Investigation of the cytotoxic implications of metal chelators against melanoma and approaches to improve the cytotoxicity profiles of metal coordinating agents

Akladios FN, Andrew SD, Parkinson CJ (2015) Selective induction of oxidative stress in cancer cells via synergistic combinations of agents targeting redox homeostasis. Bioorg Med Chem 23:3097–3104 Akladios FN, Andrew SD, Parkinson CJ (2016) Improved cytotoxicity of pyridyl-substituted thiosemicarbazones against MCF-7 when used as metal ionophores. Biometals 29(1):157–170 Bacchi A, Carcelli M, Pelagatti P, Pelizzi C, Pelizzi G, Zani F (1999) Antimicrobial and mutagenic activity of some carbono-and thiocarbonohydrazone ligands and their copper (II), iron (II) and zinc (II) complexes. J Inorg Biochem 75(2):123–133 Becker EM, Lovejoy DB, Greer JM, Watts R, Richardson DR (2003) Identification of the di-pyridyl ketone isonicotinoyl hydrazone (PKIH) analogues as potent iron chelators and anti-tumour agents. Br J Pharmacol 138(5):819–830 Bernhardt PV, Caldwell LM, Chaston TB, Chin P, Richardson DR (2003) Cytotoxic iron chelators: characterization of the structure, solution chemistry and redox activity of ligands and iron complexes of the di-2-pyridyl ketone isonicotinoyl hydrazone (HPKIH) analogues. J Biol Inorg Chem 8:866–880 Blatt J, Stitely S (1987) Antineuroblastoma activity of desferoxamine in human cell lines. Cancer Res 47(7):1749–1750 Bogojeski J, Petrović B, Bugarčić ŽD (2012) Interactions of the platinum (II) complexes with nitrogen-and sulfur-bonding bio-molecules. In: Oppezzo P. (ed) Chronic lymphocytic leukemia. InTech. doi:10.5772/1156 Bustos C, Burckhardt O, Schrebler R, Carrillo D, Arif A, Cowley A, Nunn C (1990) Synthesis, characterization, and electrochemistry of cis-dioxomolybdenum (VI) complexes of Schiff bases derived from carbohydrazide, thiocarbohydrazide, and salicylaldehyde. Crystal structures of [MoO2 (o-OC6H4CH: NN: CSNHN: CHC6H4OH-o) Me2SO] and [(MoO2) 2 (o-OC6H4CH: NN: CONN: CHC6H4O-o)(Me2SO) 2]. cntdot. 0.5 Me2SO. Inorg Chem 29(20):3996–4001 Chou TC (2006) Theoretical basis, experimental design, and computerized simulation of synergism and antagonism in drug combination studies. Pharmacol Rev 58(3):621–681 Chou TC (2010) Drug combination studies and their synergy quantification using the Chou-Talalay method. Cancer Res 70(2):440–446. doi:10.1158/0008-5472.can-09-1947 Darnell G, Richardson D (1999) The potential of iron chelators of the pyridoxal isonicotinoyl hydrazone class as effective antiproliferative agents III: the effect of the ligands on molecular targets involved in proliferation. Blood 94(2):781–792 Dragancea D, Arion VB, Shova S, Rentschler E, Gerbeleu NV (2005) Azine-bridged octanuclear copper (II) complexes assembled with a one-stranded ditopic thiocarbohydrazone ligand. Angew Chem Int Ed Engl 44(48):7938–7942 Fruehauf JP, Trapp V (2008) Reactive oxygen species: an Achilles’ heel of melanoma? Expert Rev Anticancer Ther 8(11):1751–1757 Gao J, Richardson DR (2001) 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 98(3):842–850 Giles GI (2006) The redox regulation of thiol dependent signaling pathways in cancer. Curr Pharm Des 12(34):4427–4443 Hauschild A, Eggermont A, Jacobson E, O’Day S (2009) Phase III, randomized, double-blind study of elesclomol and paclitaxel versus paclitaxel alone in stage IV metastatic melanoma (MM). Paper presented at the American Society of Clinical Oncology (ASCO) Annual Meeting, May 29–June 2, Orlando, Florida Jansson PJ, Sharpe PC, Bernhardt PV, Richardson DR (2010) Novel thiosemicarbazones of the ApT and DpT series and their copper complexes: identification of pronounced redox activity and characterization of their antitumor activity. J Med Chem 53(15):5759–5769 Kalinina E, Chernov N, Saprin A (2008) Involvement of thio-, peroxi-, and glutaredoxins in cellular redox-dependent processes. Biochemistry (Mosc) 73(13):1493–1510 Kalinowski DS, Richardson DR (2007) Future of toxicology iron chelators and differing modes of action and toxicity: the changing face of iron chelation therapy. Chem Res Toxicol 20(5):715–720 Kalinowski DS, Yu Y, Sharpe PC, Islam M, Liao YT, Lovejoy DB, Richardson DR (2007) Design, synthesis, and characterization of novel iron chelators: structure-activity relationships of the 