Azaaurones as Potent Antimycobacterial Agents Active against MDR- and XDR-TB

Herein we report the screening of a small library of aurones and their isosteric counterparts, azaaurones and N-acetylazaaurones, against Mycobacterium tuberculosis. Aurones were found to be inactive at 20 μm , whereas azaaurones and N-acetylazaaurones emerged as the most potent compounds, with nine derivatives displaying MIC₉₉ values ranging from 0.4 to 2.0 μm . In addition, several N-acetylazaaurones were found to be active against multidrug-resistant (MDR) and extensively drug-resistant (XDR) clinical M. tuberculosis isolates. The antimycobacterial mechanism of action of these compounds remains to be determined; however, a preliminary mechanistic study confirmed that they do not inhibit the mycobacterial cytochrome bc1 complex. Additionally, microsomal metabolic stability and metabolite identification studies revealed that N-acetylazaaurones are deacetylated to their azaaurone counterparts. Overall, these results demonstrate that azaaurones and their N-acetyl counterparts represent a new entry in the toolbox of chemotypes capable of inhibiting M. tuberculosis growth.     

Production of microparticles from milk fat products using the Supercritical Melt Micronization (ScMM) process

The ScMM (Supercritical Melt Micronization) process was applied for the production of microparticles from anhydrous milk fat (AMF) and a diacylglycerol-based modified milk fat (D-AMF). Both fats were able to dissolve ca. 30 wt% CO₂ in the studied pressure and temperature ranges, being the CO₂ amount slightly higher for AMF. A melting point depression was observed in both systems in the presence of CO₂. Two powder morphologies were obtained (spherical hollow particles and a mass sponge-like broken particles) depending on the ScMM process conditions. The concentration of CO₂ in the fat melt was the main process variable affecting the particle morphology, followed by the temperature of the melt. The small broken particles originated from the breakage of spherical fat particles that solidified before all CO₂ could escape from the atomized droplets. While the hollow spheres had a tendency to agglomerate, the broken microparticles constituted a free-flowing powder as long as they were stored at low temperatures (up to −18 °C). Both types of particles have a potential for being incorporated in refrigerated or frozen food products as a structuring agent.     

Evolution of directly-spinnable carbon nanotube growth by recycling analysis

Carbon nanotubes (CNTs) grown on substrate-bound catalysts by CVD are influenced by the catalyst, which changes over the course of the process. The evolution of the CNT growth is revealed by breaking the process into recycling increments and using the phenomenon of ‘direct spinnability’ as a target characteristic.Using acetylene alone, it was found that the first four cycles gave 100% regrowth in height and mass yield of CNTs, with both properties falling to around 20% on the 5th cycle. A decrease in nanotube diameter was observed whilst the areal density increased. With the addition of hydrogen a 100% regrowth for the second cycle was observed, followed by a decrease to around 55%, 18% and 11% in both height and yield for subsequent cycles. The diameter increased, whilst the areal density decreased in subsequent cycles.In the absence of hydrogen the CNTs have around seven walls, decreasing to about three by the seventh cycle. With hydrogen, CNTs have five or six walls for all cycles. Raman spectroscopy indicates an increase in disorder in later cycles. Spinnability is high for initial cycles but drops sharply on the fourth cycle, or third cycle with hydrogen, as the nanotube forest tortuosity markedly increases.     

Surface characteristics and electrochemical capacitances of carbon aerogels obtained from resorcinol and pyrocatechol using boric and oxalic acids as polymerization catalysts

Carbon aerogels were prepared by carbonizing (at 500–1500 °C) organic aerogels obtained from the polymerization reaction of resorcinol and/or pyrocatechol with formaldehyde using boric and oxalic acids as polymerization catalysts. Prepared samples were characterized by different techniques to ascertain their composition, surface chemistry, morphology, and surface physics, determining their electrochemical capacitances in acidic medium. The use of pyrocatechol yielded carbon aerogels that were micro–mesoporous, showing Type IV N₂ adsorption isotherms with Type H2 hysteresis cycles. The volume and size of mesopores depended on the acid catalyst used and the temperature at which the carbon aerogel was obtained. Conversely, the sample prepared with resorcinol and boric acid as catalyst was micro–macroporous and that obtained with a resorcinol–pyrocatechol mixture was micro–mesoporous but with large mesopores. Most of the boric acid used was lost during the exchange of water with acetone in the organic hydrogels before their supercritical CO₂ drying. Carbon aerogels obtained at 900 °C and using boric acid as polymerization catalyst showed a capacitance between 17 and 24 μF/cm². Boron influenced the capacitance because it increased the oxygen content. Sample synthesized using pyrocatechol, formaldehyde, and oxalic acid and heat-treated at 900 °C had the highest capacitance, 34 μF/cm².     

