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溴取代席夫碱有机化合物的合成及细胞毒性研究。

Synthesis and Cytotoxicity Studies of Br-Substituted Salphen Organic Compounds.

机构信息

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.

出版信息

Chem Biodivers. 2023 May;20(5):e202200972. doi: 10.1002/cbdv.202200972. Epub 2023 May 4.

Abstract

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.

摘要

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。

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