Probing the Possible Molecular Origin of the Highly Selective Toxicity of Antimalarial Peroxide Qinghaosu (Artemisinin)

Chemical Research in Toxicology

Volumn 16, Issue 10, 2003, Pages 1202-1206

  Wu, Yikang ^a   Liu, He Hua ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIMALARIAL AGENT; ARTEMISININ;

ANTIMALARIAL ACTIVITY; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; LD 50; MALARIA; MULTIDRUG RESISTANCE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE;

ANIMALS; ANTIMALARIALS; ARTEMISININS; LETHAL DOSE 50; MICE; MOLECULAR STRUCTURE; PEROXIDES; RATS; SESQUITERPENES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0142232014     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx034133k     Document Type: Article

References (25)

1. Li, Y., and Wu, Y.-L. (1998) How Chinese scientists discovered qinghaosu (artemisinin) and develop its derivatives? What are the future perspectives? Med. Trop. (Marseille) 58 (Suppl. 3), 9-12 and the references therein.
2. Klayman, D. L. (1985) Qinghaosu (artemisinin): an antimalarial drug from China. Science 228, 1049-1055.
3. Ziffer, H., Highet, R. J., and Klayman, D. L. (1997) Artemisinin: an endoperoxidic antimalarial from Artemisia annuua L. Prog. Chem. Org. Nat. Prod. 72, 121-214.
4. Haynes, R. K., and Vonwiller, S. C. (1997) From Qinghao, Marvelous Herb of Antiquity, to the Antimalarial Trioxane Qinghaosu. Some Remarkable New Chemistry. Acc. Chem. Res. 30, 73-79.
5. Liu, J.-M., Ni, M.-Y., Fan, J.-F., Tu, Y.-Y., Wu, Z.-H., Wu, Y.-L., and Chou, W.-S. (1979) Structure and reaction of arteannuin. Acta Chim. Sin. 37, 129-143.
6. China Cooperative Research Group (1982) Antimalarial efficacy and mode of action of qinghaosu and its derivatives in experimental modes. J. Trad. Chin. Med. 2, 17-24.
7. Mackenzie, D. (1999) The comeback killer. New Sci. 163, 13-13.
8. Butler, D. (1997) Time to put malaria control on the global agenda. Nature 386, 535-536.
9. Riedley, R. G. (2002) Medical need, scientific opportunity and drive for antimalarial drugs. Nature 415, 686-693.
10. Guerin, P. J., Olliaro, P., Nosten, F., Druilhe, P., Laxminarayan, R., Binka, F., Kilama, W. L., Ford, N., and White, N. J. (2002) Malaria: current status of control, diagnosis, treatment, and a proposed agenda for research and development. Lancet Infect. Dis. 2, 564-573.
11. See, for example: (1997) Free Radical Toxicology (Wallace, K. B., Ed.) Taylor & Francis, Washington, DC.
12. Wu, W.-M., Wu, Y.-K., Wu, Y.-L., Yao, Z.-J., Zhou, C.-M., Li, Y., and Shan, F. (1998) Unified mechanistic framework for the Fe(II)-induced cleavage of qinghaosu and derivatives/analogues. The first spin-trapping evidence for the previously postulated secondary C-4 radical. J. Am. Chem. Soc. 120, 3316-3325 and 13002 (addition/correction).
13. Posner, G. H., Cumming, J. N., Ploypradith, P., and Oh, C. H. (1995) Evidence for Fe(IV)=O in the molecular mechanism of action of the trioxane antimalarial artemisinin. J. Am. Chem. Soc. 117, 5885-5886 and references therein.
14. Jefford, C. W., Vicente, M. G. H., Jacquier, Y., Favarger, F., Mareda, J., Millasson-Schmidt, P., Brunner, G., and Burger, U. (1996) The deoxygenation and isomerization of artemisinin and artemether and their relevance to antimalarial action. Helv. Chim. Acta 79, 1475-1487.
15. Haynes, R. K., and Vonwiller, S. C. (1996) The behavior of qinghaosu (artemisinin) in the presence of heme iron(II) and (III). Tetrahedron Lett. 37, 253-256.
16. Haynes, R. K., and Vonwiller, S. C. (1996) The behavior of qinghaosu (Artemisinin) in the presence of non-heme iron(II) and (III). Tetrahedron Lett. 37, 257-260.
17. Avery, M. A., Fan, P.-C., Karle, J. M., Bonk, J. D., Miller, R., and Goins, D. K. (1996) Structure-activity relationship of the antimalarial agent artemisinin. 3. Total synthesis of (+)-13-carbaartemisinin and related tetra-and tricyclic structures. J. Med. Chem. 39, 1885-1897.
18. Wu, Y.-K., Yue, Z.-Y., and Wu, Y.-L. (1999) Interaction of qinghaosu (artemisinin) with cysteine sulfhydryl mediated by traces of non-heme iron. Angew. Chem., Int. Ed. 38, 2580-2582.
19. Wang, D.-Y., and Wu, Y.-L. (2000) A possible antimalarial action mode of qinghaosu (artemisinin) series compounds. Alkylation of reduced glutathione by C-centered primary radicals produced from antimalarial compound qinghaosu and 12-(2,4-dimethoxyphenyl)-12-deoxyqinghaosu. J. Chem. Soc., Chem. Commun. 2193-2194.
20. Wu, W.-M., and Wu, Y.-L. (2000) Chemical and electro-chemical reduction ofqinghaosu (artemisinin). J. Chem. Soc., Perkin Trans. 1 4279-4283.
21. Wu, Y.-K., Yue, Z.-Y., and Liu, H.-H. (2001) New Insights into the degradation of qinghaosu (artemisinin) mediated by non-heme-iron chelates, and their relevance to the antimalarial mechanism. Helv. Chim. Acta 84, 928-932.
22. Wu, Y.-K. (2002) How might qinghaosu (artemisinin) and related compounds kill the intraerythrocytic malaria parasite? A chemist's view. Acc. Chem. Res. 35, 255-259.
23. Wu, Y.-K., and Ahlberg, P. (1992) Intramolecularity and the Function of the Side Arm Base of Simple Model of Transaminases. J. Org. Chem. 57, 6324-6327.
24. China Cooperative Research Group on Qinghaosu and Its Derivatives as Antimalarials (1982) Studies on the toxicity of qinghaosu and its derivatives. J. Trad. Chin. Med. 2, 31-38.
25. The NIOSH Registry of Toxic Effects of Chemical Substances (RTECS(R)) Database (January, 2001) Compiled by the National Institute for Occupational Safety and Health of the U.S. Department of Health and Human Services.