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Evaluation of structural, spectral characterization and in vitro cytotoxic activity studies of some polycyclic aromatic compounds
Arabian Journal of Chemistry ( IF 5.3 ) Pub Date : 2020-06-01 , DOI: 10.1016/j.arabjc.2020.03.021
Majid Rezaeivala , Koray Sayin , Serap Şahin-Bölükbaşı , Derya Tandoğan , Muhammet Kose , Aysegül Kose

Abstract The present study aims to introduce three known and three new stable polycyclic aromatic compounds synthesized. With MALDI-Mass, 1H and 13C NMR spectroscopy, all new compounds were characterized. In the DMF solution were carried out the electrochemical and photophysical properties of the polyaromatic compounds. The compounds are highly fluorescent showing green-red emission when excited at one single wavelength. For the compound 3, it was shown that the highest Stokes Shift (191 nm) appeared which may be due to the excited state energy transfer. The compounds also indicated the blue-orange region of the electromagnetic spectrum strong emission bands. Additionally, compounds 1, 3, 4, and 5 were investigated for their in vitro cytotoxic activities against PC-3 prostate cancer cells, L-929 non-cancerous cells, and MDA-MB-231 breast cancer for 24 h, 48 h and 72 h. The results obtained from the experiment demonstrated that compounds had different cytotoxic activity against cell lines. Compound 3 was indicated to be inactive against L-929 cells and MDA-MB-231 cancer cells, whereas compounds 1, 4 and 5 indicated a dose and time-dependent cytotoxic activity against PC-3, MDA-MB-231, and L-929 cell lines. It was found that the most sensitive cells to compound 5 were MDA-MB-231 human breast cancer cells. Additionally, it became clear that compounds 1 and 3 had significant selectivity for human PC-3 prostate cancer cells, and compounds 1, 4 and 5 had considerable selectivity for human MDA-MB-231 breast cancer cells. Also, the quantum chemical examinations of six organic compounds were conducted at the B3LYP/6-31G level in the gas phase and water. According to calculated results, compound 5 was found to be the best candidate for NLO applications.

中文翻译:

一些多环芳族化合物的结构、光谱表征和体外细胞毒活性研究的评估

摘要 本研究旨在介绍合成的三种已知的和三种新的稳定的多环芳族化合物。使用 MALDI-Mass、1H 和 13C NMR 光谱,表征了所有新化合物。在 DMF 溶液中进行了多环芳烃化合物的电化学和光物理性能。当在一个单一波长下激发时,这些化合物具有很强的荧光性,显示出绿色-红色发射。对于化合物 3,显示最高斯托克斯位移 (191 nm) 出现,这可能是由于激发态能量转移。这些化合物还表明电磁光谱强发射带的蓝橙色区域。此外,还研究了化合物 1、3、4 和 5 对 PC-3 前列腺癌细胞、L-929 非癌细胞、和 MDA-MB-231 乳腺癌治疗 24 小时、48 小时和 72 小时。实验结果表明,化合物对细胞系具有不同的细胞毒活性。表明化合物 3 对 L-929 细胞和 MDA-MB-231 癌细胞无活性,而化合物 1、4 和 5 表明对 PC-3、MDA-MB-231 和 L 具有剂量和时间依赖性细胞毒活性-929 细胞系。发现对化合物5最敏感的细胞是MDA-MB-231人乳腺癌细胞。此外,很明显,化合物 1 和 3 对人 PC-3 前列腺癌细胞具有显着的选择性,而化合物 1、4 和 5 对人 MDA-MB-231 乳腺癌细胞具有相当大的选择性。此外,在气相和水中以 B3LYP/6-31G 水平对六种有机化合物进行了量子化学检测。
更新日期:2020-06-01
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