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1.
Chem Commun (Camb) ; 55(87): 13140-13143, 2019 Oct 29.
Artigo em Inglês | MEDLINE | ID: mdl-31617528

RESUMO

In this work, we depleted glutathione (GSH) by releasing SO2 with internal stimulus GSH itself, and also selectively marked the cancer cells followed by release of anticancer drug using another orthogonal stimulus i.e., two-photon (TP) NIR light by a single naphthalene based chromophore (TP absorbance 77 GM and uncaging cross-section 21 GM). We demonstrated the improved therapeutic efficacy of chlorambucil by the stepwise dual stimuli approach and dual surveillance of both the drug uncaging process in real-time using in vitro studies.


Assuntos
Alquilantes/farmacologia , Antineoplásicos Alquilantes/farmacologia , Clorambucila/farmacologia , Resistência a Múltiplos Medicamentos/efeitos dos fármacos , Resistencia a Medicamentos Antineoplásicos/efeitos dos fármacos , Naftalenos/farmacologia , Fótons , Alquilantes/química , Antineoplásicos Alquilantes/química , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Clorambucila/química , Liberação Controlada de Fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Glutationa/metabolismo , Humanos , Raios Infravermelhos , Estrutura Molecular , Naftalenos/química , Imagem Óptica , Dióxido de Enxofre/metabolismo
2.
Chem Commun (Camb) ; 55(92): 13808-13811, 2019 Nov 14.
Artigo em Inglês | MEDLINE | ID: mdl-31613284

RESUMO

Precise spatiotemporal control of singlet oxygen generation is of immense importance considering its involvement in photodynamic therapy. In this work, we present a rational design for an endoperoxide which is highly stable at ambient temperatures yet, can rapidly be converted into a highly labile endoperoxide, thus releasing the "stored" singlet oxygen on demand. The "off-on" chemical switching from the stable to the labile form is accomplished by the reaction with fluoride ions. The potential utility of controlled singlet oxygen release was demonstrated in cell cultures.


Assuntos
Materiais Biocompatíveis/química , Oxigênio Singlete/química , Materiais Biocompatíveis/farmacologia , Sobrevivência Celular/efeitos dos fármacos , Fluoretos/química , Humanos , Células MCF-7 , Microscopia Confocal , Naftalenos/química , Compostos de Amônio Quaternário/química , Oxigênio Singlete/toxicidade , Temperatura Ambiente
3.
J Phys Chem Lett ; 10(19): 5861-5867, 2019 Oct 03.
Artigo em Inglês | MEDLINE | ID: mdl-31464127

RESUMO

Circularly polarized luminescence (CPL) reflects the excited-state properties of the chiral system. However, compared to the singlet and triplet excited states, there are still many unknowns about CPL from the double excited state. Here, using the self-assembly strategy of a dipeptide substituted naphthalenediimide (NDI-GE) and the photogenerated radical anions, we have explored the ground-state (CD) and excited-state (CPL) chiral characteristics of neutral NDI and NDI•- radical anion assemblies. The neutral gelator assemblies showed CPL with the dissymmetry factor glum on the order of 10-3; the radical anion exhibited an inversed CPL signal with a significantly enhanced glum of 10-1. Time-dependent density functional theory calculation revealed that upon formation of the radical anions, the direction of the dipole moment changed, thus leading to the inversion of CD and CPL. The present work reveals a new platform for developing CPL materials based on the doublet excited state.


Assuntos
Dipeptídeos/química , Imidas/química , Naftalenos/química , Ânions/química , Teoria da Densidade Funcional , Dimerização , Cinética , Luminescência , Modelos Químicos , Modelos Moleculares , Processos Fotoquímicos , Solventes/química
4.
Chem Pharm Bull (Tokyo) ; 67(8): 775-777, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31366826

RESUMO

Nocardia is a potent bacterial producer of bioactive compounds. From a culture of Nocardia beijingensis NBRC 16342, we isolated four aromatic compounds, named beijinchromes A-D (1-4). We purified them by silica gel chromatography and reverse phase HPLC, and identified their structures by NMR and high resolution (HR)-MS analyses. 1, 2, and 4 are novel 1,2,3,8-tetrasubstituted naphthalenes, and 3 is a novel 3,8-disubstituted ortho-naphthoquinone. 1 and 2 exert antioxidant activities, and 3 exhibits antibiotic activity. Remarkably, the putative biosynthetic gene clusters for 1-4 are widely distributed in 37 Nocardia species, implying their potential to produce this family of compounds and important biological functions of beijinchromes.


