Structure-activity relationships of peroxide-based artemisinin antimalarials

Biologically Active Natural Products: Pharmaceuticals

Volumn , Issue , 1999, Pages 115-126

  Avery, Mitchell A ^a   McLean, Graham ^b   Edwards, Geoff ^b   Ager, Arba ^c  

^a UNIVERSITY OF MISSISSIPPI   (United States)

^b UNIVERSITY OF LIVERPOOL   (United Kingdom)

^c UNIVERSITY OF MIAMI MILLER SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0345606841     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1201/9781420048650     Document Type: Chapter

References (30)

1. Klayman, D.L. Qinghaosu (Artemisinin): an antimalarial drug from China, Science, 228, 1049, 1985.
2. Haynes, R.K. and Vonwiller, S.C. From: Qinghao, marvelous herb of antiquity, to the antimalarial trioxane Qinghaosu. Some remarkable new chemistry, Acc. Chem. Res., 30, 73, 1997.
3. Akhila, A.R.K. and Thakur, R.S. Biosynthesis of artemisinic acid in Artemisia annua, Phytochemistry, 29, 2129, 1990.
4. Acton, N. and Roth, R.J. On the conversion of dihydroartemisinic acid into artemisinin, J. Org. Chem., 57, 3610, 1992.
5. Haynes, R.K. and Vonwiller, S.C. Extraction of artemisinin and artemisinic acid: preparation of artemether and new analogs, Trans. R. Soc. Trop. Med. Hyg., 88, 23, 1994.
6. Qinghaosu Antimalarial Coordinating Research Group. Antimalaria studies on Qinghaosu, Chin. Med. J., 92, 811, 1979.
7. Li, Y., Yu, P.L., Chen, Y.X., Li, L.Q., Gai, Y.Z., Wang, D.S., and Zheng, Y.P. Studies on artemisinine analogs. I. Synthesis of ethers, carboxylates and carbonates of dihydroartemisinine, Yaoxue Xuebao, 16, 429, 1981.
8. Titulaer, H.A.C., Zuidema, J., Kager, P.A., Wetsteyn, J.C.F. M., Lugt, C.B., and Merkus, F.W.H.M. The pharmacokinetics of artemisinin after oral, intramuscular and rectal administration to volunteers, J. Pharm. Pharmacol., 42, 810, 1990.
9. Brewer, T.G., Peggins, J.O., Grate, S.J., Petras, J.M., Levine, B.S., Weina, P.J., Swearengen, J., Heiffer, M.H., and Shuster, B.G. Neurotoxicity in animals due to arteether and artemether, Trans. R. Soc. Trop. Med. Hyg., 88, 33, 1994.
10. Brewer, T.G., Grate, S.J., Peggins, J.O., Weina, P.J.P., J.M., Levine, B.S., Heiffer, M.H., and Schuster, B.G. Fatal neurotoxicity of arteether and artemether, Am. J. Trop. Med. Hyg., 51, 251, 1994.
11. Wesche, D.L., DeCoster, M.A., Tortella, F.C., and Brewer, T.G. Neurotoxicity of Artemisinin analogs in vitro, Antimic. Agents Chemother., 38, 1813, 1994.
12. Fishwick, J. and Edwards, G. The toxicity of artemisinin and related compounds on neuronal and glial cells in culture, Chem. Biol. Interact., 96, 263, 1995.
13. Smith, S.L., Fishwick, J., McLean, W.G., Edwards, G., and Ward, S.A. Enhanced in vitro neurotoxicity of artemisinin derivatives in the presence of hemin, Biochem. Pharmacol., 53, 5, 1997.
14. Kamchonwongpaisan, S., McKeever, P., Hossler, P., Ziffer, H., and Meshnick, S.R. Artemisinin neurotoxicity: neuropathology in rats and mechanistic studies in vitro, Am. J. Trop. Med. Hyg., 56, 7, 1997.
15. Meshnick, S.R., Thomas, A., Ranz, A., Xu, C.M., and Pan, H. Artemisinin (Qinghaosu), the role of intracellular hemin in its mechanism of antimalarial action, Mol. Biochem. Parasitol., 49, 181, 1991.
