Membrane transport and intracellular sequestration of novel thiosemicarbazone chelators for the treatment of cancer

Molecular Pharmacology

Volumn 78, Issue 4, 2010, Pages 675-684

  Merlot, Angelica M ^a   Pantarat, Namfon ^a   Lovejoy, David B ^a   Kalinowski, Danuta S ^a   Richardson, Des R ^a  

^a UNIVERSITY OF SYDNEY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

2 BENZOYLPYRIDINE 4 ETHYL 3 THIOSEMICARBAZONE; ANTINEOPLASTIC AGENT; CARBON 14; CHELATING AGENT; PYRIDOXAL ISONICOTINOYLHYDRAZONE; THIOSEMICARBAZONE; UNCLASSIFIED DRUG; IRON CHELATING AGENT; THIOSEMICARBAZONE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL; CELL MEMBRANE; CONTROLLED STUDY; CYTOTOXICITY; DRUG TRANSPORT; DRUG UPTAKE; HUMAN; HUMAN CELL; HYDROPHILICITY; ISOTOPE LABELING; MEMBRANE PERMEABILITY; MEMBRANE TRANSPORT; NEUROEPITHELIOMA; PH MEASUREMENT; PRIORITY JOURNAL; TEMPERATURE DEPENDENCE; TUMOR MICROENVIRONMENT; CHEMISTRY; COMPARATIVE STUDY; INTRACELLULAR FLUID; METABOLISM; NEOPLASMS; PHYSIOLOGY; TRANSPORT AT THE CELLULAR LEVEL; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; BIOLOGICAL TRANSPORT; CELL LINE, TUMOR; HUMANS; INTRACELLULAR FLUID; IRON CHELATING AGENTS; NEOPLASMS; THIOSEMICARBAZONES;

EID: 77957244799     PISSN: 0026895X     EISSN: 15210111     Source Type: Journal    
DOI: 10.1124/mol.110.066126     Document Type: Article

References (38)

