Evaluation of structural, spectral characterization and in vitro cytotoxic activity studies of some polycyclic aromatic compounds


Rezaeivala M., SAYIN K. , Şahin-Bölükbaşı S. , Tandoğan D., Kose M., Kose A.

ARABIAN JOURNAL OF CHEMISTRY, vol.13, no.6, pp.5593-5604, 2020 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 13 Issue: 6
  • Publication Date: 2020
  • Doi Number: 10.1016/j.arabjc.2020.03.021
  • Title of Journal : ARABIAN JOURNAL OF CHEMISTRY
  • Page Numbers: pp.5593-5604

Abstract

The present study aims to introduce three known and three new stable polycyclic aromatic compounds synthesized. With MALDI-Mass, H-1 and C-13 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. (C) 2020 The Author(s). Published by Elsevier B.V. on behalf of King Saud University.