N-acetylcysteine prevents the geldanamycin cytotoxicity by forming geldanamycin-N-acetylcysteine adduct

Chemico-Biological Interactions

Volumn 220, Issue , 2014, Pages 248-254

  Mlejnek, Petr ^a   Dolezel, Petr ^a  

^a PALACKÝ UNIVERSITY   (Czech Republic)

Author keywords

Cell death; Geldanamycin glutathione adduct; Geldanamycin N acetylcysteine adduct; Glutathione depletion; K562 cells

Indexed keywords

ACETYLCYSTEINE; CHEMICAL COMPOUND; GELDANAMYCIN; GELDANAMYCIN ADDUCT; GELDANAMYCIN GLUTATHIONE ADDUCT; GELDANAMYCIN N ACETYLCYSTEINE ADDUCT; GLUTATHIONE; HEAT SHOCK PROTEIN 90; UNCLASSIFIED DRUG; ANTINEOPLASTIC ANTIBIOTIC; BENZOQUINONE DERIVATIVE; MACROCYCLIC LACTAM;

APOPTOSIS; ARTICLE; CELL CYCLE PROGRESSION; CELL LEVEL; CELL PROLIFERATION; CELL PROTECTION; CELL STRUCTURE; CELL VIABILITY; CONCENTRATION (PARAMETERS); CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG EFFECT; HUMAN; HUMAN CELL; INCUBATION TIME; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PROTEIN DEPLETION; ANALOGS AND DERIVATIVES; CELL CYCLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; K562 CELL LINE; METABOLISM;

ACETYLCYSTEINE; ANTIBIOTICS, ANTINEOPLASTIC; APOPTOSIS; BENZOQUINONES; CELL CYCLE; GLUTATHIONE; HUMANS; K562 CELLS; LACTAMS, MACROCYCLIC; MOLECULAR STRUCTURE;

EID: 84907312991     PISSN: 00092797     EISSN: 18727786     Source Type: Journal    
DOI: 10.1016/j.cbi.2014.06.025     Document Type: Article

References (28)

