Novel Multi-Target Agents Based on the Privileged Structure of 4-Hydroxy-2-quinolinone.

In this work, the privileged scaffold of 4-hydroxy-2quinolinone is investigated through the synthesis of carboxamides and hybrid derivatives, as well as through their bioactivity evaluation, focusing on the ability of the molecules to inhibit the soybean LOX, as an indication of their anti-inflammatory activity. Twenty-one quinolinone carboxamides, seven novel hybrid compounds consisting of the quinolinone moiety and selected cinnamic or benzoic acid derivatives, as well as three reverse amides are synthesized and classified as multi-target agents according to their LOX inhibitory and antioxidant activity. Among all the synthesized analogues, quinolinone-carboxamide compounds 3h and 3s, which are introduced for the first time in the literature, exhibited the best LOX inhibitory activity (IC50 = 10 µM). Furthermore, carboxamide 3g and quinolinone hybrid with acetylated ferulic acid 11e emerged as multi-target agents, revealing combined antioxidant and LOX inhibitory activity (3g: IC50 = 27.5 µM for LOX inhibition, 100% inhibition of lipid peroxidation, 67.7% ability to scavenge hydroxyl radicals and 72.4% in the ABTS radical cation decolorization assay; 11e: IC50 = 52 µM for LOX inhibition and 97% inhibition of lipid peroxidation). The in silico docking results revealed that the synthetic carboxamide analogues 3h and 3s and NDGA (the reference compound) bind at the same alternative binding site in a similar binding mode.

Synthesis of Polyamide-Based Microcapsules via Interfacial Polymerization: Effect of Key Process Parameters.

Polyamide microcapsules have gathered significant research interest during the past years due to their good barrier properties; however, the potential of their application is limited due to the fragility of the polymeric membrane. Fully aliphatic polyamide microcapsules (PA MCs) were herein prepared from ethylene diamine and sebacoyl chloride via interfacial polymerization, and the effect of key encapsulation parameters, i.e., monomers ratio, core solvent, stirring rate and time during the polymerization step, were examined concerning attainable process yield and microcapsule properties (shell molecular weight and thermal properties, MC size and morphology). The process yield was found to be mainly influenced by the nature of the organic solvent, which was correlated to the diffusion potential of the diamine from the aqueous phase to the organic core through the polyamide membrane. Thus, spherical microcapsules with a size between 14 and 90 µm and a yield of 33% were prepared by using toluene as core solvent. Milder stirring during the polymerization step led to an improved microcapsule morphology; yet, the substantial improvement of mechanical properties remains a challenge.

Encapsulation of Antifouling Organic Biocides in Poly(lactic acid) Nanoparticles.

The scope of the current research was to assess the feasibility of encapsulating three commercial antifouling compounds, Irgarol 1051, Econea and Zinc pyrithione, in biodegradable poly(lactic acid) (PLA) nanoparticles. The emulsification-solvent evaporation technique was herein utilized to manufacture nanoparticles with a biocide:polymer ratio of 40%. The loaded nanoparticles were analyzed for their size and size distribution, zeta potential, encapsulation efficiency and thermal properties, while the relevant physicochemical characteristics were correlated to biocide-polymer system. In addition, the encapsulation process was scaled up and the prepared nanoparticles were dispersed in a water-based antifouling paint in order to examine the viability of incorporating nanoparticles in such coatings. Metallic specimens were coated with the nanoparticles-containing paint and examined regarding surface morphology.