This study aimed to obtain and characterize extracted hemp oil enriched in cannabidiol (CBD) by decarboxylation of cannabidiolic acid (CBDA) and to give new insights into its antioxidant and anticancer effects. Optimization of CBDA decarboxylation in hemp oil was performed, and CBD and CBDA contents and purities were determined by flash chromatography, 1H- and 13C-NMR. The antioxidant properties of CBD-enriched oil were investigated by Fe2+ chelating activity, Fe3+ reducing antioxidant power assay, O2●− scavenging activity, HO● scavenging ability and lipid peroxidation inhibitory assay, and its cytotoxicity, apoptosis- and oxidative stress-inducing effects on NHDF, MeWo, HeLa, HepG2 and HOS cells were determined. The CBD concentration in hemp oil was increased by CBDA soft decarboxylation optimized at 90 °C, for 1 h and the resulting oil was capable of reducing iron, scavenging free radicals and inhibiting lipid peroxidation in cell-free oxidative conditions. CBD-enriched oil promoted NHDF proliferation at up to 15 µg CBD/mL, while inducing apoptosis and ROS production and modulating antioxidant enzymes’ gene expression in cancer cells, being selective for osteosarcoma cells, and induced apoptosis by p53- and ROS-independent mechanisms. CBD-enriched hemp oil demonstrated antioxidant properties in oxidative conditions and promoted normal fibroblasts’ proliferation, while inducing apoptosis and ROS production in cancer cells.
Microporous chitosan nanofibers functionalized with different amounts of an antimicrobial agent via imine linkage were prepared by a three-step procedure including the electrospinning of a chitosan/PEO blend, PEO removal and acid condensation reaction in a heterogeneous system with 2-formylphenylboronic acid. The fibers’ characterization was undertaken keeping in mind their application to wound healing. Thus, by FTIR and 1H-NMR spectroscopy, it was confirmed the successful imination of the fibers and the conversion degree of the amine groups of chitosan into imine units. The fiber morphology in terms of fiber diameter, crystallinity, inter- and intra-fiber porosity and strength of intermolecular forces was investigated using scanning electron microscopy, polarized light microscopy, water vapor sorption and thermogravimetric analysis. The swelling ability was estimated in water and phosphate buffer by calculating the mass equilibrium swelling. The fiber biodegradation was explored in five media of different pH, corresponding to different stages of wound healing and the antimicrobial activity against the opportunistic pathogens inflicting wound infection was investigated according to standard tests. The biocompatibility and bioadhesivity were studied on normal human dermal fibroblast cells by direct contact procedure. The dynamic character of the imine linkage of the functionalized fibers was monitored by UV-vis spectroscopy. The results showed that the functionalization of the chitosan microporous nanofibers with antimicrobial agents via imine linkage is a great route towards bio-absorbable wound dressings with “on demand” antimicrobial properties and biodegradation rate matching the healing stages.
The paper aims to investigate the antitumor activity of a series of phenothiazine derivatives in order to establish a structure–antitumor activity relationship. To this end, PEGylated and TEGylated phenothiazine have been functionalized with formyl units and further with sulfonamide units via dynamic imine bonds. Their antitumor activity was monitored in vitro against seven human tumors cell lines and a mouse one compared to a human normal cell line by MTS assay. In order to find the potential influence of different building blocks on antitumor activity, the antioxidant activity, the ability to inhibit farnesyltransferase and the capacity to bind amino acids relevant for tumor cell growth were investigated as well. It was established that different building blocks conferred different functionalities, inducing specific antitumor activity against the tumor cells.
The study presents the achievement of a new assembly with antioxidant behaviour based on a copolymacrolactone structure that encapsulates erythritol (Eryt). Poly(ethylene brassylate-co-squaric acid) (PEBSA) was synthesised in environmentally friendly conditions, respectively, through a process in suspension in water by opening the cycle of ethylene brassylate macrolactone, followed by condensation with squaric acid. The compound synthesised in suspension was characterised by comparison with the polymer obtained by polymerisation in solution. The investigations revealed that, with the exception of the molecular masses, the compounds generated by the two synthetic procedures present similar properties, including good thermal stability, with a Tpeak of 456 °C, and the capacity for network formation. In addition, the investigation by dynamic light scattering techniques evidenced a mean diameter for PEBSA particles of around 596 nm and a zeta potential of −25 mV, which attests to their stability. The bio-based copolymacrolactone was used as a matrix for erythritol encapsulation. The new PEBSA–Eryt compound presented an increased sorption/desorption process, compared with the PEBSA matrix, and a crystalline morphology confirmed by X-ray diffraction analysis. The bioactive compound was also characterised in terms of its biocompatibility and antioxidant behaviour.
Nanomedicine has garnered significant attention due to the advantages it offers in the treatment of cancer-related disorders, some of the deadliest diseases affecting human lives. Conventional medication formulations often encounter issues of instability or insolubility in biological environments, resulting in low bioavailability. Nanocarriers play a crucial role in transporting and safeguarding drugs at specific sites of action, enabling gradual release under particular conditions. This study focuses on methotrexate (MTx) and cytarabine (Cyt), essential antitumoral drugs, loaded into PEGylated squalene micellar structures to enhance therapeutic effectiveness and minimize drawbacks. The micelles were prepared using ultrasound-assisted methods in both water and phosphate buffer saline solutions. Evaluation of drug-loaded micelles encompassed parameters such as particle size, colloidal stability, surface charge, morphology, encapsulation efficiency, drug loading capacity, and in vitro release profiles under simulated physiological and tumoral conditions. In vitro cell inhibition studies conducted on MCF-7 and HeLa cell lines demonstrated higher antitumoral activity for the drug-encapsulated micelles compared to free drugs. The encapsulation effectively addressed the burst effect, providing sustained release for at least 48 h while enhancing the drug’s protection under physiological conditions.
Background/Objectives: Antimicrobial resistance (AMR) presents a medical risk as well as a significant global socioeconomic challenge. Key contributors to AMR include the excessive use and incorrect application of antibiotics in humans and agriculture, nosocomial infections, and the absence of new classes of antibiotics. Methods: Novel dibrominated tricyclic flavonoids have been synthesized from the corresponding 3-dithiocarbamic flavanones and their antimicrobial and cytotoxicity properties have been investigated. Results: It has been found that these tricyclic flavonoids exhibit strong antimicrobial properties against clinically relevant pathogens such as Staphylococcus aureus, Acinetobacter baumannii, and Escherichia coli with MIC and MBC values against S. aureus ATCC 25923 as low as 0.12 µg/mL and 1.9 µg/mL, respectively. Conclusions: The synthetic tricyclic flavonoids exhibit strong antibacterial activity against selected WHO priority pathogens, including Staphylococcus aureus and Acinetobacter baumannii, surpassing the efficacy of both natural and synthetic flavonoids and several conventional antibiotics.