Anticancer activity of artemisinin-derived trioxanes

Bibliography

• WARHURST D: Drug resistance in Plasmodioum falciparum malaria. Infection (1999) 27:S55-S58.
   Google Scholar
• LI Y, WU YL: An over four millennium story behind qinghaosu (artemisinin) – a fantastic antimalarial drug from a traditional chinese herb. Curr. Med. Chem. (2003) 10:2197-2230.
   PubMed Web of Science ®Google Scholar
• O’NEILL PM, POSNER GH: A medicinal chemistry perspective on artemisinin and related endoperoxides. J. Med. Chem. (2004) 47:2945-2964.
   PubMed Web of Science ®Google Scholar
• KAWABATA H, NAKAMAKI T, IKONOMI P, SMITH RD, GERMAIN RS, KOEFFLER HP: Expression of transferrin receptor 2 in normal amd neoplastic hemaotpoietic cells. Blood (2001) 98:2714-2719.
   PubMed Web of Science ®Google Scholar
• LAI H, SINGH NP: Selective cancer cell cytotoxicity from exposure to dihydroartemisinin and holotransferrin. Cancer Lett. (1995) 91:41-46.
   PubMed Web of Science ®Google Scholar
• WOERDENBAG HJ, MOSKAL TA, PRAS N et al.: Cytotoxicity of artemisinin-related endoperoxides to ehrlich ascites tumor cells. J. Nat. Prod. (1993) 56:849-856.
   PubMed Web of Science ®Google Scholar
• POSNER GH, PLOYPRADITH P, HAPANGAMA W et al.: Trioxane dimers have potent antimalarial, antiproliferative and antitumor activities in vitro. Bioorg. Med. Chem. (1997) 5:1257-1265.
   PubMedGoogle Scholar
• BEEKMAN AC, BARENTSEN AR, WOERDENBAG HJ et al.: Stereochemistry-dependent cytotoxicity of some artemisinin derivatives. J. Nat. Prod. (1997) 60:325-330.
   PubMed Web of Science ®Google Scholar
• LI Y, SHAN F, WU J-M et al.: Novel antitumor artemisinin derivatives targeting G1 phase of the cell cycle. Bioorg. Med. Chem. Lett. (2001) 11:5-8.
   PubMed Web of Science ®Google Scholar
• OH S, JEONG IH, AHN CM, SHIN W-S, LEE S: Synthesis and antiangiogenic activity of thioacetal artemisinin derivatives. Bioorg. Med. Chem. (2004) 12:3783-3790.
   PubMedGoogle Scholar
• JEYADEVAN JP, BRAY PG, CHADWICK J et al.: Antimalarial and antitumor evaluation of novel C-10 non-acetal dimers of 10β-(2-hydroxyethyl- )deoxo-artemisinin. J. Med. Chem. (2004) 47:1290-1298.
   PubMedGoogle Scholar
• LIU Y, WONG VK-W, KO BC-B, WONG M-K, CHE C-M: Synthesis and cytotoxicity studies of artemisinin derivatives containing lipophilic alkyl carbon chains. Org. Lett. (2005) 7(8):1561-1564.
   PubMed Web of Science ®Google Scholar
• POSNER GH, PLOYPRADITH P, PARKER MH et al.: Antimalarial, antiproliferative and antitumor activities of artemisinin-derived, chemically robust, trioxane dimers. J. Med. Chem. (1999) 42:4275-4280.
   PubMedGoogle Scholar
• JUNG M, LEE S, HAM J, LEE K, KIM H, KIM SK: Antitumor activity of novel deoxoartemisinin monomers, dimers, and trimer. J. Med. Chem. (2003) 46:987-994.
   PubMed Web of Science ®Google Scholar
• POSNER GH, MCRINER AJ, PAIK I-H et al.: Anticancer and antimalarial efficacy and safety of artemisinin-derived trioxane dimers in rodents. J. Med. Chem. (2004) 47:1299-1301.
   PubMed Web of Science ®Google Scholar
• ALAGBALA AA, MCRINER AJ, BORSTNIK K et al.: Biological mechanisms of action of novel C-10 non-acetal trioxane dimers in prostate cancer cell lines. J. Med. Chem. In press.
