New 5-Aryl-1H-imidazoles display in vitro antitumor activity against apoptosis-resistant cancer models, including melanomas, through mitochondrial targeting.
Mathieu, Véronique; Van Den Brege, E; Ceusters, Justineet al.
2013 • In Journal of Medicinal Chemistry, 56 (17), p. 6626-6637
Ceusters, Justine ; Université de Liège - ULiège > Clinique des grands animaux (chirurgie)
Konopka, T
Cops, A
Bruyère, C
Pirker, C
Berger, W
Trieu-Van, T
Serteyn, Didier ; Université de Liège - ULiège > Dép. clinique des animaux de compagnie et des équidés (DCA) > Anesthésiologie gén. et pathologie chirurg. des grds animaux
Kiss, R
Robiette, R
Language :
English
Title :
New 5-Aryl-1H-imidazoles display in vitro antitumor activity against apoptosis-resistant cancer models, including melanomas, through mitochondrial targeting.
Publication date :
September 2013
Journal title :
Journal of Medicinal Chemistry
ISSN :
0022-2623
eISSN :
1520-4804
Publisher :
American Chemical Society, Washington, United States - District of Columbia
Talbäck, M.; Stenbeck, M.; Rosén, M.; Barlow, L.; Glimelius, B. Cancer survival in Sweden 1960-1998: developments across 4 decades Acta Oncol. 2003, 42, 637-659
Verdecchia, A.; Francisci, S.; Brenner, H.; Gatta, G.; Micheli, A.; Mangone, L.; Kunkler, I.; EUROCARE-4 Working Group. Recent cancer survival in Europe: a 2000-02 period analysis of EUROCARE-4 data Lancet Oncol. 2007, 8, 784-796
Erratum in Lancet Oncol. 2008, 9, 416.
Chen, K. G.; Sikic, B. I. Molecular pathways: regulation and therapeutic implications of multidrug resistance Clin. Cancer Res. 2012, 18, 1863-1869
Wilting, R. H.; Dannenberg, J. H. Epigenetic mechanisms in tumorigenesis, tumor cell heterogeneity and drug resistance Drug Resist Updates 2012, 15, 21-38
Wilson, T. R.; Johnston, P. G.; Longley, D. B. Anti-apoptotic mechanisms of drug resistance in cancer Curr. Cancer Drug Targets 2009, 9, 307-319
Wong, R. S. Apoptosis in cancer: from pathogenesis to treatment J. Exp. Clin. Cancer Res. 2011, 30, 87
Savage, P.; Stebbing, J.; Bower, M.; Crook, T. Why does cytotoxic chemotherapy cure only some cancers? Nat. Clin. Pract. Oncol. 2009, 6, 43-52
Lefranc, F.; Brotchi, J.; Kiss, R. Possible future issues in the treatment of glioblastomas, with a special emphasis on cell migration and the resistance of migrating glioblastoma cells to apoptosis J. Clin. Oncol. 2005, 23, 2411-2422
Soengas, M. S.; Lowe, S. W. Apoptosis and melanoma chemoresistance Oncogene 2003, 22, 3138-3151
La Porta, C. A. Mechanism of drug sensitivity and resistance in melanoma Curr Cancer Drug Targets 2009, 9, 391-397
Han, S.; Roman, J. Targeting apoptotic signaling pathways in human lung cancer Curr. Cancer Drug Targets 2010, 10, 566-574
Sugerman, P. B.; Joseph, B. K.; Savage, N. W. Review article: The role of oncogenes, tumour suppressor genes and growth factors in oral squamous cell carcinoma: a case of apoptosis versus proliferation Oral Dis. 1995, 1, 172-188
D'Amico, T. A.; Harpole, D. H., Jr. Molecular biology of esophageal cancer Chest Surg. Clin. North Am. 2000, 10, 451-469
Wong, H. H.; Lemoine, N. R. Pancreatic cancer: molecular pathogenesis and new therapeutic targets Nat. Rev. Gastroenterol. Hepatol. 2009, 6, 412-422
Bellina, F.; Cauteruccio, S.; Rossi, R. Synthesis and biological activity of vicinal diaryl-substituted 1 H -imidazoles Tetrahedron 2007, 63, 4571-4624
Bellina, F.; Cauteruccio, S.; Di Fiore, A.; Marchetti, C.; Rossi, R. Highly selective synthesis of 4(5)-aryl-, 2,5(5)-diaryl-, and 4,5-diaryl-1 H -imidazoles via Pd-catalyzed direct C-5 arylation of 1-benzyl-1 H -imidazole Tetrahedron 2008, 64, 6060-6072
Chen, J.; Ahn, S.; Wang, J.; Lu, Y.; Dalton, J. T.; Miller, D. D.; Li, W. Discovery of novel 2-aryl-4-benzoyl-imidazole (ABI-III) analogues targeting tubulin polymerization as antiproliferative agents J. Med. Chem. 2012, 55, 7285-7289
