3 years ago

Kinetic parameters for the reaction of 1,2,4-trioxolanes and artemisinin with iron(II): New evidence for the source of antimalarial activity

Kinetic parameters for the reaction of 1,2,4-trioxolanes and artemisinin with iron(II): New evidence for the source of antimalarial activity
Luiz Francisco M. L. Ciscato, Nicolas S. Lopes
The Fenton-like reductive cleavage of antimalarial peroxides like artemisinin by iron(II) species is a chemical reaction whose mechanistic pathway has not been yet fully understood; it is, however, known that there is considerable production of radical species centered at both the oxygen and carbon, which are important to the therapeutical effects of those compounds. This article reports kinetic data for the reaction of artemisinin and two model 1,2,4-trioxolanes with iron(II) species and also a mechanistic interpretation of this reductive cleavage from transition state thermodynamics. The suggestion of the presence of an enhancing specific factor inside the plasmodium is made. The antimalarial activity of three organic peroxides has been rationalized in view of their reactivity with iron(II) species, showing no direct correlation and pointing to structural or spatial effects.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1111/cbdd.13056

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