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1.
Chempluschem ; 88(8): e202300264, 2023 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-37540494

RESUMO

A novel cyanine compound based on the conjugated perylene-benzothiazole system (PBI) as a colorimetric and fluorometric dual-channel sensor for cyanide (CN- ) detection was synthesized and characterized via UV-vis and fluorescence spectroscopy. PBI exhibited a high sensitivity and rapid optical response for CN- due to the intramolecular charge transfer (ICT) mechanism. The detection limit of PBI for CN- was 1.15×10-7  M in the mixture of DMSO/H2 O (1 : 1, v/v). Moreover, probe PBI demonstrated high selectivity and sensitivity for CN- over other common anions, including Cl- , Br- , F- , I- , AcO- , ClO4 - , HSO4 - , SO4 2- , NO2 - , NO3 - and SCN- . This work provided a simple and effective approach to trace the toxic CN- ion with rapid response, high selectivity, and sensitivity that is possibly applied in environmental control and agricultural management.

2.
Nat Prod Res ; 37(15): 2541-2550, 2023.
Artigo em Inglês | MEDLINE | ID: mdl-35337215

RESUMO

Two new xanthones, oblongixanthones I (1) and J (2), and seven known compounds (3-9), were isolated from an EtOAc extract of the twigs of Garcinia oblongifolia. Their structures were elucidated using spectroscopic methods, mainly 1 D and 2 D NMR. The antidiabetic effects of the two new compounds were evaluated using α-glucosidase and PTP1B inhibition assays. Both compounds displayed strong inhibition towards α-glucosidase with IC50 values of 258.7 ± 49.3 and 187.1 ± 27.5 µM, respectively (compared with acarbose, IC50 = 900.0 ± 3.0 µM) and moderate effects against PTP1B with IC50 values of 93.9 ± 12.3 and 64.1 ± 5.8 µM, respectively (compared with RK682, IC50 = 4.4 ± 0.3 l µM).


Assuntos
Garcinia , Xantonas , Xantonas/química , Xantonas/farmacologia , Hipoglicemiantes/química , Hipoglicemiantes/farmacologia , Estrutura Molecular , Garcinia/química , alfa-Glucosidases/metabolismo
3.
Nat Prod Res ; 37(5): 750-758, 2023 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-35727176

RESUMO

Nine compounds including a new one, garcichaudiic acid (1), were isolated from the bark of G. gaudichaudii and their structures were characterized mainly by 1 D and 2 D NMR experiments. The antioxidant capacity of the isolated compounds was determined using DPPH radical scavenging assay and the anti-hyperglycemic activity was assessed by measuring the inhibitory effect against α-glucosidase. Among them, compound 4 showed higher antioxidant activity than the positive control, ascorbic acid, while both compounds 1 and 7 exhibited more significant α-glucosidase inhibitory activity than the reference drug acarbose. Molecular docking analysis of the bioactive compounds was also performed to examine the binding modes and key interactions with the catalytic site.


Assuntos
Antioxidantes , Garcinia , Antioxidantes/química , alfa-Glucosidases/metabolismo , Inibidores de Glicosídeo Hidrolases/química , Simulação de Acoplamento Molecular , Garcinia/química
4.
Nat Prod Res ; 37(2): 240-247, 2023 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-34351811

RESUMO

Two new triterpenoids, entanolide (1) and methyl 3,4-secotirucalla-23-oxo-4(28),7,24-trien-21-al-3-oate (2), together with nine known compounds (3-11), were isolated from the bark of Entandrophragma angolense. Their structures were elucidated based on spectroscopic analyses, mainly 1 D and 2 D NMR spectral data. Compounds 1-6 and 8 were evaluated for their cytotoxicity against HepG2 cells, and compounds 2-5 exhibited weak activities.


