Biomedical and biochemical applications of self-assembled metallacycles and metallacages

Accounts of Chemical Research

Volumn 46, Issue 11, 2013, Pages 2464-2474

  Cook, Timothy R ^a   Vajpayee, Vaishali ^b   Lee, Min Hyung ^b   Stang, Peter J ^a   Chi, Ki Whan ^b  

^a UNIVERSITY OF UTAH   (United States)

^b University of Ulsan   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; BIOMATERIAL; DNA; METAL; PROTEIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HUMAN; TUMOR CELL LINE; X RAY CRYSTALLOGRAPHY;

ANTINEOPLASTIC AGENTS; BIOCOMPATIBLE MATERIALS; CELL LINE, TUMOR; CRYSTALLOGRAPHY, X-RAY; DNA; HUMANS; METALS; MOLECULAR STRUCTURE; PROTEINS;

EID: 84888620584     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar400010v     Document Type: Article

References (52)

1. Kraatz, H.-B.; Metzler-Nolte, N. Concepts and models in bioinorganic chemistry; Wiley-VCH: Weinheim, 2006.
2. Bhattacharya, P. K. Metal Ions in Biochemistry; Alpha Science International Limited: Harrow, Middlesex, U.K., 2005.
3. Sherman, S. E.; Lippard, S. J. Structural aspects of platinum anticancer drug interactions with DNA Chem. Rev. 1987, 87, 1153-1181
4. Jung, Y.; Lippard, S. J. Direct Cellular Responses to Platinum-Induced DNA Damage Chem. Rev. 2007, 107, 1387-1407
5. Kelland, L. The resurgence of platinum-based cancer chemotherapy Nat. Rev. Cancer 2007, 7, 573-584
6. Jaouen, G., Ed. Bioorganometallics: Biomolecules, Labeling, Medicine; John Wiley & Sons: Weinheim, Germany, 2006.
7. Chatterjee, S.; Kundu, S.; Bhattacharyya, A.; Hartinger, C.; Dyson, P. The ruthenium(II)-arene compound RAPTA-C induces apoptosis in EAC cells through mitochondrial and p53-JNK pathways JBIC, J. Biol. Inorg. Chem. 2008, 13, 1149-1155
8. Cook, T. R.; Zheng, Y.-R.; Stang, P. J. Metal-Organic Frameworks and Self-Assembled Supramolecular Coordination Complexes: Comparing and Contrasting the Design, Synthesis, and Functionality of Metal-Organic Materials Chem. Rev. 2013, 113, 734-777
9. James, S. L. Metal-organic frameworks Chem. Soc. Rev. 2003, 32, 276-288
10. Chakrabarty, R.; Mukherjee, P. S.; Stang, P. J. Supramolecular Coordination: Self-Assembly of Finite Two- and Three-Dimensional Ensembles Chem. Rev. 2011, 111, 6810-6918
11. Wang, M.; Lan, W.-J.; Zheng, Y.-R.; Cook, T. R.; White, H. S.; Stang, P. J. Post-Self-Assembly Covalent Chemistry of Discrete Multicomponent Metallosupramolecular Hexagonal Prisms J. Am. Chem. Soc. 2011, 133, 10752-10755
12. Wang, M.; Vajpayee, V.; Shanmugaraju, S.; Zheng, Y.-R.; Zhao, Z.; Kim, H.; Mukherjee, P. S.; Chi, K.-W.; Stang, P. J. Coordination-Driven Self-Assembly of M3L2 Trigonal Cages from Preorganized Metalloligands Incorporating Octahedral Metal Centers and Fluorescent Detection of Nitroaromatics Inorg. Chem. 2011, 50, 1506-1512
13. Therrien, B. Drug Delivery by Water-Soluble Organometallic Cages. In Chemistry of Nanocontainers; Albrecht, M.; Hahn, E., Eds.; Springer: Berlin Heidelberg, 2011; Vol. 319; pp 35-55.
14. Matsumura, Y.; Maeda, H.; New, A. Concept for Macromolecular Therapeutics in Cancer Chemotherapy: Mechanism of Tumoritropic Accumulation of Proteins and the Antitumor Agent Smancs Cancer Res. 1986, 46, 6387-6392
15. Dale, L. D.; Tocher, J. H.; Dyson, T. M.; Edwards, D. I.; Tocher, D. A. Studies on DNA Damage and Induction of SOS Repair by Novel Multifunctional Bioreducible Compounds. II. A Metronidazole Adduct of a Ruthenium-arene Compound Anti-Cancer Drug Des. 1992, 7, 3-14
16. Therrien, B.; Süss-Fink, G.; Govindaswamy, P.; Renfrew, A. K.; Dyson, P. J. The "Complex-in-a-Complex" Cations [(acac) 2MâŠRu6(p-iPrC6H4Me)6(tpt)2(dhbq)3]6+: A Trojan Horse for Cancer Cells Angew. Chem., Int. Ed. 2008, 47, 3773-3776
