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Synthesis, Characterization, and Antiproliferative Properties of New Bio-Inspired Xanthylium Derivatives.

ABSTRACT: Xanthylium derivatives are curcumin analogs showing photochromic properties. Similarly, to anthocyanins, they follow the same multistate network of chemical species that are reversibly interconverted by external stimuli. In the present work, two new asymmetric monocarbonyl analogues of curcumin, 4-(4-hydroxy-3-metoxybenzylidene)-1,2,3,4-tetrahydroxanthylium chloride (compound 3) and 4-(4-hydroxybenzylidene)-6-methoxy-1,2,3,4-tetrahydroxanthylium chloride (compound 4) were synthesized, and their photochromic and biological properties were investigated. The UV-Vis spectroscopy and the direct and reverse pH-jumps studies confirmed the halochromic properties and the existence of different molecular species. A network of chemical reactions of these species was proposed. Furthermore, the antiproliferative properties of both compounds were evaluated using P19 murine embryocarcinoma cells and compared with each other. The results demonstrate that both new xanthylium derivatives modify the progression through the cell cycle of P19 cells, which translates into a significant antiproliferative effect. The effect of the methoxy group position is discussed and several checkpoint proteins are advanced as putative targets.

SUBMITTER: Koch C

PROVIDER: S-EPMC9921969 | biostudies-literature | 2023 Jan

REPOSITORIES: biostudies-literature

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Synthesis, Characterization, and Antiproliferative Properties of New Bio-Inspired Xanthylium Derivatives.

Koch Claudia C Dreavă Diana-Maria DM Todea Anamaria A Péter Francisc F Medeleanu Mihai M Păușescu Iulia I Samoilă Corina C Sîrbu Ioan Ovidiu IO

Molecules (Basel, Switzerland) 20230122 3

Xanthylium derivatives are curcumin analogs showing photochromic properties. Similarly, to anthocyanins, they follow the same multistate network of chemical species that are reversibly interconverted by external stimuli. In the present work, two new asymmetric monocarbonyl analogues of curcumin, 4-(4-hydroxy-3-metoxybenzylidene)-1,2,3,4-tetrahydroxanthylium chloride (compound <b>3</b>) and 4-(4-hydroxybenzylidene)-6-methoxy-1,2,3,4-tetrahydroxanthylium chloride (compound <b>4</b>) were synthesiz ...[more]

PMID: 36770768

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Project description:Ceramic materials possessing the properties of high-strength and rigidity are widely used in industry. The shell nacre has a layered structure containing both macroscopic and microscopic levels and is equipped with superior qualities regarding hardness and strength. Therefore, the ceramic composites with a nacre-like layered structure have the potential to be utilized as sliding bearings employed in the harsh conditions of wells. For the purpose of this paper, a porous Al?O? ceramics skeleton with nanometer powder is prepared using the freeze-casting method. Then the porous ceramic skeleton is filled with polymer polymethyl methacrylate (PMMA) through mass polymerization to produce a bionic Al?O?/PMMA composite with a lamellar structure. The properties of the prepared composite are determined by the analysis of micro-hardness, fracture toughness, friction coefficient, wear scar diameter, and the morphology of the worn surface. Consequent results indicate that elevation in the A1?O? powder, which acts as the initial solid phase content, prompts the ceramic slurry to exhibit an increase in viscosity and a gradual decrease in the pore size of the ceramic skeleton. The prepared layered Al?O?/PMMA composite possesses high fracture toughness, which closely resembles that of Al, is approximately four times that of the matrix of the Al?O? ceramics and 16 times that of the PMMA. Three kinds of composites containing different solid phase content are subjected to testing involving lubrication by water-based drilling fluid to determine the friction coefficient of each. The results indicate that an increased load leads to a decreased friction coefficient while the impact of speed is not evident. Under dry conditions, the friction coefficient of three different composites tested, declines with elevated load and speed. With the use of water-based drilling fluid as lubrication, the wear scar diameter increases at higher speed, while dry conditions denote increased load. Abrasive wear is determined to be the principal form of erosion of layered Al?O?/PMMA composites.

Dataset Information

Synthesis, Characterization, and Antiproliferative Properties of New Bio-Inspired Xanthylium Derivatives.

Publications

Synthesis, Characterization, and Antiproliferative Properties of New Bio-Inspired Xanthylium Derivatives.

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