Assuntos
Meliaceae , Triterpenos , Humanos , Triterpenos/química , Estrutura Molecular , Casca de Planta/química , Espectroscopia de Ressonância Magnética , Células Hep G2 , Meliaceae/química
5.
Nat Prod Res ; 36(6): 1494-1502, 2022 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-33703953

RESUMO

Two new rocaglamides, 8b-O-5-oxohexylrocaglaol (1) and elaeagnin (2), together with twelve known compounds, were isolated from the bark of Aglaia elaeagnoidea and the whole tree of A. odorata. Their structures were determined using spectroscopic methods, mainly 1D and 2D NMR. Cytotoxic activity against HepG2 human liver cancer cells of the isolated compounds was evaluated in vitro using the SRB assay. Three rocaglamide derivatives, dehydroaglaiastatin (13), 8b-O-5-oxohexylrocaglaol (1) and rocaglaol (5), exhibited significant effects with IC50 values of 0.69, 4.77 and 7.37 µM, respectively.


Assuntos
Aglaia , Aglaia/química , Células Hep G2 , Humanos , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/farmacologia
6.
Fitoterapia ; 133: 75-79, 2019 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-30576797

RESUMO

Three new limonoids, walsucochinones A-C (1-3), along with eight known compounds, were isolated from an ethyl acetate extract of the bark of Walsura cochinchinensis. Their structures were determined using spectroscopic techniques, mainly 1-D and 2-D NMR. The ethyl acetate extract showed cytotoxic activity against MCF-7 human breast cancer cells and cytotoxicity of the isolated compounds were evaluated in vitro using the SRB assay. Walsucochinone C (3) exhibited the most active effect with IC50 value of 16.4 ±â€¯0.2 µM.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Limoninas/farmacologia , Meliaceae/química , Casca de Planta/química , Antineoplásicos Fitogênicos/isolamento & purificação , Humanos , Concentração Inibidora 50 , Limoninas/isolamento & purificação , Células MCF-7 , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Vietnã
7.
Chem Cent J ; 11(1): 135, 2017 Dec 21.
Artigo em Inglês | MEDLINE | ID: mdl-29270833

RESUMO

BACKGROUND: Although poly(N-acyl dithieno[3,2-b:2',3'-d]pyrrole)s have attracted great attention as a new class of conducting polymers with highly stabilized energy levels, hyperbranched polymers based on this monomer type have not yet been studied. Thus, this work aims at the synthesis of novel hyperbranched polymers containing N-benzoyl dithieno[3,23,2-b:2',3'-d]pyrrole acceptor unit and 3-hexylthiophene donor moiety via the direct arylation polymerization method. Their structures, molecular weights and thermal properties were characterized via 1H NMR and FTIR spectroscopies, GPC, TGA, DSC and XRD measurements, and the optical properties were investigated by UV-vis and fluorescence spectroscopies. RESULTS: Hyperbranched conjugated polymers containing N-benzoyl dithieno[3,23,2-b:2',3'-d]pyrrole acceptor unit and 3-hexylthiophene donor moiety, linked with either triphenylamine or triphenylbenzene as branching unit, were obtained via direct arylation polymerization of the N-benzoyl dithieno[3,23,2-b:2',3'-d]pyrrole, 2,5-dibromo 3-hexylthiophene and tris(4-bromophenyl)amine (or 1,3,5-tris(4-bromophenyl)benzene) monomers. Organic solvent-soluble polymers with number-average molecular weights of around 18,000 g mol-1 were obtained in 80-92% yields. The DSC and XRD results suggested that the branching structure hindered the stacking of polymer chains, leading to crystalline domains with less ordered packing in comparison with the linear analogous polymers. The results revealed that the hyperbranched polymer with triphenylbenzene as the branching unit exhibited a strong red-shift of the maximum absorption wavelength, attributed to a higher polymer stacking order as a result of the planar structure of triphenylbenzene. CONCLUSION: Both hyperbranched polymers with triphenylamine/triphenylbenzene as branching moieties exhibited high structural order in thin films, which can be promising for organic solar cell applications. The UV-vis absorption of the hyperbranched polymer containing triphenylbenzene as branching unit was red-shifted as compared with the triphenylamine-containing polymer, as a result of a higher chain packing degree.

