The potential of iron chelators of the pyridoxal isonicotinoyl hydrazone class as effective antiproliferative agents III: The effect of the ligands on molecular targets involved in proliferation

Blood

Volumn 94, Issue 2, 1999, Pages 781-792

  Darnell, G ^a   Richardson, D R ^a,b  

^a UNIVERSITY OF QUEENSLAND   (Australia)

^b ROYAL BRISBANE AND WOMEN'S HOSPITAL   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

2 HYDROXY 1 NAPHTHYLALDEHYDE ISONICOTINOYLHYDRAZONE; CYCLOHEXIMIDE; DEFEROXAMINE; DNA; IRON; IRON CHELATING AGENT; PROTEIN P53; PYRIDOXAL ISONICOTINOYLHYDRAZONE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CELL CYCLE; CELL PROLIFERATION; DNA REPAIR; GENE ACTIVATION; HUMAN; HUMAN CELL; IRON CHELATION; IRON TRANSPORT; LIGAND BINDING; LYMPHOPROLIFERATIVE DISEASE; NEUROBLASTOMA CELL; PRIORITY JOURNAL;

EID: 0033566305     PISSN: 00064971     EISSN: None     Source Type: Journal    
DOI: 10.1182/blood.v94.2.781.414k32_781_792     Document Type: Article

References (60)

