Mixed steroidal tetraoxanes induce apoptotic cell death in tumor cells

Investigational New Drugs

Volumn 27, Issue 5, 2009, Pages 432-439

  Žižak, Željko ^a   Juranić, Zorica ^a   Opsenica, Dejan ^b   Šolaja, Bogdan A ^c  

^a INSTITUTE FOR ONCOLOGY AND RADIOLOGY OF SERBIA   (Serbia)

^b UNIVERSITY OF BELGRADE   (Serbia)

^c UNIVERSITY OF BELGRADE   (Serbia)

Author keywords

Anticancer agents; Apoptosis; Cytotoxicity; Tetraoxanes

Indexed keywords

PHYTOHEMAGGLUTININ; TETRAOXANE DERIVATIVE;

APOPTOSIS; ARTICLE; CELL CYCLE ARREST; CELL CYCLE G1 PHASE; CELL DEATH; CELL GROWTH; CELL PROLIFERATION; CELL STRUCTURE; CELL SURVIVAL; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY; DNA FRAGMENTATION; GROWTH INHIBITION; HELA CELL; HUMAN; HUMAN CELL; IC 50; PERIPHERAL BLOOD MONONUCLEAR CELL; PRIORITY JOURNAL; TUMOR CELL LINE;

APOPTOSIS; CELL PROLIFERATION; DNA FRAGMENTATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; FLOW CYTOMETRY; G1 PHASE; HELA CELLS; HUMANS; LEUKOCYTES, MONONUCLEAR; MOLECULAR STRUCTURE; NEOPLASMS; STEROIDS; TETRAOXANES;

EID: 70349248154     PISSN: 01676997     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10637-008-9197-1     Document Type: Article

References (26)