Assuntos
Naftalenos/química , Naftoquinonas/química , Nocardia/química , Estrutura Molecular , Naftalenos/isolamento & purificação , Naftalenos/farmacologia , Naftoquinonas/isolamento & purificação , Naftoquinonas/farmacologia , Estereoisomerismo
5.
Environ Sci Pollut Res Int ; 26(24): 25154-25166, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31256397

RESUMO

This study evaluated an enhancement of simultaneous polycyclic aromatic hydrocarbon (PAH) biodegradation and lipid accumulation by Rhodococcus opacus using biochar derived cheaply from biomass gasification effluent. The chemical, physical, morphological, thermal, and magnetic properties of the cheaply derived biochar were initially characterized employing different techniques, which indicated that the material is easy to separate, recover, and reuse for further application. Batch experiments were carried out to study biochar-aided PAH biodegradation by R. opacus clearly demonstrating its positive effect on PAH biodegradation and lipid accumulation by the bacterium utilizing the synthetic media containing 2-, 3- or 4-ring PAH compounds, at an initial concentration in the range 50-200 mg L-1, along with 10% (w/v) inoculum. An enhancement in PAH biodegradation from 79.6 to 92.3%, 76.1 to 90.5%, 74.1 to 88.2%, and 71.6 to 82.3% for naphthalene, anthracene, phenanthrene, and fluoranthene, respectively, were attained with a corresponding lipid accumulation of 68.1%, 74.2%, 72.4%, and 63% (w/w) of cell dry weight (CDW). From contact angle measurements carried out in the study, enhancement in PAH biodegradation and lipid accumulation due to the biochar was attributed to an improved bioavailability of PAH to the degrading bacterium.


Assuntos
Lipídeos/química , Naftalenos/química , Fenantrenos/química , Hidrocarbonetos Policíclicos Aromáticos/química , Rhodococcus/química , Biodegradação Ambiental , Biomassa , Carvão Vegetal , Hidrocarbonetos Policíclicos Aromáticos/metabolismo , Rhodococcus/metabolismo
6.
Eur J Med Chem ; 180: 224-237, 2019 Oct 15.
Artigo em Inglês | MEDLINE | ID: mdl-31306909

RESUMO

Cytotoxic effects of (R)-4'-methylklavuzon were investigated on hepatocellular carcinoma cells (HuH-7 and HepG2) and HuH-7 EpCAM+/CD133+ cancer stem cells. IC50 of (R)-4'-methylklavuzon was found as 1.25 µM for HuH-7 parental cells while it was found as 2.50 µM for HuH-7 EpCAM+/CD133+ cancer stem cells. (R)-4'-methylklavuzon tended to show more efficient in vitro cytotoxicity with its lower IC50 values on hepatocellular carcinoma cell lines compared to its lead molecule, goniothalamin and FDA-approved drugs, sorafenib and regorafenib. Cell-based Sirtuin/HDAC enzyme activity measurements revealed that endogenous Sirtuin/HDAC enzymes were reduced by 40% compared to control. SIRT1 protein levels were upregulated indicating triggered DNA repair mechanism. p53 was overexpressed in HepG2 cells. (R)-4'-methylklavuzon inhibited CRM1 protein providing increased retention of p53 and RIOK2 protein in the nucleus. HuH-7 parental and EpCAM+/CD133+ cancer stem cell spheroids lost intact morphology. 3D HepG2 spheroid viabilities were decreased in a correlation with upregulation in p53 protein levels.


