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

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 26, Issue 2, 2011, Pages 204-215

  Latxague, Laurent ^a   Gaboriau, François ^b   Chassande, Olivier ^a   Leger, Jean Michel ^a   Pires, Viviane ^c   Rouge, Pascal ^c   Dassonville Klimpt, Alexandra ^c   Fardeau, Sylvain ^c   Jarry, Christian ^a   Lescoat, Gerard ^b   Guillon, Jean ^a   Sonnet, Pascal ^c  

^a UNIVERSITÉ DE BORDEAUX   (France)

^b UNIVERSITÉ DE RENNES 1   (France)

^c UNIVERSITÉ DE PICARDIE JULES VERNE   (France)

Author keywords

antiproliferative effect; Calix 4 arene; HepaRG cell line; hepatocyte; iron chelation

Indexed keywords

25 [3 [BIS (METHOXYCARBONYLMETHYL)AMINO]PROPOXY]CALIX[4]ARENE; 25 [3 [BIS(2 HYDROXYETHYL)AMINO]PROPOXY]CALIX[4]ARENE; 25,26,27,28 TETRA[5 (4 AMIDINOPHENOXY)PENTOXY]CALIX[4]ARENE; 25,26,27,28 TETRA[5 (4 CYANOPHENOXY)PENTOXY]CALIX[4]ARENE; 25,26,27,28 TETRA[5 [4 (N HYDROXYAMIDINOPHENOXY)PENTOXY]]CALIX[4]ARENE; 25,27 BIS [3 [BIS(2 HYDROXYETHYL)AMINO]PROPOXY]CALIX[4]ARENE; 25,27 BIS [3 [BIS(HYDROXYCARBONYLMETHYL)AMINO]PROPOXY]CALIX[4]ARENE; 25,27 BIS [3 [BIS(METHOXYCARBONYLMETHYL)AMINO]PROPOXY]CALIX[4]ARENE; AMINE; CALIXARENE; DEFERASIROX; FLUORESCENT DYE; HOE 33342; LACTATE DEHYDROGENASE; N 3 BROMOPROPYL N,N BIS(METHOXYCARBONYL METHYL)AMINE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; AQUEOUS SOLUTION; ARTICLE; CANCER CELL CULTURE; CELL CYCLE PROGRESSION; CELL NUCLEUS; CELL PROLIFERATION; CELL VIABILITY; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG SOLUBILITY; DRUG SYNTHESIS; FEMALE; HUMAN; HUMAN CELL; IC 50; IRON DEPLETION; LIVER CELL CARCINOMA; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; CALIXARENES; CELL LINE, TUMOR; CELL PROLIFERATION; CELLS, CULTURED; FEMALE; HEPATOCYTES; HUMANS; LIVER; MOLECULAR STRUCTURE; PHENOLS; SOLUBILITY;

EID: 79952751964     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756366.2010.489898     Document Type: Article

References (60)

