Chiral Ruthenium(II) Polypyridyl Complexes: Stabilization of G-Quadruplex DNA, Inhibition of Telomerase Activity and Cellular Uptake

PLoS ONE

Volumn 7, Issue 12, 2012, Pages

  Yu, Qianqian ^a   Liu, Yanan ^a,b   Wang, Chuan ^a   Sun, Dongdong ^a   Yang, Xingcheng ^a   Liu, Yanyu ^a   Liu, Jie ^a  

^a JINAN UNIVERSITY   (China)

^b CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

BIS(1,10 PHENANTHROLINE) 2 (4 HYDROXY PHENYL) IMIDAZO [4,5 F] [1,10] PHENANTHROLINE RUTHENIUM; DNA; GUANINE QUADRUPLEX; RUTHENIUM DERIVATIVE; TELOMERASE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL; CHIRALITY; CONFOCAL MICROSCOPY; CONTROLLED STUDY; CYTOPLASM; DRUG EFFICACY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; GENE TARGETING; HUMAN; HUMAN CELL; TELOMERE; TELOMERIC REPEAT AMPLIFICATION PROTOCOL; TREATMENT RESPONSE;

EID: 84870860613     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0050902     Document Type: Article

References (56)

1. Davis JT, (2004) G-Quartets 40 Years Later: From 5′-GMP to Molecular Biolog and Supramolecular Chemistry. Angew Chem Int Ed 43: 668-698.
2. Huppert JL, (2008) Four-stranded nucleic acids: structure, function and targeting of G-quadruplexes. Chem Soc Rev 37: 1375-1384.
3. Wang JT, Li Y, Tan JH, Ji LN, Mao ZW, (2011) Platinum (II)-triarylpyridines complexes with electropositive pendants as efficient G-quadruplex binders. Dalt Trans 40: 564-566.
4. Murat P, Singh Y, Defrancq E, (2011) Methods for Investigating G-Quadruplex DNA/Ligand Interactions. Chem Soc Rev 40: 5293-5307.
5. Huffman KE, Levene SD, Tesmer VM, Shay JW, Wright WE, (2000) Telomere shortening is proportional to the size of the G-rich telomeric 3′-overhang. J Biol Chem 275: 19719-19722.
6. Kim NW, Piatyszek MA, Prowse KR, Harley CB, West MD, et al. (1994) Specific association of human telomerase activity with immortal cells and cancer. Science 266: 2011-2015.
7. Nugent CI, Lundblad V, (1998) The telomerase reverse transcriptase: components and regulation. Genes & development 12: 1073.
8. De Cian A, Lacroix L, Douarre C, Temime-Smaali N, Trentesaux C, et al. (2008) Targeting telomeres and telomerase. Biochimie 90: 131-155.
9. Zahler AM, Williamson JR, Cech TR, Prescott DM, (1991) Inhibition of telomerase by G-quartet DMA structures. Nature 350: 718-720.
10. Sun J, An Y, Zhang L, Chen H-Y, Han Y, et al. (2011) Studies on synthesis, characterization, and G-quadruplex binding of Ru(II) complexes containing two dppz ligands. Inorg Bio Chem 105: 149-154.
11. Shi S, Geng X, Zhao J, Yao T, Wang C, et al. (2010) Interaction of [Ru(bpy)2(dppz)]2+ with human telomeric DNA: Preferential binding to G-quadruplexes over i-motif. Biochimie 92: 370-377.
12. Anantha NV, Azam M, Sheardy RD, (1998) Porphyrin Binding to Quadruplexed T4G4. Biochemistry 37: 2709-2714.
13. Reed JE, Arnal AA, Neidle S, Vilar R, (2006) Stabilization of G-Quadruplex DNA and Inhibition of Telomerase Activity by Square-Planar Nickel(II) Complexes. J Am Chem Soc 128: 5992-5993.
14. Reed JE, Neidle S, Vilar R, (2007) Stabilisation of human telomeric quadruplex DNA and inhibition of telomerase by a platinum-phenanthroline complex. Chem Commun 42: 4366-4368.
15. Wheelhouse RT, Sun D, Han H, Han FX, Hurley LH, (1998) Cationic porphyrins as telomerase inhibitors: the interaction of tetra-(N-methyl-4-pyridyl) porphine with quadruplex DNA. J Am Chem Soc 120: 3261-3262.
16. Gao F, Chao H, Ji LN, (2008) DNA Binding, Photocleavage, and Topoisomerase Inhibition of Functionalized Ruthenium (II)-Polypyridine Complexes. Chemistry & biodiversity 5: 1962-1979.
17. Georgiades SN, Abd Karim NH, Suntharalingam K, Vilar R, (2010) Interaction of Metal Complexes with G-Quadruplex DNA Angew. Chem Int Ed 49: 4020-4034.
18. Parkinson GN, Lee MPH, Neidle S, (2002) Crystal structure of parallel quadruplexes from human telomeric DNA. Nature 417: 876-880.
