3-[(E)-(acridin-9'-ylmethylidene)amino]-1-substituted thioureas and their biological activity

Spectrochim Acta A Mol Biomol Spectrosc. 2017 Jun 5:180:234-241. doi: 10.1016/j.saa.2017.03.014. Epub 2017 Mar 8.

Abstract

This paper describes the synthesis of a novel series of acridine thiosemicarbazones through a two-step reaction between various isothiocyanates and hydrazine followed by treatment with acridin-9-carbaldehyde. The properties of this series of seven new derivatives are studied using NMR and biochemical techniques, and the DNA-binding properties of the compounds are determined using spectrophotometric studies (UV-vis absorption, fluorescence, and circular/linear dichroism) and viscometry. The binding constants K are estimated as being in the range of 2.2 to 7.8×104M-1 and the percentage of hypochromism was found to be 22.11-49.75% (from UV-vis spectral titration). Electrophoretic experiments prove that the novel compounds demonstrate moderate inhibitory effects against Topo I activity at a concentration of 60×10-6M.

Keywords: Acridine; DNA-binding; Spectroscopic study; Thiosemicarbazone; Topoisomerase I.

MeSH terms

  • Acridines* / analysis
  • Acridines* / chemistry
  • Acridines* / metabolism
  • Circular Dichroism
  • DNA / chemistry
  • DNA / metabolism
  • DNA Topoisomerases, Type I
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Spectrophotometry, Ultraviolet
  • Thiosemicarbazones / analysis
  • Thiosemicarbazones / chemistry
  • Thiosemicarbazones / metabolism
  • Thiourea* / analysis
  • Thiourea* / chemistry
  • Thiourea* / metabolism
  • Topoisomerase I Inhibitors* / analysis
  • Topoisomerase I Inhibitors* / chemistry
  • Topoisomerase I Inhibitors* / metabolism

Substances

  • Acridines
  • Thiosemicarbazones
  • Topoisomerase I Inhibitors
  • DNA
  • DNA Topoisomerases, Type I
  • Thiourea