Regression of lung cancer by hypoxia-sensitizing ruthenium polypyridyl complexes

Molecular Cancer Therapeutics

Volumn 12, Issue 5, 2013, Pages 643-653

  Yadav, Abhishek ^a   Janaratne, Thamara ^a   Krishnan, Arthi ^a   Singhal, Sharad S ^c   Yadav, Sushma ^c   Dayoub, Adam S ^a   Hawkins, Doyle L ^b   Awasthi, Sanjay ^c   MacDonnell, Frederick M ^a,b  

^a Department of Chemistry and Biochemistry ^*  (United States)

^b UNIVERSITY OF TEXAS AT ARLINGTON   (United States)

^c CITY OF HOPE NATIONAL MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CISPLATIN; DNA; FREE RADICAL; RUTHENIUM COMPLEX; RUTHENIUM POLYPYRIDYL COMPLEX; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; COORDINATION COMPOUND; RUTHENIUM;

ANIMAL EXPERIMENT; ANIMAL MODEL; APOPTOSIS; ARTICLE; CANCER CELL; CANCER CELL CULTURE; CELL HYPOXIA; CHEMOSENSITIVITY; CONTROLLED STUDY; CYTOTOXICITY; DNA CLEAVAGE; DRUG EXCRETION; DRUG METABOLISM; DRUG STABILITY; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; LD 50; LUNG NON SMALL CELL CANCER; MALE; MOUSE; NONHUMAN; PRIORITY JOURNAL; SIGNAL TRANSDUCTION; TUMOR GROWTH; TUMOR XENOGRAFT; URINARY EXCRETION; ANIMAL; CARCINOMA, NON-SMALL-CELL LUNG; CELL PROLIFERATION; CHEMISTRY; DRUG EFFECTS; DRUG SCREENING; IC50; LUNG NEOPLASMS; METABOLISM; NUDE MOUSE; PATHOLOGY; TOXICITY; TUMOR CELL LINE; TUMOR VOLUME;

ANIMALS; ANTINEOPLASTIC AGENTS; APOPTOSIS; CARCINOMA, NON-SMALL-CELL LUNG; CELL HYPOXIA; CELL LINE, TUMOR; CELL PROLIFERATION; COORDINATION COMPLEXES; DNA CLEAVAGE; HUMANS; INHIBITORY CONCENTRATION 50; LUNG NEOPLASMS; MALE; MICE; MICE, NUDE; RUTHENIUM; TUMOR BURDEN; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 84877645679     PISSN: 15357163     EISSN: 15388514     Source Type: Journal    
DOI: 10.1158/1535-7163.MCT-12-1130     Document Type: Article

References (47)

