Antiproliferative effect on HepaRG cell cultures of new calix[4]arenes

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 25, Issue 2, 2010, Pages 216-227

  Rouge, Pascal ^a   Pires, Viviane Silva ^a   Gaboriau, François ^b   Dassonville Klimpt, Alexandra ^a   Guillon, Jean ^c   Nascimento, Sophie Da ^a   Leger, Jean Michel ^c   Lescoat, Gerard ^b   Sonnet, Pascal ^a  

^a UNIVERSITÉ DE PICARDIE JULES VERNE   (France)

^b UNIVERSITÉ EUROPÉENNE DE BRETAGNE   (France)

^c Laboratoire de Pharmacochimie   (France)

Author keywords

Antiproliferative effect; Calix 4 arene; HepaRG cell line; Hepatocyte; Iron chelation

Indexed keywords

25 HYDROXY 26,27,28 TRI(ETHOXYCARBONYLBUTOXY)TERTBUTYL CALIX[4]ARENE; 25,26,27 TRIHYDROXY 28 (ETHOXYCARBONYLBUTOXY)TERT BUTYL CALIX[4]ARENE; 25,27 DIHYDROXY 26,28 BIS(ACIDBUTOXY)TERT BUTYL CALIX[4]ARENE; 25,27 DIHYDROXY 26,28 BIS(ACIDHEXOXY)TERT BUTYL CALIX[4]ARENE; 25,27 DIHYDROXY 26,28 BIS(ACIDPENTOXY)TERT BUTYL CALIX[4]ARENE; 25,27 DIHYDROXY 26,28 BIS(ETHOXYCARBONYLBUTOXY)TERT BUTYL CALIX[4]ARENE; 25,27 DIHYDROXY 26,28 BIS(ETHOXYCARBONYLPENTOXY)TERT BUTYL CALIX[4]ARENE; 25,27 DIHYDROXY 26,28 BIS(ETHOXYCARBONYLPROPOXY)CALIX[4]ARENE; 25,27 DIHYDROXY 26,28 BIS(ETHOXYCARBONYLPROPOXY)TERT BUTYL CALIX[4]ARENE; 25,27,26,28 TETRA(ETHOXYCARBONYLBUTOXY)CALIX[4]ARENE; 25,27,26,28 TETRA(ETHOXYCARBONYLMETHOXY)CALIX[4]ARENE; ALKYL GROUP; CALIX[4]ARENE; DEFERASIROX; IRON CHELATE; LACTATE DEHYDROGENASE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

CANCER CELL CULTURE; CELL CULTURE; CELL PROLIFERATION; CONFERENCE PAPER; CONTROLLED STUDY; CYTOTOXICITY; DRUG EFFECT; ENZYME ACTIVITY; HUMAN; HUMAN CELL; IRON DEPLETION; LIVER CELL CARCINOMA; PRIORITY JOURNAL;

BENZOIC ACIDS; CALIXARENES; CELL LINE, TUMOR; CELL PROLIFERATION; DRUG DESIGN; HUMANS; IRON; IRON CHELATING AGENTS; PHENOLS; TRIAZOLES;

EID: 77949469490     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756360903169949     Document Type: Conference Paper

References (51)