1. JL Vennerstrom HN Fu WY Ellis AL Ager Jr JK Wood SL Andersen L Gerena WK Milhous 1992 Dispiro-1,2,4,5-tetraoxanes: a new class of antimalarial peroxides J Med Chem 35 3023 3027 1501229 10.1021/jm00094a015 1:CAS:528:DyaK38XkvFSht74%3D
2. NM Todorovic M Stefanovic B Tinant JP Declercq MT Makler BA Solaja 1996 Steroidal geminal dihydroperoxides and 1,2,4,5-tetraoxanes: structure determination and their antimalarial activity Steroids 61 688 696 8987137 10.1016/S0039-128X(96)00203-6 1:CAS:528:DyaK2sXlsVOj (Pubitemid 27031003)
3. Y Dong H Matile J Chollet R Kaminsky JK Wood JL Vennerstrom 1999 Synthesis and antimalarial activity of 11 dispiro-1,2,4,5-tetraoxane analogues of WR 148999. 7,8,15,16-Tetraoxadispiro[5.2.5.2]hexadecanes substituted at the 1 and 10 positions with unsaturated and polar functional groups J Med Chem 42 1477 1480 10212135 10.1021/jm980698f 1:CAS:528:DyaK1MXhvFOmsLg%3D (Pubitemid 29200885)
4. JL Vennerstrom Y Dong SL Andersen AL Ager Jr H Fu RE Miller DL Wesche DE Kyle L Gerena SM Walters JK Wood G Edwards AD Holme WG McLean WK Milhous 2000 Synthesis and antimalarial activity of sixteen dispiro-1,2,4, 5-tetraoxanes: alkyl-substituted 7,8,15,16-tetraoxadispiro[5.2.5. 2]hexadecanes J Med Chem 43 2753 2758 10893313 10.1021/jm0000766 1:CAS:528:DC%2BD3cXkslSkt7o%3D (Pubitemid 30463924)
5. JL Vennerstrom AL Ager Jr SL Andersen JM Grace V Wongpanich CK Angerhofer JK Hu DL Wesche 2000 Assessment of the antimalarial potential of tetraoxane WR 148999 Am J Trop Med Hyg 62 573 578 11289666 1:STN:280:DC%2BD3M7pvFejtA%3D%3D
6. D Opsenica G Pocsfalvi Z Juranic B Tinant JP Declercq DE Kyle WK Milhous BA Solaja 2000 Cholic acid derivatives as 1,2,4,5-tetraoxane carriers: structure and antimalarial and antiproliferative activity J Med Chem 43 3274 3282 10966746 10.1021/jm000952f 1:CAS:528:DC%2BD3cXlsVejtbo%3D (Pubitemid 30681546)
7. AK Bhattacharjee KA Carvalho D Opsenica BA Solaja 2005 Structure-activity relationship study of steroidal 1,2,4,5-tetraoxane animalarials using computational procedures J Serb Chem Soc 70 329 345 10.2298/JSC0503329B 1:CAS:528:DC%2BD2MXkt1Cgu78%3D (Pubitemid 43166580)
8. Doorenbos HE, Decker DL (1973) Antimalarial Synthesis, Annual Technical Report No. Am-1A-73. The Dow Chemical Company
9. I Opsenica N Terzic D Opsenica G Angelovski M Lehnig P Eilbracht B Tinant Z Juranic KS Smith YS Yang DS Diaz PL Smith WK Milhous D Dokovic BA Solaja 2006 Tetraoxane antimalarials and their reaction with Fe(II) J Med Chem 49 3790 3799 16789736 10.1021/jm050966r 1:CAS:528:DC%2BD28XlvFentro%3D (Pubitemid 43970709)
10. R Amewu AV Stachulski SA Ward NG Berry PG Bray J Davies G Labat L Vivas PM O'Neill 2006 Design and synthesis of orally active dispiro 1,2,4,5-tetraoxanes; synthetic antimalarials with superior activity to artemisinin Org Biomol Chem 4 4431 4436 17268634 10.1039/b613565j 1:CAS:528:DC%2BD28Xht1OhsbbF (Pubitemid 44847966)
11. HJ Woerdenbag TA Moskal N Pras TM Malingré FS el-Feraly HH Kampinga AW Konings 1993 Cytotoxicity of artemisinin-related endoperoxides to Ehrlich ascites tumor cells J Nat Prod 56 849 856 8350087 10.1021/np50096a007 1:CAS:528:DyaK3sXlslemur4%3D
12. T Efferth G Rücker M Falkenberg D Manns A Olbrich U Fabry R Osieka 1996 Detection of apoptosis in KG-1a leukemic cells treated with investigational drugs Arzneimittelforschung 46 196 200 8720313 1:CAS:528:DyaK28XhvFOqtrw%3D
13. D Opsenica G Angelovski G Pocsfalvi Z Juranic Z Zizak D Kyle WK Milhous BA Solaja 2003 Antimalarial and antiproliferative evaluation of bis-steroidal tetraoxanes Bioorg Med Chem 11 2761 2768 12788350 10.1016/S0968-0896(03)00224-4 1:CAS:528:DC%2BD3sXkt1Okt7s%3D (Pubitemid 36683000)
14. BA Solaja N Terzic G Pocsfalvi L Gerena B Tinant D Opsenica WK Milhous 2002 Mixed steroidal 1,2,4,5-tetraoxanes: antimalarial and antimycobacterial activity J Med Chem 45 3331 3336 12139444 10.1021/jm020891g 1:CAS:528: DC%2BD38XkvVygtbk%3D (Pubitemid 34824022)
15. N Terzic D Opsenica D Milic B Tinant KS Smith WK Milhous BA Solaja 2007 Deoxycholic acid-derived tetraoxane antimalarials and antiproliferatives(1) J Med Chem 50 5118 5127 17887664 10.1021/jm070684m 1:CAS:528:DC%2BD2sXhtVGqt7jJ (Pubitemid 47585709)
16. T Mosmann 1983 Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays J Immunol Methods 65 55 63 6606682 10.1016/0022-1759(83)90303-4 1:STN:280:DyaL2c%2FovFSmtw%3D%3D
17. M Ohno T Abe 1991 Rapid colorimetric assay for the quantification of leukemia inhibitory factor (LIF) and interleukin-6 (IL-6) J Immunol Methods 145 199 203 1765652 10.1016/0022-1759(91)90327-C 1:CAS:528:DyaK38XotFKhtQ%3D%3D
18. SJ Martin SV Lennon AM Bonham TG Cotter 1990 Induction of apoptosis (programmed cell death) in human leukemic HL-60 cells by inhibition of RNA or protein synthesis J Immunol 145 1859 1867 2167911 1:CAS:528:DyaK3cXmtV2rsbk%3D
19. M Carbonari T Tedesco M Fiorilli 2001 A unified procedure for conservative (morphology) and integral (DNA and immunophenotype) cell staining for flow cytometry Cytometry 44 120 125 11378862 10.1002/1097-0320(20010601)44: 2<120::AID-CYTO1090>3.0.CO;2-7 1:STN:280:DC%2BD3M3pslensg%3D%3D (Pubitemid 32525396)
20. AH Wyllie 1980 Glucocorticoid-induced thymocyte apoptosis is associated with endogenous endonuclease activation Nature 284 555 556 6245367 10.1038/284555a0 1:CAS:528:DyaL3cXktlOrur4%3D
21. PM O'Neill GH Posner 2004 A medicinal chemistry perspective on artemisinin and related endoperoxides J Med Chem 47 2945 2964 15163175 10.1021/jm030571c (Pubitemid 38702690)
22. U Eckstein-Ludwig RJ Webb ID Van Goethem JM East AG Lee M Kimura PM O'Neill PG Bray SA Ward S Krishna 2003 Artemisinins target the SERCA of Plasmodium falciparum Nature 424 957 961 12931192 10.1038/nature01813 1:CAS:528:DC%2BD3sXmsV2isL4%3D (Pubitemid 37051688)
23. PA Berman PA Adams 1997 Artemisinin enhances heme-catalysed oxidation of lipid membranes Free Radic Biol Med 22 1283 1288 9098103 10.1016/S0891-5849(96) 00508-4 1:CAS:528:DyaK2sXisFyns7s%3D (Pubitemid 27171971)
24. N Shterman B Kupfer C Moroz 1991 Comparison of transferrin receptors, iron content and isoferritin profile in normal and malignant human breast cell lines Pathobiology 59 19 25 2043266 10.1159/000163611 1:CAS:528: DyaK3MXlsFKisr8%3D
25. D Hanahan RA Weinberg 2000 The hallmarks of cancer Cell 100 57 70 10647931 10.1016/S0092-8674(00)81683-9 1:CAS:528:DC%2BD3cXks1CktA%3D%3D
26. JA Collins CA Schandi KK Young J Vesely MC Willingham 1997 Major DNA fragmentation is a late event in apoptosis J Histochem Cytochem 45 923 934 9212818 1:CAS:528:DyaK2sXkt1Cjtb8%3D