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1.
J Chromatogr A ; 1623: 461174, 2020 Jul 19.
Artigo em Inglês | MEDLINE | ID: mdl-32505278

RESUMO

A new class of chitosan derivatives with an isopropylthiourea at the 2-position and various carbamates at the 3,6-positions of the glucosamine skeleton was synthesized by the selective thiocarbamoylation of the 2-amino group. The chiral stationary phases (CSPs) were then prepared by coating the obtained chitosan 2-isopropylthiourea-3,6-dicarbamate derivatives onto silica gel. The enantioseparation property of the chitosan-based CSPs was assessed with twelve racemates by high-performance liquid chromatography (HPLC). The CSPs displayed a characteristic enantioseparation power, which seemed to be significantly affected by the 3,6-substituents of the glucosamine unit. The chitosan derivatives with the 3,6-diphenylcarbamate, except for 2-methylphenylcarbamate, possessed higher enantioseparation abilities than those with the 3,6-dicyclohexylcarbamate. Compared to other chitosan derivatives with 2-various substituents and commercialized Chiralcel OD, the chitosan 2-isopropylthiourea derivatives revealed a relatively higher enantioselectivity for some racemic compounds.


Assuntos
Quitosana/análogos & derivados , Cromatografia Líquida de Alta Pressão/métodos , Carbamatos/química , Celulose/análogos & derivados , Celulose/química , Glucosamina/química , Fenilcarbamatos/química , Sílica Gel/química , Estereoisomerismo , Tioureia/análogos & derivados
2.
J Anim Physiol Anim Nutr (Berl) ; 104(4): 1067-1074, 2020 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-31953905

RESUMO

A study was conducted to investigate the effects of oregano essential oil (EO) on growth performance, nutrients utilization, intestinal morphology, intestinal barrier-related gene expression and antioxidant capability in meat ducks. A total of 360 1-day-old ducks were divided into three groups (12 replicates pens per diet of 10 ducks in each pen): negative control (no essential oil or antibiotic), positive control (antibiotic: 500 mg/kg aureomycin of diet) and oregano EO (100 mg/kg of diet). The experiment was carried out for 35 days. Ducks were given feed and water ad libitum. Ducks fed EO supplement showed similar body weight and feed to gain ratio to antibiotic fed ducks. EO supplementation significantly increased (p < .05) feed intake (day 1-35), jejunal villus height (VH) to crypt depth (CD) ratio, serum superoxide dismutase activities (SOD) and jejunal total antioxidant capacity (T-AOC) of ducks compared to controls. Ducks fed diets supplemented with oregano EO also had decreased (p < .05) jejunal CD, serum and hepatic malondialdehyde (MDA) concentration, and the mRNA expression of jejunal zonula occludens-3 (ZO-3) and secretory immunoglobulin A (sIgA) genes in comparison to the control group. Compared to the antibiotic supplementation group, the mRNA expression of claudin1 (CLND1) and CLND2 significantly increased (p < .05), but the mRNA expression of ZO-3 and mucin 2 markedly decreased (p < .05) in the jejunum of ducks in oregano EO supplementation group. These results suggest that oregano EO improves the antioxidant capacity and intestinal defence and structural measures and may aide in helping to maintain enteric health in production without growth-promoting antibiotics.

3.
Angew Chem Int Ed Engl ; 58(35): 12223-12230, 2019 08 26.
Artigo em Inglês | MEDLINE | ID: mdl-31211884

RESUMO

Herein we show that by appending bulky ß-cyclodextrin (CD) groups onto sheet-forming peptoids, we obtain cylindrical micelles that further assembly into membranes and intertwined ribbons on substrates in aqueous solution, depending on the choice of solution and substrate conditions. In situ atomic force microscopy (AFM) shows that micelle assembly occurs in two steps, starting with "precursor" particles that transform into worm-like micelles, which extend and coalesce to form the higher order structures with a rate and a degree of cooperativity dependent on pH and Ca2+ concentration. After co-assembly with hydrophobic 4-(2-hydroxyethylamino)-7-nitro-2,1,3-benzoxadiazole (NBD) donors that occupy the hydrophobic core, followed by exposure to hydrophilic Rhodamine B as acceptors that insert into cyclodextrin, the micelles exhibit highly efficient Förster resonance energy transfer efficiency in aqueous solution, thereby mimicking natural light harvesting systems.

