Search Results (19)

Glioblastoma multiforme (GBM) is an aggressive brain cancer characterized by highly invasive growth driven by glial-mesenchymal transition (GMT). Given the urgent need for effective therapies targeting this process, we aimed to discover potential GMT inhibitors using transcriptomic-based repurposing applied to both approved and experimental drugs. Deep bioinformatic analysis of transcriptomic data from GBM patient tumors and GBM cell lines with mesenchymal phenotype using gene set variation analysis (GSVA), weighted gene co-expression network analysis (WGCNA), reconstruction of GMT-related gene association networks, gene set enrichment analysis (GSEA), and the search for correlation with transcriptomic profiles of known GMT markers, revealed a novel 31-gene GMT signature applicable as relevant input data for the connectivity map-based drug repurposing study. Using this gene signature, a number of small-molecule compounds were predicted as potent anti-GMT agents. Further ranking according to their blood–brain barrier permeability, as well as structural and transcriptomic similarities to known anti-GBM drugs, revealed SP600125, vemurafenib, FG-7142, dibenzoylmethane, and phensuximide as the most promising for GMT inhibition. In vitro validation showed that SP600125, which is most closely associated with GMT-related hub genes, effectively inhibited TGF-β1- and chemical hypoxia-induced GMT in U87 GBM cells by reducing morphological changes, migration, vasculogenic mimicry, and mesenchymal marker expression. These results clearly demonstrate the applicability of connectivity mapping as a powerful tool to accelerate the discovery of effective GMT-targeting therapies for GBM and significantly expand our understanding of the antitumor potential of SP600125. Full article

The aim of this study was to determine the types of UV filters used in adult and children’s sunscreen products sold in Poland (part of the EU market) and their frequency of use. The INCI compositions of sunscreen products were collected and analyzed for the presence of UV filters. The study included 150 randomly selected preparations for adults (from 71 brands) and 50 for children (from 33 brands). The survey concerned the UV filters listed in Annex VI to Regulation (EC) No 1223/2009 of the European Parliament and Council of 30 November 2009 on cosmetic products. The most frequently used UV filters in the child sunscreens were triazine derivatives: bis-ethylhexyloxyphenol methoxyphenyl triazine (60.0%) and ethylhexyl triazone (52.0%), and ethylhexyl salicylate (46.0%), a derivative of salicylic acid. The most common in adult sunscreens were butyl methoxydibenzoylmethane (56.0%), a dibenzoylmethane derivative, followed by the salicylic acid derivative ethylhexyl salicylate (54.7%) and the triazine derivatives bis-ethylhexyloxyphenol methoxyphenyl triazine (54.7%) and ethylhexyl triazone (50.0%). Physical filters, including their nano and non-nano forms, were more popular in sunscreens for children, i.e., 50.0% (TiO₂) and 22.0% (ZnO), than for adults: 21.3% (TiO₂) and 6.7% (ZnO). For both adults and children, many cosmetic products contained four or five UV filters per preparation; however, the child preparations often used two UV filters. To summarize, the following UV filters dominate in photoprotectors for both adults and children: butyl methoxydibenzoylmethane, bis-ethylhexyloxyphenol methoxyphenyl triazine, ethylhexyl triazone, ethylhexyl salicylate, and diethylamino hydroxybenzoyl hexyl benzoate. Full article

Sunscreens reduce the occurrence risk of skin disorders such as sunburn, skin aging, and cancer through their ability to absorb, reflect, and scatter ultraviolet (UV) radiation. This review provides an overview of UV filters as active ingredients of sunscreen products, emphasizing their classification and structural characteristics. Their photostability, mechanism of action of ultraviolet radiation absorption, optical properties, and regulatory status are discussed based on their chemical structure. The main classes of organic UV filters presented include aminobenzoic acid derivatives, salicylic acid derivatives, cinnamic acid derivatives, benzophenones, dibenzoylmethane derivatives, benzylidene camphor derivatives, triazines, benzimidazole derivatives, and benzotriazole derivatives. The pursuit of new UV filters through research is crucial in advancing sunscreen technology and ensuring the availability of effective and safe options for sun protection. Full article

