Antimalarial activities and therapeutic properties of febrifugine analogs

Antimicrobial Agents and Chemotherapy

Volumn 49, Issue 3, 2005, Pages 1169-1176

  Jiang, Suping ^a   Zeng, Qiang ^a   Gettayacamin, Montip ^b   Tungtaeng, Anchalee ^b   Wannaying, Srisombat ^b   Lim, Apassorn ^b   Hansukjariya, Pranee ^b   Okunji, Christopher O ^a   Zhu, Shuren ^a   Fang, Daohe ^c  

^a WALTER REED ARMY INSTITUTE OF RESEARCH   (United States)

^b ARMED FORCES RESEARCH INSTITUTE OF MEDICAL SCIENCES   (Thailand)

^c Washington Natural Care Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIMALARIAL AGENT; FEBRIFUGINE; HALOFUGINONE; UNCLASSIFIED DRUG; WR 059421; WR 088442; WR 090212; WR 092103; WR 139672; WR 140085; WR 146115; WR 221232; WR 222048;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CHINESE HERB; CONTROLLED STUDY; DICHROA FEBRIFUGA; GASTROINTESTINAL TOXICITY; IC 50; MACROPHAGE; MALARIA; MOUSE; NONHUMAN; PARASITEMIA; PLANT ROOT; PLASMODIUM BERGHEI; PRIORITY JOURNAL;

ANIMALS; ANTIMALARIALS; CELL LINE; MACROPHAGES; MICE; MICE, INBRED ICR; PIPERIDINES; QUINAZOLINES;

EID: 20044367655     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/AAC.49.3.1169-1176.2005     Document Type: Article

References (35)