   Google Scholar
• BAEGE AC, POSNER GH: unpublished results.
   Google Scholar
• EKTHAWATCHAI S, KAMCHONWONGPAISAN S, KONGSAEREE P, TARNCHOMPOO B, THEBTARANONTH Y, YUTHAVONG Y: C-16 artemisinin derivatives and their antimalarial and cytotoxic activities: syntheses of artemisinin monomers, dimers, trimers and tetramers by nucleophilic additions to artemisitene. J. Med. Chem. (2001) 44:4688-4695.
   PubMed Web of Science ®Google Scholar
• EFFERTH T, DUNSTAN H, SAUERBREY A, MIYACHI H, CHITAMBAR CR: The anti-malarial artesunate is also active against cancer. Int. J. Oncol. (2001) 18:767-773.
   PubMed Web of Science ®Google Scholar
• LAI HC, SINGH NP: Selective cancer cell cytotoxicity from exposure to dihydroartemisinin and holotransferrin. Cancer Lett. (1995) 91:41-46.
   PubMed Web of Science ®Google Scholar
• KWOK JC, RICHARDSON DR: The iron metabolism of neoplastic cells: alterations that facilitate proliferation? Crit. Rev. Oncol. Hematol. (2002) 42:65-78.
   PubMed Web of Science ®Google Scholar
• CHITAMBAR CR, SELIGMAN PA: Effects of different transferrin forms on transferrin receptor expression, iron uptake and cellular proliferation of human-leukemic HL60 cells – mechanisms responsible for the specific cytotoxicity of transferrin-gallium. J. Clin. Invest. (1986) 78:1538-1546.
   PubMed Web of Science ®Google Scholar
• LEBMAN D, TRUCCO M, BOTTERO L, LANGE B, PESSANO S, ROVERA G: A mAb that detects expression of transferrin receptor in human erythroid precursor cells. Blood (1982) 59:671-678.
   PubMed Web of Science ®Google Scholar
• SINGH NP, LAI HC: Selective toxicity of dihydroartemisinin and holotransferrin toward human breast cancer cells. Life Sci. (2001) 70:49-56.
   PubMed Web of Science ®Google Scholar
• EFFERTH T, BENAKIS A, ROMERO MR et al.: Enhancement of cytotoxicity of artemisinins toward cancer cells by ferrous iron. Free Rad. Biol. Med. (2004) 37:998-1009.
   PubMed Web of Science ®Google Scholar
• KIM SJ, KIM MS, LEE JW et al.: Dihydroartemisinin enhances radiosensitivity of human glioma cells in vitro. J. Cancer Res. Clin. Oncol. (2006) 132:129-135.
   PubMed Web of Science ®Google Scholar
• WU WM, YAO ZJ, WU YL et al.: Ferrous ion induced cleavage of the peroxy bond in qinghaosu and its derivatives and the DNA damage associated with this process. Chem. Comun. (1996) 18:2213-2214.
   Google Scholar
• LI W, MO WK, SHEN D et al.: Yeast model uncovers dual roles of mitochondria in the action of artemisinin. PLOS Genetics (2005) 1:329-334.
   Web of Science ®Google Scholar
• SADAVA D, PHILLIPS T, LIN C, KANE SE: Transferrin overcomes drug resistance to artemisinin in human small-cell lung carcinoma cells. Cancer Lett. (2002) 179:151-156.
   PubMed Web of Science ®Google Scholar
• SINGH NP, LAI HC, Artemisinin induces apoptosis in human cancer cells. Anticancer Res. (2004) 24:2277-2280.
   PubMed Web of Science ®Google Scholar
• DISBROW GL, BAEGE AC, KIERPIEC KA et al.: Dihydroartemisinin is cytotoxic to papillomavirus-expressing epithelial cells in vitro and in vivo. Cancer Res. (2005) 65:10854-10861.
   PubMed Web of Science ®Google Scholar
• SEARLE J, KERR JF, BISHOP CJ: Necrosis and apoptosis – distinct modes of cell-death with fundamentally different significance. Pathol. Annu. (1982) 17:229-259.
   PubMed Web of Science ®Google Scholar
• PARK BK, O'NEILL PM, MAGGS JL, PIRMOHAMED M: Safety assessment of peroxide antimalarials: clinical and chemical perspectives. Br. J. Clin. Pharmacol. (1998) 46:521-529.