1. Baker E, Richardson D, Gross S, and Ponka P (1992) Evaluation of the iron chelation potential of hydrazones of pyridoxal, salicylaldehyde and 2-hydroxy-1-naphthylaldehyde using the hepatocyte in culture. Hepatology 15:492-501.
2. Becker EM, Lovejoy DB, Greer JM, Watts R, and Richardson DR (2003) Identification of the di-pyridyl ketone isonicotinoyl hydrazone (PKIH) analogues as potent iron chelators and anti-tumour agents. Br J Pharmacol 138:819-830. (Pubitemid 36390638)
3. Buss JL, Arduini E, and Ponka P (2002) Mobilization of intracellular iron by analogs of pyridoxal isonicotinoyl hydrazone (PIH) is determined by the membrane permeability of the iron-chelator complexes. Biochem Pharmacol 64:1689-1701. (Pubitemid 35351576)
4. Buss JL, Arduini E, Shephard KC, and Ponka P (2003) Lipophilicity of analogs of pyridoxal isonicotinoyl hydrazone (PIH) determines the efflux of iron complexes and toxicity in K562 cells. Biochem Pharmacol 65:349-360. (Pubitemid 36084552)
5. Carmeliet P and Jain RK (2000) Angiogenesis in cancer and other diseases. Nature 407:249-257.
6. Cavanaugh PG, Jia L, Zou Y, and Nicolson GL (1999) Transferrin receptor overexpression enhances transferrin responsiveness and the metastatic growth of a rat mammary adenocarcinoma cell line. Breast Cancer Res Treat 56:203-217. (Pubitemid 29495652)
7. Curado MP, Edwards B, Shin HR, Ferlay J, Heanue M, Boyle P, and Storm H (2007) Cancer Incidence in Five Continents, Volume IX, International Agency for Research on Cancer, Lyon, France.
8. Doungdee P, Sarel S, Wongvisetsirikul N, and Avramovici-Grisaru S (1995) Iron chelators of the pyridoxal 2-pyridyl hydrazone class. Part 4. pKa values of the chelators and their relevance to biological properties. J Chem Soc Perkin Trans 2:319-323.
9. Elford HL, Freese M, Passamani E, and Morris HP (1970) Ribonucleotide reductase and cell proliferation. I. Variations of ribonucleotide reductase activity with tumor growth rate in a series of rat hepatomas. J Biol Chem 245:5228-5233.
10. Gottesman MM, Fojo T, and Bates SE (2002) Multidrug resistance in cancer: role of ATP-dependent transporters. Nat Rev Cancer 2:48-58. (Pubitemid 37328807)
11. Grahame-Smith DG and Aronson JK (2006) Clinical Pharmacology and Drug Therapy, Oxford University Press, New York.
12. Greish K (2007) Enhanced permeability and retention of macromolecular drugs in solid tumors: a royal gate for targeted anticancer nanomedicines. J Drug Target 15:457-464.
13. Helmlinger G, Yuan F, Dellian M, and Jain RK (1997) Interstitial pH and pO2 gradients in solid tumors in vivo: high-resolution measurements reveal a lack of correlation. Nat Med 3:177-182. (Pubitemid 27064702)
14. Henderson GB and Zevely EM (1984) Transport routes used by L1210 cells for the influx and efflux of methotrexate. J Biol Chem 259:1526-1531. (Pubitemid 14104204)
15. Hodges YK, Antholine WE, and Horwitz LD (2004) Effect on ribonucleotide reductase of novel lipophilic iron chelators: the desferri-exochelins. Biochem Biophys Res Commun 315:595-598.
16. Huang AR and Ponka P (1983) A study of the mechanism of action of pyridoxal isonicotinoyl hydrazone at the cellular level using reticulocytes loaded with non-heme 59Fe. Biochim Biophys Acta 757:306-315.
17. Kalinowski DS and Richardson DR (2005) The evolution of iron chelators for the treatment of iron overload disease and cancer. Pharmacol Rev 57:547-583. (Pubitemid 43036441)
18. Kalinowski DS, Yu Y, Sharpe PC, Islam M, Liao YT, Lovejoy DB, Kumar N, Bernhardt PV, and Richardson DR (2007) Design, synthesis, and characterization of novel iron chelators: structure-activity relationships of the 2-benzoylpyridine thiosemicarbazone series and their 3-nitrobenzoyl analogues as potent antitumor agents. J Med Chem 50:3716-3729.
19. Kolberg M, Strand KR, Graff P, and Andersson KK (2004) Structure, function, and mechanism of ribonucleotide reductases. Biochim Biophys Acta 1699:1-34. (Pubitemid 38680791)
20. Le NT and Richardson DR (2002) The role of iron in cell cycle progression and the proliferation of neoplastic cells. Biochim Biophys Acta 1603:31-46. (Pubitemid 35257983)
21. Le NT and Richardson DR (2004) Iron chelators with high antiproliferative activity up-regulate the expression of a growth inhibitory and metastasis suppressor gene: a link between iron metabolism and proliferation. Blood 104:2967-2975.
22. Maeda H (2001) The enhanced permeability and retention (EPR) effect in tumor vasculature: the key role of tumor-selective macromolecular drug targeting. Adv Enzyme Regul 41:189-207.
23. Pahl PM and Horwitz LD (2005) Cell permeable iron chelators as potential cancer chemotherapeutic agents. Cancer Invest 23:683-691.
24. Qian ZM and Morgan EH (1991) Effect of metabolic inhibitors on uptake of non-transferrin-bound iron by reticulocytes. Biochim Biophys Acta 1073:456-462.
25. Richardson DR (1997) Mobilization of iron from neoplastic cells by some iron chelators is an energy-dependent process. Biochim Biophys Acta 1320:45-57.
26. Richardson DR and Baker E (1990) The uptake of iron and transferrin by the human malignant melanoma cell. Biochim Biophys Acta 1053:1-12.
27. Richardson DR and Ponka P (1994) The iron metabolism of the human neuroblastoma cell: lack of relationship between the efficacy of iron chelation and the inhibition of DNA synthesis. J Lab Clin Med 124:660-671.
28. Richardson DR, Sharpe PC, Lovejoy DB, Senaratne D, Kalinowski DS, Islam M, and Bernhardt PV (2006) Dipyridyl thiosemicarbazone chelators with potent and selective antitumor activity form iron complexes with redox activity. J Med Chem 49:6510-6521.
29. Richardson DR, Tran EH, and Ponka P (1995) The potential of iron chelators of the pyridoxal isonicotinoyl hydrazone class as effective antiproliferative agents. Blood 86:4295-4306.
30. Richardson DR, Vitolo LM, Hefter GT, May PM, Clare BW, Webb J, and Wilairat P (1990) Iron chelators of the pyridoxal isonicotinoyl hydrazone class. Part I. Ionisation characteristics of the ligands and their relevance to biological properties. Inorganica Chim Acta 170:165-170.
31. Svec F (1985) Relationship between intact cell ATP levels and glucocorticoid receptor-binding capacity in the AtT-20 cell. Biochim Biophys Acta 847:147-154.
32. Trinder D and Baker E (2003) Transferrin receptor 2: a new molecule in iron metabolism. Int J Biochem Cell Biol 35:292-296.
33. van der Veldt AA, Luurtsema G, Lubberink M, Lammertsma AA, and Hendrikse NH (2008) Individualized treatment planning in oncology: role of PET and radiolabelled anticancer drugs in predicting tumour resistance. Curr Pharm Des 14: 2914-2931.
34. Warburg O (1956) On the origin of cancer cells. Science 123:309-314.
35. Whitnall M, Howard J, Ponka P, and Richardson DR (2006) A class of iron chelators with a wide spectrum of potent antitumor activity that overcomes resistance to chemotherapeutics. Proc Natl Acad Sci USA 103:14901-14906.
36. Yu Y, Kovacevic Z, and Richardson DR (2007) Tuning cell cycle regulation with an iron key. Cell Cycle 6:1982-1994.
37. Yuan J, Lovejoy DB, and Richardson DR (2004) Novel di-2-pyridyl-derived iron chelators with marked and selective antitumor activity: in vitro and in vivo assessment. Blood 104:1450-1458.
38. Zimmer G and Schirmer H (1974) Viscosity changes of erythrocyte membrane and membrane lipids at transition temperature. Biochim Biophys Acta 345:314-320.