Phosphorus‐containing soybean‐oil copolymers: Cross‐metathesis of fatty acid derivatives as an alternative to phosphorus‐containing reactive flame retardants

Two different approaches to the creation of phosphorus‐containing soybean‐oil copolymers were investigated. First, two phosphorus‐containing styrene (ST) derivatives, diphenyl styryl phosphine oxide and dimethyl‐p‐vinylbenzylphosphonate (STP2), where tested as comonomers in the cationic copolymerization of soybean oil (SOY), ST, and divinylbenzene (DVB), to obtain heterogeneous systems in all cases. To overcome this drawback, the cross‐metathesis reaction of methyl 10‐undecenoate and STP2 was carried out to link the phosphorus moiety to the vegetable‐oil derivative. This second approach permitted the synthesis of a new reactive phosphorus‐containing plant‐oil derivative, which was incorporated into the soybean oil, ST, and DVB system. The cationic copolymerization was investigated, and the structure, thermal stability, and mechanical and flame‐retardant properties of the resulting copolymers were studied. Thermosets with moderate glass‐transition temperatures were obtained; this showed that the cross‐metathesis reaction is a convenient way to produce oil‐compatible monomers able to undergo homogeneous polymerization reactions. The resulting thermosets with 1% phosphorus had limiting oxygen index values about 24.0; this indicated an improvement in the fire‐retardant properties of the soybean‐oil‐based copolymers. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2011     

A process for the production of a diacylglycerol‐based milk fat analogue

We propose a novel process for the production of a DAG‐rich acylglycerol mixture derived from milk fat. This product has potentially interesting nutritional properties, derived from both its high content of DAG and of short‐chain fatty acids (FAs). The proposed process consists of three steps: lipase‐catalysed partial ethanolysis of milk fat, extraction of the by‐product fatty acid ethyl esters (FAEEs) using supercritical carbon dioxide (SC‐CO₂) and isomerization of DAG to increase the proportion of 1,3‐DAG. The experimental investigation of the process steps was done using milk fat and trilaurin. Several lipases were tested for maximizing the percentage of DAG in the acylglycerol mixture produced by ethanolysis. The selectivity of the chosen lipase was such that the produced AG mixture was enriched in short‐chain FAs in relation to the original milk fat. FAEEs were completely extracted from the ethanolysis mixture by SC‐CO₂. In the final process step, we explored the reaction conditions for facilitating acyl migration in the DAG mixture, so that the equilibrium proportion of 1,3‐DAG (～64%) was attained. Our results set the basis for the development of a simple process for the production of a DAG‐rich milk fat analogue.     

Dynamic colorimetric properties of mixed thermochromic printing inks

Leuco dye‐based thermochromic inks reversibly change from the coloured to the discoloured state in a defined, comparatively wide temperature region. Inside this region, the colour of a sample depends on the temperature and thermal history, which is known as the hysteresis effect. The colour of such a sample as a function of temperature has the shape of a hysteresis loop. Commercially available thermochromic inks have different loops, narrow or broad, and their shapes range from approximately symmetric to highly asymmetric. These properties are also important in mixtures of inks. The hysteresis loop of a mixture reveals its binary nature if the individual pure inks have well‐separated hysteresis. When inks with close‐separated loops, i.e. with similar activation temperatures, are mixed together, the loop of the mixture fuses together into an apparently single loop. Our research shows that some of their dynamic colour properties could be predicted in advance. However, optic and colorimetric properties of mixtures are not additive.     

The Effect of Exogenous Application of Quercetin Derivative Solutions on the Course of Physiological and Biochemical Processes in Wheat Seedlings

Quercetin, classified as a flavonoid, is a strong antioxidant that plays a significant role in the regulation of physiological processes in plants, which is particularly important in the case of biotic and abiotic stresses. The study investigated the effect of the use of potassium quercetin solutions in various concentrations (0.5%, 1.0%, 3.0% and 5.0%) on the physiological and biochemical properties of wheat seedlings. A pot experiment was carried out in order to determine the most beneficial dose of this flavonoid acting as a bio-stimulant for wheat plants. Spraying with quercetin derivative solutions was performed twice, and physiological measurements (chlorophyll content and fluorescence as well as gas exchange) were carried out on the first and seventh days after each application. The total phenolic compounds content and the total antioxidant capacity were also determined. It was shown that the concentrations of potassium quercetin applied have a stimulating effect on the course of physiological processes. In the case of most of the tested physiological parameters (chlorophyll content and fluorescence and gas exchange) and the total antioxidant capacity, no significant differences were observed in their increase as a result of application with concentrations of 3.0 and 5.0%. Therefore, the beneficial effect of quercetin on the analysed parameters is already observed when spraying with a concentration of 3.0%.     

Microstructured Lipid Carriers (MLC) Based on N-Acetylcysteine and Chitosan Preventing Pseudomonas aeruginosa Biofilm

The aim of this work was the development of microstructured lipid carriers (MLC) based on chitosan (CH) and containing N-acetylcysteine (NAC), a mucolytic and antioxidant agent, to inhibit the formation of Pseudomonas aeruginosa biofilm. MLC were prepared using the high shear homogenization technique. The MLC were characterized for morphology, particle size, Z potential, encapsulation efficiency and drug release. The antioxidant properties of NAC-loaded microstructured carriers were evaluated through an in vitro spectrophotometer assay. Finally, the activity of NAC-CH-MLC on biofilm production by Pseudomonas aeruginosa was also evaluated. Results obtained from this study highlighted that the use of chitosan into the inner aqueous phase permitted to obtain microstructured particles with a narrow size range and with good encapsulation efficiency. NAC-loaded MLC showed higher antioxidant activity than the free molecule, demonstrating how encapsulation increases the antioxidant effect of the molecule. Furthermore, the reduction of biofilm growth resulted extremely high with MLC being 64.74% ± 6.2% and 83.74% ± 9.95%, respectively, at 0.5 mg/mL and 2 mg/mL. In conclusion, this work represents a favorable technological strategy against diseases in which bacterial biofilm is relevant, such as cystic fibrosis.