8.
Bioorg Med Chem Lett ; 27(15): 3301-3304, 2017 08 01.
Artigo em Inglês | MEDLINE | ID: mdl-28624142

RESUMO

An ethyl acetate extract the bark of Garcinia xanthochymus exhibited strong inhibition towards α-glucosidase and PTP1B with IC50 values of 0.3±0.1µg/mL and 2.3±0.4µg/mL, respectively. Chemical constituents of the extract were therefore examined, and two new compounds, xanthochymusxanthones A (1) and B (2), along with ten known xanthones (3-12), were isolated. Their structures were determined using spectroscopic methods, mainly 1D and 2D NMR. Inhibitory activity of the isolated compounds was then tested, and subelliptenone F (12) showed significant effect towards α-glucosidase with IC50 value of 4.1±0.3µM (compared with acarbose, IC50=900.0±3.0µM) whilst xanthochymusxanthone B (2) exhibited remarkable activity towards PTP1B with IC50 value of 8.0±0.6µM (compared with RK682, IC50=4.4±0.3µM).


Assuntos
Garcinia/química , Inibidores de Glicosídeo Hidrolases/química , Inibidores de Glicosídeo Hidrolases/farmacologia , Proteína Tirosina Fosfatase não Receptora Tipo 1/antagonistas & inibidores , Xantonas/química , Xantonas/farmacologia , Diabetes Mellitus/tratamento farmacológico , Diabetes Mellitus/metabolismo , Inibidores de Glicosídeo Hidrolases/isolamento & purificação , Humanos , Hipoglicemiantes/química , Hipoglicemiantes/isolamento & purificação , Hipoglicemiantes/farmacologia , Modelos Moleculares , Casca de Planta/química , Proteína Tirosina Fosfatase não Receptora Tipo 1/metabolismo , Xantonas/isolamento & purificação , alfa-Glucosidases/metabolismo
9.
Chem Cent J ; 9: 10, 2015.
Artigo em Inglês | MEDLINE | ID: mdl-25763100

RESUMO

BACKGROUND: Carbon nanotube (CNT) characteristics, besides the processing conditions, can change significantly the microwave absorption behavior of CNT/polymer composites. In this study, we investigated the influence of three commercial multi-walled CNT materials with various diameters and length-to-diameter aspect ratios on the X-band microwave absorption of epoxy nanocomposites with CNT contents from 0.125 to 2 wt%, prepared by two dispersion methods, i.e. in solution with surfactant-aiding and via ball-milling. RESULTS: The laser diffraction particle size and TEM analysis showed that both methods produced good dispersions at the microscopic level of CNTs. Both a high aspect ratio resulting in nanotube alignment trend and good infiltration of the matrix in the individual nanotubes, which was indicated by high Brookfield viscosities at low CNT contents of CNT/epoxy dispersions, are important factors to achieve composites with high microwave absorption characteristics. The multi-walled carbon nanotube (MWCNT) with the largest aspect ratio resulted in composites with the best X-band microwave absorption performance, which is considerably better than that of reported pristine CNT/polymer composites with similar or lower thicknesses and CNT loadings below 4 wt%. CONCLUSIONS: A high aspect ratio of CNTs resulting in microscopic alignment trend of nanotubes as well as a good level of micro-scale CNT dispersion resulting from good CNT-matrix interactions are crucial to obtain effective microwave absorption performance. This study demonstrated that effective radar absorbing MWCNT/epoxy nanocomposites having small matching thicknesses of 2-3 mm and very low filler contents of 0.25-0.5 wt%, with microwave energy absorption in the X-band region above 90% and maximum absorption peak values above 97%, could be obtained via simple processing methods, which is promising for mass production in industrial applications. Graphical AbstractComparison of the X-band microwave reflection loss of epoxy composites of various commercial multi-walled carbon nanotube materials.

