Faculty of Industrial Chemistry and Environmental Engineering, Politehnica University Timişoara, Carol Telbisz 6, 300001 Timisoara, Romania.
Biochemistry Department, Faculty of Pharmacy, University of Medicine and Pharmacy "Victor Babeş", Eftimie Murgu 2, 300041 Timisoara, Romania.
Molecules. 2023 Jan 22;28(3):1102. doi: 10.3390/molecules28031102.
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 ) and 4-(4-hydroxybenzylidene)-6-methoxy-1,2,3,4-tetrahydroxanthylium chloride (compound ) 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.
姜黄素类似物是具有光致变色性质的黄烷酮衍生物。与花青素类似，它们遵循相同的多态网络化学物质，这些化学物质可以通过外部刺激可逆地相互转化。在本工作中，合成了两种新的不对称单羰基姜黄素类似物，4-(4-羟基-3-甲氧基苯亚甲基)-1,2,3,4-四氢黄烷酮氯化物（化合物 ）和 4-(4-羟基苯亚甲基)-6-甲氧基-1,2,3,4-四氢黄烷酮氯化物（化合物 ），并研究了它们的光致变色和生物性质。紫外可见光谱和直接和反向 pH 跳跃研究证实了卤代性质和不同分子物种的存在。提出了这些物质的化学反应网络。此外，还使用 P19 鼠胚癌细胞评估了这两种化合物的抗增殖特性，并相互进行了比较。结果表明，两种新的黄烷酮衍生物都改变了 P19 细胞通过细胞周期的进程，从而产生显著的抗增殖作用。讨论了甲氧基位置的影响，并提出了几种检查点蛋白作为潜在的靶标。
