Spectrophotometric and ESI-MS/HPLC studies reveal a common mechanism for the reaction of various artemisinin analogues with hemin.
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.
Department of Chemistry, University of Florence, Via della Lastruccia 3, I-50019 Sesto Fiorentino, Florence, Italy. messori@cerm.unifi.it
Luigi
L
Messori
Francesca
F
Piccioli
Brigitte
B
Eitler
Maria Camilla
MC
Bergonzi
Anna Rita
AR
Bilia
Franco Francesco
FF
Vincieri
D037621:Artemisinins / Q000138:chemical synthesis / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D006427:Hemin / Q000737:chemistry*; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000138:chemical synthesis / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods; D013053:Spectrophotometry; D013329:Structure-Activity Relationship
D037621:Artemisinins; D012717:Sesquiterpenes; D006427:Hemin; C031327:artemisinin