Activation of C-H bonds in nitrones leads to iridium hydrides with antitumor activity

Journal of Medicinal Chemistry

Volumn 56, Issue 16, 2013, Pages 6531-6535

  Song, Xiaoda ^a   Qian, Yong ^a   Ben, Rong ^a   Lu, Xiang ^a   Zhu, Hai Liang ^a   Chao, Hui ^a,c   Zhao, Jing ^a,b  

^a NANJING UNIVERSITY   (China)

^b PEKING UNIVERSITY   (China)

^c SUN YAT SEN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CISPLATIN; IRIDIUM COMPLEX; N TERT BUTYL ALPHA PHENYLNITRONE; NITRONE DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CELL STRAIN HEPG2; CHEMICAL BOND; CONTROLLED STUDY; DRUG DESIGN; DRUG DNA INTERACTION; DRUG EFFICACY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; INSTITUTE FOR CANCER RESEARCH MOUSE; MOUSE; NONHUMAN; TUMOR XENOGRAFT;

ANIMALS; ANTINEOPLASTIC AGENTS; CARBON; HYDROGEN; IRIDIUM; MICE; MICE, INBRED ICR; MODELS, MOLECULAR; NITROGEN OXIDES;

EID: 84883161413     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm4004973     Document Type: Article

References (35)

