School of Chemistry, National Autonomous University of Mexico (UNAM) Circuito Escolar s/n, Ciudad Universitaria, 04510, Mexico City, Mexico.
Departamento de Investigaciones Científicas y Tecnológicas, Universidad de Sonora. Blvd. Luis Donaldo Colosio s/n, 83000, Hermosillo, Sonora, Mexico.
Chem Biodivers. 2023 May;20(5):e202200972. doi: 10.1002/cbdv.202200972. Epub 2023 May 4.
We present the synthesis and characterization of organic Salphen compounds containing bromine substituents at the para/ortho-para positions, in their symmetric and non-symmetric versions, and describe the X-ray structure and full characterization for the new unsymmetrical varieties. We report for the first time antiproliferative activity in metal-free brominated Salphen compounds, by evaluations in four human cancer cell lines, cervix (HeLa), prostate (PC-3), lung (A549) and colon (LS 180) and one non-cancerous counterpart (ARPE-19). We assessed in vitro cell viability against controls using the MTT assay ((3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide)) and determined the concentration required for 50 % growth inhibition (IC ), together with their selectivity vs. non-cancerous cells. We found promising results against prostate (9.6 μM) and colon (13.5 μM) adenocarcinoma cells. We also found a tradeoff between selectivity (up to 3-fold vs. ARPE-19) and inhibition, depending upon the symmetry and bromine-substitution of the molecules, showing up to 20-fold higher selectivity vs. doxorubicin controls.
我们介绍了含有溴取代基的有机 Salphen 化合物的合成和表征，包括对位/邻位-对位取代基的对称和非对称版本，并描述了新的非对称变体的 X 射线结构和全谱表征。我们首次报道了无金属溴化 Salphen 化合物的抗增殖活性，通过在四种人类癌细胞系（宫颈（HeLa）、前列腺（PC-3）、肺（A549）和结肠（LS 180）和一种非癌对照（ARPE-19）中的评估来实现。我们使用 MTT 测定法（（3-(4,5-二甲基噻唑-2-基)-2,5-二苯基-2H-四唑溴化物））评估了对对照物的体外细胞活力，并确定了 50%生长抑制所需的浓度（IC ），以及它们与非癌细胞的选择性。我们发现对前列腺（9.6 μM）和结肠（13.5 μM）腺癌细胞有很好的效果。我们还发现，分子的对称性和溴取代基之间存在选择性（高达 3 倍 vs. ARPE-19）和抑制之间的权衡，与多柔比星对照物相比，选择性高达 20 倍。
