Anticancer and Antimalarial Efficacy and Safety of Artemisinin-Derived Trioxane Dimers in Rodents

Journal of Medicinal Chemistry

Volumn 47, Issue 5, 2004, Pages 1299-1301

  Posner, Gary H ^a,b   McRiner, Andrew J ^a   Paik, Ik Hyeon ^a   Sur, Surojit ^a   Borstnik, Kristina ^a   Xie, Suji ^b   Shapiro, Theresa A ^b,c   Alagbala, Adebusola ^d   Foster, Barbara ^d  

^a JOHNS HOPKINS UNIVERSITY   (United States)

^b JOHNS HOPKINS BLOOMBERG SCHOOL OF PUBLIC HEALTH   (United States)

^c JOHNS HOPKINS UNIVERSITY SCHOOL OF MEDICINE   (United States)

^d ROSWELL PARK CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTEMISININ DERIVATIVE; ARTESUNATE; DOXORUBICIN; GEMCITABINE; ISOBUTYRIC ACID; ISONICOTINATE N OXIDE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANTIMALARIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; DOSE RESPONSE; DRUG EFFICACY; DRUG SAFETY; MOUSE; NONHUMAN; PROSTATE ADENOCARCINOMA;

ADENOCARCINOMA; ADMINISTRATION, ORAL; ANIMALS; ANTIMALARIALS; ANTINEOPLASTIC AGENTS; ARTEMISININS; CELL LINE, TUMOR; DIMERIZATION; DRUG RESISTANCE; DRUG SCREENING ASSAYS, ANTITUMOR; FLOW CYTOMETRY; INJECTIONS, INTRAVENOUS; MALE; MICE; PLASMODIUM FALCIPARUM; PROSTATIC NEOPLASMS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 1242296302     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0303711     Document Type: Article

References (16)

1. Borstnik, K.; Paik, I.-P.; Posner, G. H. Malaria: New Chemotherapeutic Peroxide Drugs. Mini-Rev. Med. Chem. 2002, 2, 573-583.
2. Robert, A.; Decky-Cabaret, O.; Cazelles, J.; Meunier, B. From Mechanistic Studies on Artemisinin Derivatives to New Modular Antimalarial Drugs. Acc. Chem. Res. 2002, 35, 167-174.
3. Dadava, D.; Phillips, T.; Lin, C.; Kane, S. E. Transferrin Overcomes Drug Resistance to Artemisinin in Human Small-Cell Lung Carcinoma Cells. Cancer Lett. 2002, 179, 151-156.
4. Jung, M.; Lee, S.; Ham, J.; Lee, K.; Kim, H.; Kim, S. K. Antitumor Activity of Novel Deoxoartemisinin Monomers, Dimers, and Trimer. J. Med. Chem. 2003, 46, 987-994.
5. Chen, H.-H.; Zhou, H.-J.; Fang, X. Inhibition of Human Cancer Cell Line Growth and Human Umbilical Vein Endothelial Cell Angiogenesis by Artemisinin Derivatives in Vitro. Pharm. Res. 2003, 48, 231-236.
6. Posner, G. H.; Paik, I.-H.; Sur, S.; McRiner, A. J.; Borstnik, K.; Xie, S.; Shapiro, T. A. Orally Active, Antimalarial, Anticancer, Artemisinin-Derived Trioxane Dimers with High Stability and Efficacy. J. Med. Chem. 2003, 46, 1060-1065.
7. Cancer Facts & Figures 2003; http: //www.cancer.org/docroot/stt/stt_0.asp.
8. Foster, B. A.; Gingrich, J. R.; Kwon, E. D.; Madias, C.; Greenberg, N. M. Characterization of prostatic epithelial cell lines derived from transgenic adenocarcinoma of the mouse prostate (TRAMP) model. Cancer Res. 1997, 57, 3325-3330.
9. Han, G.; Foster, B. A.; Mistry, S.; Buchanan, G.; Harris, J. M.; Tilley, W. D.; Greenberg, N. M. Hormone status selects for spontaneous somatic androgen receptor variants that demonstrate specific ligand and cofactor dependent activities in autochthonous prostate cancer. J. Biol. Chem. 2001, 276 (14), 11204-11213.
10. China Cooperative Research Group on Qinghaosu and Its Derivatives as Antimalarials. The chemistry and synthesis of qinghaosu derivatives. J. Trad. Chim. Med. 1982, 2, 9-16.
11. For experimental details of the testing protocol, including references to development of the assay, see the following. Posner, G. H.; González, L.; Cumming, J. N.; Klinedinst, D.; Shapiro, T. A. Synthesis and Antimalarial Activity of Heteroatom-Containing Bicyclic Endoperoxides. Tetrahedron 1997, 53, 37-50.
12. Peters, W.; Robinson, B. L.; Rossiter, J. C.; Jefford, C. W. The Chemotherapy of Rodent Malaria. XLVIII. The Activities of Some Synthetic 1,2,4-Trioxanes against Chloroquine-Sensitive and Chloroquine-Resistant Parasites. Part 1: Studies Leading to the Development of Novel cis-Fused Cyclopenteno Derivatives. Ann. Trop. Med. Parasitol. 1993, 87, 1-7.
13. Avery, M. A.; Alvim-Gaston, M.; Vroman, J. A.; Wu, B.; Ager, A.; Peters, W. Structure-Activity Relationships of the Antimalarial Agent Artemisinin. 7. Direct Modification of (+)-Artemisinin and in Vivo Antimalarial Screening of New, Potential Preclinical Antimalarial Candidates. J. Med. Chem. 2002, 45, 4321-4335.
14. Bachi, M. D.; Korshin, E. E.; Hoos, R.; Szpilman, A. M.; Ploypradith, P. ; Xie, S. J.; Shapiro, T. A.; Posner, G. H. A Short Synthesis and Biological Evaluation of Potent and Nontoxic Antimalarial Bridged Bicyclic β-Sulfonyl-Endoperoxides. J. Med. Chem. 2003, 46, 2516-2533.
15. Cronauer, M. V.; Klocker, H.; Talasz, H.; Geisen, F. H.; Hobisch, A.; Radmayr, C.; Bock, G.; Culig, Z.; Schirmer, M.; Reissigl, A.; Bartsch, G.; Konwalinka, G. Inhibitory Effects of the Nucleoside Analogue Gemcitabine on Prostatic Carcinoma Cells. Prostate 1996, 28, 172-181.
16. See the following related publication in this issue. Jeyadevan, J. P.; Bray, P. G.; Chadwick, J.; Mercer, A. E.; Byrne, A.; Ward, S. A.; Park, B. K.; Williams, D. P.; Cosstick, R.; Davies, J.; Higson, A. P.; Irving, E.; Posner, G. H.; O'Neill, P. M. Antimalarial and Antitumor Evaluation of Novel C-10 Non-Acetal Dimers of 10β-(2-Hydroxyethyl)deoxoartemisinin. J. Med. Chem. 2004, 47, 1290-1298.