Synthesis, molecular structure and cytotoxicity of molecular materials based on water soluble half-sandwich Rh(III) and Ir(III) tetranuclear metalla-cycles

Materials

Volumn 6, Issue 11, 2013, Pages 5352-5366

  Gupta, Gajendra ^a   Murray, Benjamin S ^b   Dyson, Paul J ^b   Therrien, Bruno ^a  

^a UNIVERSITY OF NEUCHÂTEL   (Switzerland)

^b EPFL   (Switzerland)

Author keywords

Anticancer activity; Bioorganometallic chemistry; Half sandwich complexes; Metal based drugs; Metalla cycles; Metalla rectangles

Indexed keywords

ANTICANCER ACTIVITIES; BIO-ORGANOMETALLIC CHEMISTRY; HALF-SANDWICH COMPLEXES; METAL-BASED DRUGS; METALLA-CYCLES; METALLA-RECTANGLES;

CELL CULTURE; CHLORINE COMPOUNDS; CYTOTOXICITY; DYES; ETHYLENE; GEOMETRY; IRIDIUM; KETONES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLATINUM COMPOUNDS; RHODIUM; SYNTHESIS (CHEMICAL);

RHODIUM COMPOUNDS;

EID: 84888999423     PISSN: None     EISSN: 19961944     Source Type: Journal    
DOI: 10.3390/ma6115352     Document Type: Article

References (43)