This study investigated the impact of surface basicity on the performance of layered double hydroxides (LDHs) as heat stabilizers for polyvinyl chloride (PVC). LDHs with varying surface basicity were synthesized and characterized using XRD, SEM, BET, and CO₂-TPD. The LDHs were then combined with zinc stearate and dibenzoylmethane to create an environmentally friendly heat stabilizer and added to PVC. The resulting PVC composites were evaluated for thermal stability using the oven-aging method. The results showed that a lower Mg/Al molar ratio (2.0) improved the initial whiteness and long-term thermal stability of PVC composites compared to higher ratios (2.5, 3.0, and 3.5). Replacing Mg with Zn in the LDHs had a similar effect to that of reducing the Mg/Al ratio. Crosslinking the laminae of LDHs with 5% silane coupling agent KH-560 reduced the surface basicity of LDHs by 79%, increasing the chromaticity index, b*, and thermal stability time of PVC composites by 48% and 14%, respectively. A descriptive relationship was established between the structure and surface basicity of LDHs and the initial whiteness and long-term thermal stability of PVC composites. Full article

In the present work, the intramolecular O-H···O hydrogen bonding in 3-hydroxy-1,3-diphenylprop-2-en-1-one (keto-enol form of dibenzoylmethane, DBM) was investigated. For this purpose, the Raman spectra of polycrystalline samples of ordinary (H-DBM) and deuterated (D-DBM) 3-hydroxy-1,3-diphenylprop-2-en-1-one in the temperature range of 5–300 K were measured. It was found that low-temperature hydrogen bonding is extremely strong, the proton and deuteron are located in the midpoint of the O···O segment, and their ground and first excited vibrational states are located above the barrier U₀ between the local minima. The vibrational frequencies, in this case, are 1543 and 1709 cm⁻¹ for the proton and 1045 and 1087 cm⁻¹ for the deuteron. As the temperature rises and the barrier height increases in H-DBM, the zero-point vibrational state of the proton begins to move into one of the local minima at T > 50 K, while the excited state remains in the broad single-well potential. The same is observed in D-DBM, but with a significant temperature delay. Compounds with donor (−OCH₃) and acceptor (−NO₂) substituents in the phenyl ring were also synthesized and their spectra were obtained. Both results confirm existing ideas about the nature of the extremely strong hydrogen bond. The quantum-chemical calculation of the vibrational spectrum of H-DBM and D-DBM is consistent with the experimental results. Full article

Due to the medical importance of dibenzoylmethane, one of the aims of the study was to find an appropriate packing material and a biologically friendly co-solvent to help its introduction into living systems. Accordingly, redox properties of dibenzoylmethane were investigated on glassy carbon electrodes in acetonitrile and in 1-propanol with cyclic voltammetry, and showed a diffusion-controlled process. In the anodic window, an oxidation peak appeared at around 1.9 V in both solvents. Cycling repeatedly between 0 and 2 V, the reproducibility of this peak was acceptable, but when extending the window to higher potentials, the electrode deactivated, obviously due to electrode material. The addition of the investigated tetrakis(3,5-dicarboxyphenoxy) cavitand did not significantly change the voltammograms. Further electrochemical experiments showed that the coexistence of water in acetonitrile and 1-propanol drastically reduces the solubility of dibenzoylmethane. Moreover, very rapid electrode deactivation occurred and this fact made the use of electrochemical methods complicated. Considering that both the cavitand and dibenzoylmethane are soluble in dimethyl sulfoxide, the interaction of these species was investigated and formation of stable complexes was detected. This observation was verified with fluorescence quenching studies. The mixture of water and dimethyl sulphoxide also dramatically improved the solubility of the cavitand–dibenzoylmethane complex at high excess of water. The addition of cavitand improved the solubility of dibenzoylmethane, a property which supports the application of dibenzoylmethane in therapy. Full article

A novel multi-channel barcode module was developed by using chiral co-crystals which contain field-induced SMM behavior and different emission bands. The chiral co-crystals [Zn(H₂L)Dy(DBM)₂]₄(ClO₄)₄⋅9CH₃OH⋅H₂O (1a) and [Zn(H₂L)Dy(DBM)₂]₄(ClO₄)₄⋅8CH₃OH⋅0.5H₂O (1b) (H₄L = 2,2′-[1,2-ethanediylbis[(hydroxyethylimino)methylene]]bis[6-methoxy-4-methyl-phenol], HDBM = dibenzoylmethane) were obtained through one-pot reaction of Zn^II and Dy^III with the achiral ligands H₄L and HDBM. X-ray single crystal diffraction and CD spectroscopy confirmed that they are enantiomers crystallized in P4₃ (1a) and P4₁ (1b), both consisting of two ∆-[Zn(H₂L)Dy(DBM)₂]⁺ cations, two Λ-[Zn(H₂L)Dy(DBM)₂]⁺ cations and four (ClO₄)⁻ anions. The presence of Dy^III ions endow them with the property of field-induced slow magnetic relaxation. The relatively low energy barrier of 35.0(9) K for complex 1 may be due to the poor axiality of the ligand field caused by the long Dy-O_phenoxy bond lengths and the small O_phenoxy-Dy-O_phenoxy bond angles. Moreover, when the organic ligands H₄L (λ_ex = 350 nm) and Dy^III (λ_ex = 420 nm) are excited, different emission spectra are observed. Full article

