especially posterior (P) and dorsocaudal belt (DCB) fields. Visual responses emerged first in fields P and DCB and then spread rostroventrally to core and ventrocaudal belt (VCB) fields. Absolute values of positive and negative peak amplitudes of visual responses were both larger in fields P and DCB than in core and VCB fields. When combined visual and auditory stimuli were applied, fields P and DCB were more inhibited than core and VCB fields beginning approximately 110 ms after stimuli. Correspondingly, differences between responses to auditory stimuli alone and combined audiovisual stimuli became larger in fields P and DCB than in core and VCB fields after approximately 110 ms after stimuli. These data indicate that visual influences are most salient in fields P and DCB, which manifest mainly as inhibition, and that they enhance differences in auditory responses among fields.


Assuntos
Córtex Auditivo/fisiologia , Percepção Auditiva/fisiologia , Percepção Visual/fisiologia , Estimulação Acústica , Potenciais de Ação , Animais , Córtex Auditivo/anatomia & histologia , Fenômenos Eletrofisiológicos , Corantes Fluorescentes , Cobaias , Masculino , Imagem Óptica , Estimulação Luminosa , Tempo de Reação , Estirenos
17.
Med Chem ; 13(5): 448-452, 2017.
Artigo em Inglês | MEDLINE | ID: mdl-27585570

RESUMO

BACKGROUND: Many 2-substituted quinolines and especially 2-arylvinyl derivatives isolated from plants or prepared by synthesis have been designed from ethnopharmacological studies. OBJECTIVE: In order to explore new aspects of the structure-antituberculosis activity relationship, a series of styrylquinoline derivatives was prepared. METHOD: A series of styrylquinoline derivatives was prepared from quinaldic acid and a variety of arylbenzaldehydes under eco-friendly conditions via Knoevenagel reaction and trifluoroacetic acid (TFA) as catalyst. RESULTS: The products were obtained in short reaction times and good yields and were evaluated for growth inhibitory activity towards Mycobacterium tuberculosis H37Rv (Mtb) through the National Institute of Allergy and Infectious Diseases (NIAID, USA). CONCLUSION: Three compounds had activity under aerobic conditions.


Assuntos
Antituberculosos/farmacologia , Quinolinas/farmacologia , Estirenos/farmacologia , Antituberculosos/síntese química , Química Verde , Micro-Ondas , Mycobacterium tuberculosis/efeitos dos fármacos , Quinolinas/síntese química , Estereoisomerismo , Estirenos/síntese química
18.
Neurotox Res ; 30(3): 407-26, 2016 10.
Artigo em Inglês | MEDLINE | ID: mdl-27149969

RESUMO

The development of agents that affect two or more relevant targets has drawn considerable attention in treatment of AD. Diallyl disulfide (DADS), an active principle of garlic, has been reported to prevent APP processing by amyloidogenic pathway. Recently, we have reported a new series of DADS derivatives and our findings revealed that compound 7k and 7l could provide good templates for developing new multifunctional agents for AD treatment. Thus, the present study was constructed to investigate the neuroprotective effect of DADS analogues (7k and 7l) against Aß-induced neurotoxicity in SH-SY5Y human neuroblastoma cells and in ameliorating the cognition deficit induced by scopolamine in rat model. The results indicated that compound 7k and 7l significantly inhibited Aß1-42-induced neuronal cell death by inhibiting ROS generation. Moreover, they prevented apoptosis, in response to ROS, by restoring normal Bax/Bcl-2 ratio. Furthermore, it was observed that scopolamine-induced memory impairment was coupled by alterations in neurotransmitters, acetylcholinesterase activity and oxidative stress markers. Histological analysis revealed severe damaging effects of scopolamine on the structure of cerebral cortex and hippocampus. Administration of compounds 7k and 7l at 5 mg/kg significantly reversed scopolamine-induced behavioural, biochemical, neurochemical and histological changes in a manner comparable to standard donepezil. Together the present findings and previous studies indicate that compounds 7k and 7l have neuroprotective and cognition-enhancing effects, which makes them a promising multi-target candidate for addressing the complex nature of AD.


