EPR evidence for the involvement of free radicals in the iron-catalysed decomposition of qinghaosu (artemisinin) and some derivatives; antimalarial action of some polycyclic endoperoxides

Free Radical Research

Volumn 28, Issue 5, 1998, Pages 471-476

  Butler, Anthony R ^a   Gilbert, Bruce C ^b   Hulme, Philippa ^a   Irvine, Lee R ^b   Renton, Louise ^a   Whitwood, Adrian C ^b  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

^b UNIVERSITY OF YORK   (United Kingdom)

Author keywords

Alkoxyl antimalarial; Artemisinin; Electron paramagnetic resonance; Peroxides; Peroxygen; Qinghaosu; Radical fragmentation; Radical rearrangement; Spin trapping

Indexed keywords

ACETONITRILE; ANTIMALARIAL AGENT; ARTEMISININ; ENDOPEROXIDE; FERROUS ION; FREE RADICAL; IRON;

ANTIMALARIAL ACTIVITY; ARTICLE; CATALYSIS; CONTROLLED STUDY; DRUG DECOMPOSITION; ELECTRON SPIN RESONANCE;

EID: 0031874783     PISSN: 10715762     EISSN: None     Source Type: Journal    
DOI: 10.3109/10715769809066884     Document Type: Article

References (21)

1. J.-M. Liu, M.-Y. Ni, J.-F. Fan, Y-Y. Tu, Z.-H. Wu, Y.-L. Wu and W.-S. Chou, "Structure and reaction of arteannuin", Acta Chimica Sinica, 1979, 37, 129-143.
2. China Cooperative Research Group, Journal of Traditional Chinese Medicine, "Qinghaosu and its derivatives as antimalarials", 1982, 2, 45-50.
3. H.-M. Gu, B.-F. Lu and Z.-X. Qu, "Antimalarial activities of derivatives of artemisinin against chloroquine-resistant plasmodium berghei", Acta Pharmacology Sinica, 1980, 1, 48-50; B. Ye,Y.-L. Wu, G.-F. Li and X.-Q. Jiao, "Antimalarial Activity of Deoxoqinghaosu", Acta Pharmaceutica Sinica, 1991, 26, 228-300.
4. H.-M. Gu, B.-F. Lu and Z.-X. Qu, "Antimalarial activities of derivatives of artemisinin against chloroquine-resistant plasmodium berghei", Acta Pharmacology Sinica, 1980, 1, 48-50; B. Ye,Y.-L. Wu, G.-F. Li and X.-Q. Jiao, "Antimalarial Activity of Deoxoqinghaosu", Acta Pharmaceutica Sinica, 1991, 26, 228-300.
5. C.W. Jefford, F. Favarger, M. da G.H. Vincente and Y. Jacquier, "The Decomposition of cis-fused cyclopenteno1,2,4-trioxanes induced by ferrous salts and some oxophilic reagents", Helvetica Chimica Acta, 1995, 78, 452-458.
6. G.H. Posner, J.N. Cumming, P. Ploypradith and C.H. Oh, "Evidence for Fe(IV)=O in the molecular mechanism of action of the trioxane antimalarial artemisinin", Journal of the American Chemical Society, 1995, 117, 5885-5886.
7. G.H. Posner, S.B. Park, L. González, D. Wang, J.N. Cumming, D. Klinedinst, T.A. Shapiro and M.D. Bachi, "Evidence for the importance of high-valent Fe=O and of a diketone in the molecular mechanism of action of antimalarial trioxane analogs of artemisinin", Journal of the American Chemical Society, 1996, 118, 3537-3538.
8. W.-M. Wu, Z.-J. Yao, Y.-L. Wu, K. Jiang, Y.-F. Wang, H.-B. Chen, F. Shan and Y. Li, "Ferrous ion-induced cleavage of the peroxy bond in qinghaosu and its derivatives and the DNA-damage associated with this process", Chemical Communications, 1996, 2213-2214.
9. S.R. Krungkrai and Y. Tuthavong, "The antimalarial action on plasmodium-falciparum of qinghaosu and artesunate in combination with agents which modulate oxidant stress", Transactions of the Royal Society of Tropical Medicine and Hygiene, 1987, 81, 710-714.
10. S.R. Meshnick, T.W. Tsang, F.-B. Lin, H.-Z. Pan, C-N. Chang, F. Kuypers, D. Chiu and B. Lubin, "Activated oxygen mediates the antimalarial activity of qinghaosu", Progress in Clinical Biological Research, 1989, 313, 95-104.
11. H. Kaur, K.H.W. Leung and M.J. Perkins, "A Water-soluble, nitroso-aromatic spin-trap", Journal of the Chemical Society, Chemical Communications, 1981, 142-143.
12. W. Bors, C. Michel and K. Stettmaier, "Radical species produced from the photolytic and pulse-radiolytic degradation of cert-butyl hydroperoxide - An EPR spin trapping investigation", J. Chem. Soc., Perkin Trans. 2, 1992, 1513-1517.
13. 2 in aqueous-solution - direct evidence for the formation of the hydroxyl radical", Free Radical Research Communications, 1992, 17, 21-39.
14. B.C. Gilbert and S. Silvester, "EPR studies of the role of copper in bio-organic free radical reactions. Coppercatalysed oxidations of thiols with peroxides, especially those involving glutathione", Nukleonika, 1997, 42, 307-322.
15. M.J. Davies, "Detection of peroxyl and alkoxyl radicals produced by reaction of hydroperoxides with hemeproteins by electron-spin resonance spectroscopy", Biochimica et Biophysics Acta, 1988, 964, 28-35.
16. I. Leban, L. Golu and M. Japelj, "Crystal and molecular-structure of qinghaosu - a rdetermination", Acta Pharmaceutica Jugoslavica, 1988, 38, 71-77.
17. 3C-O moiety due to the reduction of molecular symmetry - X-ray, conformational, and quantum-chemical study", Journal of Molecular Structure, 1984, 112, 127-140.
18. J.-M. Savariault and M.S. Lehmann, "Experimental determination of the deformation electron density in hydrogen peroxide by combination of X-ray and neutron diffraction measurements", Journal of the American Chemical Society, 1980, 102, 1298.
19. A.J. Lin, D.L. Klayman, J.M. Hoch, J.V. Silverton and C.F. George, "Thermal rearrangement and decomposition products of artemisinin (qinghaosu)", Journal of Organic Chemistry, 1985, 50, 4504-4508.
20. M. Erben-Russ, C. Michel, W. Bors and M. Saran, "Absolute rate constants of alkoxyl radical reactions in aqueous-solution", Journal of Physical Chemistry, 1987, 91, 2362-2365.
21. C. Walling and A. Padwa, "Positive halogen compounds VII. Intramolecular chlorinations with long-chain hypochlorites", Journal of the American Chemical Society, 1963, 85, 1597.