Nshimyumukiza, P.; Van Den Berge, E.; Delest, B.; Mijatovic, T.; Kiss, R.; Marchand-Brynaert, J.; Robiette, R. Synthesis and biological evaluation of novel imidazole-containing macrocycles Tetrahedron 2010, 66, 4515-4520
Hanahan, D.; Weinberg, R. A. Hallmarks of cancer: the next generation Cell 2011, 144, 646-674
Delest, B.; Nshimyumukiza, P.; Fasbender, O.; Tinant, B.; Marchand-Brynaert, J.; Darro, F.; Robiette, R. Divergent and regioselective synthesis of 1,2,4- and 1,2,5-trisubstituted imidazoles J. Org. Chem. 2008, 73, 6816-6823
Van Den Berge, E.; Pospisil, J.; Tran, T. V.; Collard, L.; Robiette, R. Planar chirality of imidazole-containing macrocycles: understanding and tuning atropoisomerism Eur. J. Org. Chem. 2011, 6649-6655
Ermolat'ev, D. S.; Abaev, E. V.; Van der Eycken, E. V. Efficient one pot, two step, microwave-assisted procedure for the synthesis of polysubstituted 2-aminoimidazoles Org. Lett. 2006, 8, 5781-5784
Ermolat'ev, D. S.; Alifanov, V. L.; Rybakov, V. B.; Babaev, E. V.; Van der Eycken, E. V. A concise microwave-assisted synthesis of 2-aminoimidazole marine sponge alkaloids of the isonaamines series Synthesis 2008, 13, 2083-2088
Van Goietsenoven, G.; Hutton, J.; Becker, J. P.; Lallemand, B.; Robert, F.; Lefranc, F.; Pirker, C.; Vandenbussche, G.; Van Antwerpen, P.; Evidente, A.; Berger, W.; Prévost, M.; Pelletier, J.; Kiss, R.; Kinzy, T. G.; Kornienko, A.; Mathieu, V. Targeting of eEF1A with Amaryllidaceae isocarbostyrils as a strategy to combat melanomas FASEB J. 2010, 24, 4575-4584
Dumont, P.; Ingrassia, L.; Rouzeau, S.; Ribaucour, F.; Thomas, S.; Roland, I.; Darro, F.; Lefranc, F.; Kiss, R. The Amaryllidaceae isocarbostyril narciclasine induces apoptosis by activation of the death receptor and/or mitochondrial pathways in cancer cells but not in normal fibroblasts Neoplasia 2007, 9, 766-776
Yao, Y.; Jia, X. Y.; Tian, H. Y.; Jiang, Y. X.; Xu, G. J.; Qian, Q. J.; Zhao, F. K. Comparative proteomic analysis of colon cancer cells in response to oxaliplatin treatment Biochim. Biophys. Acta 2009, 1794, 1433-1440
Branle, F.; Lefranc, F.; Camby, I.; Jeuken, J.; Geurts-Moespot, A.; Sprenger, S.; Sweep, F.; Kiss, R.; Salmon, I. Evaluation of the efficiency of chemotherapy in in vivo orthotopic models of human glioma cells with and without 1p19q deletions and in C6 rat orthotopic allografts serving for the evaluation of surgery combined with chemotherapy Cancer 2002, 95, 641-655
Ingrassia, L.; Lefranc, F.; Dewelle, J.; Pottier, L.; Mathieu, V.; Spiegl-Kreinecker, S.; Sauvage, S.; El Yazidi, M.; Dehoux, M.; Berger, W.; Van Quaquebeke, E.; Kiss, R. Structure-activity relationship analysis of novel derivatives of narciclasine (an Amaryllidaceae isocarbostyril derivative) as potential anticancer agents J. Med. Chem. 2009, 52, 1100-1114
Mijatovic, T.; Mathieu, V.; Gaussin, J. F.; De Nève, N.; Ribaucour, F.; Van Quaquebeke, E.; Dumont, P.; Darro, F.; Kiss, R. Cardenolide-induced lysosomal membrane permeabilization demonstrates therapeutic benefits in experimental human non-small cell lung cancers Neoplasia 2006, 8, 402-412
Paull, K. D.; Shoemaker, R. H.; Hodes, L.; Monks, A.; Scudiero, D. A.; Rubinstein, L.; Plowman, J.; Boyd, M. R. Display and analysis of patterns of differential activity of drugs against human tumor cell lines: development of mean graph and COMPARE algorithm J. Natl. Cancer Inst. 1989, 81, 1088-1092
Chan, J.; Khan, S. N.; Harvey, I.; Merrick, W.; Pelletier, J. Eukaryotic protein synthesis inhibitors identified by comparison of cytotoxicity profiles RNA 2004, 10, 528-543
