Spectrophotometric and ESI-MS/HPLC studies reveal a common mechanism for the reaction of various artemisinin analogues with hemin

Bioorg Med Chem Lett. 2003 Nov 17;13(22):4055-7. doi: 10.1016/j.bmcl.2003.08.032.

Abstract

The reaction of hemin with three well known artemisinin analogues, namely dihydroartemisinin, artemether and artesunate, was independently analysed by visible spectrophotometry and by ESI-MS/HPLC. A very similar reaction pathway emerges for all these compounds that matches closely the reaction profile previously described for artemisinin. In the course of the reaction characteristic isomeric 1:1 drug-hemin adducts are formed as in the case of artemisinin; eventual disruption of the porphyrin ring takes place in all cases, most likely through oxidative degradation.

MeSH terms

  • Artemisinins / chemical synthesis
  • Artemisinins / chemistry*
  • Chromatography, High Pressure Liquid
  • Hemin / chemistry*
  • Molecular Structure
  • Sesquiterpenes / chemical synthesis
  • Sesquiterpenes / chemistry*
  • Spectrometry, Mass, Electrospray Ionization / methods
  • Spectrophotometry
  • Structure-Activity Relationship

Substances

  • Artemisinins
  • Sesquiterpenes
  • Hemin
  • artemisinin