   PubMed Web of Science ®Google Scholar
• CHEN HH, ZHOU HJ, FAN X: Inhibition of human cancer cell line growth and human umbilical vein endothelial cell angiogenesis by artemisinin derivatives in vitro. Pharmacol. Res. (2003) 48:231-236.
   PubMed Web of Science ®Google Scholar
• DELL'EVA R, PFEFFER U, VENE R et al.: Inhibition of angiogenesis in vivo and growth of Kaposi's sarcoma xenograft tumors by the anti-malarial artesunate. Biochem. Pharm. (2004) 68:2359-2366.
   PubMed Web of Science ®Google Scholar
• CHEN HH, ZHOU HJ, WANG WQ, WU GD: Antimalarial dihydroartemisinin also inhibits angiogenesis. Cancer Chemo. Pharmacol. (2004) 53:423-432.
   PubMed Web of Science ®Google Scholar
• FOLKMAN J, BACH M, ROWE JW et al.: Tumor angiogenesis – therapeutic implications. NEJM (1971) 285:1182-1202.
   PubMed Web of Science ®Google Scholar
• CHEN HH, ZHOU HJ, WU GD, LOU XE: Inhibitory effects of artesunate on angiogenesis and on expressions of vascular endothelial growth factor and VEGF receptor KDR/flk-1. Pharmacol. (2004) 71:1-9.
   PubMed Web of Science ®Google Scholar
• LAI HC, SINGH NP: Oral artemisinin prevents and delays the development of 7,12-dimethylbenz[a]anthracene (DMBA)-induced breast cancer in the rat. Cancer Lett. (2006) 231:43-48.
   PubMed Web of Science ®Google Scholar
• BERGER TG, DIECKMANN D, EFFERTH T et al.: Artesunate in the treatment of metastatic uveal melanoma – first experiences. Oncol. Rep. (2005) 14:1599-1603.
   PubMed Web of Science ®Google Scholar
• PANOSSIAN LA, GARGA NI, PELLETIER D: Toxic brainstem encephalopathy after artemisinin treatment for breast cancer. Annal. Neurol. (2005) 58:812-813.
   PubMed Web of Science ®Google Scholar
• WHITE NJ, ASHLEY EA, NOSTEN F: Toxic brainstem encephalopathy after artemisinin treatment for breast cancer. Annal. Neurol. (2006) 59:725-726.
   PubMedGoogle Scholar
• PARSONS M, PEPPER E, CHAN V et al.: Toxic brainstem encephalopathy after artemisinin treatment for breast cancer – reply. Annal. Neurol. (2006) 59:726-726.
   PubMedGoogle Scholar
• BREWER TG, PEGGINS JO, GRATE SJ et al.: Neurotoxicity in animals due to arteether and artemether. Trans. R. Soc. Trop. Med. Hyg. (1994) 88:33-36.
   PubMed Web of Science ®Google Scholar
• PETRAS JM, YOUNG GD, BAUMAN RA et al.: Arteether-induced brain injury in Macaca mulatta. I. The precerebellar nuclei: the lateral reticular nuclei, paramedian reticular nuclei, and perihypoglossal nuclei. Anat. Embryol. (2000) 201:383-397.
   PubMedGoogle Scholar
• TOOVEY S, JAMIESON A: Audiometric changes associated with the treatment of uncomplicated falciparum malaria with co-artemether. Trans. R. Soc. Trop. Med. Hyg. (2004) 98:261-267.
   PubMed Web of Science ®Google Scholar
• EFFERTH T, BRIEHL MM, TOME ME: Role of antioxidant genes for the activity of artesunate against tumor cells. Int. J. Oncol. (2003) 23:1231-1235.
   PubMedGoogle Scholar
• EFFERTH T: Mechanistic perspectives for 1,2,4-trioxanes in anti-cancer therapy. Drug Res. Updat. (2005) 8:85-97.
   Google Scholar
• LAI H, SASAKI T, SINGH NP: Targeted treatment of cancer with artemisinin and artemisinin-tagged iron-carrying compounds. Expert Opin. Ther. Targets (2005) 9:995-1007.
   PubMed Web of Science ®Google Scholar