1. Brabec, V. DNA modifications by antitumor platinum and ruthenium compounds: their recognition and repair Prog. Nucleic Acid Res. Mol. Biol. 2002, 71, 1-68
2. Clarke, M. J. Ruthenium metallopharmaceuticals Coord. Chem. Rev. 2003, 236, 209-233
3. Keppler, B., Ed. Metal Complexes in Cancer Chemotherapy; VCH, Weinheim, Germany; New York, 1993.
4. Hartinger, C. G.; Dyson, P. J. Bioorganometallicchemistry-from teaching paradigms to medicinal applications Chem. Soc. Rev. 2009, 38, 391-401
5. Hartinger, C. G.; Metzler-Nolte, N.; Dyson, P. J. Challenges and opportunities in the development of organometallic anticancer drugs Organometallics 2012, 31, 5677-5685
6. Wirth, S.; Rohbogner, C. J.; Cieslak, M.; Julia, K. B.; Donevski, S.; Nawrot, B.; Lorenz, I. P. Rhodium(III) and iridium(III) complexes with 1,2-naphthoquinone-1-oximate as a bidentate ligand: synthesis, structure, and biological activity J. Biol. Inorg. Chem. 2010, 15, 429-440
7. Wong, E.; Giandomenico, C. M. Current status of platinum-based antitumor drugs Chem. Rev. 1999, 99, 2451-2466
8. Guo, Z.; Sadler, P. J. Metals in medicine Angew. Chem., Int. Ed. Engl. 1999, 38, 1512-1531
9. Ho, Y. P.; AuYeung, S. C. F.; To, K. K. W. Platinum-based anticancer agents: innovative design strategies and biological perspectives Med. Res. Rev. 2003, 23, 633-655
10. Bruijnincx, P. CA.; Sadler, P. J. Controlling platinum, ruthenium, and osmium reactivity for anticancer drug design Curr. Opin. Chem. Biol. 2008, 12, 197-206
11. Sava, G.; Bergamo, A. \Ruthenium-based compounds and tumour growth control Int. J. Oncol. 2000, 17, 353-365
12. Galanski, M.; Arion, V. B.; Jakupec, M. A.; Keppler, B. K. Recent developments in the field of tumor-inhibiting metal complexes Curr. Pharm. Des. 2003, 9, 2078-2089
13. Habtemariam, A.; Melchart, M.; Fernandez, R.; Parsons, S.; Oswald, I. D. H.; Parkin, A.; Fabbiani, F. P. A.; Davidson, J. E.; Dawson, A.; Aird, R. E.; Jodrell, D. I.; Sadler, P. J. Structure-activity relationships for cytotoxic ruthenium(II) arene complexes containing N, N -, N, O -, and O, O -chelating ligands J. Med. Chem. 2006, 49, 6858-6868
14. Hartinger, C. G.; Jakupec, M. A.; Zorbas-Seifried, S.; Groessl, M.; Egger, A.; Berger, W.; Zorbas, H.; Dyson, P. J.; Keppler, B. K. KP1019, a new redox-active anticancer agent-preclinical development and results of a clinical phase I study in tumor patients Chem. Biodiversity 2008, 5, 2140-2155
15. Lau, J. S.; Lee, P. K.; Tsang, K. H.; Ng, C. H.; Lam, Y. W.; Cheng, S. H.; Lo, K. K. Luminescent cyclometalated iridium(III) polypyridine indole complexes-synthesis, photophysics, electrochemistry, protein-binding properties, cytotoxicity, and cellular uptake Inorg. Chem. 2009, 48, 708-718
16. Amouri, H.; Moussa, J.; Renfrew, A. K.; Dyson, P. J.; Rager, M. N.; Chamoreau, L. M. Discovery, structure, and anticancer activity of an iridium complex of diselenobenzoquinone Angew. Chem., Int. Ed. Engl. 2010, 49, 7530-7533
17. Liu, Z.; Habtemariam, A.; Pizarro, A. M.; Fletcher, S. A.; Kisova, A.; Vrana, O.; Salassa, L.; Bruijnincx, P. C.; Clarkson, G. J.; Brabec, V.; Sadler, P. J. Organometallic half-sandwich iridium anticancer complexes J. Med. Chem. 2011, 54, 3011
18. Wilbuer, A.; Vlecken, D. H.; Schmitz, D. J.; Kräling, K.; Harms, K.; Bagowski, C. P.; Meggers, E. Iridium complex with antiangiogenic properties Angew. Chem., Int. Ed. Engl. 2010, 49, 3839-3842
19. Leung, C. H.; Zhong, H. J.; Yang, H.; Cheng, Z.; Chan, D. S.; Ma, V. P.; Wong, C. Y.; Ma, D. L. A metal-based inhibitor of tumor necrosis factor-α Angew. Chem., Int. Ed. Engl. 2012, 51, 9010-9014
20. 2CS) on the intercalation of (g5-pentamethylcyclopentadienyl)-iridium(III)- dipyridoquinoxaline and -dipyridophenazine complexes J. Organomet. Chem. 2007, 692, 1300-1309
21. Schmitt, F.; Govindaswamy, P.; Süss-Fink, G.; Ang, W. H.; Dyson, P. J.; Jeanneret, L. J.; Therrien, B. Ruthenium porphyrin compounds for photodynamic therapy of cancer J. Med. Chem. 2008, 51, 1811-1816
22. 2{d(pGpG}], the principal adduct formed by cis -diamminedichloroplatinum(II) with DNA J. Am. Chem. Soc. 1988, 110, 7368-7738
23. Huang, H.; Zhu, L.; Reid, B. R.; Drobny, G. P.; Hopkins, P. B. Solution structure of a cisplatin-induced DNA interstrand cross-link Science 1995, 270, 1842-1844
24. Wang, D.; Lippard, S. J. Cellular processing of platinum anticancer drugs Nature Rev. Drug Discovery 2005, 4, 307-320
25. Bernotas, R. C.; Thomas, C. E.; Carr, A. A.; Nieduzak, T. R.; Adams, G.; Ohlweiler, D. F.; Hay, D. A. Synthesis and radical scavenging activity of 3,3-dialkyl-3,4-dihydro-isoquinoline 2-oxides Bioorg. Med. Chem. Lett. 1996, 6, 1105-1110
26. Nakae, D.; Kishida, H.; Enami, T.; Konishi, Y.; Hensley, K. L.; Floyd, R. A.; Kotake, Y. Effects of phenyl N-tert -butyl nitrone and its derivatives on the early phase of hepatocarcinogenesis in rats fed a choline-deficient, l -amino acid-defined diet Cancer Sci 2003, 94, 26-31
27. Floyd, R. A.; Kopke, R. D.; Choi, C. H.; Foster, S. B.; Doblas, S.; Towner, R. A. Nitrones as therapeutics Free Radical Biol. Med. 2008, 45, 1361-1374
28. Floyd, R. A.; Towner, R. A.; Wu, D.; Abbott, A.; Cranford, R.; Branch, D.; Guo, W. X.; Foster, S. B.; Jones, I.; Alam, R.; Moore, D.; Allen, T.; Huycke, M. Anti-cancer activity of nitrones in the ApcMin/+ model of colorectal cancer Free Radical Res. 2010, 44, 108
29. Floyd, R. A.; Chandru, H. K.; He, T.; Towner, R. Anti-cancer activity of nitrones and observations on mechanism of action Anticancer Agents Med. Chem. 2011, 11, 373-379
30. Crabtree, R. H.; Parnell, C. P. Arene and cyclohexadienyl complexes as intermediates in the selective catalytic dehydrogenation of cyclohexenes to arenes Organometallics 1985, 4, 519-523
31. 50 is very close to the results reported in Sbovata, S. M.; Bettio, F.; Mozzon, M.; Bertani, R.; Venzo, A.; Benetollo, F.; Michelin, R. A.; Gandin, V.; Marzano, C. Cisplatinum and transplatinum complexes with benzyliminoether ligands: synthesis, characterization, structure-activity relationships, and in vitro and in vivo antitumor efficacy J. Med. Chem. 2007, 50, 4775-4784
32. Jung, Y.; Lippard, S. J. Direct cellular responses to platinum-induced DNA damage Chem. Rev. 2007, 107, 1387-1407
33. Bosea, R. N.; Maurmann, L.; Mishur, R. L.; Yasui, L.; Gupta, S.; Grayburn, W. S.; Hofstetter, H.; Salley, T. Non-DNA-binding platinum anticancer agents: cytotoxic activities of platinum-phosphato complexes towards human ovarian cancer cells Proc. Natl. Acad. Sci. U. S. A. 2008, 105, 18314-18319
34. Fu, Y.; Romero, M. J.; Habtemariam, A.; Snowden, M. E.; Song, L.; Clarkson, G. J.; Qamar, J.; Pizarro, A. M.; Unwin, P. R.; Sadler, P. J. The contrasting chemical reactivity of potent isoelectronic iminopyridine and azopyridineosmium(II) arene anticancer complexes Chem. Sci. 2012, 3, 2485-2494
35. Betanzos-Lara, S.; Liu, Z.; Habtemariam, A.; Pizarro, A. M.; Qamar, B.; Sadler, P. J. Organometallic ruthenium and iridium transfer-hydrogenation catalysts using coenzyme NADH as a cofactor Angew. Chem., Int. Ed. 2012, 51, 3897-3900