Frédérick, R.; Bruyère, C.; Vancraeynest, C.; Reniers, J.; Meinguet, C.; Pochet, L.; Backlund, A.; Masereel, B.; Kiss, R.; Wouters, J. Novel trisubstituted harmine derivatives with original in vitro anticancer activity J. Med. Chem. 2012, 55, 6489-6501
Mathieu, V.; Pirker, C.; Schmidt, W. M.; Spiegl-Kreinecker, S.; Lötsch, D.; Heffeter, P.; Hegedus, B.; Grusch, M.; Kiss, R.; Berger, W. Aggressiveness of human melanoma xenograft models is promoted by aneuploidy-driven gene expression deregulation Oncotarget 2012, 3, 399-413
Le Mercier, M.; Mathieu, V.; Haibe-Kains, B.; Bontempi, G.; Mijatovic, T.; Decaestecker, C.; Kiss, R.; Lefranc, F. Knocking down galectin 1 in human hs683 glioblastoma cells impairs both angiogenesis and endoplasmic reticulum stress responses J. Neuropathol. Exp. Neurol. 2008, 67, 456-469
Gautam, P.; Upadhyay, S. K.; Hassan, W.; Madan, T.; Sirdeshmukh, R.; Sundaram, C. S.; Gade, W. N.; Basir, S. F.; Singh, Y.; Sarma, P. U. Transcriptomic and proteomic profile of Aspergillus fumigatus on exposure to artemisinin Mycopathologia 2011, 172, 331-346
Cui, Y.; Paules, R. S. Use of transcriptomics in understanding mechanisms of drug-induced toxicity Pharmacogenomics 2010, 11, 573-585
Blackman, R. K.; Cheung-Ong, K.; Gebbia, M.; Proia, D. A.; He, S.; Kepros, J.; Jonneaux, A.; Marchetti, P.; Kluza, J.; Rao, P. E.; Wada, Y.; Giaever, G.; Nislow, C. Mitochondrial electron transport is the cellular target of the oncology drug elesclomol PLoS One 2012, 7, e29798
O'Day, S.; Gonzalez, R.; Lawson, D.; Weber, R.; Hutchins, L.; Anderson, C.; Haddad, J.; Kong, S.; Williams, A.; Jacobson, E. Phase II, randomized, controlled, double-blinded trial of weekly elesclomol plus paclitaxel versus paclitaxel alone for stage IV metastatic melanoma J. Clin. Oncol. 2009, 27, 5452-5458
Warburg, O. Versuche am überlebenden karzinomgewebe Biochem. Z. 1923, 142, 317-333
Montero, A. J.; Jassem, J. Cellular redox pathways as a therapeutic target in the treatment of cancer Drugs 2011, 71, 1385-1396
Filipp, F. V.; Ratnikov, B.; De Ingeniis, J.; Smith, J. W.; Osterman, A. L.; Scott, D. A. Glutamine-fueled mitochondrial metabolism is decoupled from glycolysis in melanoma Pigm. Cell Melanoma Res. 2012, 25, 732-739
Wenner, C. E. Targeting mitochondria as a therapeutic target in cancer J Cell. Physiol. 2012, 227, 450-456
Murphy, M. P. Mitochondrial thiols in antioxidant protection and redox signaling: distinct roles for glutathionylation and other thiol modifications Antioxid Redox Signaling 2012, 16, 476-95
Indran, I. R.; Tufo, G.; Pervaiz, S.; Brenner, C. Recent advances in apoptosis, mitochondria and drug resistance in cancer cells Biochim. Biophys. Acta 2011, 1807, 735-745
Burhans, W. C.; Heintz, N. H. The cell cycle is a redox cycle: linking phase-specific targets to cell fate Free Radical Biol. Med. 2009, 47, 1282-1293
Debeir, O.; Mégalizzi, V.; Warzée, N.; Kiss, R.; Decaestecker, C. Videomicroscopic extraction of specific information on cell proliferation and migration in vitro Exp. Cell Res. 2008, 314, 2985-2998
Le Calvé, B.; Lallemand, B.; Perrone, C.; Lenglet, G.; Depauw, S.; Van Goietsenoven, G.; Bury, M.; Vurro, M.; Herphelin, F.; Andolfi, A.; Zonno, M. C.; Mathieu, V.; Dufrasne, F.; VanAntwerpen, P.; Poumay, Y.; David-Cordonnier, M. H.; Evidente, A.; Kiss, R. In vitro anticancer activity, toxicity and structure-activity relationships of phyllostictine A, a natural oxazatricycloalkenone produced by the fungus Phyllostictacirsii Toxicol. Appl. Pharmacol. 2011, 254, 8-17
Gnoula, C.; Mégalizzi, V.; De Nève, N.; Sauvage, S.; Ribaucour, F.; Guissou, P.; Duez, P.; Dubois, J.; Ingrassia, L.; Lefranc, F.; Kiss, R.; Mijatovic, T. Balanitin-6 and -7:diosgenylsaponins isolated from Balanites aegyptiaca Del. display significant anti-tumor activity in vitro and in vivo Int. J. Oncol. 2008, 32, 5-15
