Role of zinc and iron chelation in apoptosis mediated by tachpyridine, an anti-cancer iron chelator

Biochemical Pharmacology

Volumn 67, Issue 9, 2004, Pages 1677-1688

  Zhao, Rong ^a,b   Planalp, Roy P ^c   Ma, Rong ^a,b   Greene, Bryan T ^a,b   Jones, Bradley T ^d   Brechbiel, Martin W ^e   Torti, Frank M ^a,b   Torti, Suzy V ^a,b  

^a WAKE FOREST SCHOOL OF MEDICINE   (United States)

^b WAKE FOREST UNIVERSITY HEALTH SCIENCES   (United States)

^c Univ of New Hampshire   (United States)

^d WAKE FOREST UNIVERSITY   (United States)

^e NATIONAL INSTITUTES OF HEALTH   (United States)

Author keywords

Apoptosis; Caspase; Chelator; Chemotherapeutic agent; Internal standard; Iron; IS; PBS; Phosphate buffered saline; Solid phase extraction; SPE; Zinc

Indexed keywords

ANTINEOPLASTIC AGENT; CASPASE 3; CASPASE 9; IRON; IRON CHELATING AGENT; METAL COMPLEX; N,N',N'' TRIS(2 PYRIDYLMETHYL) 1,3,5 TRIAMINOCYCLOHEXANE; UNCLASSIFIED DRUG; ZINC;

ARTICLE; CELL PROTECTION; CHEMICAL REACTION KINETICS; CONTROLLED STUDY; CULTURE MEDIUM; CYTOTOXICITY; DRUG ACTIVITY; DRUG TARGETING; ENZYME ACTIVATION; FEMALE; HUMAN; HUMAN CELL; IRON CHELATION; OXIDATION KINETICS; PRIORITY JOURNAL; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

APOPTOSIS; CASPASES; CYCLOHEXYLAMINES; ENZYME ACTIVATION; EXTRACELLULAR SPACE; HELA CELLS; HUMANS; INTRACELLULAR SPACE; IRON; IRON CHELATING AGENTS; KINETICS; PYRIDINES; TUMOR CELLS, CULTURED; ZINC;

EID: 1842785914     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bcp.2003.12.036     Document Type: Article

References (45)