1. rd 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, Powell LW, Halliday JW. Preneoplastic signifcance of hepatic iron-free foci in genetic hemochromatosis: a study of 185 patients. Hepatology 1993;18:1363-1369. (Pubitemid 23348423)
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. (Pubitemid 30010408)
6. Kalinowski DS, Richardson DR, Te evolution of iron chelators for the treatment of iron overload disease and cancer. Pharmacol Rev 2005;57:547-583. (Pubitemid 43036441)
7. Soyano A, Chinea M, Romano EL. Te efect of desferrioxamine on the proliferative response of rat lymphocytes stimulated with various mitogens in vitro. Immunopharmacol 1984;8:163-169. (Pubitemid 16162326)
8. Polson RJ, Jenkins R, Lombard M, Williams AC, Roberts S, Nouri-Aria K, Williams R, Bomford A. Mechanisms of inhibition of mononuclear cell activation by the iron-chelating agent desferrioxamine. Immunology 1990;71:176-181. (Pubitemid 20341214)
9. Richardson DR, Milnes K. Te potential of iron chelators of the pyridoxal isonicotinoyl hydrazone class as efective 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. (Pubitemid 27172591)
10. Chenouf N, Bafet G, Drénou B, Cariou S, Desille M, Clément B, Brissot P, Lescoat G, Loréal O. 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, Pierre JL, Brissot P, Lescoat G. Antiproliferative and apoptotic efects of O-Trensox, a new synthetic iron chelator, on diferentiated human hepatoma cell lines. Carcinogenesis 2000;21:943-51. (Pubitemid 30265138)
12. Richardson DR. Potential of iron chelators as efective antiproliferative agents. Can J Physiol Pharmacol 1997;75:1164-1180. (Pubitemid 28033934)
13. Hann HWL, Stahlhut MW, Blumberg BS. Iron mutation and tumor growth: decreased tumor growth in iron defcient mice. Cancer Res 1988;48:4168-4170.
14. Le NTV, Richardson DR, Te role of iron in cell cycle progression and the proliferation of neoplastic cells. Biochim 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 of Hematology 2003;73:200-210. (Pubitemid 36753964)
16. Richardson DR. Iron chelators as therapeutic agents for the treatment of cancer. Crit Rev Oncol/Hematol 2002;42:267-281. (Pubitemid 34615689)
17. Richardson DR, Sharpe PC, Lovejoy DB, Senaratne D, Kalinowski DS, Islam M, Bernhardt PV. Dipyridyl thiosemicarbazone chelators with potent and selective antitumor activity form iron complexes with redox activity. J Med Chem 2006;49:6510-6521. (Pubitemid 44657445)
18. Gao J, Richardson DR. Te potential of iron chelators of the pyridoxal isonicotinoyl hydrazone class as efective antiproliferative agents: IV. Te 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, Cheng Y, Sartorelli AC Triapine (3-aminopyridine-2-carboxaldehyde-thiosemicarbazone):a potent inhibitor of ribonucleotide reductase activity with broad spectrum antitumor activity. Biochem Pharmacol 2000;59:938-91.
20. Brodie C, Siriwardana G, Lucas J, Schleicher R, Terada N, Szepesi A, Gelfand E, Seligman P. Neuroblastoma sensitivity to growth inhibition by desferrioxamine: evidence for a block in G1 phase of the cell cycle. Cancer Res 1993;53:3968-3975. (Pubitemid 23267697)
21. Glickstein H, Breuer W, Loyevsky M, Konijn AM, Shanzer A,Cabantchik ZI. Diferential cytotoxicity of iron chelators on malaria-infected cells versus mammalian cells. Blood 1996;87:4871-4878. (Pubitemid 26162391)
22. A-Valle P, Timeus F, Piglione M, Rosso P, di Montezemolo LC, Crescenzio N, Marranca D, Ramenghi U. Efect of diferent exposures to desferrioxamine on neuroblastoma cell lines. Pediatr Hematol Oncol 1995;12:439-446.
23. Cappellini MD, Cohen A, Piga A, Bejaoui M, Perrotta S, Agaoglu L, Aydinok Y, Kattamis A, Kilinc Y Porter J, et al. A phase 3 study of deferasirox (ICL670), A once-daily oral iron chelator, in patients with beta-thalassemia. Blood 2006;107:3455-3462.
24. 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. (Pubitemid 28087409)
25. Olivieri NF, Koren G, Matsui D, Liu PP, Blendis L, Cameron R, McClelland RA, Templeton DM. 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.
26. Al-Refaie FN, Wonke B, Hofbrand AV, Wickens DG, Nortey P, Kontoghiorges GJ. Efcacy and possible adverse efects of the oral iron chelator 1,2-dimethyl-3-hydroxypyrid-4-one (L1) in thalassemia major. Blood 1992;80:593-599.
27. Collins AF, Fassos FF, Stobie S, Lewis N, Shaw D, Fry M, Templeton DM, McClelland RA, Koren G, Olivieri NF. 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.
28. 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.
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. (Pubitemid 34761134)
30. Bergeron RJ, Wiegand J, McManis JS, Bharti N. Te design, synthesis and evaluation of organ-specifc iron chelators. J Med Chem 2006;49:7032-7073.
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. Medicinal Res Rev 2002;22:26-64. (Pubitemid 34023572)
33. Sansone F, Segura M, Ungaro R. Calixarenes in Bioorganic and Biomimetic Chemistry. In: Asfari Z, Böhmer V, Harrowfeld J, Vicens J, eds. Calixarenes 2001. Dordrecht, Te 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. (Pubitemid 351883823)
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, Royal society of Chemistry. London, 1989.