17. 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, 0, 4345-4350
18. Paul, L. E. H.; Therrien, B.; Furrer, J. Investigation of the Reactivity between a Ruthenium Hexacationic Prism and Biological Ligands Inorg. Chem. 2011, 51, 1057-1067
19. Vajpayee, V.; Yang, Y. J.; Kang, S. C.; Kim, H.; Kim, I. S.; Wang, M.; Stang, P. J.; Chi, K.-W. Hexanuclear self-assembled arene-ruthenium nano-prismatic cages: potential anticancer agents Chem. Commun. 2011, 47, 5184-5186
20. Linares, F. t.; 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
21. Mattsson, J.; Govindaswamy, P.; Renfrew, A. K.; Dyson, P. J.; StěpničkaA, P.; Süss-Fink, G.; Therrien, B. Synthesis, Molecular Structure, and Anticancer Activity of Cationic Arene Ruthenium Metallarectangles Organometallics 2009, 28, 4350-4357
22. 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.; Chi, K.-W. Self-Assembly of Cationic, Hetero- or Homonuclear Ruthenium(II) Macrocyclic Rectangles and Their Photophysical, Electrochemical, and Biological Studies Organometallics 2011, 30, 6482-6489
23. Vajpayee, V.; Lee, S.; Kim, S.-H.; Kang, S. C.; Cook, T. R.; Kim, H.; Kim, D. W.; Verma, S.; Lah, M. S.; Kim, I. S.; Wang, M.; Stang, P. J.; Chi, K.-W. Self-assembled metalla-rectangles bearing azodipyridyl ligands: Synthesis, characterization and antitumor activity Dalton Trans. 2013, 42, 466-475
24. Vajpayee, V.; Song, Y. H.; Jung, Y. J.; Kang, S. C.; Kim, H.; Kim, I. S.; Wang, M.; Cook, T. R.; Stang, P. J.; Chi, K.-W. Coordination-driven self-assembly of ruthenium-based molecular-rectangles: Synthesis, characterization, photo-physical and anticancer potency studies Dalton Trans. 2012, 41, 3046-3052
25. Vajpayee, V.; Song, Y. H.; Yang, Y. J.; Kang, S. C.; Kim, H.; Kim, I. S.; Wang, M.; Stang, P. J.; Chi, K.-W. Coordination-Driven Self-Assembly and Anticancer Activity of Molecular Rectangles Containing Octahedral Ruthenium Metal Centers Organometallics 2011, 30, 3242-3245
26. Mishra, A.; Jung, H.; Park, J. W.; Kim, H. K.; Kim, H.; Stang, P. J.; Chi, K.-W. Anticancer Activity of Self-Assembled Molecular Rectangles via Arene-Ruthenium Acceptors and a New Unsymmetrical Amide Ligand Organometallics 2012, 31, 3519-3526
27. 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
28. 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
29. Morakot, N.; Rakrai, W.; Keawwangchai, S.; Kaewtong, C.; Wanno, B. Design and synthesis of thiourea based receptor containing naphthalene as oxalate selective sensor J. Mol. Model. 2010, 16, 129-136
30. Pal, R.; Parker, D.; Costello, L. C. A europium luminescence assay of lactate and citrate in biological fluids Org. Biomol. Chem. 2009, 7, 1525-1528
31. Costello, L. C.; Franklin, R. B. Prostatic fluid electrolyte composition for the screening of prostate cancer: A potential solution to a major problem Prostate Cancer Prostatic Dis. 2008, 12, 17-24
32. Mishra, A.; Vajpayee, V.; Kim, H.; Lee, M. H.; Jung, H.; Wang, M.; Stang, P. J.; Chi, K.-W. Self-assembled metalla-bowls for selective sensing of multi-carboxylate anions Dalton Trans. 2012, 41, 1195-1201
33. Hannon, M. J.; Painting, C. L.; Jackson, A.; Hamblin, J.; Errington, W. An inexpensive approach to supramolecular architecture Chem. Commun. 1997, 1807-1808
34. Hannon, M. J.; Moreno, V.; Prieto, M. J.; Moldrheim, E.; Sletten, E.; Meistermann, I.; Isaac, C. J.; Sanders, K. J.; Rodger, A. Intramolecular DNA Coiling Mediated by a Metallo-Supramolecular Cylinder Angew. Chem., Int. Ed. 2001, 40, 879-884