1. Le N., Richardson D. The role of iron in cell cycle progression and the proliferation of neoplastic cells. Biochim. Biophys. Acta. 1603:2002;31-46.
2. Buss J.L., Torti F.M., Torti S.V. The role of iron chelation in cancer therapy. Curr. Med. Chem. 10:2003;1021-1034.
3. Estrov Z., Tawa A., Wang X.H., Dube I.D., Sulh H., Cohen A.et al. In vitro and in vivo effects of deferoxamine in neonatal acute leukemia. Blood. 69:1987;757-761.
4. Dezza L., Cazzola M., Danova M., Carlo-Stella C., Bergamaschi G., Brugnatelli S.et al. Effects of desferrioxamine on normal and leukemic human hematopoietic cell growth: in vitro and in vivo studies. Leukemia. 3:1989;104-107.
5. Donfrancesco A., Deb G., Dominici C., Pileggi D., Castello M.A., Helson L. Effects of a single course of deferoxamine in neuroblastoma patients. Cancer Res. 50:1990;4929-4930.
6. Frantz C.N., Bernstein M., Castleberry R., Vietti T. Proc. Am. Soc. Clin. Oncol. 13:1994;416.
7. Blatt J. Deferoxamine in children with recurrent neuroblastoma. Anticancer Res. 14:1994;2109-2112.
8. Donfrancesco A., De Bernardi B., Carli M., Mancini A., Nigro M., De Sio L.et al. Deferoxamine followed by cyclophosphamide, etoposide, carboplatin, thiotepa, induction regimen in advanced neuroblastoma: preliminary results. Italian Neuroblastoma Cooperative Group. Eur. J. Cancer. 31:1995;612-615.
9. Donfrancesco A., Deb G., Angioni A., Maurizio C., Cozza R., Jenkner A.et al. D-CECaT: a breakthrough for patients with neuroblastoma. Anticancer Drugs. 4:1993;317-321.
10. Park G, Przyborowska A, Ye N, Tsoupas N, Bauer C, Broker G, et al. Steric effects caused by N-alkylation of the tripodal chelator N,N′,N″- tris(2-pyridylmethyl)-cis,cis-1,3,5-triaminocyclohexane (tachpyr): structural and electronic properties of the Mn(II), Co(II), Ni(II), Cu(II) and Zn(II) complexes. J Chem Soc, Dalton Trans 2003;318.
11. Planalp RP, Lai S, Lu G, Przyborowska AM, Park G, Rogers RD, et al. Biometals 2002: 3rd International Biometals Symposium, London, UK, April 2002, p. E4.
12. Park G., Lu F., Ye N., Brechbiel M., Torti S., Torti F.et al. Novel iron complexes and chelators based on cis,cis-1,3,5-triaminocyclohexane: iron-mediated ligand oxidation and biochemical properties. J. Biol. Inorg. Chem. 3:1998;449-457.
13. Torti S.V., Torti F.M., Whitman S.P., Brechbiel M.W., Park G., Planalp R.P. Tumor cell cytotoxicity of a novel metal chelator. Blood. 92:1998;1384-1389.
14. Greene B.T., Thorburn J., Willingham M.C., Thorburn A., Planalp R.P., Brechbiel M.W.et al. Activation of caspase pathways during iron chelator-mediated apoptosis. J. Biol. Chem. 277:2002;25568-25575.
15. Abeysinghe R.D., Greene B.T., Haynes R., Willingham M.C., Turner J., Planalp R.P.et al. p53-independent apoptosis mediated by tachpyridine, an anti-cancer iron chelator. Carcinogenesis. 22:2001;1607-1614.
16. Bowen T., Planalp R.P., Brechbiel M.W. An improved synthesis of cis,cis-1,3,5-triaminocyclohexane. Synthesis of novel hexadentate ligand derivatives for the preparation of gallium radiopharmaceuticals. Bioorg. Med. Chem. Lett. 6:1996;807.
17. Planalp R.P., Przyborowska A.M., Park G., Ye N., Lu F.H., Rogers R.D.et al. Novel cytotoxic chelators that bind iron(II) selectively over zinc(II) under aqueous aerobic conditions. Biochem. Soc. Trans. 30:2002;758-762.
18. Boyd G., Smyth J.F., Jodrell D.I., Cummings J. High-performance liquid chromatographic technique for the simultaneous determination of lactone and hydroxy acid forms of camptothecin and SN-38 in tissue culture media and cancer cells. Anal. Biochem. 297:2001;15-24.
19. Berquin I.M., Dziubinski M.L., Nolan G.P., Ethier S.P. A functional screen for genes inducing epidermal growth factor autonomy of human mammary epithelial cells confirms the role of amphiregulin. Oncogene. 20:2001;4019-4028.
20. Cheng Y.F., Neue U.D., Bean L. Straightforward solid-phase extraction method for the determination of verapamil and its metabolite in plasma in a 96-well extraction plate. J. Chromatogr. A. 828:1998;273-281.
21. Cheng Y.F., Neue U.D., Woods L.L. Novel high-performance liquid chromatographic and solid-phase extraction methods for quantitating methadone and its metabolite in spiked human urine. J. Chromatogr. B: Biomed. Sci. Appl. 729:1999;19-31.