1. Hoffbrand AV, Ganeshaguru K, Hooton JWL, Tatersall MHN: Effect of iron deficiency and desferrioxamine on DNA synthesis in human cells. Br J Haematol 33:517, 1976
2. Bergeron RJ, Cavanaugh PF Jr, Kline SJ, Hughes RG Jr, Elliot GT, Porter CW: Antineoplastic and antiherpetic activity of spermidine catecholamide iron chelators. Biochem Biophys Res Commun 121:848, 1984
3. Hoyes KP, Hider RC, Porter JB: Cell cycle synchronization and growth inhibition by 3-hydroxypyridin-4-one iron chelators in leukemic cell lines. Cancer Res 52:4591, 1992
4. Seligman PA, Schleicher RB, Siriwardana G, Domenico J, Gelfand EW: Effects of agents that inhibit cellular iron incorporation on bladder cell proliferation. Blood 82:1608, 1993
5. Torti SV, Torti FM, Whitman SP, Brechbiel MW, Park G, Planap RP: Tumor cell cytotoxicity of a novel metal chelator. Blood 92:1384, 1998
6. Richardson DR: Potential of iron chelators as effective anti-proliferative agents. Can J Physiol Pharmacol 75:1164, 1997
7. Becton DL, Bryles P: Deferoxamine inhibition of human neuroblastoma viability and proliferation. Cancer Res 48:7189, 1988
8. Blatt J, Taylor SR, Stitely S: Mechanism of antineuroblastoma activity of deferoxamine in vitro. J Lab Clin Med 112:433, 1988
9. Blatt J, Taylor SR, Kontoghiorghes GJ: Comparison of activity of deferoxamine with that of oral iron chelators against human neuroblastoma cell lines. Cancer Res 49:2925, 1989
10. Brodie C, Siriwardana G, Lucas J, Schleicher R, Terada N, Szepesi A, Gelfand E, Seligman P: Neuroblastoma sensitivity to growth inhibition by deferoxamine: Evidence for a block in the G1 phase of the cell cycle. Cancer Res 53:3968, 1993
11. Becton DL, Roberts B: Antileukemic effects of desferrioxamine on human myeloid leukemia cell lines. Cancer Res 49:4809, 1989
12. Estrov Z, Tawa A, Wang X-H, Dube ID, Sulh H, Cohen A, Gelfand EW, Freedman MH: In vivo and in vitro effects of desferrioxamine in neonatal acute leukemia. Blood 69:757, 1987
13. Donfrancesco A, Deb G, Dominici C, Pileggi D, Castello MA, Helson L: Effects of a single course of deferoxamine in neuroblastoma patients. Cancer Res 50:4929, 1990
14. Donfrancesco A, Deb G, Dominici C, Angioni A, Caniglia M, De Sio L, Fidani P, Amici A, Helson L: Deferoxamine, cyclophosphamide, etoposide, carboplatin, and thiotepa (D-CECat): A new cytoreductive chelation-chemotherapy regimen in patients with advanced neuroblastoma. Am J Clin Oncol 15:319, 1992
15. Richardson DR, Hefter GT, May PM, Webb J, Baker E: Iron chelators of the pyridoxal isonicotinoyl hydrazone class III. Formation constants with calcium(II), magnesium(II) and zinc(II). Biol Metals 2:161, 1989
16. Vitolo LMW, Hefter GT, Clare BW, Webb J: Iron chelators of the pyridoxal isonicotinoyl hydrazone class. Part 2. Formation constants with iron(III) and iron(II). Inorg Chim Acta 170: 171, 1990
17. Ponka P, Borova J, Neuwirt J, Fuchs O: Mobilization of iron from reticulocytes. Identification of pyridoxal isonicotinoyl hydrazone as a new iron chelating agent. FEBS Lett 97:317, 1979
18. Ponka P, Borova J, Neuwirt J, Fuchs O, Necas E: A study of intracellular iron metabolism using pyridoxal isonicotinoyl hydrazone and other synthetic chelating agents. Biochim Biophys Acta 586:278, 1979
19. Hershko C, Avramovici-Grisaru S, Link G, Gelfand L, Sarel S: Mechanisms of in vivo chelation by pyridoxal isonicotinoyl hydrazone and other imino derivatives of pyridoxal. J Lab Clin Med 98:99, 1981
20. Richardson DR, Ponka P: Pyridoxal isonicotinoyl hydrazone and its analogs: Potential orally effective iron-chelating agents for the treatment of iron overload disease. J Lab Clin Med 131:306, 1998
21. Richardson DR, Tran E, Ponka P: The potential of iron chelators of the pyridoxal isonicotinoyl hydrazone class as effective anti-proliferative agents. Blood 86:4295, 1995
22. Richardson DR, Milnes K: The potential of iron chelators of the pyridoxal isonicotinoyl hydrazone class as effective anti-proliferative agents II: The mechanism of action of ligands derived from salicylaldehyde benzoyl hydrazone and 2-hydroxy-1-naphthylaldehyde benzoyl hydrazone. Blood 89:3025, 1997
23. Thelander L, Reichard P: Reduction of ribonucleotides. Annu Rev Biochem 48:133, 1979
24. Thelander L, Graslund A, Thelander M: Continual presence of oxygen and iron is required for mammalian ribonucleotide reduction: Possible regulation mechanism. Biochem Biophys Res Commun 110: 859, 1983
25. Lederman HM, Cohen A, Lee JWW, Freedman MH, Gelfand EW: Deferoxamine: A reversible S-phase inhibitor of human lymphocyte proliferation. Blood 64:748, 1984
26. Nyholm S, Mann GJ, Johansson AG, Bergeron RJ, Graslund A, Thelander L: Role of ribonucleotide reductase in inhibition of mammalian cell growth by potent iron chelators. J Biol Chem 268:26200, 1993
27. Klausner RD, Harford JB: Cis-trans models for post-transcriptional gene regulation. Science 246:870, 1989
28. Hentze MW, Kühn LC: Molecular control of vertebrate iron metabolism: mRNA-based regulatory circuits operated by iron, nitric oxide, and oxidative stress. Proc Natl Acad Sci USA 93:8175, 1996
29. Richardson DR, Ponka P: The molecular mechanisms of the metabolism and transport of iron in normal and neoplastic cells. Biochim Biophys Acta 1331:1, 1997
30. Xiong Y, Hannon GJ, Zhang H, Casso D, Kobayashi R, Beach D: p21 is a universal inhibitor of cyclin kinases. Nature 366:701, 1993