Assuntos
Antígeno AC133/antagonistas & inibidores , Antineoplásicos/farmacologia , Carcinoma Hepatocelular/tratamento farmacológico , Molécula de Adesão da Célula Epitelial/antagonistas & inibidores , Carioferinas/antagonistas & inibidores , Neoplasias Hepáticas/tratamento farmacológico , Naftalenos/farmacologia , Receptores Citoplasmáticos e Nucleares/antagonistas & inibidores , Sirtuína 1/antagonistas & inibidores , Antígeno AC133/metabolismo , Antineoplásicos/síntese química , Antineoplásicos/química , Carcinoma Hepatocelular/metabolismo , Carcinoma Hepatocelular/patologia , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Molécula de Adesão da Célula Epitelial/metabolismo , Células Hep G2 , Humanos , Carioferinas/metabolismo , Neoplasias Hepáticas/metabolismo , Neoplasias Hepáticas/patologia , Estrutura Molecular , Naftalenos/síntese química , Naftalenos/química , Receptores Citoplasmáticos e Nucleares/metabolismo , Sirtuína 1/metabolismo , Relação Estrutura-Atividade , Células Tumorais Cultivadas
7.
Environ Sci Pollut Res Int ; 26(24): 25142-25153, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31254193

RESUMO

The three-dimensional quantitative structure-activity relationship (3D-QSAR) model is established for polychlorinated naphthalenes (PCNs) using the biological degradability (total score) results to modify CN-56 to design 37 new derivatives with higher degradability (increased by 14.55-38.79%). Furthermore, five new CN-56 derivatives are selected through evaluation of their persistent organic pollutant properties (toxicity, bioconcentration, long-range transport) and practicability (stability, insulativity, flame retardancy) using 3D-QSAR, density functional theory (DFT) and molecular docking methods. Environmental and health-based risk assessments are conducted using the multimedia fugacity model and fuzzy theory for complete screening of the new CN-56 derivatives. Whereas CN-56 is classed as high risk, three new derivatives can be classed as medium risk. The biodegradability mechanism analysis of the PCNs indicates that the electrostatic property is the main factor that affects the degradability, which provides a favorable theoretical reference to obtain environmentally friendly fire retardant and insulating materials.


Assuntos
Poluentes Ambientais/análise , Naftalenos/análise , Biodegradação Ambiental , Poluentes Ambientais/química , Simulação de Acoplamento Molecular , Naftalenos/química , Relação Quantitativa Estrutura-Atividade , Medição de Risco , Eletricidade Estática
8.
Eur J Med Chem ; 178: 648-666, 2019 Sep 15.
Artigo em Inglês | MEDLINE | ID: mdl-31226656

RESUMO

Targeting autophagy is a promising therapeutic strategy for cancer treatment. As a result, the identification of novel autophagy inhibitors is an emerging field of research. Herein, we report the development of a novel AlphaScreen HTS assay that combined with a MS-based assay and a structure-based high-throughput virtual screening have enabled the identification of benzo[cd]indol-2(1H)-one as a novel scaffold that targets Atg4B. Thus, an initial screening campaign led to the identification of NSC126353 and NSC611216 bearing a chlorohydrin moiety. Structural-activity relationship analysis of the initial hits provided an optimized lead, compound 33, bearing a 7-aminobenzo[cd]indol-2-[1H]-one scaffold and a propyl group replacing the chlorine. Inhibition of autophagy was also investigated in cells by measuring LC3-II and p62 protein levels. Moreover, the synergistic effect of 33 combined with oxaliplatin resulted in an enhanced cell death in the human colorectal adenocarcinoma cell line HT-29. We are convinced that the developed AlphaScreen and MS-based assays can be key tools enabling the high-throughput identification of novel Atg4B inhibitors. Moreover, the aminobenzo[cd]indol-2-[1H]-one scaffold represents a novel chemotype for the further development of small molecule inhibitors of Atg4B.


Assuntos
Proteínas Relacionadas à Autofagia/antagonistas & inibidores , Lactamas/farmacologia , Naftalenos/farmacologia , Proteínas Relacionadas à Autofagia/metabolismo , Cisteína Endopeptidases/metabolismo , Relação Dose-Resposta a Droga , Avaliação Pré-Clínica de Medicamentos , Humanos , Lactamas/síntese química , Lactamas/química , Modelos Moleculares , Estrutura Molecular , Naftalenos/síntese química , Naftalenos/química , Relação Estrutura-Atividade
9.
Eur J Med Chem ; 178: 571-588, 2019 Sep 15.
Artigo em Inglês | MEDLINE | ID: mdl-31220675