4.
Nat Commun ; 9(1): 270, 2018 01 18.
Artigo em Inglês | MEDLINE | ID: mdl-29348551

RESUMO

Despite recent advances in the assembly of organic nanotubes, conferral of sequence-defined engineering and dynamic response characteristics to the tubules remains a challenge. Here we report a new family of highly designable and dynamic nanotubes assembled from sequence-defined peptoids through a unique "rolling-up and closure of nanosheet" mechanism. During the assembly process, amorphous spherical particles of amphiphilic peptoid oligomers crystallize to form well-defined nanosheets before folding to form single-walled nanotubes. These nanotubes undergo a pH-triggered, reversible contraction-expansion motion. By varying the number of hydrophobic residues of peptoids, we demonstrate tuning of nanotube wall thickness, diameter, and mechanical properties. Atomic force microscopy-based mechanical measurements show peptoid nanotubes are highly stiff (Young's Modulus ~13-17 GPa). We further demonstrate the precise incorporation of functional groups within nanotubes and their applications in water decontamination and cellular adhesion and uptake. These nanotubes provide a robust platform for developing biomimetic materials tailored to specific applications.


Assuntos
Nanotubos/química , Peptoides/química , Dobramento de Proteína , Multimerização Proteica , Células A549 , Cristalografia por Raios X , Humanos , Concentração de Íons de Hidrogênio , Interações Hidrofóbicas e Hidrofílicas , Microscopia de Força Atômica , Microscopia Confocal , Microscopia Eletrônica de Transmissão , Nanotubos/ultraestrutura , Peptidomiméticos/química , Água/química
5.
Phys Chem Chem Phys ; 19(24): 16047-16056, 2017 Jun 21.
Artigo em Inglês | MEDLINE | ID: mdl-28597883

RESUMO

The adsorption and viscoelastic properties of a micellar solution of 2-hydroxyl-propanediyl-1,3-bis(hexadecyldimethylammonium bromide), abbreviated as 16-3OH-16, have been investigated by surface tension and rheological measurements. Meanwhile, an aqueous solution of propanediyl-1,3-bis(hexadecyldimethylammonium bromide), abbreviated as 16-3-16, was also examined. From the steady state and oscillatory rheological results, a notable difference in shear viscosities between the two systems was observed. Zeta potentials and size distributions confirm the change in the potentials and hydrodynamic diameters, and these results are in good agreement with the rheological results. The differences of the two solutions were attributed to the effect of the hydroxyl group on the spacer of 16-3OH-16. Molecular dynamic simulations and density functional theory (DFT) calculations were performed to investigate the non-covalent interactions in the solution and the difference between the molecular orbitals and the electrostatic potentials. Our research shows that a more uniform distribution of positive charges around the spacer could result in a more effective electrostatic screening effect between the charged headgroups, and promote the formation of a worm-like micelle. Also, hyperconjugation becomes stronger when the hydroxyl group is introduced on the spacer of the gemini molecule.

6.
Langmuir ; 33(17): 4319-4327, 2017 05 02.
Artigo em Inglês | MEDLINE | ID: mdl-28391678

RESUMO

Smart wormlike micelles with stimuli-tunable rheological properties may be useful in a variety of applications, such as in molecular devices and sensors. The formation of triplestimuli-responsive systems so far has been a challenging and important issue. In this work, a novel triplestimuli (photo-, pH-, and thermoresponsive) wormlike micelle is constructed with N-cetyl-N-methylmorpholinium bromide and trans-cinnamic acid (CA). The corresponding multiresponsive behaviors of wormlike micellar system were revealed using cryogenic transmission electron microscopy, a rheometer, and 1H NMR. The rheological properties of wormlike micellar system under different temperatures, pH conditions, and UV irradiation times are measured. As confirmed by 1H NMR, chemical structure of a CA molecule can be altered by the multiple stimulation from an exotic environment. We expect it to be a good model for triple-responsive wormlike micelles, which is helpful to understand the mechanism of triple-responsiveness and widen their applications.