2-benzoylpyridine thiosemicarbazone series and their 3-nitrobenzoyl analogues as potent antitumor agents. J Med Chem 50(15):3716–3729 Liu F, Garcia AMG, Meyskens FL (2012) NADPH oxidase 1 overexpression enhances invasion via matrix metalloproteinase-2 and epithelial–mesenchymal transition in melanoma cells. J Invest Dermatol 132(8):2033–2041 Lovejoy DB, Richardson DR (2002) Novel “hybrid” iron chelators derived from aroylhydrazones and thiosemicarbazones demonstrate selective antiproliferative activity against tumor cells. Blood 100(2):666–676 Lovejoy DB, Jansson PJ, Brunk UT, Wong J, Ponka P, Richardson DR (2011) Antitumor activity of metal-chelating compound Dp44mT is mediated by formation of a redox-active copper complex that accumulates in lysosomes. Cancer Res 71(17):5871–5880 Manoj E, Kurup MP, Fun H-K, Punnoose A (2007) Self-assembled macrocyclic molecular squares of Ni (II) derived from carbohydrazones and thiocarbohydrazones: structural and magnetic studies. Polyhedron 26(15):4451–4462 Moubaraki B, Murray KS, Ranford JD, Vittal JJ, Wang X, Xu Y (1999) Preparation, characterisation and structures of copper (II) complexes of an asymmetric anti-cancer drug analogue†. J Chem Soc Dalton Trans 20:3573–3578 Nagai M, Vo NH, Ogawa LS, Chimmanamada D, Inoue T, Chu J, Barsoum J (2012) The oncology drug elesclomol selectively transports copper to the mitochondria to induce oxidative stress in cancer cells. Free Radic Biol Med 52(10):2142–2150 Noulsri E, Richardson DR, Lerdwana S, Fucharoen S, Yamagishi T, Kalinowski DS, Pattanapanyasat K (2009) Antitumor activity and mechanism of action of the iron chelator, Dp44mT, against leukemic cells. Am J Hematol 84(3):170–176 O’Day S, Gonzalez R, Lawson D, Weber R, Hutchins L, Anderson C, Jacobson E (2009) Phase II, randomized, controlled, double-blinded trial of weekly elesclomol plus paclitaxel versus paclitaxel alone for stage IV metastatic melanoma. J Clin Oncol 27(32):5452–5458 Peethambaram P, Burton J, Oberg A, Gomez-Dahl L, Isham C, Tibodeau J, Erlichman C (2007) A phase 2 trial of flavopiridol and cisplatin in platinum-resistant ovarian cancer. Mol Cancer Ther 6(11 Supplement):A140 Richardson DR, Sharpe PC, Lovejoy DB, Senaratne D, Kalinowski DS, Islam M, Bernhardt PV (2006) Dipyridyl thiosemicarbazone chelators with potent and selective antitumor activity form iron complexes with redox activity. J Med Chem 49(22):6510–6521 Sander C, Hamm F, Elsner P, Thiele J (2003) Oxidative stress in malignant melanoma and non-melanoma skin cancer. Br J Dermatol 148(5):913–922 Sathisha MP, Revankar VK, Pai KSR (2007) Synthesis, structure, electrochemistry, and spectral characterization of bis-isatin thiocarbohydrazone metal complexes and their antitumor activity against ehrlich ascites carcinoma in swiss albino mice. Met-Based Drugs 2008:362105. doi:10.1155/2008/362105 Shah MA, Schwartz GK (2001) Cell cycle-mediated drug resistance an emerging concept in cancer therapy. Clin Cancer Res 7(8):2168–2181 Siriwardana G, Seligman PA (2015) Iron depletion results in Src kinase inhibition with associated cell cycle arrest in neuroblastoma cells. Physiol Rep 3(3):e12341 Tas F (2012) Metastatic behavior in melanoma: timing, pattern, survival, and influencing factors. J Oncol 2012:9. doi:10.1155/2012/647684 Tew KD, Townsend DM (2011) Redox platforms in cancer drug discovery and development. Curr Opin Chem Biol 15(1):156–161. doi:10.1016/j.cbpa.2010.10.016 Venza M, Visalli M, Beninati C, De Gaetano GV, Teti D, Venza I (2015) Cellular mechanisms of oxidative stress and action in melanoma. Oxid Med Cell Longev 2015:11. doi:10.1155/2015/481782 Whitnall M, Howard J, Ponka P, Richardson DR (2006) A class of iron chelators with a wide spectrum of potent antitumor activity that overcomes resistance to chemotherapeutics. Proc Nat Acad Sci 103(40):14901–14906 Yamaura M, Mitsushita J, Furuta S, Kiniwa Y, Ashida A, Goto Y, Takata M (2009) NADPH oxidase 4 contributes to transformation phenotype of melanoma cells by regulating G2-M cell cycle progression. Cancer Res 69(6):2647–2654 Yu Y, Kalinowski DS, Kovacevic Z, Siafakas AR, Jansson PJ, Stefani C, Richardson DR (2009) Thiosemicarbazones from the old to new: iron chelators that are more than just ribonucleotide reductase inhibitors. J Med Chem 52(17):5271–5294