37. Asfari Z, Böhmer V, Harrowfeld J, Vicens J, Calixarene. Dordrecht: Kluwer Academic, 2001.
38. Guillon J, Léger JM, Sonnet P, Jarry C, Robba M. Synthesis of cone, partial-cone 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.
39. Guillon J, Sonnet P, Malval JP, Massip S, Gosse I, Léger JM, Lapouyade R, Rochette J, Monti JP, Jarry C Synthesis and cesium binding afnity of new 25,27-bis(alkyloxy)calix[4]arene-crown-6 conformers in relation to the alkyl pendent moiety. Supramol Chem 2002;14:437-450.
40. Guillon J, Léger JM, Dapremont C, Denis LA, Sonnet P, Massip S, Jarry C First synthesis of 1,3-alternate 25,27-dialkyloxy-5,17-diarylcalix[4] arenes-crown-6 as new cesium selective extracants by Suzuki cross-coupling reaction. Supramol Chem 2004;16:319-329. (Pubitemid 39077667)
41. Pires VS, Gaboriau F, Guillon J, Nascimento S, Dassonville A, Lescoat G, Desplat V, Rochette J, Jarry C, Sonnet P. Modulation of cell proliferation in rat liver cell cultures by new calix[4]arenes. J Enzyme Inhib Med Chem 2006;21:261-70. (Pubitemid 44083954)
42. Rouge P, Silva Pires V, Gaboriau F, Dassonville-Klimpt A, Guillon J, Da Nascimento S, Léger JM, Lescoat G, Sonnet P. Antiproliferative efect on HepaRG cell cultures of new calix[4]arenes. J Enzyme Inhib Med Chem 2009;25:216-227.
43. Gripon P, Rumin S, Urban S, Le Seyec J, Glaise D, Cannie I, Guyomard C, Lucas J, Trepo C and Guguen-Guillouzo C Infection of a human hepatoma cell line by hepatitis B virus. Proc Natl Acad Sci USA 2002;99:15655-15660. (Pubitemid 35403987)
44. Troadec MB, Glaise D, Lamirault G, Le Cunf M, Guerin E, Le Meur N, Detivaud L, Zindy P, Leroyer P, Guisle I, Duval H, Gripon P, Teret N, Boudjema K, Guguen-Guillouzo C, Brissot P, Leger JJ and Loreal O. Hepatocyte iron loading capacity is associated with diferentiation and repression of motility in the HepaRG cell line. Genomics 2006;87:93-103. (Pubitemid 43005105)
45. Rouan MC, Marfl F, Mangoni P, Sechaud R, Humbert H and 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. (Pubitemid 32324086)
46. Tomas F, Serratrice G, Beguin C, Aman ES, Pierre JL, Fontecave M, Laulhere JP. Calcein as a fuorescent probe for ferric iron. Application to iron nutrition in plant cells. J Biol Chem 1999;274:13375-13383.
47. Hasinof BB. Te intracellular iron sensor calcein is catalytically oxidatively degraded by iron(II) in a hydrogen peroxide-dependent reaction. J Inorg Biochem 2003;95:157-164.
48. Rodbard D, McClean SW. Automated computer analysis for enzyme multiplied immunological techniques. Clin Chem 1977;23:112-115. (Pubitemid 8015720)
49. Bonache MC, Chamorro C, Velasquez S, De Clercq E, Balzarini J, Rodriguez Barrios F, Gago F, Camarasa MJ, San-Felix A. Improving the antiviral efocoency and selectivity of HIV-1 reverse transcriptase inhibithor TSAO-T by the introduction of functional groups at the N-3 position. J Med Chem 2005;48:6653-6660. (Pubitemid 41509181)
50. Mallia MB, Subramanian S, Mathur A, Sarma HD, Venkatesh M, Banerjee S. On the isolation and evaluation of a novel unsubstituted 5-nitroimidazole derivative as an agent to target tumor hypoxia. Bioorg Med Chem Lett 2008;18:5233-5237.
51. Gutsche CD, Lee-Gin L. Calixarenes 12. Te synthesis of functionalized calixarenes. Tetrahedron 1986;42:1633-1640.
52. Casnati A, Arduini A, Ghidini E, Pochini A, Ungaro R. A general synthesis of calix[4]arene monoalkyl ethers. Tetrahedron 1991;47:2221-2228.
53. Berg SS, Newbery G. Chemotherapeutic amidines. X. Substituted 4,4'-diamidino-ω,ω-diphenoxyalkanes and-diphenylethers. J Chem Soc 1949; 642-648.
54. Barboso S, Garcia Carrera A, Matthews SE, Arnaud-Neu F, Böhmer V, Dozol JF, Rouquette H, Schwing-Weill MJ. Calix[4]arenes with CMPO functions at the narrow rim. Synthesis and extraction properties. J Chem Soc, Perkin Trans 2 1999;4:719-723. (Pubitemid 129639866)
55. Rudzevich Y, Rudzevich V, Moon C, Schnell I, Fischer K, Böhmer V. Self-assembly of programmed building blocks into structurally uniform dendrimers. J Am Chem Soc 2005;127:14168-14169. (Pubitemid 41457566)
56. Clark TE, Makha M, Raston CL, Sobolev AN. Supersized bilayers based on an O-alkyl substituted calix[4]arene. CrystEngComm 2006;8:707-711. (Pubitemid 44372580)
57. Ismail MA, Arafa RK, Brun R, Wenzler T, Miao Y, Wilson WD, Generaux C, Bridges A, Hall JE, Boykin DW. Synthesis, DNA afnity, and antiprotozoal activity of linear dications: terphenyl diamidines and analogues. J Med Chem 2006;49:5324-5332. (Pubitemid 44260226)
58. Dalai S, Belov VN, Nizamov S, Rauch K, Finsinger D, de Meijere A. Access to Variously Substituted 5,6,7,8-Tetrahydro-3H-quinazolin-4-ones via Diels-Alder Adducts of Phenyl Vinyl Sulfone to Cyclobutene-Annelated Pyrimidinones. Eur J Org Chem 2006;12:2753-2765.
59. Ismail MA, Arafa RK, Wenzler T, Brun R, Tanious FA, Wilson WD, Boykin DW. Synthesis and antiprotozoal activity of novel bis-benzamidinoimidazo[1,2-a] pyridines and 5,6,7,8-tetrahydroimidazo[1,2-a]pyridines. Bioorg Med Chem 2008;16:683-691. (Pubitemid 351163070)
60. Supplementary X-ray crystallographic data of compounds 1, 2 and 3 (CCDC-748460, CCDC-748458 and CCDC-748459): Cambridge Crystallographic Data Centre, University Chemical Lab, 12 Union Road, Cambridge, CB2 1EZ, UK; E-mail: deposit@ccdc.cam.ac.uk.