10.
Langmuir ; 26(17): 14073-80, 2010 Sep 07.
Artigo em Inglês | MEDLINE | ID: mdl-20707322

RESUMO

The effect of annealing on the structure and the helix orientation in Langmuir-Blodgett (LB) monolayers of diblock copolymers (PLGA-b-PMLGSLGs) of poly(alpha-L-glutamic acid) (PLGA) and poly(gamma-methyl-L-glutamate-ran-gamma-stearyl-L-glutamate) with 30 mol % of stearyl substituents (PMLGSLG) with unidirectional helix orientation deposited on hydrophilic silicon substrates was characterized by means of small-angle X-ray reflectivity, transmission Fourier transform infrared spectroscopy, and atomic force microscopy. Upon annealing at 100 degrees C for 24 h, the alpha-helices became less tilted toward the substrate surface normal. Surface area shrinkage accompanied the change in tilt, indicated by an increase in both film thickness and electron density, resulting in more compact and uniform films. The enhancement of the helix orientation by thermal annealing was greater for the PMLGSLG block and for the diblock copolymers with the shorter block lengths. For these diblock copolymers, annealing resulted in postorientation of the PMLGSLG block helices almost perpendicular to the substrate surface. This effect originates from a considerable increase in intermolecular packing of the PLGA block caused by hydrogen bonds between the carboxylic groups upon annealing, as well as the high mobility of the PMLGSLG block helices for rearrangement favored by the melted side chain mantle at elevated temperatures.


Assuntos
Membranas Artificiais , Peptídeos/química , Ácido Poliglutâmico/química , Estrutura Molecular , Propriedades de Superfície
11.
Langmuir ; 26(13): 11018-24, 2010 Jul 06.
Artigo em Inglês | MEDLINE | ID: mdl-20509643

RESUMO

The azimuthal helix orientation of the rigid-rod amphiphilic diblock copolypeptides (PLGA-b-PMLGSLGs) of poly(alpha-L-glutamic acid) (PLGA) and poly(gamma-methyl-L-glutamate-ran-gamma-stearyl-L-glutamate) with 30 mol % of stearyl substituents (PMLGSLG) in Langmuir-Blodgett (LB) monolayers was investigated using polarized transmission Fourier transform infrared spectroscopy. The relative position of dipping with respect to the previous transfer position can be used to manipulate the azimuthal orientation of the helices parallel to or tilted by an angle of 45 degrees with respect to the dipping direction in the transferred films. The study of the azimuthal order for the LB monolayers of PLGA-b-PMLGSLGs of various block lengths revealed that the observed effect arises mainly from the deformation of the PMLGSLG top brush layer, induced by the flow orientation around the transfer region. In those cases where the PMLGSLG block is tilted by a sufficiently large angle with respect to the surface normal, high azimuthal order parameters of 0.5-0.75 were obtained.


Assuntos
Peptídeos/química , Polímeros/química , Ácido Láctico/química , Ácido Poliglicólico/química , Copolímero de Ácido Poliláctico e Ácido Poliglicólico , Espectroscopia de Infravermelho com Transformada de Fourier
12.
Langmuir ; 26(9): 6515-21, 2010 May 04.
Artigo em Inglês | MEDLINE | ID: mdl-20041640

RESUMO

The surface potentials and effective dipole moments of alpha-helical amphiphilic diblock copolypeptides during monolayer compression at the air-water interface are reported. Amphiphilic diblock copolypeptides (PLGA-b-PMLGSLGs) of poly(alpha-L-glutamic acid) (PLGA) and poly(gamma-methyl-L-glutamate-ran-gamma-stearyl-L-glutamate) with 30 mol % of stearyl substituents (PMLGSLG) of various block lengths were studied during the double-brush formation process at the water surface. Upon monolayer spreading of PLGA-b-PMLGSLGs, surface potentials of hundreds of millivolts were recorded, attributed to the dipole moments of water molecules reorienting due to interactions with the monolayers. Upon compression, the effective dipole moments derived from the surface potentials of the PLGA-b-PMLGSLG monolayers decrease gradually, most likely as a result of the immersion of the hydrophilic block in water and cancellation of the interactions between the hydrophobic block and the underlying water molecules. The polypeptide macrodipole moment immersed in water was apparently effectively screened out. The remaining effective dipole moment of the monolayer contributes mainly to the hydrophobic block, and upon tilting away from the water surface toward the surface normal, it was found to increase with the hydrophobic block length, indicating the gradual formation of unidirectional aligned polypeptide molecules in the double-brush monolayer.


Assuntos
Peptídeos/química , Polímeros/química , Ar , Modelos Moleculares , Conformação Molecular , Propriedades de Superfície , Água/química
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