16. Meshnick, S.R. Is hemozoin a target for antimalarial drugs? Ann. Trop. Med. Parasitol., 90, 367, 1996.
17. Posner, G.H. and Oh, C. A regiospecifically oxygen-18 labeled 1,2,4-trioxane: a simple chemical model system to probe the mechanism(s) for the antimalarial activity of artemisinin (Qinghaosu), J. Am. Chem. Soc., 114, 8328, 1992.
18. Cumming, J.N., Ploypradith, P., and Posner, G.H. Antimalarial activity of artemisinin (Qinghaosu) and related trioxanes: mechanism(s) of action, Adv. Pharmacol., 37, 253, 1997.
19. Asawamahasakda, W., Ittarat, I., Pu, Y.-M., Ziffer, H., and Meshnick, S.R. Reaction of antimalarial endoperoxides with specific parasite proteins, Antimicrob. Agents Chemother., 38, 1854, 1994
20. Yang, Y.-Z., Little, B., and Meshnick, R. Alkylation of proteins by artemisinin effects of heme, pH, and drug structure, Biochem. Pharmacol., 48, 569, 1994.
21. Bhisutthibhan, J., Pan, X.-O., Hossler, P.A., Walker, D.J., Yowell, C.A., Carlton, J., Dame, J.B., and Meshnick, S.R. The plasmodium falciparum translationally controlled tumor protein homolog and its reaction with the antimalarial drug artemisinin, J. Biol. Chem., 273, 16192, 1998.
22. Avery, M.A., Chong, W.K.M., and Jennings-White, C. Stereoselective total synthesis of (+)-artemisinin, the antimalarial constituent of Artemisia annua L., J. Am. Chem. Soc., 114, 974, 1992.
23. Avery, M.A., Bonk, J.D., and Bupp, J. Radiolabeled antimalarials: synthesis of 14C-artemisinin, J. Labelled Comp. Radiopharm., 38, 263, 1996.
24. Avery, M.A., Bonk, J., Mehrotra, S., Chong, W.K.M., Miller, R., Milhous, W.K., Goins, K.D., Venkatesan, S., Wyandt, C., Khan, I., and Avery, B.A. Structure-activity relationships of the antimalarial agent artemisinin. 2. Effect of heteroatom substitution at O-11: synthesis and bioassay of N-alkyl-11-aza-9-desmethylartemisinins, J. Med. Chem., 38, 5038, 1995.
25. Avery, M.A., Gao, F., Chong, W.K.M., Mehrotra, S., and Milhous, W.K. Structure-activity relationships of the antimalarial agent artemisinin. I. Synthesis and comparative molecular field analysis of C-9 analogs of artemisinin and 10-deoxoartemisinin, J. Med. Chem., 36, 4264, 1993.
26. Avery, M.A., Mehrotra, S., Bonk, J.D., Vroman, J.A., Goins, K., and Miller, R. Structure-activity relationships of the antimalarial agent artemisinin. 4. Effect of substitution at C-3, J. Med. Chem., 39, 2900, 1996.
27. Avery, M.A., Mehrotra, S., Johnson, T., and Miller, R. Structure-activity relationships of the antimalarial agent artemisinin. 5. Analogs of 10-deoxoartemisinin substituted at C-3 and C-9, J. Med. Chem., 39, 4149, 1996.
28. Cramer III, R.D., Patterson, D.E., and Bunce, J.D. Comparative molecular field analysis (CoMFA).Effect of shape on binding of steroids to carrier proteins, J. Am. Chem. Soc., 110, 5959, 1988.
29. Posner, G.H., Oh, C.H., Gerena, L., and Milhous, W.K. Extraordinarily potent antimalarial compounds: new, structurally simple, easily synthesized, tricyclic 1,2,4-trioxanes, J. Med. Chem., 35, 2459, 1992.
30. Vroman, J.A., Khan, I., and Avery, M.A. Copper (I) catalyzed conjugate addition of Grignard reagents to acrylic acids: homologation of artemisinic acid and subsequent conversion to 9-substituted artemisinin analogs, Tetrahedron Lett., 38, 6173, 1997.