Synthesis, Raman, FT-IR, NMR spectroscopic characterization, antimicrobial activity, cytotoxicity and DNA binding of new mixed aza-oxo-thia macrocyclic compounds


Aghatabay N. M. , Bas A., Kircali A., Sen G., Yazicioglu M. B. , Guecin F., ...More

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, vol.44, no.11, pp.4681-4689, 2009 (Journal Indexed in SCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 44 Issue: 11
  • Publication Date: 2009
  • Doi Number: 10.1016/j.ejmech.2009.07.003
  • Title of Journal : EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
  • Page Numbers: pp.4681-4689

Abstract

Series of new mixed aza-oxo-thia macrocyclic ligands 1,9(2,6)-ditriazina-2,8,10,16-tetraaza-3,7,11,15-tetraoxo-5,13-dithia-cyclohexadecaphan-1(4),9(4)-diphenyl (L-1); 1,10(2,6)-ditriazina-2,9,11,18-tetraaza-3,8,12, 17-tetraoxo-5,6,14,15-tetrathia-cyclooctadecaphan-1(4),10(4)-diphenyI (L-2); 1,11(2,6)-ditriazina-2,10,12,20-tetraaza-3,9,13,19-tetraoxo-6,16-dithia-cyclocosa-phan-1(4),11(4)-diphenyl (L-3); 1,12(2,6)-ditriazina-2,11,13,22-tetraaza-3,10,14,21-tetraoxo-6,7,17,18-tetrathia-cyclodocosaphan-1(4),12(4)-diphenyl (L-4) were synthesised. The structural features of the compounds have been studied by elemental analyses, Mass, FT-Raman, FT-IR, H-1 and C-13 NMR spectroscopy. The antimicrobial activities of the ligands were evaluated using disk diffusion method in dimethyl sulfoxide (DMSO) as well as the minimal inhibitory concentration (MIC) dilution method, against several bacteria and yeast cultures. The obtained results from both methods were assessed in side-by-side comparison with commercial antibacterial and antifungal agents. In most cases, the compounds show strong antifungal activity in the comparison tests. Cytotoxic activities of the ligands against two different human cancer cell lines, stomach (23132/87) and lung (A549) were determined by MTT assay. DNA fragmentation assay tested cell lines were used to analyze the DNA ladder formation which is a characteristic of apoptotic cell death. The binding of the ligands with calf thymus DNA (CT-DNA) has also been investigated by absorption spectroscopy. (C) 2009 Elsevier Masson SAS. All rights reserved.