1. Lippert B, Editor. Cisplatin chemistry and biochemistry of a leading anticancer drug. Weinheim, Germany: Wiley-VCH; 1999.
2. Clarke MJ. Ruthenium metallopharmaceuticals. Coord Chem Rev 2003;236:209-33.
3. Jakupec MA, Galanski M, Arion VB, Hartinger CG, Keppler BK. Antitumour metal compounds: more than theme and variations. Dalton Trans 2008:183-94.
4. Allardyce CS, Dyson PJ. Ruthenium in medicine: current clinical uses and future prospects. Platin Met Rev 2001;45:62-9.
5. Bergamo A, Gava B, Alessio E, Mestroni G, Serli B, Cocchietto M, et al. Ruthenium-based NAMI-A type complexes with in vivo selective metastasis reduction and in vitro invasion inhibition unrelated to cell cytotoxicity. Int J Oncol 2002;21:1331-8.
6. Depenbrock H, Schmelcher S, Peter R, Keppler BK, Weirich G, Block T, et al. Preclinical activity of trans-indazolium [tetrachlorobisindazoleruthenate(III)] (NSC 666158; IndCR; KP 1019) against tumour colony-forming units and haematopoietic progenitor cells. Eur J Cancer 1997;33:2404-10.
7. Lentz F, Drescher A, Lindauer A, Henke M, Hilger RA, Hartinger CG, et al. Pharmacokinetics of a novel anticancer ruthenium complex (KP1019, FFC14A) in a phase I dose-escalation study. Anticancer Drugs 2009;20:97-103.
8. Hartinger CG, Jakupec MA, Zorbas-Seifried S, Groessl M, Egger A, Berger W, et al. KP1019, a new redox-active anticancer agent-preclinical development and results of a clinical phase I study in tumor patients. Chem Biodivers 2008;5:2140-55.
9. Morris RE, Aird RE, Murdoch PDS, Chen H, Cummings J, Hughes ND, et al. Inhibition of cancer cell growth by ruthenium(II) arene complexes. J Med Chem 2001;44:3616-21.
10. Meng X, Leyva ML, Jenny M, Gross I, Benosman S, Fricker B, et al. A ruthenium-containing organometallic compound reduces tumor growth through induction of the endoplasmic reticulum stress gene CHOP. Cancer Res 2009;69:5458-66.
11. Shulman A, Dwyer FP. Metal chelates in biological systems. In:Dwyer FP, Mellor DP, editors. Chelating agents and metal chelates. New York, NY: Academic Press; 1964. p. 383-439.
12. Beccari E. Pharmacological studies on the ferrous tri-2,20-bipyridyl complex. IV. Relation between concentration in the blood and action on the central nervous system. Boll Soc Ital Biol Sper 1941;16:216-8.
13. Koch JH, Rogers WP, Dwyer FP, Gyarfas EC. The metabolic fate of tris-1,10-phenanthroline ruthenium-106 (II) perchlorate, a compound with anticholinesterase and curare-like activity. Aust J Biol Sci 1957;10: 342-50.
14. Dwyer FP, Mayhew E, Roe EMF, Shulman A. Inhibition of Landschuetz ascites tumor growth by metal chelates derived from 3,4,7,8-tetramethyl-1,10- phenanthroline. Br J Cancer 1965;19:195-9.
15. Koch JH, Gyarfas EC, Dwyer FP. Biological activity of complexions. Mechanism of inhibition of acetylcholinesterase. Aust J Biol Sci 1956;9:371-81.
16. Dwyer FP, Gyarfas EC, Rogers WP, Koch JH. Biological activity of complex ions. Nature 1952;170:190-1.
17. White DO, Harris AW, Cheyne IM, Shew M. Actions of metal chelates of substituted 1,10-phenanthrolines on viruses and cells. 3. Actions on cultured cells. Aust J Exp Biol Med Sci 1969;47:81-9.
18. Augustyn KE, Pierre VC, Barton JK, editors. Metallointercalators as probes of DNA recognition and reactions. Wiley encyclopedia of chemical biology London, England: John Wiley & Sons, Inc.; 2009.
19. Pisani MJ, Weber DK, Heimann K, Collins JG, Keene FR. Selective mitochondrial accumulation of cytotoxic dinuclear polypyridyl ruthenium( II) complexes. Metallomics 2010;2:393-6.
20. 2 with N-N 1/4; bpy, phen, dpq, dppz, and dppn. Chem Med Chem 2008;3:1104-9.
21. Pascu G, Hotze A, Sanchez-Cano C, Kariuki B, Hannon M. Dinuclear ruthenium(II) triple-stranded helicates: luminescent supramolecular cylinders that bind and coil dna and exhibit activity against cancer cell lines. Angew Chem Int Ed 2007;46:4374-8.
22. Gill MR, Garcia-Lara J, Foster SJ, Smythe C, Battaglia G, Thomas JA.A ruthenium(II) polypyridyl complex for direct imaging of DNAstructure in living cells. Nat Chem 2009;1:662-7.