1. Abramovitch, R., H. Dafni, M. Neeman, A. Nagler, and M. Pines. 1999. Inhibition of neovascularization and tumor growth, and facilitation of wound repair, by halofuginone, an inhibitor of collagen type I synthesis. Neoplasia 1:321-329.
2. Chien, P. L., and C. C. Cheng. 1970. Structural modification of febrifugine. Some methylenedioxy analogs. J. Med. Chem. 13:867-870.
3. Desjardins, R. E., C. J. Canfield, J. D. Haynes, and J. D. Chulay. 1979. Quantitative assessment of antimalarial activity in vitro by a semiautomated microdilution technique. Antimicrob. Agents Chemother. 16:710-718.
4. Geary, T. G., A. A. Divo, and J. B. Jensen. 1983. An in vitro assay system for the identification of potential antimalarial drugs. J. Parasitol. 69:577-583.
5. Halevy, O., A. Nagler, F. Levi-Schaffer, O. Genina, and M. Pines. 1996. Inhibition of collagen type I synthesis by skin fibroblasts of graft versus host disease and scleroderma patients: effect of halofuginone. Biochem. Pharmacol. 52:1057-1063.
6. Hirai, S., H. Kikuchi, H. Kim, K. Begum, Y. Wataya, H. Tasaka, Y. Miyazawa, K. Yamamoto, and Y. Oshima. 2003. Metabolites of febrifugine and its synthetic analogue by mouse liver S9 and their antimalarial activity against Plasmodium malarial parasite. J. Med. Chem. 46:4351-4359.
7. Jang, C. S., F. Y. Fu, C.Y. Wang, K.C. Huang, G. Lu, and T. C. Chou. 1946. Chang shan, a Chinese antimalarial herb. Science 103:59.
8. Jang, C. S., F. Y. Fu, K.C. Huang, and C. Y. Wang. 1948. Pharmacology of chang shan (Dichroa febrifuga), a Chinese antimalarial herb. Nature 161:400-401.
9. Jiang, S., S. T. Prigge, L. Wei, L., Y. Gao, T. H. Hudson, L. Gerena, J. B. Dame, and D. E. Kyle. 2001. New class of small nonpeptidyl compounds blocks Plasmodium falciparum development in vitro by inhibiting plasmepsins. Antimicrob. Agents Chemother. 45:2577-2584.
10. Keys, J. D. 1981. Chinese herbs. Charles E. Tuttle Company, Rutland, Vt.
11. Kikuchi, H., H. Tasaka, S. Hirai, Y. Takaya, Y. Iwabuchi, H. Ooi, S. Hatakeyama, H. S. Kim, Y. Wataya, and Y. Oshima. 2002. Potent antimalarial febrifugine analogues against the plasmodium malaria parasite. J. Med. Chem. 6:2563-2570.
12. Koepfli, J. B. 1947. An alkaloid with high antimalarial activity from Dichroa febrifuga. J. Am. Chem. Soc. 69:1837.
13. Koepfli, J. B., J. A. Brockman, Jr., and J. Moffat. 1950. Structure of febrifugine and isofebrifugine. J. Am. Chem. Soc. 72:3323.
14. Koepfli, J. B., J. F. Mead, and J. A. Brockman, Jr. 1948. Alkaloids of Dichroa febrifuga. I. Isolation and degradative studies. J. Am. Chem. Soc. 70:1048-1054.
15. Kuehl, K. A., Jr., C. F. Spencer, and K. Folkers. 1948. Alkaloids of Dichroa febrifuga Lour. J. Am. Chem Soc. 70:2091-2093.
16. Lei, S. H., and G. Bodeker. 2003. Changshan (Dechroa febrifuga)-ancient febrifuge and modern antimalarial: lessons for research from a forgotten tale. In M. Willcox, G. Bodeker, and P. Rasaoanaivo (ed.), Traditional medicinal plants and malaria. Harwood Press, Taylor & Francis Publishing, London, United Kingdom.
17. Li, S. 1593. Ben Cao Gang Mu (Systema Materia Medica). [Reprint, China Archive Press. Beijing, China, 1999.]
18. Liu, K., S. Sekine, Y. Goto, K. Iijima, I. Yamagishi, K. Kondon, M. Matsukawa, and T. Abe. 1998. Halofuginone inhibits neointimal formation of cultured rat aorta in a concentration-dependent fashion in vitro. Heart Vessels 13:18-23.
19. Murata, K., F. Takano, S. Fushiya, and Y. Oshima. 1998. Enhancement of NO production in activated macrophages in vivo by an antimalarial crude drug, Dichroa febrifuga. J. Nat. Prod. 61:729-733.
20. Murata, K., F. Takano, S. Fushiya, and Y. Oshima. 1999. Potentiation by febrifugine of host defense in mice against Plasmodium berghei NK65. Biochem. Pharmacol. 58:1593-1601.
21. Nagler, A., N. Firman, R. Feferman, S. Cotev, M. Pines, and S. Shoshan. 1996. Reduction in pulmonary fibrosis in vivo by halofuginone. Am. J. Respir. Crit. Care Med. 154:1082-1086.
22. 21a. National Research Council, Institute of Laboratory Animal Resources. 1996. Guide for the care and use of laboratory animals. National Academy Press, Washington, D.C.
23. Nyska, M., A. Nyska, E. Rivlin, S. Porat, M. Pines, S. Shoshan, and A. Nagler. 1996. Topically applied halofuginone, an inhibitor of collagen type I transcription, reduces peritendinous fibrous adhesions following surgery. Connect. Tissue Res. 34:97-103.
24. Olliaro, P. 2001. Mode of action and mechanisms of resistance for antimalarial drugs. Pharmacol. Ther. 89:207-219.
25. Pines, M., V. Knopov, O. Genina, I. Lavelin, and A. Nagler. 1997. Halofuginone, a specific inhibitor of collagen type I synthesis, prevents dimethylnitrosamine-induced liver cirrhosis. J. Hepatol. 27:391-398.
26. Pines, M., and A. Nagler. 1998. Halofuginone: a novel antifibrotic therapy. Gen. Pharmacol. 30:445-450.
27. Pines, M. I., Vlodavsky, and A. Nagler. 2000. Halofuginone: from veterinary use to human therapy. Drug Dev. Res. 50:371-378.
28. Ridley, R. G. 1999. Planting the seeds of new antimalarial drugs. Science 285:1502-1503.
29. Ryley, J. F., and M. J. Betts. 1973. Chemotherapy of chicken coccidiosis. Adv. Pharmacol. Chemother. 10:221-293.
30. Siegfried, J. 1986. Quinazoline alkaloids. The Alkaloides. 29:99-140.
31. Skehan, P., R. Storeng, D. Scudiero, A. Monks, J. McMahon, D. Vistica, J. T. Warren, H. Bokesch, S. Kenney, and M. R. Boyd. 1990. New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl. Cancer Inst. 82:1107-1112.
32. Takaya, Y., H. Tasaka, T. Chiba, K. Uwai, M. Tanitsu, H. S. Kim, Y. Wataya, M. Miura, M. Takeshita, and Y. Oshima. 1999. New type of febrifugine analogues, bearing a quinolizidine moiety, show potent antimalarial activity against Plasmodium malaria parasite. J. Med. Chem. 42:3163-3166.
33. Takeuchi, Y., M. Hattori, H. Abe, and T. Harayama. 1999. Synthesis of D/L-febrifugine and D/L-isofebrifugine. Synthesis 10:1814-1818.
34. Trager, W., and J. B. Jensen. 1976. Human malaria parasites in continuous culture. Science 193:674-675.
35. World Health Organization. 2001. Roll back malaria. Malaria at a glance. World Health Organization, Geneva, Switzerland.