RESUMO

In order to obtain novel pharmacological tools and to investigate a multitargeting analgesic strategy, the CB1 and CB2 cannabinoid receptor agonist JWH-018 was conjugated with the opiate analgesic oxycodone or with an enkephalin related tetrapeptide. The opioid and cannabinoid pharmacophores were coupled via spacers of different length and chemical structure. In vitro radioligand binding experiments confirmed that the resulting bivalent compounds bound both to the opioid and to the cannabinoid receptors with moderate to high affinity. The highest affinity bivalent derivatives 11 and 19 exhibited agonist properties in [35S]GTPγS binding assays. These compounds activated MOR and CB (11 mainly CB2, whereas 19 mainly CB1) receptor-mediated signaling, as it was revealed by experiments using receptor specific antagonists. In rats both 11 and 19 exhibited antiallodynic effect similar to the parent drugs in 20 µg dose at spinal level. These results support the strategy of multitargeting G-protein coupled receptors to develop lead compounds with antinociceptive properties.


Assuntos
Analgésicos Opioides/farmacologia , Encefalinas/farmacologia , Indóis/farmacologia , Naftalenos/farmacologia , Oxicodona/farmacologia , Receptor CB1 de Canabinoide/antagonistas & inibidores , Receptor CB2 de Canabinoide/antagonistas & inibidores , Receptores Opioides mu/antagonistas & inibidores , Analgésicos Opioides/síntese química , Analgésicos Opioides/química , Animais , Relação Dose-Resposta a Droga , Encefalinas/química , Indóis/química , Camundongos , Estrutura Molecular , Naftalenos/química , Oxicodona/química , Ratos , Receptor CB1 de Canabinoide/metabolismo , Receptor CB2 de Canabinoide/metabolismo , Receptores Opioides mu/metabolismo , Relação Estrutura-Atividade
10.
Chemistry ; 25(47): 11085-11097, 2019 Aug 22.
Artigo em Inglês | MEDLINE | ID: mdl-31219221

RESUMO

Naphthalene diimide (NDI) dyads exhibiting a different substitution pattern and linker length have been synthesised and evaluated as G-quadruplex (G4) ligands, by investigating their cytotoxicity in selected cell lines. The dyads with the long C7 linker exhibit extremely low IC50 values, below 10 nm, on different cancer cell lines. Contrary, the dyads with the shorter C4 linker were much less effective, with IC values increasing up to 1 µm. Among the three dyads with the longest linker, small differences in the IC50 values emerge, suggesting that the linker length plays a more important role than the substitution pattern. We have further shown that the dyads are able to induce cellular DNA damage response, which is not limited to the telomeric regions and is likely the origin of their cytotoxicity. Both absorption titration and dynamic light scattering of the most cytotoxic dyads in the presence of hTel22 highlight their ability to induce effective G4 aggregation, acting as non-covalent cross-linking agents.


Assuntos
Dano ao DNA/efeitos dos fármacos , Reparo do DNA/efeitos dos fármacos , Quadruplex G , Imidas/farmacologia , Naftalenos/farmacologia , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Imidas/síntese química , Imidas/química , Ligantes , Metáfase/efeitos dos fármacos , Microscopia de Fluorescência , Naftalenos/síntese química , Naftalenos/química , Proteínas Proto-Oncogênicas c-kit/genética , Proteínas Proto-Oncogênicas c-kit/metabolismo , Proteínas Proto-Oncogênicas c-myc/genética , Proteínas Proto-Oncogênicas c-myc/metabolismo , Telômero/efeitos dos fármacos , Telômero/metabolismo
11.
Anal Chim Acta ; 1069: 82-88, 2019 Sep 03.
Artigo em Inglês | MEDLINE | ID: mdl-31084744

