Synthesis, anticancer evaluation and in silico ADMET studies on urea/thiourea derivatives from gabapentin

Phosphorus Sulfur and Silicon and The Related Elements Pub Date : 2020-11-25 DOI:10.1080/10426507.2020.1845678

S. Türk, F. Tok, Ö. Erdoğan, Ö. Çevik, T. Tok, B. Koçyiğit-Kaymakçıoğlu, S. Karakuş

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引用次数: 3

Abstract

Abstract 2-(1-((3-Substitutedureido/thioureido)methyl)cyclohexyl)acetic acid derivatives (1–9) were synthesized from gabapentin. All the synthesized compounds were characterized by using IR, 1H-NMR, 13C-NMR spectroscopy, mass spectrometry and elemental analysis. Urea and thiourea derivatives were investigated for their potential in vitro anticancer activities on PC3 and MCF7 cancer cell lines using MTT assay. Cell apoptosis was detected by with Annexin V Assay. Our results showed that compound 8 {2-(1-((3-(2,6-dichlorophenyl)ureido)methyl)cyclohexyl)acetic acid} significantly inhibited the proliferation and growing of PC3 and MCF7 cells. Both cell types showed dysfunction of cellular morphology which induced apoptosis 10 µM concentration of compound 8 treated cells. Our results indicate that compound 8 might have significance as an anti-tumor agent against human prostate and breast cancer. The theoretical structure and activity estimation via in silico ADMET was also examined. Graphical Abstract

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加巴喷丁脲/硫脲衍生物的合成、抗癌评价及硅ADMET研究

摘要以加巴喷丁为原料合成了2-(1-((3-取代脲基/硫脲基)甲基)环己基)乙酸衍生物(1- 9)。所有合成的化合物都通过IR、1H-NMR、13C-NMR、质谱和元素分析进行了表征。采用MTT法研究了尿素和硫脲衍生物对PC3和MCF7癌细胞的体外抑癌活性。Annexin V法检测细胞凋亡。结果表明，化合物8{2-(1-((3-(2,6-二氯苯)脲基)甲基)环己基)乙酸}显著抑制PC3和MCF7细胞的增殖和生长。10µM浓度的化合物8处理后，两种细胞均表现出细胞形态功能障碍，诱导细胞凋亡。提示化合物8可能具有抗人前列腺癌和乳腺癌的作用。并对其理论结构和活度估计进行了验证。图形抽象

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Phosphorus Sulfur and Silicon and The Related Elements

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