Assuntos
Doença de Alzheimer/tratamento farmacológico , Disfunção Cognitiva/tratamento farmacológico , Dissulfetos/farmacologia , Nootrópicos/farmacologia , Estirenos/farmacologia , Doença de Alzheimer/metabolismo , Doença de Alzheimer/patologia , Peptídeos beta-Amiloides/metabolismo , Peptídeos beta-Amiloides/toxicidade , Anidridos , Animais , Apoptose/efeitos dos fármacos , Apoptose/fisiologia , Encéfalo/efeitos dos fármacos , Encéfalo/metabolismo , Encéfalo/patologia , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Sobrevivência Celular/fisiologia , Disfunção Cognitiva/metabolismo , Disfunção Cognitiva/patologia , Modelos Animais de Doenças , Avaliação Pré-Clínica de Medicamentos , Humanos , Masculino , Atividade Motora/efeitos dos fármacos , Fragmentos de Peptídeos/metabolismo , Fragmentos de Peptídeos/toxicidade , Distribuição Aleatória , Ratos Wistar , Espécies Reativas de Oxigênio/metabolismo , Escopolamina
19.
Artigo em Inglês | MEDLINE | ID: mdl-27050484

RESUMO

The aim of this paper was to compare two kinds of adsorbents (walnut shell and polymeric resins) in terms of their efficiency to remove oil from water, since walnut shell losses weight during the process requiring interruption, while polymeric resins do not. Polymeric resins based on glycidyl methacrylate and divinylbenzene (GMA-DVB) and styrene and divinylbenzene (STY-DVB) were synthesized and characterized. All adsorbents were tested by continuous flow process, eluting 3,000 bed volumes of synthetic oily water, and the oil content was monitored by fluorescence spectroscopy. Although the walnut shell presented high efficiency (∼94%), STY-DVB was even better (∼100%) besides presenting better mechanical resistance. Moreover, polymeric resins, mainly when based on GMA, can be chemically modified to remove specific contaminants still remaining in water after conventional treatment.


Assuntos
Resíduos Industriais , Juglans , Petróleo , Estirenos/química , Poluentes Químicos da Água/química , Purificação da Água/métodos , Humanos , Polímeros/química
20.
Drug Des Devel Ther ; 10: 1235-42, 2016.
Artigo em Inglês | MEDLINE | ID: mdl-27042015

RESUMO

BACKGROUND: Acne is a prominent skin condition affecting >80% of teenagers and young adults and ~650 million people globally. Isotretinoin, a vitamin A derivative, is currently the standard of care for treatment. However, it has a well-established teratogenic activity, a reason for the development of novel and low-risk treatment options for acne. OBJECTIVE: To investigate the effectiveness of Zolav(®), (a p-carboethoxy-tristyrylbenzene derivative) [corrected] a novel antibiotic as a treatment for acne vulgaris. MATERIALS AND METHODS: Minimum inhibitory concentration of Zolav(®) (a p-carboethoxy-tristyrylbenzene derivative) against Propionibacterium acnes was determined by following a standard protocol using Mueller-Hinton broth and serial dilutions in a 96-well plate. Cytotoxicity effects on human umbilical vein endothelial cells and lung cells in the presence of Zolav(®) (a p-carboethoxy-tristyrylbenzene derivative) were investigated by determining the growth inhibition (GI50) concentration, total growth inhibition concentration, and the lethal concentration of 50% (LC50). The tryptophan auxotrophic mutant of Escherichia coli strain, WP2 uvrA (ATCC 49979), was used for the AMES assay with the addition of Zolav(®) (a p-carboethoxy-tristyrylbenzene derivative) tested for its ability to reverse the mutation and induce bacterial growth. The in vivo effectiveness of Zolav(®) (a p-carboethoxy-tristyrylbenzene derivative) was tested in a P. acnes mouse intradermal model where the skin at the infection site was removed, homogenized, and subjected to colony-forming unit (CFU) counts. RESULTS: Susceptibility testing of Zolav(®) (a p-carboethoxy-tristyrylbenzene derivative) against P. acnes showed a minimum inhibitory concentration of 2 µg/mL against three strains with no cytotoxicity and no mutagenicity observed at the highest concentrations tested, 30 µM and 1,500 µg/plate, respectively. The use of Zolav(®) (a p-carboethoxy-tristyrylbenzene derivative) at a concentration of 50 µg/mL (q8h) elicited a two-log difference in CFU/g between the treatment group and the control. CONCLUSION: This study demonstrates the potential of Zolav(®) (a p-carboethoxy-tristyrylbenzene derivative) as a novel treatment for acne vulgaris.


Assuntos
Acne Vulgar/tratamento farmacológico , Acne Vulgar/microbiologia , Antibacterianos/farmacologia , Antibacterianos/uso terapêutico , Derivados de Benzeno/farmacologia , Derivados de Benzeno/uso terapêutico , Estirenos/farmacologia , Estirenos/uso terapêutico , Animais , Antibacterianos/química , Derivados de Benzeno/química , Morte Celular/efeitos dos fármacos , Linhagem Celular , Química Farmacêutica , Relação Dose-Resposta a Droga , Escherichia coli/efeitos dos fármacos , Feminino , Humanos , Masculino , Camundongos , Camundongos Endogâmicos BALB C , Testes de Sensibilidade Microbiana , Propionibacterium acnes/efeitos dos fármacos , Ratos , Ratos Sprague-Dawley , Relação Estrutura-Atividade , Estirenos/química
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