31. El-Deiry WS, Tokino T, Velculescu VE, Levy DB, Parsons R, Trent JM, Lin D, Mercer E, Kinzler KW, Vogelstein B: WAF1, a potent mediator of p53 suppression. Cell 75:817, 1993
32. Harper JW, Adam GR, Wei N, Keyomars K, Elledge SJ: The p21 Cdk-interacting protein Cip 1 is a potent inhibitor of G1 cyclin-dependent kinases. Cell 75:805, 1993
33. Levine AJ: p53, the cellular gatekeeper for growth and division. Cell 88:323, 1997
34. Agarwal ML, Agarwal A, Taylor WR, Stark GR: p53 controls both the G2/M and the G1 cell cycle checkpoints and mediates reversible growth arrest in human fibroblasts. Proc Natl Acad Sci USA 92:8493, 1995
35. Kastan MB, Zhan Q, El-Deiry WS, Carrier F, Jacks T, Walsh WV, Plunkett BS, Vogelstein B, Fornace AJ Jr: A mammalian cell cycle check point pathway utilizing p53 and gadd45 is defective in ataxia telangiectasia. Cell 71:587, 1992
36. Wu X, Bayle JH, Olson D, Levine AJ: The p53-mdm2 autoregulatory feedback loop. Genes Dev 7:1126, 1993
37. Momand J, Zambetti GP, Olson DC, George D, Levine AJ: The mdm-2 oncogene product forms a complex with the p53 protein and inhibits p53-mediated transactivation. Cell 69:1237, 1992
38. Michieli P, Chedid M, Lin D, Pierce JH, Mercer WE, Givol D: Induction of WAF1/CIP1 by a p53-independent pathway. Cancer Res 54:3391, 1994
39. Zeng Y-X, El-Deiry WS: Regulation of p21 WAF1/CIP1 expression by p53-independent pathways. Oncogene 12:1557, 1996
40. Johnson DK, Murphy TB, Rose NJ, Goodwin WH, Pickart L: Cytotoxic chelators and chelates I. Inhibition of DNA synthesis in cultured rodent and human cells by aroylhydrazones and by a copper(II) complex of salicylaldehyde benzoyl hydrazone. Inorg Chim Acta 67:159, 1982
41. Richardson DR, Bernhardt P: Crystal and molecular structure of 2-hydroxy-1-naphthylaldehyde isonicotinoyl hydrazone (NIH) and its iron(III) complex: An iron chelator with anti-tumour activity. J Biol Inorg Chem (in press)
42. Richardson DR: Cytotoxic analogues of the iron(III) chelator pyridoxal isonicotinoyl hydrazone: Effect of complexation with copper(II), gallium(III), and iron(III) on their anti-proliferative activity. Antimicrob Agents Chemother 41:2061, 1997
43. Richardson DR, Baker E: The uptake of iron and transferrin by the human melanoma cell. Biochim Biophys Acta 1053:1, 1990
44. Leibold EA, Munro HN: Cytoplasmic protein binds in vitro to a highly conserved sequence in the 5′ untranslated region of ferritin heavy-and light-subunit mRNAs. Proc Natl Acad Sci USA 85:2171, 1988
45. Müllner EW, Neupert B, Kühn LC: A specific mRNA binding factor regulates the iron-dependent stability of the cytoplasmic transferrin receptor mRNA. Cell 58:373, 1989
46. Mahmoudi M, Lin VK: Comparison of two different hybridization systems in northern transfer analysis. Biotechniques 7:331, 1989
47. Chitambar CR, Wereley JP: Effect of hydroxyurea on cellular iron metabolism in human leukemic CCRF-CEM cells: Changes in iron uptake and the regulation of transferrin receptor and ferritin gene expression following inhibition of DNA synthesis. Cancer Res 55:4361, 1995
48. Brodeur GM, Seeger RC, Schwab M, Varmus HE, Bishop JM: Amplification of N-myc in untreated human neuroblastomas correlates with advanced disease stage. Science 224:1121, 1984
49. Frantz CN, Iyer J, Frick KK, Eskenazi AE, Derg PE: Iron and N-myc expression in neuroblastoma. Neuroblastoma Research Meeting. Philadelphia, PA, 1993
50. Frantz CN, Eskenazi AE, Overman D: Iron chelation cancer therapy for neuroblastoma. Proceedings of the International Conference on Bioiron. April 16-21, 1995. Asheville, NC, 1995, p 195
51. Linke SP, Clarkin KC, DiLeonardo A, Tsao A, Wahl GM: A reversible, p53-dependent Go/G1 cell cycle arrest induced by ribonucleotide depletion in the absence of detectable DNA damage. Genes Dev 10:934, 1996
52. Davidoff AM, Pence JC, Shorter NA, Ingelhart JD, Marks JR: Expression of p53 in human neuroblastoma-and neuroepithelioma-derived cell lines. Oncogene 7:127, 1992
53. Moll UM, Ostermeyer AG, Haladay R, Winkfield B, Frazier M, Zambetti G: Cytoplasmic sequestration of wild-type p53 protein impairs the G1 checkpoint after DNA damage. Mol Cell Biol 16:1126, 1996
54. Bi S, Hughes T, Bungey J, Chase A, de Fabritiis P, Goldman JA: p53 in chronic myeloid leukemia cell lines. Leukemia 6:839, 1992
55. Ehinger M, Nilsson E, Persson A-M, Olsson I, Gullberg U: Involvement of the tumor suppressor gene p53 in tumor necrosis factor-induced differentiation of the leukemic cell line K562. Cell Growth Diff 6:9, 1995
56. Zeng Y-X, Somasundaram K, El-Deiry W: AP2 inhibits cancer cell growth and activates p21WAF1/CIP1 expression. Nat Genet 15:78, 1997
57. Billon N, van Grunsven LA, Rudkin BB: The CDK inhibitor p21WAF1/Cip1 is induced through a p300-dependent mechanism during NGF-mediated neuronal differentiation of PC12 cells. Oncogene 13:2047, 1996
58. Pantopoulos K, Weiss G, Hentze MW: Nitric oxide and oxidative stress (H202) control mammalian iron metabolism by different pathways. Mol Cell Biol 16:3781, 1996
59. Constable A, Quick S, Gray NK, Hentze MW: Modulation of the RNA-binding activity of a regulatory protein by iron in vitro: Switching between enzymatic and genetic function. Proc Natl Acad Sci USA 89:4554, 1992
60. Haile DJ, Rouault TA, Harford JB, Kennedy MC, Blondin GA, Beinert H, Klausner RD: Cellular regulation of the iron-responsive element binding protein: Disassembly of the cubane iron-sulfur cluster results in high-affinity RNA binding. Proc Natl Acad Sci USA 89:11735, 1992