Relationship between electronic structure and cytotoxic activity of azulenes

In Vivo. 2006 May-Jun;20(3):385-9.

Abstract

The structure-activity relationship of the cytotoxic activity of azulene and azulene derivatives was discussed, using theoretically calculated results. In order to clearly divide the azulenes into three groups according to their functional groups, the CC50, four different dipole moments (muG, muESP-G, muwand muESP-W) and heats of formation (deltaHf) of the azulenes [1-24] were separately calculated in two states, gas-phase and water, by the conductor-like screening model/parametric method 3 (COSMO/PM3). For the halogenated azulenes and isopropyl azulenes, the cytotoxic activity might follow the three quantitative structure-activity relationship (QSAR) parameters: deltadeltaHf, HOMO energy and muw Whereas, for the other ten compounds [3-5, 7-8, 10, 15-18], the cytotoxic activity might be related to the three QSAR parameters, deltadeltaHf, LUMO energy and muG

Publication types

  • Comparative Study

MeSH terms

  • Antineoplastic Agents* / chemistry
  • Antineoplastic Agents* / toxicity
  • Azulenes / chemical synthesis
  • Azulenes / chemistry*
  • Azulenes / toxicity*
  • Cell Line
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Chemical Phenomena
  • Chemistry, Physical
  • Humans
  • Hydrophobic and Hydrophilic Interactions
  • Models, Chemical
  • Molecular Structure
  • Quantitative Structure-Activity Relationship
  • Statistics as Topic
  • Thermodynamics
  • Water / chemistry

Substances

  • Antineoplastic Agents
  • Azulenes
  • Water