Diazenecarboxamide UP-91, a potential anticancer agent, acts by reducing cellular glutathione content

Pharmacology and Toxicology

Volumn 91, Issue 5, 2002, Pages 258-263

  Moskatelo, Dubravka ^a   Polanc, Slovenko ^b   Košmrlj, Janez ^b   Vuković, Lidija ^a   Osmak, Maja ^a  

^a RUDER BO KOVI INSTITUTE   (Croatia)

^b UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; CISPLATIN; GLUTATHIONE; JK 1013; JK 914; JK 918; THIOPHENOL; UNCLASSIFIED DRUG; UP 91; VINCRISTINE; IMIDE; PYRIDINE DERIVATIVE; UP-91;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CELL SURVIVAL; CHROMATOGRAPHY; COLORIMETRY; CONTROLLED STUDY; CYTOTOXICITY; DRUG STRUCTURE; HUMAN; HUMAN CELL; PRIORITY JOURNAL; SPECTROPHOTOMETRY; STRUCTURE ANALYSIS; CELL CULTURE; DOSE RESPONSE; DRUG RESISTANCE; HELA CELL; METABOLISM;

ANTINEOPLASTIC AGENTS; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG RESISTANCE, NEOPLASM; GLUTATHIONE; HELA CELLS; HUMANS; IMIDES; PYRIDINES; TUMOR CELLS, CULTURED;

EID: 1842855165     PISSN: 09019928     EISSN: None     Source Type: Journal    
DOI: 10.1034/j.1600-0773.2002.910507.x     Document Type: Article

References (32)