RESUMO

Nerve agent metabolites (NAMs) derived from alkyl methyl phosphonic acids, such as ethyl methylphosphonic acid (EMPA), isopropyl methylphosphonic acid (IMPA), and pinacolyl methylphosphonic acid (PMPA), were extracted from human urine using diethyl ether as an extractant. After exchanging the diethyl ether solvent to acetonitrile, the analytes were derivatized with 2-(bromomethyl)naphthalene (BMN). The reaction products of the BMN and NAMs, i.e., MN-EMPA, MN-IMPA, and MN-PMPA, were separated by gas chromatography (GC) and measured by mass spectrometry (MS) using a femtosecond laser emitting at 267 nm as the ionization source for resonance-enhanced two-photon ionization (RE2PI). The limits of detection (LOD) were <1 ng/mL for these analytes. The use of BMN increased the volatility of the analytes for separation by GC and also increased the ionization efficiency via the RE2PI process as the result of presence of a naphthalene functional group. A two-dimensional GC-MS display can be used for comprehensive analysis of NAMs, by-products, and impurities in the sample. Then, this approach could be used to confirm the use of chemical weapons and for forensic identification.


Assuntos
Lasers , Naftalenos/química , Agentes Neurotóxicos/análise , Agentes Neurotóxicos/metabolismo , Urinálise/métodos , Humanos , Espectrometria de Massas , Fatores de Tempo , Urinálise/instrumentação
12.
Chemistry ; 25(44): 10464-10471, 2019 Aug 06.
Artigo em Inglês | MEDLINE | ID: mdl-31111971

RESUMO

Programmable assembly of biomolecules is a fast growing research area that aims to emulate nature's elegance in creating numerous hierarchical self-assembled structures, which are responsible for unimaginably difficult biological functions. Protein assembly is a particularly challenging task, owing to their structural diversity, conformational heterogeneity, and high molecular weight. This article reveals the ability of a supramolecular structure-directing unit (SSDU) to regulate the entropically favourable supramolecular assembly of a covalently conjugated protein (bovine serum albumin (BSA)) to produce well-defined protein-decorated micelles with remarkably high thermal stability, suppression of the thermal denaturation of the protein, and retention of enzymatic activity. Furthermore, a SSDU-appended thermo-responsive poly(N-isopropylacrylamide) (PNIPAM) co-assembles with the SSDU-BSA conjugate because, in both cases, assembly was primarily driven by specific molecular recognition between the SSDUs. However, the resulting supramolecular protein-polymer conjugate exhibits distinctly different polymersome structure to that of the micellar particle produced by the protein-SSDU conjugate. In this case, the enzymatic activity can be significantly suppressed above the lower critical solution temperature of supramolecularly conjugated PNIPAM, possibly due to collapse of the de-solvated polymer chains on the protein surface.


Assuntos
Resinas Acrílicas/química , Soroalbumina Bovina/química , Imidas/química , Micelas , Nanopartículas/química , Naftalenos/química , Temperatura Ambiente , Termodinâmica
13.
Nat Commun ; 10(1): 2074, 2019 05 06.
Artigo em Inglês | MEDLINE | ID: mdl-31061390

RESUMO

Hydride transfers play a crucial role in a multitude of biological redox reactions and are mediated by flavin, deazaflavin or nicotinamide adenine dinucleotide cofactors at standard redox potentials ranging from 0 to -340 mV. 2-Naphthoyl-CoA reductase, a key enzyme of oxygen-independent bacterial naphthalene degradation, uses a low-potential one-electron donor for the two-electron dearomatization of its substrate below the redox limit of known biological hydride transfer processes at E°' = -493 mV. Here we demonstrate by X-ray structural analyses, QM/MM computational studies, and multiple spectroscopy/activity based titrations that highly cooperative electron transfer (n = 3) from a low-potential one-electron (FAD) to a two-electron (FMN) transferring flavin cofactor is the key to overcome the resonance stabilized aromatic system by hydride transfer in a highly hydrophobic pocket. The results evidence how the protein environment inversely functionalizes two flavins to switch from low-potential one-electron to hydride transfer at the thermodynamic limit of flavin redox chemistry.