19. Gill MR, Garcia-Lara J, Foster SJ, Smythe C, Battaglia G, et al. (2009) A ruthenium (II) polypyridyl complex for direct imaging of DNA structure in living cells. Nature 1: 662-667.
20. Shinohara K, Sannohe Y, Kaieda S, Tanaka K, Osuga H, et al. (2010) A chiral wedge molecule inhibits telomerase activity. J Am Chem Soc 132: 3778-3782.
21. Yu H, Wang X, Fu M, Ren J, Qu X, (2008) Chiral metallo-supramolecular complexes selectively recognize human telomeric G-quadruplex DNA. Nucl Acids Res 36: 5695-5703.
22. Zhao C, Geng J, Feng L, Ren J, Qu X (2010) Chiral Metall-qoupramolecular Complexes Selectively Induce Human Telomeric G-quadruplex Formation under Salt eficient Conditions. In: Qu X, editor: Chem-Eur J 17: 8209-8215.
23. Marzilli LG, Intini FP, Kiser D, Wong HC, Susan O, et al. (1998) Chirality-Controlling Chelate (CCC) Ligands in Analogues of Platinum Anticancer Agents. Influence of N9 Substituents of Guanine Derivatives (G) on the Distribution of Chiral Conformers of (CCC) PtG2 with CCC = N, N′-Dimethyl-2, 3-diaminobutane. Inorg Chem pp. 6898-6905.
24. Shi S, Liu J, Li J, Zheng KC, Tan CP, et al. (2005) Electronic effect of different positions of the-NO2 group on the DNA-intercalator of chiral complexes [Ru (bpy) 2L] 2+(L = o-npip, m-npip and p-npip). Dalton Trans pp. 2038-2046.
25. Svensson FR, Abrahamsson M, Stro-mberg N, Ewing AG, Lincoln P, (2011) Ruthenium (II) Complex Enantiomers as Cellular Probes for Diastereomeric Interactions in Confocal and Fluorescence Lifetime Imaging Microscopy. J Phys Chem Lette 2: 397-401.
26. Sun D, Liu Y, Liu D, Zhang R, Yang X, et al. (2012) Stabilization of G-quadruplex DNA, Inhibition of Telomerase Activity and Live Cell Imaging Studies of Chiral Ruthenium (II) Complexes. Chem Eur J pp. 4285-4295.
27. Cantor CR, Warshaw MM, Shapiro H, (1970) Oligonucleotide interactions. 3. Circular dichroism studies of the conformation of deoxyoligonucleotides. Biopolymers 9: 1059-1077.
28. Sullivan BP, Salmon DJ, Meyer TJ, (1978) Mixed phosphine 2, 2′-bipyridine complexes of ruthenium. Inorg Chem 17: 3334-3341.
29. Vrábel M, Hocek M, Havran L, Fojta M, Votruba I, et al. (2007) Purines Bearing Phenanthroline or Bipyridine Ligands and Their RuII Complexes in Position 8 as Model Compounds for Electrochemical DNA Labeling - Synthesis, Crystal Structure, Electrochemistry, Quantum Chemical Calculations, Cytostatic and Antiviral Activity. Eur J Inorg Chem 12: 1752-1769.
30. Morgan O, Wang S, Bae SA, Morgan RJ, Baker AD, et al. (1997) Two complete stereochemical sets of dinuclear ruthenium complexes. J Chem Soc, Dalton Trans pp. 3773-3776.
31. Kurzeev SA, Vilesov AS, Fedorova TV, Stepanova EV, Koroleva OV, et al. (2009) Kinetic and theoretical comprehension of diverse rate laws and reactivity gaps in Coriolus hirsutus laccase-catalyzed oxidation of acido and cyclometalated Ru(II) complexes. Biochemistry 48: 4519-4527.
32. Velders AH, Kooijman H, Spek AL, Haasnoot JG, de Vos D, et al. (2000) Strong differences in the in vitro cytotoxicity of three isomeric dichlorobis (2-phenylazopyridine) ruthenium (II) complexes. Inorg Chem 39: 2966-2967.
33. Kim NW, Wu F, (1997) Advances in quantification and characterization of telomerase activity by the telomeric repeat amplification protocol (TRAP). Nucleic Acids Res 25: 2595.
34. Krupp G, Kühne K, Tamm S, Klapper W, Heidorn K, et al. (1997) Molecular basis of artifacts in the detection of telomerase activity and a modified primer for a more robust 'TRAP'assay. Nucleic Acids Res 25: 919.
35. Tan C, Lai S, Wu S, Hu S, Zhou L, et al. (2010) Nuclear Permeable Ruthenium (II) β-Carboline Complexes Induce Autophagy To Antagonize Mitochondrial-Mediated Apoptosis. J Med Chem 53: 7613-7624.
36. Xu L, Zhang D, Huang J, Deng M, Zhang M, et al. (2009) High fluorescence selectivity and visual detection of G-quadruplex structures by a novel dinuclear ruthenium complex. Chem Commun 46: 743-745.