1. Cook, T.R.; Vajpayee, V.; Lee, M.H.; Stang, P.J.; Chi, K.-W. Biomedical and biochemical applications of self-assembled metallacycles and metallacages. Acc. Chem. Res. 2013, 46, 2464-2474.
2. Therrien, B. Drug delivery by water-soluble organometallic cages. Top Curr. Chem. 2012, 319, 35-56.
3. Smith, G.S.; Therrien, B. Targeted and multifunctional arene ruthenium chemotherapeutics. Dalton Trans. 2011, 40, 10793-10800.
4. Mishra, A.; Kang, S.C.; Chi, K.-W. Coordination-driven self-assembly of arene-ruthenium compounds. Eur. J. Inorg. Chem. 2013, 5222-5232.
5. Hartinger, C.G.; Phillips, A.D.; Nazarov, A.A. Polynuclear ruthenium, osmium and gold complexes. The quest for innovative chemotherapeutics. Curr. Top Med. Chem. 2011, 11, 2688-2702.
6. Hartinger, C.G.; Metzler-Nolte, N.; Dyson, P.J. Challenges and opportunities in the development of organometallic anticancer drugs. Organometallics 2012, 31, 5677-5685.
7. Mattsson, J.; Govindaswamy, P.; Renfrew, A.K.; Dyson, P.J.; Štěpnička, P.; Süss-Fink, G.; Therrien, B. Synthesis, molecular structure, and anticancer activity of cationic arene ruthenium metallarectangles. Organometallics 2009, 28, 4350-4357.
8. Barry, N.P.E.; Zava, O.; Furrer, J.; Dyson, P.J.; Therrien, B. Anticancer activity of opened arene ruthenium metalla-assemblies. Dalton Trans. 2010, 39, 5272-5277.
9. Barry, N.P.E.; Edafe, F.; Therrien, B. Anticancer activity of tetracationic arene ruthenium metalla-cycles. Dalton Trans. 2011, 40, 7172-7180.
10. Vajpayee, V.; Song, Y.H.; Yang, Y.J.; Kang, S.C.; Cook, T.R.; Kim, D.W.; Lah, M.S.; Kim, I.S.; Wang, M.; Stang, P.J.; et al. Self-assembly of cationic, hetero-or homonuclear ruthenium(II) macrocyclic rectangles and their photophysical, electrochemical, and biological studies. Organometallics 2011, 30, 6482-6489.
11. Vajpayee, V.; Lee, S.m.; Park, J.W.; Dubey, A.; Kim, H.; Cook, T.R.; Stang, P.J.; Chi, K.-W. Growth inhibitory activity of a bis-benzimidazole-bridged arene ruthenium metalla-rectangle and -prism. Organometallics 2013, 32, 1563-1566.
12. Jung, H.; Dubey, A.; Koo, H.J.; Vajpayee, V.; Cook, T.R.; Kim, H.; Kang, S.C.; Stang, P.J.; Chi, K.-W. Self-assembly of ambidentate pyridyl-carboxylate ligands with octahedral ruthenium metal centers: Self-selection for a single-linkage isomer and anticancer-potency studies. Chem. Eur. J. 2013, 19, 6709-6717.
13. Linares, F.; Galindo, M.A.; Galli, S.; Romero, M.A.; Navarro, J.A.R.; Barea, E. Tetranuclear coordination assemblies based on half-sandwich ruthenium(II) complexes: Noncovalent binding to DNA and cytotoxicity. Inorg. Chem. 2009, 48, 7413-7420.
14. Linares, F.; Procopio, E.Q.; Galindo, M.A.; Romero, M.A.; Navarro, J.A.R.; Barea, E. Molecular architecture of redox-active half-sandwich Ru(II) cyclic assemblies. Interactions with biomolecules and anticancer activity. CrystEngComm 2010, 12, 2343-2346.
15. Vajpayee, V.; Song, Y.H.; Lee, M.H.; Kim, H.; Wang, M.; Stang, P.J.; Chi, K.-W. Self-assembled arene-ruthenium-based rectangles for the selective sensing of multi-carboxylate anions. Chem. Eur. J. 2011, 17, 7837-7844.
16. Severin, K. Research in the laboratory of supramolecular chemistry: Functional nanostructures, sensors, and catalysts. Chimia 2011, 65, 680-682.
17. Gao, J.; Rochat, S.; Qian, X.; Severin, K. A simple assay for the fluorometric detection of lithium ions in aqueous solution. Chem. Eur. J. 2010, 16, 5013-5017.
18. Mendoza-Ferri, M.-G.; Hartinger, C.G.; Eichinger, R.E.; Stolyarova, N.; Severin, K.; Jakupec, M.A.; Nazarov, A.A.; Keppler, B.K. Influence of the spacer length on the in vitro anticancer activity of dinuclear ruthenium-arene compounds. Organometallics 2008, 27, 2405-2407.
19. Mendoza-Ferri, M.-G.; Hartinger, C.G.; Nazarov, A.A.; Kandioller, W.; Severin, K.; Keppler, B.K. Modifying the structure of dinuclear ruthenium complexes with antitumor activity. Appl. Organometal. Chem. 2008, 22, 326-332.
20. Liu, H.-K.; Sadler, P.J. Metal complexes as DNA intercalators. Acc. Chem. Res. 2011, 44, 349-359.
21. Barry, N.P.E.; Edafe, F.; Dyson, P.J.; Therrien, B. Anticancer activity of osmium metalla-rectangles. Dalton Trans. 2010, 39, 2816-2820.