Assuntos
Proteínas de Bactérias/química , Coenzimas/química , Flavinas/química , Modelos Moleculares , Oxirredutases/química , Proteínas de Bactérias/isolamento & purificação , Proteínas de Bactérias/metabolismo , Coenzimas/metabolismo , Simulação por Computador , Cristalografia por Raios X , Transporte de Elétrons , Flavinas/metabolismo , Naftalenos/química , Naftalenos/metabolismo , Oxirredutases/isolamento & purificação , Oxirredutases/metabolismo , Estrutura Terciária de Proteína , Proteínas Recombinantes/química , Proteínas Recombinantes/isolamento & purificação , Proteínas Recombinantes/metabolismo , Análise Espectral
14.
Chemistry ; 25(42): 9967-9972, 2019 Jul 25.
Artigo em Inglês | MEDLINE | ID: mdl-31056773

RESUMO

3,3'-Diformyl-1,1'-bi-2-naphthol or its methoxymethyl-protected derivative is found to undergo a highly selective reaction with excess bromine in CH2 Cl2 at reflux to give the novel 5,5',6,6'-tetrabrominated product (S)- or (R)-2. The observed electrophilic substitution at the 5,5'-positons of an optically active binaphthyl compound is unprecedented. Unlike unbrominated 3,3'-diformyl-1,1'-bi-2-naphthol, which is not suitable for fluorescent recognition in water, compound (S)-2, in combination with Zn2+ , exhibits a highly enantioselective fluorescent response toward amino acids in aqueous solution (HEPES buffer, pH 7.4). It is further found that the condensation product of (R)-2 with tryptophan, (R)-3, shows dual-responsive emissions toward amino acids; the short wavelength (λ1 =350 nm) emission is sensitive to the concentration of the substrate regardless of the chiral configuration and the long wavelength (λ2 >500 nm) emission is highly enantioselective. Thus, the use of (R)-3 allows the simultaneous determination of the concentration and enantiomeric composition of an amino acid sample from one fluorescence measurement.


Assuntos
Aldeídos/química , Aminoácidos/análise , Corantes Fluorescentes/química , Naftalenos/química , Cátions Bivalentes , Conformação Molecular , Estereoisomerismo , Água , Zinco/química
15.
J Agric Food Chem ; 67(24): 6819-6827, 2019 Jun 19.
Artigo em Inglês | MEDLINE | ID: mdl-31135148

RESUMO

Napropamide [ N, N-diethyl-2-(1-naphthalenyloxy)propenamide, NAP] is a highly efficient and broad-spectrum amide herbicide. Little is known about the bacterial catabolism of its different enantiomers. Here, we report the isolation of two NAP-degrading strains of Sphingobium sp., A1 and B2, and the different catabolic pathways of different enantiomers in these two strains. Strain A1 dioxygenated NAP at different positions of the naphthalene ring of different enantiomers, leading to the complete degradation of R-NAP while producing a dead-end product from S-NAP. Strain B2 cleaved the amido bonds of both enantiomers, but only the product from S-NAP could be further transformed to form α-naphthol and mineralize in strain B2. The degradation rates of R-NAP and S-NAP in the combination degradation by strains A1 and B2 were 24.8 and 7.5 times that in the single-strain degradation by strain B2 or A1, respectively, showing enhanced synergistic catabolism between strains A1 and B2. This study provides new insights into the enantioselective catabolic network of the chiral herbicide NAP in microorganisms.


Assuntos
Herbicidas/química , Herbicidas/metabolismo , Naftalenos/química , Naftalenos/metabolismo , Sphingomonadaceae/metabolismo , Biodegradação Ambiental , Sphingomonadaceae/química , Estereoisomerismo
16.
J Agric Food Chem ; 67(22): 6414-6422, 2019 Jun 05.
Artigo em Inglês | MEDLINE | ID: mdl-31088051

RESUMO

The C13-norisoprenoid aroma compounds 1,1,6-trimethyl-1,2-dihydronaphthalene (TDN) and isomeric 2,10,10-trimethyl-6-methylene-1-oxaspiro[4.5]dec-7-enes, so-called vitispiranes, are considered to be biosynthetically related. They occur at higher concentrations in bottle-aged Riesling wines especially and are important contributors to the varietal aroma of Riesling wines. Because of the variation of the quantitative methods and data reported in the literature, a redetermination of concentration levels for both free and total TDN and isomeric vitispiranes, especially in German Riesling wines, was performed using a stable-isotope-dilution assay (SIDA). For this purpose, a novel six-step synthetic route to TDN and deuterium-labeled TDN was developed. A standardized sample preparation for TDN and vitispiranes and a rapid acid-hydrolysis method at genuine wine-pH conditions for the conversion of the precursors into TDN and vitispiranes were also developed. Automated HS-SPME was applied to 250 wine samples from two wine competitions, and analysis was performed by gas chromatography-mass spectrometry with selected-ion monitoring (GC-SIM-MS) as well as selected-reaction monitoring (GC-SRM-MS).