37. Wei C, Jia G, Yuan J, Feng Z, Li C, (2006) A spectroscopic study on the interactions of porphyrin with G-quadruplex DNAs. Biochemistry 45: 6681-6691.
38. Haq I, Trent JO, Chowdhry BZ, Jenkins TC, (1999) Intercalative G-tetraplex stabilization of telomeric DNA by a cationic porphyrin1. J Am Chem Soc 121: 1768-1779.
39. Tan JH, Ou TM, Gu LQ, (2009) Isaindigotone Derivatives: A New Class of Highly Selective Ligands for Telomeric G-Quadruplex DNA. J Med Chem 52: 2825-2835.
40. Jin R, Gaffney BL, Wang C, Jones RA, Breslauer KJ, (1992) Thermodynamics and structure of a DNA tetraplex: a spectroscopic and calorimetric study of the tetramolecular complexes of d (TG3T) and d (TG3T2G3T). Proc Natl Acad Sci 89: 8832.
41. Hänsel R, Löhr F, Foldynová-Trantírková S, Bamberg E, Trantírek L, et al. (2011) The parallel G-quadruplex structure of vertebrate telomeric repeat sequences is not the preferred folding topology under physiological conditions. Nucleic Acids Res 39: 5768-5775.
42. Ambrus A, Chen D, Dai J, Bialis T, Jones RA, et al. (2006) Human telomeric sequence forms a hybrid-type intramolecular G-quadruplex structure with mixed parallel/antiparallel strands in potassium solution. Nucleic Acids Res 34: 2723.
43. Teulade-Fichou MP, Carrasco C, Guittat L, Bailly C, Alberti P, et al. (2003) Selective recognition of G-quadruplex telomeric DNA by a bis (quinacridine) macrocycle. J Am Chem Soc 125: 4732-4740.
44. Han H, Cliff CL, Hurley LH, (1999) Accelerated assembly of G-quadruplex structures by a small molecule. Biochemistry 38: 6981-6986.
45. Sun D, Zhang R, Yuan F, Liu D, Zhou Y, et al. (2012) Studies on characterization, telomerase inhibitory property and G-quadruplex binding of η6-arene ruthenium complexes with 1, 10-phenanthroline-derived ligands. Datl Trans 41: 1734-1741.
46. Mergny J-L, Maurizot J-C, (2001) Fluorescence Resonance Energy Transfer as a Probe for G-Quartet Formation by a Telomeric Repeat. Chem Bio Chem 2: 124-132.
47. Moorhouse AD, Santos AM, Gunaratnam M, Moore M, Neidle S, et al. (2006) Stabilization of G-quadruplex DNA by highly selective ligands via click chemistry. J Am Chem Soc 128: 15972-15973.
48. Wang JT, Li Y, Tan JH, Ji LN, Mao ZW, (2011) Platinum(II)-triarylpyridines complexes with electropositive pendants as efficient G-quadruplex binders. Datlon. Trans 40: 564-566.
49. Ren L, Zhang A, Huang J, Wang P, Weng X, et al. (2007) Quaternary Ammonium Zinc Phthalocyanine: Inhibiting Telomerase by Stabilizing G quadruplexes and Inducing G-quadruplex Structure Transition and Formation. J Am Chem Soc 128: 775-780.
50. Lau JSY, Lee PK, Tsang KHK, Ng CHC, Lam YW, et al. (2008) Luminescent Cyclometalated Iridium (III) Polypyridine Indole Complexes-Synthesis, Photophysics, Electrochemistry, Protein-Binding Properties, Cytotoxicity, and Cellular Uptake. Inorg Chem 48: 708-718.
51. Elmes RBP, Orange KN, Cloonan SM, Williams DC, Gunnlaugsson T, (2011) Luminescent ruthenium (II) polypyridyl functionalized gold nanoparticles; their DNA binding abilities and application as cellular imaging agents. J Am Chem Soc 133: 15862-15865.
52. Puckett CA, Barton JK, (2007) Methods to explore cellular uptake of ruthenium complexes. J Am Chem Soc 129: 46-47.
53. Puckett CA, Barton JK, (2008) Mechanism of Cellular Uptake of a Ruthenium Polypyridyl Complex. Biochemistry 47: 11711-11716.
54. Tan C, Lai S, Wu S, Hu S, Zhou L, et al. (2010) Nuclear Permeable Ruthenium (II) β-Carboline Complexes Induce Autophagy To Antagonize Mitochondrial-Mediated Apoptosis. J Med Chem 53: 7613-7624.
55. Levina A, Mitra A, Lay PA, (2009) Recent developments in ruthenium anticancer drugs. Metallomics 1: 458-470.
56. Noor F, Wüstholz A, Kinscherf R, Metzler-nolte N, (2005) A Cobaltocenium-peptide Bioconjugate Shows Enhanced Cellular Uptake and Directed Nuclear Delivery. Angew Chem Int Ed 44: 2429-2432.