1. Brittenham GM. Disorders of iron metabolism: iron deficiency and overload. In: Hoffman R, Benz EJ, Shattil SJ, Furie B, Cohen HJ, et al., eds. Hematology: basic principles and practise, 3rd ed. New York: Churchill Livingstone, 2000:397-428.
2. McCance RA, Widdowson EM. Absorption and excretion of iron. Lancet 1937;ii:680-684
3. Deugnier Y, Charalambous P, Le Quilleuc D, Turlin B, Searle J, Brissot P, et al. Preneoplastic significance of hepatic iron-free foci in genetic hemochromatosis: a study of 185 patients. Hepatology 1993; 18:1363-1369
4. Hsing AW, McLaughlin JK, Olsen JH, Mellemkjar L, Wacholder S, Fraumeni JF. Cancer risk following primary hemochromatosis: a population-based cohort study in Denmark. Int J Cancer 1995; 60:160-162
5. Andrews NC. Disorders of iron metabolism. N Engl J Med 1999;341:1986-1995
6. Kalinowski DS, Richardson DR. The evolution of iron chelators for the treatment of iron overload disease and cancer. Pharmacol Rev 2005;57:547-583
7. Soyano A, Chinea M, Romano EL. The effect of desferrioxamine on the proliferative response of rat lymphocytes stimulated with various mitogens in vitro. Immunopharmacology 1984;8:163-169
8. Polson RJ, Jenkins R, Lombard M, Williams AC, Roberts S, Nouri-Aria K, et al. Mechanisms of inhibition of mononuclear cell activation by the iron-chelating agent desferrioxamine. Immunology 1990;71:176-181
9. Richardson DR, Milnes K. The potential of iron chelators of the pyridoxal isonicotinoyl hydrazone class as effective antiproliferative agents. II: The mechanism of action of ligands derived from salicylaldehyde benzoyl hydrazone and 2-hydroxy-1-naphthylaldehyde benzoyl hydrazone. Blood 1997;89:3025-3038
10. Chenoufi N, Baffet G, Drénou B, Cariou S, Desille M, Clément B, et al. Deferoxamine arrests in vitro the proliferation of porcine hepatocyte in G1 phase of the cell cycle. Liver 1997;18:60-67
11. Rakba N, Loyer P, Gilot D, Delcros JG, Glaise D, Baret P, et al. Antiproliferative and apoptotic effects of O-Trensox, a new synthetic iron chelator, on differentiated human hepatoma cell lines. Carcinogenesis 2000;21:943-951
12. Richardson DR. Potential of iron chelators as effective antiproliferative agents. Can J Physiol Pharmacol 1997;75:1164-1180
13. Hann HWL, Stahlhut MW, Blumberg BS. Iron mutation and tumor growth: decreased tumor growth in iron deficient mice. Cancer Res 1988;48:4168-4170
14. Le NT, Richardson DR. The role of iron in cell cycle progression and the proliferation of neoplastic cells. Biochem Biophys Acta 2002; 1603:31-46.
15. Chaston TB, Richardson DR. Iron chelators for the treatment of iron overload disease: relationship between structure, redox activity and toxicity. Am J Hematol 2003;73:200-210
16. Richardson DR. Iron chelators as therapeutic agents for the treatment of cancer. Crit Rev Oncol Hematol 2002;42:267-281
17. Richardson DR, Sharpe PC, Lovejoy DB, Senaratne D, Kalinowski DS, Islam M, et al. Dipyridyl thiosemicarbazone chelators with potent and selective antitumor activity form iron complexes with redox activity. J Med Chem 2006;49:6510-6521
18. Gao J, Richardson DR. The potential of iron chelators of the pyridoxal isonicotinoyl hydrazone class as effective antiproliferative agents: IV. The mechanisms involved in inhibiting cell-cycle progression. Blood 2001;98:842-850
19. Finch RA, Liu M, Grill SP, Rose WC, Loomis R, Vasquez KM, et al. Triapine (3-aminopyridine-2-carboxaldehyde-thiosemicarbazone): a potent inhibitor of ribonucleotide reductase activity with broad spectrum antitumor activity. Biochem Pharmacol 2000;59:938-991
20. Brodie C, Siriwardana G, Lucas J, Schleicher R, Terada N, Szepesi A, et al. Neuroblastoma sensitivity to growth inhibition by desferrioxamine: evidence for a block in G1 phase of the cell cycle. Cancer Res 1993;53:3968-3975
21. Glickstein H, Breuer W, Loyevsky M, Konijn AM, Shanzer A, Cabantchik ZI. Differential cytotoxicity of iron chelators on malariainfected cells versus mammalian cells. Blood 1996;87:4871-4878
22. Valle P, Timeus F, Piglione M, Rosso P, di Montezemolo LC, Crescenzio N, et al. Effect of different exposures to desferrioxamine on neuroblastoma cell lines. Pediatr Hematol Oncol 1995;12:439-446
23. Selig RA, White L, Gramacho C, Sterlinglevis K, Fraser IW, Naidoo D. Failure of iron chelators to reduce tumor growth in human neuroblastoma xenografts. Cancer Res 1998;58:473-478
24. Olivieri NF, Koren G, Matsui D, Liu PP, Blendis L, Cameron R, et al. Reduction of tissue iron stores and normalization of serum ferritin during treatment with the oral iron chelator L1 in thalassemia intermedia. Blood 1992;79:2741-2748
25. Al-Refaie FN, Wonke B, Hoffbrand AV, Wickens DG, Nortey P, Kontoghiorges GJ. Efficacy and possible adverse effects of the oral iron chelator 1,2-dimethyl-3-hydroxypyrid-4-one (L1) in thalassemia major. Blood 1992;80:593-599