Assuntos
Deutério/química , Naftalenos/química , Norisoprenoides/química , Vinho/análise , Cromatografia Gasosa-Espectrometria de Massas , Técnicas de Diluição do Indicador , Isomerismo , Naftalenos/síntese química , Vitis/química
17.
Chemosphere ; 229: 570-579, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31100628

RESUMO

Trace anionic dyes in wastewater are difficult to be rapidly and efficiently removed because they are completely soluble and poorly biodegradable. Herein, a facile and environmentally friendly adsorbent was fabricated via the surface functioned SiO2 with abundant amine groups of polyethyleneimine (PEI). The structural characterization indicated that PEI was successfully immobilized on the SiO2 surface. The adsorption performance of SiO2-PEI was evaluated using acid orange II (AOII) as model pollutant. The adsorption of AOII on SiO2-PEI displayed high removal rates in the pH range of 2.0-9.0, and exhibited ultrafast removal (99.1% removal rate at 10 min). The adsorption behavior fitted well with the Langmuir isotherm and pseudo-second-order kinetic model, and the maximum uptake capability of AOII was higher than 705.3 mg/g. The excellent adsorption capacity of AOII on SiO2-PEI mainly relied on the electrostatic attraction between the sulfonic acid group of AOII and amine group of PEI in the adsorption process. Additionally, other anionic dyes like acid fuchsin and direct sky blue 5B could also be fast and efficiently removed by SiO2-PEI. This work is expected to open new possibilities for the ultrafast removal of anionic dye pollutants.


Assuntos
Compostos Azo/isolamento & purificação , Corantes/isolamento & purificação , Nanopartículas/química , Naftalenos/isolamento & purificação , Polietilenoimina/química , Poluentes Químicos da Água/isolamento & purificação , Adsorção , Ânions , Compostos Azo/química , Benzenossulfonatos/química , Benzenossulfonatos/isolamento & purificação , Corantes/química , Cinética , Microscopia Eletrônica de Varredura , Naftalenos/química , Dióxido de Silício/química , Espectroscopia de Infravermelho com Transformada de Fourier , Termogravimetria , Eliminação de Resíduos Líquidos/instrumentação , Eliminação de Resíduos Líquidos/métodos , Águas Residuárias/química , Poluentes Químicos da Água/química , Difração de Raios X
18.
Chem Pharm Bull (Tokyo) ; 67(7): 725-728, 2019 Jul 01.
Artigo em Inglês | MEDLINE | ID: mdl-30982797

RESUMO

Eighteen novel chalcone derivatives containing indole and naphthalene moieties (2-19) were synthesized and characterized by 1H-NMR, 13C-NMR and high resolution (HR)-MS spectra. All compounds were evaluated for their in vitro cytotoxic potential against human hepatocellular carcinoma (HepG2), human colon carcinoma (HCT116) and human breast adenocarcinoma (MCF-7) cell lines. Among them, compound 2, 3, 4 and 7 showed potent activities against tested cancer cell lines. More significantly, compound 7 exhibited the most potent cytotoxic activity against HepG2, HCT116 and MCF-7 with IC50 values of 0.65, 1.13 and 0.82 µM, respectively. Furthermore, flow cytometry analysis indicated that compound 7 arrested cancer cells in G2/M phase. The compound 7 also displayed significant inhibition of tubulin polymerization (IC50 = 3.9 µM). Finally, molecular docking studies were performed to explore the possible interactions between compound 7 and tubulin binding pockets.