1. Akiyama, S. I., Z. S. Chen, T. Sumizawa & T. Furukawa: Resistance to cisplatin. Anti-Cancer Drug Design 1999, 14, 143-151.
2. Beketić-Orešković, L. & M. Osmak: Human larynx carcinoma cells resistant to cisdiamminedichloroplatinum(II) Cross-resistance pattern. Neoplasma 1994, 41, 171-176.
3. Boulton, A. J. & A. McKillop: Reactivity of six-membered rings. In: Comprehensive Heterocyclic Chemistry. Eds.: A. R. Katritzky & C. W. Rees. Pergamon Press, Oxford, 1984,Vol. 2, pp. 29-65.
4. Burdon, R. H., V. Gill & D. Alliangana: Hydrogen peroxide in relation to proliferation and apoptosis in BHK-21 hamster fibroblasts. Free Radical Res. 1996, 24, 81-83.
5. Ghibelli, L., S. Coppola, G. Rotilio, E. Lafavia, V. Maresca & M. R. Ciriolo: Non-oxidative loss of glutathione in apoptosis via GSH extrusion. Biochem. Biophys. Res. Commun. 1995, 216, 313-320.
6. Hamilton, T. C., M. A. Winker, K. G. Loui, G. Batist, B. Behrens, T. Tsuruo, K. R. Grotzinger, W. M. McKoy, R. C. Young & R. F. Ozols: Augmentation of adriamycin, melphalan, and cisplatin cytotoxicity in drug-resistant and sensitive human ovarian carcinoma cell lines by buthionine sulfoximine mediated glutathione depletion. Biochem. Pharmacol. 1985, 34, 2583-2586.
7. Hessing, A. & R. Müller-Matthesius: Die Disproportionierung von Arylsemicarbaziden. Chemische Berichte 1971, 104, 3463-3474.
8. Kearns, P. R. & A. G. Hall: Glutathione and the response of malignant cells to chemotherapy. DDT 1998, 3, 113-121.
9. Knapen, M. F. C. M., P. L. M. Zusterzeel, W. H. M. Peters & E. A. P. Stegeers: Glutathione and glutathione related enzymes in reproduction: A review. Eur. J. Obstet. Gynecol. Reprod. Biol. 1999, 82, 171-184.
10. Košmrlj, J., M. Kočevar & S. Polanc: A mild approach to ,3,4-oxidiazoles and fused 1,2,4-traizoles. Diazenes as intermediates? Synlett 1996, 652-654.
11. Košmrlj, J., M. Kočevar M & S. Polanc: Controlled oxidation of thiols to disulfides by diazenecarboxamides. J. Chem. Soc. Perkin Transaction 1 1998, 3917-3919.
12. König, J., A. T. Nies, Y. Chi, I. Leier & D. Keppler: Conjugate export pumps of the multidrug resistance protein (MRP) family: Localization, substrate specifity, and MRP2-mediated drug resistance. Biochim. Biophys. Acta 1999, 1461, 377394.
13. Lai, G. M., R. F. Ozols, R. C. Young & T. C. Hamilton: Effect of glutathione on DNA repair in cisplatin-resistant human ovarian cancer cell lines. J. Nat. Cancer Inst. 1989, 81, 535-539.
14. Meister, A.: Glutathione, ascorbate, and cellular protection. Cancer Res. 1994, 54, 1969s-1975s.
15. Mickisch, G., S. Fajta, G. Keilhauer, E. Schlike, P. Tschada & P. Alken: Chemosensitivity testing of primary human renal cell carcinoma by tetrazolium based microculture assay (MTT). Urol. Res. 1990, 18, 131-136.
16. Nielsen, D., C. Maare & T. Skovsgaard T: Cellular resistance to anthracyclines. Gen. Pharmacol. 1996, 27, 251-255.
17. Osmak, M.: Molecular alterations induced in drug-resistant cells. Radiol. Oncol. 1998, 32, 19-33.
18. Osmak, M. & D. Eljuga: The response of two vincristine resistant larynx carcinoma cell clones to chemotherapeutic drugs. Radiol. Oncol. 1992, 26, 140-144.
19. Osmak, M. & D. Eljuga: The characterization of two human cervical carcinoma HeLa sublines resistant to cisplatin. Res. Exp. Med. 1993, 193, 389-396.
20. Osmak, M., L. Beketić-Orešković, M. Matulić & J. Sorić: Resistance of human larynx carcinoma cells to cisplatin, gamma irradiation and methotrexate do not involve overexpression of c-myc or c-Ki-ras oncogenes. Murat. Res. 1993, 303, 113-120.
21. Osmak, M., T. Bordukalo, B. Jernej, J. Košmrlj & S. Polanc S: Diazene JK-279: Potential anticancer drug. Anti-Cancer Drugs 1999a, 10, 853-859
22. Osmak, M., T. Bordukalo, J. Košmrlj, M. Kvajo, Z. Marijanović, D. Eljuga & S. Polanc: Diazenes: Modificators of tumor cell resistance to cisplatin. Neoplasma 1999b, 46, 201-206.
23. Osmak, M., I. Vrhovec & J. Škrk: Cisplatin resistant glioblastoma cells may have increased concentration of urokinase plasminogen activator and plasminogen activator inhibitor type 1. J. Neuro-Oncol. 1999c, 42, 95-102.
24. Osmak, M., T. Bordukalo, A. Ambriović Ristov, B. Jernej, J. Košmrlj & S. Polanc: Diazense as modificators of drug-resistance in tumor cells. Neoplasma 2000, 476, 390-395.
25. Sandstrom, P. A., M. D. Mannie & T. M. Buttke: Inhibition of activation-induced death in T cell hybridomas by thiol antioxidants: Oxidative stress as a modulator of apoptosis. J. Leukocyte Biol. 1994, 55, 221-226.
26. Schmitt, C. A. & S. W. Lowe: Apoptosis and therapy. J. Pathol. 1999, 187, 127-137.
27. Slater, A. F. G., C. Stefan, I. Nobel, D. J. Van den Dobbelsteen & S. Orrenius: Signaling mechanisms and oxidative stress in apoptosis. Toxicol. Lett. 1995, 82, 149-153.
28. Tietze, F.: Enzymatic method for quantitative determination of nanogram amounts of total and oxidized glutathione: Applications to mammalian blood and other tissues. Analyt. Biochem. 1969, 27, 502-522.
29. Versantvoort, C. H. M., H. J. Broxterman, T. Bagrij, R. J. Scheper RJ & P. R. Twentyman: Regulation by glutathione of drug transport in multidrug resistant human lung tumour cell lines over-expressing MRP. Brit. J. Cancer 1995, 72, 82-89.
30. Voehringer, D. W. & R. E Meyn: Reversing drug resistance in bcl-2 expressing tumor cells by depleting glutathione. Drug Resistance Update 1998, 1, 345-351.
31. While, A. C., V. J. Thannickal & B. L. Fanburg: Glutathione deficiency in human disease. J. Nutrit. Biochem. 1994, 5, 218-226.
32. Zhang, K., P. Mack & K. P. Wong: Glutathione-related mechanisms in cellular resistance to anticancer drugs (review). Int. J. Oncol. 1998, 12, 871-882