Hottonia palustris L. is from the genus Hottonia (Primulaceae), and the understanding of its phytochemical and pharmacological properties is limited. In this study, the use of chromatographic techniques led to the isolation of a further eleven compounds, including three new flavonoids: 2′,5-dihydroxyflavone 2′-O-β-glucopyranoside, 5,6-dihydroxyflavone 6-O-(6”-O-glucopyranosyl)-β-glucopyranoside (hottonioside A), and 4′,5,7-trihydroxyflavone 7-O-(2”-O-β-glucuronide)-β-glucopyranoside. Their structures were determined using extensive 1D and 2D NMR data and mass spectrometry (HRMS). The qualitative assessment of the chemical composition of the investigated extracts and fractions was performed using the LC-HRMS technique. Furthermore, the antioxidant potential of extracts, fractions, and compounds and their ability to inhibit acetylcholinesterase were also evaluated. Thus, we may conclude that the observed biological effects are the result of the presence of many biologically active compounds, of which dibenzoylmethane is the most active. Therefore, H. palustris is a source of substances with desirable properties in the prevention and treatment of neurodegenerative diseases. Full article

Luminescent aerogels based on sodium alginate cross-linked with ions of rare earth elements (Eu³⁺, Tb³⁺, Sm³⁺) and containing phenanthroline, thenoyltrifluoroacetone, dibenzoylmethane, and acetylacetone as ligands introduced into the matrix during the impregnation of alginate aerogels (AEG), were obtained for the first time in a supercritical carbon dioxide medium. The impregnation method used made it possible to introduce organically soluble sensitizing ligands into polysaccharide matrices over the entire thickness of the sample while maintaining the porous structure of the aerogel. It is shown that the pore size and their specific area are 150 nm and 270 m²/g, respectively. Moreover, metal ions with content of about 23 wt.%, acting as cross-linking agents, are uniformly distributed over the thickness of the sample. In addition, the effect of sensitizing ligands on the luminescence intensity of cross-linked aerogel matrices is considered. The interaction in the resulting metal/ligand systems is unique for each pair, which is confirmed by the detection of broad bands with individual positions in the luminescence excitation spectra of photoactive aerogels. Full article

The reaction of β-diketophosphazene with the europium (III) salt synthesized the corresponding metal complex which was structured with (3-aminopropyl)triethoxysilane and treated with dibenzoylmethane for additional coordination of europium atoms. The polymer thus obtained exhibits luminescence with a maximum of 615 nm, which is characteristic of europium. The polymer is thermally stable up to 300 °C, the coating based on it has a contact angle of 101°, and the adhesive strength of the coating to non-finished glass (according to ISO 2409: 2013) is 1 point. Full article

Luminescent organic-inorganic hybrids containing lanthanides (Ln³⁺) have been prominent for applications such as luminescent bio-probes in biological assays. In this sense, a luminescent hybrid based on dense silica (SiO₂) nanospheres decorated with Eu³⁺ β–diketonate complexes using dibenzoylmethane (Hdbm) as a luminescent antenna was developed by using a hierarchical organization in four steps: (i) anchoring of 3-aminopropyltriethoxysilane (APTES) organosilane on the SiO₂ surface, (ii) formation of a carboxylic acid ligand, (iii) coordination of Eu³⁺ to the carboxylate groups and (iv) coordination of dbm⁻ to Eu³⁺. The hybrid structure was elucidated through the correlation of thermogravimetry, silicon nuclear magnetic resonance and photoluminescence. Results indicate that the carboxylic acid-Eu³⁺-dbm hybrid was formed on the surface of the particles with no detectable changes on their size or shape after all the four steps (average size of 32 ± 7 nm). A surface charge of −27.8 mV was achieved for the hybrid, assuring a stable suspension in aqueous media. The Eu³⁺ complex provides intense red luminescence, characteristic of Eu³⁺⁵D₀→⁷F_J electronic transitions, with an intrinsic emission quantum yield of 38%, even in an aqueous suspension. Therefore, the correlation of luminescence, structure, particle morphology and fluorescence microscopy images make the hybrid promising for application in bioimaging. Full article