1. C. DeBoer, P.A. Meulman, R.J. Wnuk, and D.H. Peterson Geldanamycin a new antibiotic J. Antibiot. 23 1970 442 447
2. Y. Uehara, M. Hori, T. Takeuchi, and H. Umezawa Phenotypic change from transformed to normal induced by benzoquinonoid ansamycins accompanies inactivation of p60src in rat kidney cells infected with Rous sarcoma virus Mol. Cell. Biol. 6 1986 2198 2206 (Pubitemid 17189579)
3. L. Whitesell, and P. Cook Stable and specific binding of heat shock protein 90 by geldanamycin disrupts glucocorticoid receptor function in intact cells Mol. Endocrinol. 10 1996 705 712 (Pubitemid 26176278)
4. H.S. Chen, S.S. Singh, and G.H. Perdew The Ah receptor is a sensitive target of geldanamycin-induced protein turnover Arch. Biochem. Biophys. 348 1997 190 198 (Pubitemid 27514687)
5. W.G. An, T.W. Schulte, and L.M. Neckers The heat shock protein 90 antagonist geldanamycin alters chaperone association with p210 bcr-abl and v-src proteins before their degradation by the proteasome Cell Growth Differ. 11 2000 355 360 (Pubitemid 30619563)
6. M. Sakagami, P. Morrison, and W.J. Welch Benzoquinoid ansamycins (herbimycin A and geldanamycin) interfere with the maturation of growth factor receptor tyrosine kinases Cell Stress Chaperones 4 1999 19 28 (Pubitemid 29178590)
7. H.J. Ochel, T.W. Schulte, P. Nguyen, J. Trepel, and L. Neckers The benzoquinone ansamycin geldanamycin stimulates proteolytic degradation of focal adhesion kinase Mol. Genet. Metab. 66 1999 24 30 (Pubitemid 29389926)
8. S.E. Holt, D.L. Aisner, J. Baur, V.M. Tesmer, M. Dy, M. Ouellette, J.B. Trager, G.B. Morin, D.O. Toft, J.W. Shay, W.E. Wright, and M.A. White Functional requirement of p23 and Hsp90 in telomerase complexes Genes Dev. 13 1999 817 826 (Pubitemid 29169841)
9. E. Minet, D. Mottem, G. Michel, I. Roland, M. Raes, J. Remacle, and C. Michiels Hypoxia-induced activation of HIF-1: role of HIF-1alpha-Hsp90 interaction FEBS Lett. 460 1999 251 256 (Pubitemid 29495950)
10. L. Neckers, and P. Workman Hsp90 molecular chaperone inhibitors: are we there yet? Clin. Cancer Res. 18 2012 64 76
11. D.S. Hong, U. Banerji, B. Tavana, G.C. George, J. Aaron, and R. Kurzrock Targeting the molecular chaperone heat shock protein 90 (HSP90): lessons learned and future directions Cancer Treat. Rev. 39 2013 375 387
12. N.M. Benchekroun, C.E. Myers, and B.K. Sinha Free radical formation by ansamycin benzoquinone in human breast tumor cells: implications for cytotoxicity and resistance Free Radic. Biol. Med. 17 1994 191 200 (Pubitemid 24269671)
13. C.B. Clark, M.J. Rane, D. El Mehdi, C.J. Miller, L.R. Sachleben Jr., and E. Gozal Role of oxidative stress in geldanamycin-induced cytotoxicity and disruption of Hsp90 signaling complex Free Radic. Biol. Med. 47 2009 1440 1449
14. Y. Samuni, H. Ishii, F. Hyodo, U. Samuni, M.C. Krishna, S. Goldstein, and J.B. Mitchel Reactive oxygen species mediate hepatotoxicity induced by the Hsp90 inhibitor geldanamycin and its analogs Free Radic. Biol. Med. 48 2010 1559 1563
15. A.K. McCollum, C.J. TenEyck, B.M. Sauer, D.O. Toft, and Ch. Ehrlichman Glutathione-mediated mechanism to 17-allylamino-demethoxygeldanamycin through a up-regulation of heat shock protein 27 induces resistance Cancer Res. 66 2006 10967 10975 (Pubitemid 44876996)
16. N.R. Bachur, S.L. Gordon, and M.V. Gee A general mechanism for microsomal activation of quinone anticancer agents to free radicals Cancer Res. 38 1978 1745 1750 (Pubitemid 8349723)
17. S. Dilakov, U. Landmesser, and D.G. Harrison Geldanamycin leads to superoxide formation by enzymatic and non-enzymatic redox cycling. Implications for studies of Hsp90 and endothelial cell nitric-oxide synthase J. Biol. Chem. 277 2002 25480 25485 (Pubitemid 34951862)
18. P. Mlejnek, and P. Dolezel Induction of apoptosis by A3 adenosine receptor agonist N6-(3-iodobenzyl)-adenosine-5′-N-methylcarboxamide in human leukemia cells: a possible involvement of intracellular mechanism Acta Physiol. 199 2010 171 179
19. I. Nicoleti, G. Migliorati, M.C. Pagliacci, F. Grignani, and C. Riccardi A rapid and simple method for measuring thymocyte apoptosis by propidium iodide staining and flow cytometry J. Immunol. Methods 139 2 1991 271 279
20. Z. Darzynkiewicz, S. Bruno, G. Del Bino, W. Gorczyca, M.A. Hotz, P. Lassota, and F. Traganos Features of apoptotic cells measured by flow cytometry Cytometry 13 1992 795 808
21. C.P. LeBel, H. Ischiropoulos, and S.C. Bondy Evaluation of the probe 2′,7′-dichlorofluorescein as an indicator of reactive oxygen species formation and oxidative stress Chem. Res. Toxicol. 5 1992 227 231
22. P. Mlejnek, and P. Kuglík Induction of apoptosis in HL-60 cells by N6-Benzyladenosine J. Cell. Biochem. 77 2000 6 17 (Pubitemid 30126890)
23. I. Frydrych, and P. Mlejnek Serine protease inhibitors N-α-tosyl-l-lysinyl-chloromethylketone (TLCK) and N-tosyl-l- phenylalaninyl-chloromethylketone (TPCK) are potent inhibitors of activated caspase proteases J. Cell. Biochem. 103 2008 1646 1656 (Pubitemid 351490729)
24. P. Mlejnek, O. Novak, and P. Dolezel A non-radioactive assay for precise determination of intracellular levels of imatinib and its main metabolite in Bcr-Abl positive cells Talanta 83 2011 1466 1471
25. T.W. Schulte, M.V. Blagosklonny, C. Ingui, and L. Neckers Disruption of the Raf-1-Hsp90 molecular complex results in destabilization of Raf-1 and loss of Raf-1-Ras association J. Biol. Chem. 270 1995 24585 24588
26. W.G. An, R.C. Schnur, L. Neckers, and M.V. Blagosklonny Depletion of p185erbB2, Raf-1 and mutant p53 proteins by geldanamycin derivatives correlates with antiproliferative activity Cancer Chemother. Pharmacol. 40 1997 60 64 (Pubitemid 27160962)
27. R.L. Cysyk, R.J. Parker, J.J. Barchi Jr., P.S. Steeg, N.R. Hartman, and J.M. Strong Reaction of geldanamycin and C17-substituted analogues with glutathione: product identifications and pharmacological implications Chem. Res. Toxicol. 19 2006 376 381
28. A. Samuni, and S. Goldstein Redox properties and thiol reactivity of geldanamycin and its analogues in aqueous solutions J. Phys. Chem. B 116 2012 6404 6410