23. Novakova O, Kasparkova J, Vrana O, van Vliet PM, Reedijk J, Brabec V. Correlation between cytotoxicity and DNA binding of polypyridyl ruthenium complexes. Biochemistry 1995;34:12369-78.
24. Dwyer FP, Gyarfas EC, Wright RD, Shulman A. Effect of inorganic complex ions on transmission at a neuromuscular junction. Nature 1957;179:425-6.
25. Koch JH, Gallagher CH. Effect of some neuromuscular blocking agents on mitochondrial enzyme systems. Nature 1959;184:1039-41.
26. Mayhew E, Roe EM, Shulman A. Microscopical observations on the effects of phenanthroline chelates on Landsch€utz ascites tumour cells. J R Microsc Soc 1965;84:475-83.
27. Puckett CA, Barton JK. Methods to explore cellular uptake of ruthenium complexes. J Am Chem Soc 2007;129:46-7.
28. Puckett CA, Barton JK. Mechanism of cellular uptake of a ruthenium polypyridyl complex. Biochemistry 2008;47:11711-6.
29. Brabec V, Novakova O. DNA binding mode of ruthenium complexes and relationship to tumor cell toxicity. Drug Resist Updates 2006;9: 111-22.
30. 2-carboline complexes induce autophagy to antagonize mitochondrial-mediated apoptosis. J Med Chem 2010;53:7613-24.
31. Zava O, Zakeeruddin SM, Danelon C, Vogel H, Gratzel M, Dyson PJ. A Cytotoxic ruthenium Tris(Bipyridyl) complex that accumulates at plasma membranes. Chem Bio Chem 2009;10:1796-800.
32. 2+ with visible light. Chem Commun 2010;46: 2426-8.
33. Moucheron C, Kirsch-De Mesmaeker A, Kelly JM. Photophysics and photochemistry of metal polypyridyl and related complexes with nucleic acids. Struct Bonding 1998;92:163-216.
34. Janaratne TK, Yadav A, Ongeri F, MacDonnell FM. Preferential DNA cleavage under anaerobic conditions by a dna-binding ruthenium dimer. Inorg Chem 2007;46:3420-2.
35. Sun P, Krishnan A, Yadav A, Singh S, MacDonnell FM, Armstrong DW. Enantiomeric separations of ruthenium(II) polypyridyl complexes using high-performance liquid chromatography (HPLC) with cyclodextrin chiral stationary phases (CSPs). Inorg Chem 2007;46:10312-20.
36. MacDonnell FM, Bodige S. Efficient stereospecific syntheses of chiral ruthenium dimers. Inorg Chem 1996;35:5758-9.
37. Bolger J, Gourdon A, Ishow E, Launay J-P. Mononuclear and binuclear tetrapyrido[3,2-a:20,30-c:300,200-h:2000,3000-j]phenazine (tpphz) ruthenium and osmium complexes. Inorg Chem 1996;35:2937-44.
38. W€arnmark K, Thomas JA, Heyke O, Lehn J-M. Stereoisomerically controlled inorganic architectures: synthesis of enantio-and diastereo-merically pure ruthenium-palladium molecular rods from enantiopure building blocks. Chem Commun 1996;701-2.
39. Kim M-J, Konduri R, Ye H, MacDonnell FM, Puntoriero F, Serroni S, et al. Dinuclear ruthenium(II) polypyridyl complexes containing large, redox-active, aromatic bridging ligands: synthesis, characterization, and intramolecular quenching of MLCT excited states. Inorg Chem 2002;41:2471-6.
40. Kim M-J. Chiral metallodendrimers and oligomers containing Ru(II) polypyridyl complexes [Ph. D Thesis]. Arlington, TX: University of Texas at Arlington; 2000.
41. Singhal SS, Singhal J, Yadav S, Dwivedi S, Boor PJ, Awasthi YC, et al. Regression of lung and colon cancer xenografts by depleting or inhibiting RLIP76 (ral-binding protein 1). Cancer Res 2007;67:4382-9.
42. 3. J Org Chem 2005;70:9093-102.
43. Pratviel G, Bernadou J, Meunier B. DNA and RNA cleavage by metal complexes. Adv Inorg Chem 1998;45:251-312.
44. Janaratne TK. Investigation of ruthenium (II) polypyridyl dimers as potential chemotherepeutic agents [Ph. D Thesis]. Arlington, TX: University of Texas at Arlington;2006.
45. Rajput C, Rutkaite R, Swanson L, Haq I, Thomas JA. Dinuclear monointercalating RuII complexes that display high affinity binding to duplex and quadruplex DNA. Chem Eur J 2006;12:4611-9.
46. 2 in water: insights on the mechanism of multielectron reduction and protonation of the Tatpp acceptor ligand as a function of pH. Inorg Chem 2008;47: 8847-58.
47. 4, in water: proton-coupled sequential and concerted multielectron reduction. Chem Eur J 2005;11:4327-39.