Assuntos
Antineoplásicos/síntese química , Chalconas/química , Indóis/química , Naftalenos/química , Moduladores de Tubulina/síntese química , Antineoplásicos/metabolismo , Antineoplásicos/farmacologia , Sítios de Ligação , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Chalconas/metabolismo , Chalconas/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Pontos de Checagem da Fase G2 do Ciclo Celular/efeitos dos fármacos , Humanos , Concentração Inibidora 50 , Pontos de Checagem da Fase M do Ciclo Celular/efeitos dos fármacos , Simulação de Acoplamento Molecular , Estrutura Terciária de Proteína , Relação Estrutura-Atividade , Tubulina (Proteína)/química , Tubulina (Proteína)/metabolismo , Moduladores de Tubulina/metabolismo , Moduladores de Tubulina/farmacologia
19.
Ecotoxicol Environ Saf ; 177: 86-92, 2019 Aug 15.
Artigo em Inglês | MEDLINE | ID: mdl-30974247

RESUMO

Polychlorinated naphthalenes (PCNs) in the environment in China have been studied extensively. However, there have been no reports on PCNs in human serum samples from China. In this context, we collected 480 serum samples from an industrial city in Eastern China. The concentration range for the sum of the mono-to octa-CNs was 14300-50700 pg/g lipid. The most predominant congener was CN-5/7, which accounted for 21.6%-51.1% of the total PCN concentration. Further analysis indicated that residues of PCN industrial technical products in the local environment appear to be the main source of CN-5/7 in the serum samples. On the other hand, the sum of the tetra-to octa-CNs concentration was obviously higher in males (1390 ±â€¯929 pg/g lipid) than in females (267 ±â€¯25 pg/g lipid). Moreover, the concentrations of combustion-related PCNs in the male 20-24, 25-29 and 30-34 years groups were obviously higher than those in the female samples. Therefore, industrial thermal processes are important sources of PCNs in male serum in addition to PCN products. The toxic equivalent (TEQ) concentrations of PCNs in the pooled serum samples ranged from 0.12 to 0.40 pg/g lipid. CN-10 and CN-66/67 were the dominant TEQ congeners in male serum, and CN-10, CN-1, and CN-2 were the main TEQ congeners in female serum.


Assuntos
Monitoramento Ambiental , Naftalenos/sangue , Adolescente , Adulto , China , Cidades , Feminino , Humanos , Masculino , Pessoa de Meia-Idade , Naftalenos/química , Fatores Sexuais
20.
Mar Drugs ; 17(4)2019 Apr 11.
Artigo em Inglês | MEDLINE | ID: mdl-30978906

RESUMO

In order to find out the seeds of antitumor agents, we focused on potential bioactive materials from marine-derived microorganisms. Marine products include a number of compounds with unique structures, some of which may exhibit unusual bioactivities. As a part of this study, we studied metabolites of a strain of Alternaria sp. OUPS-117D-1 originally derived from the sea urchin Anthocidaris crassispina, and isolated five new decalin derivatives, altercrasins A-E (1-5). The absolute stereostructure of altercrasins A (1) had been decided by chemical transformation and the modified Mosher's method. In this study, four decalin derivatives, altercrasins B-E (2-5) were purified by silica gel chromatography, and reversed phase high-performance liquid chromatography (RP HPLC), and their structures were elucidated on the basis of 1D and 2D nuclear magnetic resonance (NMR) spectroscopic analyses. The absolute configuration of them were deduced by the comparison with 1 in the NMR chemical shifts, NOESY correlations, and electronic circular dichroism (ECD) spectral analyses. As a result, we found out that compound pairs of 1/2 and 4/5 were respective stereoisomers. In addition, their cytotoxic activities using murine P388 leukemia, human HL-60 leukemia, and murine L1210 leukemia cell lines showed that 4 and 5 exhibit potent cytotoxicity, in especially, the activity of 4 was equal to that of 5-fluorouracil.


Assuntos
Alternaria/química , Antineoplásicos/isolamento & purificação , Naftalenos/isolamento & purificação , Ouriços-do-Mar/microbiologia , Animais , Antineoplásicos/química , Antineoplásicos/farmacologia , Linhagem Celular Tumoral , Dicroísmo Circular , Ensaios de Seleção de Medicamentos Antitumorais , Fluoruracila/farmacologia , Humanos , Espectroscopia de Ressonância Magnética , Camundongos , Estrutura Molecular , Naftalenos/química , Naftalenos/farmacologia , Estereoisomerismo
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