7.
Polymers (Basel) ; 9(7)2017 Jul 21.
Artigo em Inglês | MEDLINE | ID: mdl-30970974

RESUMO

Abstract: Water-soluble polymers are widely used in oilfields. The rheological behaviors of these polymers in high-salinity solution are very important for stimulation of high-salinity reservoirs. In this work, a novel thermal-resistant and shear-stable amphoteric polyacrylamide (PASD), prepared from acrylamide (AM), sodium styrene sulfonate (SSS), and acryloxyethyl trimethylammonium chloride (DAC) monomers, was prepared by free-radical polymerization in high-salinity solution. The amphoteric polyacrylamide was characterized by Fourier transform infrared (FTIR) spectroscopy, nuclear magnetic resonance spectroscopy (¹H NMR), elemental analysis, thermogravimetric analysis (TG), and scanning electron microscopy (SEM). The amphoteric polyacrylamide exhibited excellent salinity tolerance. The slow increase in apparent viscosity of the polymer with increase in salinity was interesting. The amphoteric polyacrylamide showed perfect temperature resistance in high-salinity solution. The viscosity retention reached 38.9% at 120 °C and was restored to 87.8% of its initial viscosity when temperature was decreased to room temperature. The retention ratio of apparent viscosity reached 49.7% at 170 s-1 and could still retain it at 25.8% at 1000 s-1. All these results demonstrated that PASD had excellent thermal-resistance and shear-stability in high-salinity solution. We expect that this work could provide a new strategy to design polymers with excellent salinity-tolerance, thermal-resistance, and shear-stability performances.

8.
Soft Matter ; 12(20): 4549-56, 2016 05 18.
Artigo em Inglês | MEDLINE | ID: mdl-27094804

RESUMO

Imagine a novel solution that can be switched reversibly from low viscosity to high viscosity with only one additive, upon different commands. To this end, we have developed a simple and effective route to form smart, multi-response wormlike micelles based on a synthesized surfactant, N-cetyl-N,N-diisopropanolammonium bromide (CDIAB). Moreover, we provide new insight into the effects of synergy on this smart wormlike micelle. Rheological measurements were used to study the morphology of the wormlike micelles; (1)H NMR spectroscopy and density functional theory (DFT) calculations were employed to investigate the molecular arrangements and mechanism of the synergy involved in the reversible reactions of pH-response and CO2-response of the micelles in solution. Based on the abovementioned results, it is encouraging to discover that binding energy and electrostatic interaction are the basic driving forces in the formation of wormlike micelles. Moreover, stable viscoelastic behavior was observed in the CDIAB system, with strong binding energy and electrostatic interactions. It is highly anticipated that the synergy observed in this surfactant will be of particular interest due to its novel mechanism and unique properties.

9.
Soft Matter ; 11(39): 7817-26, 2015 Oct 21.
Artigo em Inglês | MEDLINE | ID: mdl-26314927

RESUMO

To understand the role of electrostatic interactions and hydrogen bonds in the formation of wormlike micelles with the aid of sodium salicylate, two quaternary ammonium surfactants with the headgroup decorated by one hydroxyethyl group N-cetyl-N-(2-hydroxyethyl)dimethylammonium bromide and two hydroxyethyl groups N-cetyl-N,N-di(2-hydroxyethyl)methylammonium bromide, abbreviated as CHEMAB and CDHAB, respectively, were synthesized in this work. Single crystal X-ray diffraction was used to study the intermolecular interactions of surfactants, and (1)H NMR and rheological measurements were employed to investigate the molecular arrangement and morphology of the wormlike micelles. The synergistic interactions of hydrogen bonding and more effective shielding of electrostatic repulsion contribute to the formation and viscoelastic behavior of wormlike micelles. The results also revealed the aggregation behavior of surfactants with hydroxyethyl headgroups in aqueous solutions.

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