22. Severin, K.; Bergs, R.; Beck, W. Bioorganometallic chemistry-transition metal complexes with α-amino acids and peptides. Angew. Chem. Int. Ed. 1998, 37, 1634-1654.
23. Herberhold, M.; Yan, H.; Milius, W.; Wrackmeyer, B. Metal-induced B-H activation: Addition of methyl acetylene carboxylates to Cp*Rh-, Cp*Ir-, (p-cymene)Ru-, and (p-cymene)Os half-sandwich complexes containing the chelating 1,2-dicarba-closo-dodecaborane-1,2-dithiolate ligand. Chem. Eur. J. 2000, 6, 3026-2032.
24. Hartinger, C.G.; Dyson, P.J. Bioorganometallic chemistry-From teaching paradigms to medicinal applications. Chem. Soc. Rev. 2009, 38, 391-401.
25. Gupta, G.; Garci, A.; Murray, B.S.; Dyson, P.J.; Fabre, G.; Trouillas, P.; Giannini, F.; Furrer, J.; Süss-Fink, G.; Therrien, B. Synthesis, molecular structure, computational study and in vitro anticancer activity of dinuclear thiolato-bridged pentamethylcyclopentadienyl Rh(II) and Ir(II) complexes. Dalton Trans. 2013, 42, 15457-15463.
26. Dorcier, A.; Ang, W.H.; Bolaño, S.; Gonsalvi, L.; Juillerat-Jeanneret, L.; Laurenczy, G.; Peruzzini, M.; Phillips, A.D.; Zanobini, F.; Dyson, P.J. In vitro evaluation of rhodium and osmium RAPTA analogues: The case for organometallic anticancer drugs not based on ruthenium. Organometallics 2006, 25, 4090-4096.
27. Hearn, J.M.; Romero-Canelón, I; Qamar, B.; Liu, Z.; Hands-Portman, I.; Sadler, P.J. Organometallic iridium(III) anticancer complexes with new mechanisms of action: NCI-60 screening mitochondrial targeting, and apoptosis. ACS Chem. Biol. 2013, 8, 1335-1343.
28. Barry, N.P.E.; Sadler, P.J. Exploration of the medical periodic table: Towards new targets. Chem. Commun. 2013, 49, 5106-5131.
29. Geldmacher, Y.; Oleszak, M.; Sheldrick, W.S. Rhodium(III) and iridium(III) complexes as anticancer agents. Inorg. Chim. Acta 2012, 393, 84-102.
30. Han, Y.-F.; Jia, W.-G.; Yu, W.-B.; Jin, G.-X. Stepwise formation of organometallic macrocycles, prisms and boxes from Ir, Rh and Ru-based half-sandwich units. Chem. Soc. Rev. 2009, 38, 3419-3434.
31. Han, Y.-F.; Lin, Y.-J.; Jin, G.-X. Discrete half-sandwich Ir, Rh-based organometallic molecular boxes: Synthesis, characterization, and their properties. Dalton Trans. 2011, 40, 10370-10375.
32. Wu, T.; Lin, Y.-J.; Jin, G.-X. Stepwise formation of organometallic macrocycles and triangular prisms containing 2,2'-bisbenzimidazole ligands. Dalton Trans. 2013, 42, 82-88.
33. Yan, H.; Süss-Fink, G.; Neels, A.; Stoeckli-Evans, H. Mono-, di-and tetra-nuclear p-cymeneruthenium complexes containing oxalato ligands. J. Chem. Soc. Dalton Trans. 1997, 4345-4350.
34. Pitto-Barry, A.; Barry, N.P.E.; Zava, O.; Deschenaux, R.; Therrien, B. Encapsulation of pyrene-functionalized poly(benzyl ether) dendrons into a water-soluble organometallic cages. Chem. Asian J. 2011, 6, 1595-1603.
35. Huang, S.-L.; Lin, Y.-J.; Hor, T.S.A.; Jin, G.-X. Cp*Rh-based heterometallic metallarectangles: Size-dependent borromean link structures and catalytic acyl transfer. J. Am. Chem. Soc. 2013, 135, 8125-8128.
36. Barry, N.P.E.; Furrer, J.; Therrien, B. In-and out-of-cavity interactions by modulating the size of ruthenium metallarectangles. Helv. Chim. Acta 2010, 93, 1313-1328.
37. Barry, N.P.E.; Furrer, J.; Freudenreich, J.; Süss-Fink, G.; Therrien, B. Designing the host-guest properties of tetranuclear arene ruthenium metalla-rectangles to accommodate a pyrene molecule. Eur. J. Inorg. Chem. 2010, 725-728.
38. Kang, J.W.; Moseley, K.; Maitlis, P.M. Pentamethylcyclopentadienylrhodium and -iridium halides. Synthesis and properties. J. Am. Chem. Soc. 1969, 91, 5970-5977.
39. 5-Pentamethylcyclopenta-dienyl)rhodium and -iridium compounds. Inorg. Synth. 1992, 29, 228-234.
40. Sheldrick, G.M. A short history of SHELX. Acta Cryst. 2008, 64, 112-122.
41. Spek, A.L. Single-crystal structure validation with the program PLATON. J. Appl. Cryst. 2003, 36, 7-13.
42. Farrugia, L.J. ORTEP-3 for Windows-A version of ORTEP-III with a graphical interface (GUI) J. Appl. Cryst. 1997, 30, 565.
43. Bruno, I.J.; Cole, J.C.; Edington, P.R.; Kessler, M.; Macrae, C.F.; McCabe, P.; Pearson, J.; Taylor, R. New software for searching the Cambridge Structural Database and visualizing crystal structures. Acta Cryst. 2002, 58, 389-397.