35. Oleksi, A.; Blanco, A. G.; Boer, R.; Usón, I.; Aymamí, J.; Rodger, A.; Hannon, M. J.; Coll, M. Molecular Recognition of a Three-Way DNA Junction by a Metallosupramolecular Helicate Angew. Chem., Int. Ed. 2006, 45, 1227-1231
36. Hotze, A. C. G.; Hodges, N. J.; Hayden, R. E.; Sanchez-Cano, C.; Paines, C.; Male, N.; Tse, M.-K.; Bunce, C. M.; Chipman, J. K.; Hannon, M. J. Supramolecular Iron Cylinder with Unprecedented DNA Binding Is a Potent Cytostatic and Apoptotic Agent without Exhibiting Genotoxicity Chem. Biol. 2008, 15, 1258-1267
37. Cardo, L.; Sadovnikova, V.; Phongtongpasuk, S.; Hodges, N. J.; Hannon, M. J. Arginine conjugates of metallo-supramolecular cylinders prescribe helicity and enhance DNA junction binding and cellular activity Chem. Commun. 2011, 47, 6575-6577
38. Howson, S. E.; Bolhuis, A.; Brabec, V.; Clarkson, G. J.; Malina, J.; Rodger, A.; Scott, P. Optically pure, water-stable metallo-helical 'flexicate' assemblies with antibiotic activity Nat. Chem. 2012, 4, 31-36
39. Pascu, G. I.; Hotze, A. C. G.; Sanchez-Cano, C.; Kariuki, B. M.; Hannon, M. J. 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, 4374-4378
40. Ducani, C.; Leczkowska, A.; Hodges, N. J.; Hannon, M. J. Noncovalent DNA-Binding Metallo-Supramolecular Cylinders Prevent DNA Transactions in vitro Angew. Chem., Int. Ed. 2010, 49, 8942-8945
41. Pope, A. J.; Bruce, C.; Kysela, B.; Hannon, M. J. Issues surrounding standard cytotoxicity testing for assessing activity of non-covalent DNA-binding metallo-drugs Dalton Trans. 2010, 39, 2772-2774
42. Kieltyka, R.; Englebienne, P.; Fakhoury, J.; Autexier, C.; Moitessier, N.; Sleiman, H. F. A Platinum Supramolecular Square as an Effective G-Quadruplex Binder and Telomerase Inhibitor J. Am. Chem. Soc. 2008, 130, 10040-10041
43. Barry, N. P. E.; Abd Karim, N. H.; Vilar, R.; Therrien, B. Interactions of ruthenium coordination cubes with DNA Dalton Trans. 2009, 0, 10717-10719
44. Mishra, A.; Ravikumar, S.; Hong, S. H.; Kim, H.; Vajpayee, V.; Lee, H.; Ahn, B.; Wang, M.; Stang, P. J.; Chi, K.-W. DNA Binding and Unwinding by Self-Assembled Supramolecular Heterobimetallacycles Organometallics 2011, 30, 6343-6346
45. Sava, G.; Jaouen, G.; Hillard, E. A.; Bergamo, A. Targeted therapy vs. DNA-adduct formation-guided design: Thoughts about the future of metal-based anticancer drugs Dalton Trans. 2012, 41, 8226-8234
46. Sonpavde, G.; Sternberg, C. N. Satraplatin for the therapy of castration-resistant prostate cancer Future Oncol. 2009, 5, 931-940
47. Sanborn, R. Cisplatin Versus Carboplatin in NSCLC: Is There One "Best" Answer? Curr. Treat. Options Oncol. 2008, 9, 326-342
48. Perrone, F.; Bossi, P.; Cortelazzi, B.; Locati, L.; Quattrone, P.; Pierotti, M. A.; Pilotti, S.; Licitra, L. TP53 Mutations and Pathologic Complete Response to Neoadjuvant Cisplatin and Fluorouracil Chemotherapy in Resected Oral Cavity Squamous Cell Carcinoma J. Clin. Oncol. 2010, 28, 761-766
49. Casini, A.; Reedijk, J. Interactions of anticancer Pt compounds with proteins: an overlooked topic in medicinal inorganic chemistry? Chem. Sci. 2012, 3, 3135-3144
50. Che, C.-M.; Siu, F.-M. Metal complexes in medicine with a focus on enzyme inhibition Curr. Opin. Chem. Biol. 2010, 14, 255-261
51. Yu, H.; Li, M.; Liu, G.; Geng, J.; Wang, J.; Ren, J.; Zhao, C.; Qu, X. Metallosupramolecular complex targeting an [small alpha]/[small beta] discordant stretch of amyloid [small beta] peptide Chem. Sci. 2012, 3, 3145-3153
52. Kerckhoffs, J. M. C. A.; Peberdy, J. C.; Meistermann, I.; Childs, L. J.; Isaac, C. J.; Pearmund, C. R.; Reudegger, V.; Khalid, S.; Alcock, N. W.; Hannon, M. J.; Rodger, A. Enantiomeric resolution of supramolecular helicates with different surface topographies Dalton Trans. 2007, 734-742