Aryl hydrocarbon receptor activation of an antitumor aminoflavone: Basis of selective toxicity for MCF-7 breast tumor cells

Molecular Cancer Therapeutics

Volumn 3, Issue 6, 2004, Pages 715-725

  Loaiza Pérez, Andrea I ^a   Kenney, Susan ^b   Boswell, Jamie ^b   Hollingshead, Melinda ^b   Alley, Michael C ^b   Hose, Curtis ^b   Ciolino, Henry P ^b   Yeh, Grace C ^b   Trepel, Jane B ^a   Vistica, David T ^b   Sausville, Edward A ^a  

^a NATIONAL CANCER INSTITUTE   (United States)

^b NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 AMINO 6,8 DIFLUORO 2 (3 FLUOROPHENYL) 7 METHYL 4H 1 BENZOPYRAN 4 ONE; AMINOFLAVONE; ANTINEOPLASTIC AGENT; AROMATIC HYDROCARBON RECEPTOR; CELL DNA; CYTOCHROME P450 1A1; ETHOXYRESORUFIN DEETHYLASE; FLAVONE DERIVATIVE; MESSENGER RNA; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; BREAST CARCINOMA; CANCER CELL; CANCER CELL CULTURE; CANCER RESISTANCE; CELL NUCLEUS; CELL STRAIN MCF 7; CHEMOSENSITIVITY; COMPLEX FORMATION; CONTROLLED STUDY; CYTOPLASM; DNA PROTEIN COMPLEX; DNA RESPONSIVE ELEMENT; DRUG BINDING SITE; DRUG CYTOTOXICITY; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG STRUCTURE; ENZYME ACTIVATION; ENZYME ACTIVITY; ENZYME INDUCTION; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; MOUSE; NONHUMAN; NUCLEAR LOCALIZATION SIGNAL; PRIORITY JOURNAL; PROTEIN EXPRESSION; SIGNAL TRANSDUCTION; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; TRANSCRIPTION INITIATION; TRANSCRIPTION REGULATION; TUMOR XENOGRAFT; XENOBIOTIC METABOLISM;

EID: 4444223703     PISSN: 15357163     EISSN: None     Source Type: Journal    
DOI: 10.1158/1535-7163.715.3.6     Document Type: Article

References (36)