A series of 18 regio- and stereo-chemically diverse chiral non-racemic 1,2-, 1,3-, and 1,4-diamines have been synthesized from commercial (1S)-(+)-ketopinic acid and (1S)-(+)-10-camphorsulfonic acid. The structures of the diamines are all based on the d-(+)-camphor scaffold and feature isomeric diversity in terms of regioisomeric attachment of the primary and the tertiary amine function and the exo/endo-isomerism. Diamines were transformed into the corresponding noncovalent bifunctional thiourea organocatalysts, which have been evaluated for catalytic activity in the conjugative addition of 1,3-dicarbonyl nucleophiles (dimethyl malonate, acetylacetone, and dibenzoylmethane) to trans-β-nitrostyrene. The highest enantioselectivity was achieved in the reaction with acetylacetone as nucleophile using endo-1,3-diamine derived catalyst 52 (91.5:8.5 er). All new organocatalysts 48–63 have been fully characterized. The structures and the absolute configurations of eight intermediates and thiourea derivative 52 were also determined by X-ray diffraction. Full article

Perfluorophenyl-substituted compounds, 3-hydroxy-1,3-bis(pentafluorophenyl)-2- propen-1-one (H1) and 1,5-dihydroxy-1,5-bis(pentafluorophenyl)-1,4-pentadien-3-one (H₂2), were prepared in 56 and 30% yields, respectively, and only the enol forms were preferentially obtained among the keto-enol tautomerism. Molecular conformations and tautomerism of the fluorine-substituted compounds were certified based on X-ray crystallographic studies and density functional calculations. The solvent dependency of the absorption spectra was only observed for the fluorinated compounds. The compounds H1 and H₂2 quantitatively formed co-crystals with the corresponding non-perfluorinated compounds, dibenzoylmethane (H3) and 1,5-dihydroxy-1,5-diphenyl-1,4-pentadien-3-one (H₂4), respectively, through the arene–perfluoroarene interaction to give the 1:1 co-crystals H1•H3 and H₂2•H₂4, which were characterized by X-ray crystallographic and elemental analysis studies. Full article

Zinc orotate (ZnOr₂), which is a new kind of poly(vinyl chloride) (PVC) stabilizer, is prepared in this work through the precipitation method, and its impact on the thermal stability of PVC is measured by thermogravimetric analysis (TG), Congo red test, and discoloration test. The results exhibit that the thermal stability of PVC is positively enhanced after the addition of ZnOr₂. In contrast with a commercial thermal stabilizer, zinc stearate (ZnSt₂), a noteworthy improvement was observed that ZnOr₂ could postpone the “zinc burning” of PVC. This is principally ascribed to the Or anion in the structure of ZnOr₂ being able to absorb the HCl released by PVC, and to supersede unstable chlorine atoms in the structure of PVC. In addition, blending ZnOr₂ with calcium stearate (CaSt₂) in diverse mass ratios can significantly accelerate the thermal stability of PVC. Optimum performance was achieved with a CaSt₂:ZnOr₂ ratio of 1.8:1.2. Moreover, an outstanding synergistic effect can be observed when CaSt₂/ZnOr₂ is coupled with other commercial auxiliary stabilizers. The initial color and long-term stability of PVC including CaSt₂/ZnOr₂ is significantly increased when pentaerythritol (PER) is added, while dibenzoylmethane (DBM) can only improve its long-term thermal stability. Full article

There is still an international need to develop broad-spectrum sunscreen products with an adequate UVB/UVA balance, while the approved filters available in the UVA are scarce. Currently, one of the few UVA filters approved in the United States and Europe is tert-butylmethoxydibenzoylmethane (BMDM, avobenzone). However, this compound is unstable from aphotochemical point of view and cannot be used in combination with certain sunscreens. In this paper, we investigate the photochemical behavior of a set of dibenzoylmethanes and chalcones. In particular, we carry out their absorption and emission spectra, evaluate their photochemical degradation, and study their generation of free radicals and singlet oxygen photoproduction. Two compounds resultedin having the basic properties of UVA filters (2′-hydroxy-4-methoxychalcone and 2′-hydroxy-4-methoxydibenzoylmethane). Further studies are proposed, such as formulating the compounds into emulsions or other common cosmetic presentations, as well as combining them with broadly-used UVB filters. We have also considered the need to establish its toxicological profile. Full article