22. Rouan M.C., Marfil F., Mangoni P., Séchaud R., Humbert H., Maurer G. Determination of a new oral iron chelator, ICL670, and its iron complex in plasma by high-performance liquid chromatography and ultraviolet detection. J. Chromatogr. B. 755:2001;203-213.
23. Technical reports. Comparison guide to C18 reversed phase HPLC columns. MAC-MOD Analytical, Inc.
24. Sarzanini C. High-performance liquid chromatography: trace metal determination and speciation. Adv. Chromatogr. 41:2001;249-310.
25. Tomlinson E., Jefferies T.M., Riley C.M. Ion-pair high-performance liquid chromatography. J. Chromatogr. 159:1978;315-358.
26. Hart S.J., Tontodonati R., Calder I.C. Reversed-phase chromatography of urinary metabolites of paracetamol using ion suppression and ion pairing. J. Chromatogr. 225:1981;387-405.
27. Liang H., Kays M.B., Sowinski K.M. Separation of levofloxacin, ciprofloxacin, gatifloxacin, moxifloxacin, trovafloxacin and cinoxacin by high-performance liquid chromatography: application to levofloxacin determination in human plasma. J. Chromatogr. B. 772:2002;53-63.
28. Cory A.H., Owen T.C., Barltrop J.A., Cory J.G. Use of an aqueous soluble tetrazolium/formazan assay for cell growth assays in culture. Cancer Commun. 3:1991;207-212.
29. Epemolu R., Ackerman R., Porter J., Hider R., Damani L., Singh S. HPLC determination of 1,2-diethyl-3-hydroxypyridin-4-one (CP94), its iron complex [Fe(III) (CP94)3] and glucuronide conjugate [CP94-GLUC] in serum and urine of thalassaemic patients. J. Pharm. Biomed. Anal. 12:1994;923-930.
30. Wang P., Lee H.K. Recent applications of high-performance liquid chromatography to the analysis of metal complexes. J. Chromatog. A. 789:1997;437-451.
31. Ma D., Lu F., Overstreet T., Milenic D.E., Brechbiel M.W. Novel chelating agents for potential clinical applications of copper. Nucl. Med. Biol. 29:2002;91-105.
32. Gulumian M, Hancock RD, Rollin HB. Different fractions of metal ions in biological fluids and their physiological roles. Handbook Metal-Ligand Interact Biol Fluids: Bioinorg Chem 1995;1:93-107.
33. Burdette S.C., Walkup G.K., Spingler B., Tsien R.Y., Lippard S.J. Fluorescent sensors for Zn(2+) based on a fluorescein platform: synthesis, properties and intracellular distribution. J. Am. Chem. Soc. 123:2001;7831-7841.
34. Hirano T., Kikuchi K., Urano Y., Nagano T. Improvement and biological applications of fluorescent probes for zinc, ZnAFs. J. Am. Chem. Soc. 124:2001;6555-6562.
35. Petrat F., De Groot H., Sustmann R., Rauen U. The chelatable iron pool in living cells: a methodically defined quantity. Biol. Chem. 383:2002;489-502.
36. Tamura T., Sadakata N., Oda T., Maramatsu T. Role of zinc ions in ricin-induced apoptosis in U937 cells. Toxicol. Lett. 132:2002;141-151.
37. Breuer W., Epsztejn S., Cabantchik Z.I. Iron acquired from transferrin by K562 cells is delivered into a cytoplasmic pool of chelatable iron(II). J. Biol. Chem. 270:1995;24209-242115.
38. Minotti G., Recalcati S., Mordente A., Liberi G., Calafiore A., Mancuso C.et al. The secondary alcohol metabolite of doxorubicin irreversibly inactivates aconitase/iron regulatory protein-1 in cytosolic fractions from human myoxardium. FASEB J. 12:1998;541-552.
39. Perry D.K., Smyth M.J., Stennicke H.R., Salvesen G.S., Duriez P., Poirier G.G.et al. Zinc is a potent inhibitor of the apoptotic protease, caspase-3. A novel target for zinc in the inhibition of apoptosis. J. Biol. Chem. 272:1997;18530-18533.
40. Chimienti F., Seve M., Richard S., Mathieu J., Favier A. Role of cellular zinc in programmed cell death: temporal relationship between zinc depletion, activation of caspases, and cleavage of Sp family transcription factors. Biochem. Pharmacol. 62:2001;51-62.
41. Stennicke H.R., Salveson G.S. Biochemical characteristics of caspases-3, -6, -7, and -8. J. Biol. Chem. 272:1997;25719-25723.
42. Martell AE, Smith RM. Critical stability constants. New York: Plenum Press; 1974-1989.
43. Liu Z.D., Hider R.C. Design of clinically useful iron(III)-selective chelators. Med. Res. Rev. 22:2002;26-64.
44. MacLean K.H., Cleveland J.L., Porter J.B. Cellular zinc content is a major determinant of iron chelator-induced apoptosis of thymocytes. Blood. 98:2001;3831-3839.
45. Samuni A.M., Krishna M.D., DeGraff W., Russo A., Planalp R.P., Brechbiel M.et al. Mechanisms underlying the cytotoxic effects of Tachpyr - a novel metal chelator. Biochim. Biophys. Acta. 1571:2002;211-218.