26. Collins AF, Fassos FF, Stobie S, Lewis N, Shaw D, Fry M, et al. Iron-balance and dose-response studies of the oral iron chelator 1,2-dimethyl-3- hydroxypyrid-4-one (L1) in iron-loaded patients with sickle cell disease. Blood 1994;83:2329-2333
27. Porter JB, Davis BA. Monitoring chelation therapy to achieve optimal outcome in the treatment of thalassaemia. Best Pract Res Clin Haematol 2002;15:329-368
28. Lescoat G, Chantrel-Groussard K, Pasdeloup N, Nick H, Brissot P, Gaboriau F. Antiproliferative and apoptotic effects in rat and human hepatoma cell cultures of the orally active iron chelator ICL670 compared to CP20: a possible relationship with polyamine metabolism. Cell proliferation 2007;40:755-767
29. Lovejoy D, Richardson DR. Novel "hybrid" iron chelators derived from aroylhydrazones and thiosemicarbazones demonstrate high anti-proliferative activity that is selective for tumor cells. Blood 2002;100:666-676
30. Bergeron RJ, Wiegand J, McManis JS, Bharti N. The design, synthesis and evaluation of organ-specific iron chelators. J Med Chem 2006; 49:7032-7043
31. Liu ZD, Hider RC. Design of iron chelators with therapeutic application. Coord Chem Rev 2002;232:151-171
32. Liu ZD, Hider RC. Design of clinically useful iron-selective chelators. Med Res Rev 2002;22: 26-64.
33. Sansone F, Segura M, Ungaro R. Calixarenes in bioorganic and biomimetic chemistry. In: Asfari Z, Böhmer V, Harrowfield J, Vicens J, eds. Calixarenes 2001. Dordrecht, The Netherlands: Kluwer Academic Publishers, 2001:496-512.
34. Mutihac L. Functionalized calix[n]arenes as membrane transporters for biological compounds. A minireview. Curr Drug Discov Technol 2008;5:98-104.
35. Jose P, Menon S. Lower-rim substituted calixarenes and their applications. Bioinorg Chem Appl 2007:65815.
36. Gutsche CD. Calixarenes: Monographs in Supramolecular Chemistry. London: Royal Society of Chemistry, 1989.
37. Asfari Z, Böhmer V, Harrowfield J, Vicens J, eds. Calixarenes 2001. Dordrecht, The Netherlands: Kluwer Academic Publishers, 2001.
38. Creaven, BS, Donlon DF, McGinley J. Coordination chemistry of calix[4] arene derivatives with lower rim functionalisation and their applications. Coord Chem Rev 2009;253:893-962.
39. Ali A, Salunke-Gawali S, Rao CP, Linares J. A first report of the complexes of 5,11,17,23-tetra-tert-butyl-25,27-dicarboxymethoxy-26,28- dihydroxycalix[4]arene with Mn(II), Fe(III), Co(II), Ni(II), Cu(II) and Zn(II). Inorg Chem Commun 2004;7:1298-1301
40. Deligoz H, Ozen O, Cilgi GK. Structural analysis of calix[n]arene-iron (III) complexes (n = 4, 6, 8) and thermal decomposition of the parent calix[n] arenes. J Coord Chem 2007;60:73-83.
41. Ogden MI, Skelton BW, White AH. Syntheses, structural studies and solution properties of iron complexes of some amide-substituted calixarenes. J Chem Soc Dalton Trans 2001;20:3073-3077
42. Guillon J, Léger JM, Sonnet P, Jarry C, Robba M. Synthesis of cone, partialcone and 1,3-alternate 25,27-bis[1-(2-ethyl)hexyl]- and 25,27-bis[1- (2-tert-butoxy)ethyl]calix[4]arene-crown-6 conformers as potential selective cesium extractants. J Org Chem 2000;65:8283-8289
43. Guillon J, Sonnet P, Malval JP, Massip S, Gosse I, Léger JM, et al. Synthesis and cesium binding affinity of new 25,27-bis(alkyloxy)calix[4] arenecrown- 6 conformers in relation to the alkyl pendent moiety. Supramol Chem 2002;14:437-450
44. Guillon J, Léger JM, Dapremont C, Denis LA, Sonnet P, Massip S, et al. First synthesis of 1,3-alternate 25,27-dialkyloxy-5,17-diarylcalix[4] arenes-crown-6 as new cesium selective extracants by Suzuki crosscoupling reaction. Supramol Chem 2004;16:319-329
45. Pires VS, Gaboriau F, Guillon J, Nascimento S, Dassonville A, Lescoat G, et al. Modulation of cell proliferation in rat liver cell cultures by new calix[4]arenes. J Enzyme Inhib Med Chem. 2006; 21:261-270
46. Gripon P, Rumin S, Urban S, Le Seyec J, Glaise D, Cannie I, et al. Infection of a human hepatoma cell line by hepatitis B virus. Proc Natl Acad Sci USA 2002;99:15655-15660
47. Troadec MB, Glaise D, Lamirault G, Le Cunff M, Guerin E, Le Meur N, et al. Hepatocyte iron loading capacity is associated with differentiation and repression of motility in the HepaRG cell line. Genomics 2006;87:93-103.
48. Rouan MC, Marfil F, Mangoni P, Sechaud 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 Biomed Sci Appl 2001; 755:203-213
49. Collins EM, McKervey A, Madigan E, Moran MB, Owens M, Ferguson G, et al. Chemically modified calix[4]arenes. Regioselective synthesis of 1,3-(distal) derivatives and related compounds. X-ray crystal structure of a diphenol-dinitrile. J Chem Soc Perkin Trans 1 1991: 3137-3142
50. Collins EM, McKervey A, Harris SJ. Molecular receptors with calix[4]arene substructure. Synthesis of derivatives with mixed ligating functional groups. J Chem Soc Perkin Trans 1 1989:372-374
51. Supplementary X-ray crystallographic data of compounds 3c and 8b (CCDC-706418 and CCDC-706417): Cambridge Crystallographic Data Centre, University Chemical Laboratory, 12 Union Road, Cambridge, CB2 1EZ, UK. E-mail: deposit@ccdc.cam.ac.uk.