1. Akama T, Shida Y, Sugaya T, Ishida H, Gomi K, Kasai M. Novel 5-aminoflavone derivatives as specific antitumor agents in breast cancer. J Med Chem 1996;39:3461-9.
2. Akama T, Ishida H, Shida Y, et al. Design and synthesis of potent antitumor 5,4′-diaminoflavone derivatives based on metabolic considerations. J Med Chem 1997;40:1894-900.
3. Akama T, Ishida H, Kimura U, Gomi K, Saito H. Structure-activity relationships of the 7-substituents of 5,4′-diamino-6,8,3′-trifluoroflavone, a potent antitumor agent. J Med Chem 1998;41:2056-67.
4. Kuffel MJ, Schroeder JC, Pobst LJ, et al. Activation of the antitumor agent aminoflavone (NSC 686288) is mediated by induction of tumor cell cytochrome P450 1A1/1A2. Mol Pharmacol 2002;62:143-53.
5. Hankinson O. The aryl hydrocarbon receptor complex. Annu Rev Pharmacol Toxicol 1995;35:307-40.
6. Schmidt JV, Bradfield CA. Ah receptor signaling pathways. Annu Rev Cell Dev Biol 1996;12:55-89.
7. Poland A, Knutson, JC. 2,3,7,8-Tetrachlorodibenzo-p-dioxin and related halogenated aromatic hydrocarbons: examination of the mechanism of toxicity. Annu Rev Pharmacol Toxicol 1982;22:517-54.
8. Fernandez-Salguero PM, Hilbert DM, Rudikoff S, Ward JM, Gonzalez FJ. Aryl-hydrocarbon receptor-deficient mice are resistant to 2,3,7,8-tetrachlorodibenzo-p-dioxin-induced toxicity. Toxicol Appl Pharmacol 1996;140:173-9.
9. Whitlock JP Jr. Induction of cytochrome P4501A1. Annu Rev Pharmacol Toxicol 1999;39:103-25.
10. Ciolino HP, Dankwah M, Yeh GC. Resistance of MCF-7 cells to dimethylbenz(a)anthracene-induced apoptosis is due to reduced CYP1A1 expression. Int J Oncol 2002;21:385-91.
11. Skehan P, Storeng R, Scudiero D, et al. New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst 1990;82:1107-12.
12. Bradford MM. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 1976;72:248-54.
13. Plowman J, Dykes DJ, Hollingshead M, Simpson-Herrer L, Alley MC. Human tumor xenografts models in NCI drug development. In: Teicher B, editor. Anticancer drug development guide: practical screening, clinical trials and approval. Totowa: Humana Press, Inc.; 1997. p. 101-25.
14. Geran RI, Greenberg NH, MacDonnald MM, Schumacher AM, Abbott BJ. Protocols for screening chemical agents and natural products against animal tumors and other biological systems. Cancer Chemother Rep 1972; 3:51.
15. Kennedy SW, Jones SP. Simultaneous measurement of cytochrome P4501A catalytic activity and total protein concentration with a fluorescence plate reader. Anal Biochem 1994;222:217-23.
16. Berghard A, Gradin K, Pongratz I, Whitelaw M, Poellinger L. Cross-coupling of signal transduction pathways: the dioxin receptor mediates induction of cytochrome P-450IA1 expression via a protein kinase C-dependent mechanism. Mol Cell Biol 1993;13:677-89.
17. Nordeen SK. Luciferase reporter gene vectors for analysis of promoters and enhancers. Biotechniques 1988;6:454-8.
18. Andrews NC, Faller DV. A rapid micropreparation technique for extraction of DNA-binding proteins from limiting numbers of mammalian cells. Nucleic Acids Res 1991;19:2499.
19. Dykes DJ, Hollingshead MG, Camalier RF, Mayo JG, Sausville EA. Marked activity of an aminoflavone (NSC 696299) against human renal tumors in athymic nude mice. Proc Am Assoc Cancer Res 1999;40:118.
20. Chen L, Waxman DJ. Cytochrome P450 gene-directed enzyme prodrug therapy (GDEPT) for cancer. Curr Pharm Des 2002;8:1405-16.
21. Yu LJ, Matias J, Scudiero DA, et al. P450 enzyme expression patterns in the NO human tumor cell line panel. Drug Metab Dispos 2001; 29:304-12.
22. Allen SW, Mueller L, Williams SN, Quattrochi LC, Raucy J. The use of a high-volume screening procedure to assess the effects of dietary flavonoids on human cyp1a1 expression. Drug Metab Dispos 2001;29: 1074-9.
23. Ma Q, Baldwin KT. 2,3,7,8-Tetrachlorodibenzo-podioxin-induced degradation of aryl hydrocarbon receptor (AhR) by the ubiquitin-protesome pathway. J Biol Chem 2000;275:8432-8.
24. Ikuta T, Eguchi H, Tachibana T, Yoneda Y, Kawajiri K. Nuclear localization and export signals of the human aryl hydrocarbon receptor. J Biol Chem 1998;273:2895-904.
25. Ikuta T, Tachibana T, Watanabe J, Yoshida M, Yoneda Y, Kawajiri K. Nucleocytoplasmic shuttling of the aryl hydrocarbon receptor. J Biochem (Tokyo) 2000;127:503-9.
26. Jyonouchi H, Sun S, Iijima K, Wang M, Hecht SS. Effects of anti-7,8-dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene on human small airway epithelial cells and the protective effects of myo-inositol. Carcinogenesis 1999;20:139-45.
27. Lei W, Yu R, Mandlekar S, Kong AN. Induction of apoptosis and activation of interleukin 1β-converting enzyme/Ced-3 protease (caspase-3) and c-Jun NH2-terminal kinase 1 by benzo(a)pyrene. Cancer Res 1998; 58:2102-6.
28. Miller ML, Andringa A, Cody T, Dixon K, Albert RE. Cell proliferation and nuclear abnormalities are increased and apoptosis is decreased in the epidermis of the p53 null mouse after topical application of benzo[a]pyrene. Cell Prolif 1996;29:561-76.
29. Liang Y, Yan C, Schor NF. Apoptosis in the absence of caspase 3. Oncogene 2001;20:6570-8.
30. Mc Gee MM, Hyland E, Campiani G, Ramunno A, Nacci V, Zisterer DM. Caspase-3 is not essential for DNA fragmentation in MCF-7 cells during apoptosis induced by the pyrrolo-1,5-benzoxazepine, PBOX-6. FEBS Lett 2002;515:66-70.
31. Loaiza-Perez AI, Trapani V, Hose C, et al. Aryl hydrocarbon receptor mediates sensitivity of MCF-7 breast cancer cells to antitumor agent 2-(4-amino-3-methylphenyl) benzothiazole. Mol Pharmacol 2002;61:13-9.
32. Donohue SJ, Brown AP, Prezioso JA, et al. Toxicity findings and pharmacokinetics of benzothiazone (NSC 674498) and the lysyl prodrug 5-F-benzothiazole (NSC 710305) in Beagle dogs. Proc Am Assoc Cancer Res 2001;42:933.
33. Brown AP, Morrissey RL, Rodvold KA, et al. Intravenous plasma elimination kinetics and toxicity of an aminoflavone in the dog. Proc Am Assoc Cancer Res 1999;40:390.
34. Gradin K, McGuire J, Wenger RH, et al. Functional interference between hypoxia and dioxin signal transduction pathways: competition for recruitment of the Arnt transcription factor. Mol Cell Biol 1996;16: 5221-31.
35. Tian Y, Ke S, Denison MS, Rabson AB, Gallo MA. Ah receptor and NF-κB interactions, a potential mechanism for dioxin toxicity. J Biol Chem 1999;274:510-5.
36. Wilson CL, Thomsen J, Hoivik DJ, et al. Aryl hydrocarbon (Ah) nonresponsiveness in estrogen receptor-negative MDA-MB-231 cells is associated with expression of a variant arnt protein. Arch Biochem Biophys 1997;346:65-73.