Interactions of metal ions with DNA, its constituents and derivatives, which may be relevant for anticancer research

Current Topics in Medicinal Chemistry

Volumn 11, Issue 21, 2011, Pages 2661-2687

  Turel, Iztok ^a   Kljun, Jakob ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

Anticancer metal complex; Carcinogenic metals; Diagnostics; DNA; Metal based drug; Metal ion; Structure

Indexed keywords

ACICLOVIR; ANTINEOPLASTIC AGENT; BLEOMYCIN; BUDOTITANE; CARBOPLATIN; CISPLATIN; COBALT; DNA; FLUOROURACIL; GALLIUM NITRATE; MAGNESIUM; MERCAPTOPURINE; METAL COMPLEX; METAL ION; NICKEL; OXALIPLATIN; PENCICLOVIR; REACTIVE OXYGEN METABOLITE; RIBAVIRIN; RUBIDIUM; TEGAFUR; TITANOCENE DICHLORIDE; ZIDOVUDINE; ZINC ION;

ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; APOPTOSIS; BINDING KINETICS; BINDING SITE; BONE MARROW SUPPRESSION; CANCER DIAGNOSIS; CANCER PREVENTION; CANCER RESEARCH; CARCINOGEN DNA INTERACTION; CELL PROLIFERATION; COMPETITIVE INHIBITION; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; CRYSTALLIZATION; DNA DAMAGE; DNA STRUCTURE; DRUG CYTOTOXICITY; GENE MUTATION; HELICOBACTER INFECTION; HUMAN; HYDROGEN BOND; HYDROLYSIS; KAPOSI SARCOMA; LEUKEMIA; NAUSEA; NEPHROTOXICITY; NONHUMAN; REVIEW; SIGNAL TRANSDUCTION; STRUCTURE ACTIVITY RELATION; VOMITING; X RAY DIFFRACTION;

ANTIMETABOLITES; ANTINEOPLASTIC AGENTS; BINDING SITES; CATIONS; COORDINATION COMPLEXES; DNA; DNA CLEAVAGE; HUMANS; METAL NANOPARTICLES; METALS; MODELS, MOLECULAR; NEOPLASMS; NUCLEIC ACID CONFORMATION; NUCLEOTIDES; ORGANOMETALLIC COMPOUNDS;

EID: 80055082426     PISSN: 15680266     EISSN: 18734294     Source Type: Journal    
DOI: 10.2174/156802611798040787     Document Type: Review

References (367)

1. Dahm, R. Discovering DNA: Friedrich Miescher and the early years of nucleic acid research. Hum. Genet., 2008, 122, 565-581.
2. Levene, P. The structure of yeast nucleic acid. J. Biol. Chem., 1919, 40, 415-424.
3. Hammarsten, E. The biological significance of nucleic acid compounds. Biochem. Z., 1924, 144, 383-466.
4. Watson, J. D.; Crick, F. H. C. Molecular structure of nucleic acids a structure for deoxyribose nucleic acid. Nature, 1953, 171, 738-739.
5. Alberts, B.; Johnson, A.; Lewis, J.; Raff, M.; Roberts, K.; Walter, P. Eds. Molecular biology of the cell, Garland Science: New York, 2002.
6. Luger, K.; Mader, A. W.; Richmond, R. K.; Sargent, D. F.; Richmond, T. J. Crystal structure of the nucleosome core particle at 2.8 angstrom resolution. Nature, 1997, 389, 251-260.
7. Subirana, J. A.; Soler-Lopez, M. Cations as hydrogen bond donors: A view of electrostatic interactions in DNA. Annu. Rev. Bioph. Biom., 2003, 32, 27-45 and the references therein.
8. Calladine, C. R.; Drew, H. R.; Luisi, B. F.; Travers, A. A. Understanding DNA: The molecule & how it works, Elsevier Ltd.: London, 2004.
9. Williams, P. J. P.; Fraústo da Silva, J. J. R. Eds. The chemistry of evolution: The development of our ecosystem, Elsevier B.V.: Amsterdam, 2006.
10. Sigel, H.; Sigel, A. Eds. Metal ions in biological systems: Nucleotides and derivatives: their ligating ambivalency, vol. 8, Marcel Dekker: New York, 1979.
11. Sigel, H.; Sigel, A. Eds. Metal ions in biological systems: Interactions of metal ions with nucleotides, nucleic acids and their constituents, vol. 32, Marcel Dekker: New York, 1996.
12. Sigel, H.; Sigel, A. Eds. Metal ions in biological systems: Probing nucleic acids with metal ion complexes of small molecules, vol. 33, Marcel Dekker: New York, 1996.
13. Hud, N. V. Ed. Nucleic acid metal ion interactions, RSC Publishing: Cambridge, 2009.
14. Hadjiliadis, N.; Sletten, E. Eds. Metal complex DNA interactions, John Wiley & Sons, Inc.: Hoboken, NJ, 2009.
15. Lippert, B. Coordinative bond formation between metal ions and nucleic acid bases. In: Nucleic acid metal ion interactions, Hud, N.V., Ed.; RSC Publishing: Cambridge, 2009, pp. 39-74.
16. Hodgson, D. J. The stereochemistry of metal complexes of nucleic acid constituents. In: Progress in inorganic chemistry, Lippard, S.J., Ed.; John Wiley & Sons, Inc.: Chichester, 1977; Vol. 23, pp. 211-254.
17. Misra, V. K.; Draper, D. E. On the role of magnesium ions in RNA stability. Biopolymers, 1998, 48, 113-135.
18. McCleverty, J. A.; Meyer, T. J. Eds. Comprehensive coordination chemistry II: Bio-coordination chemistry, vol. 8, Elsevier: Amsterdam, 2005
19. Sletten, E.; Froystein, N. A. Sequence-selective binding of transition metal complexes to DNA. In: Metal complex DNA interactions, N. Hadjiliadis; E. Sletten, Eds.; John Wiley & Sons, Inc.: Chichester, 2009, pp. 1-30.
20. Dickerson, R. E.; Drew, H. R. Structure of a B-DNA dodecamer.3. Geometry of hydration. J. Mol. Biol., 1981, 149, 761-786.
21. Nerdal, W.; Hare, D. R.; Reid, B. R. Solution structure of the EcoRI SNA-sequence-refinement of NMR-derived distance geometry structures by NOESY spectrum back-calculations. Biochemistry, 1989, 28, 10008-10021.
22. Richens, D. T. Ed. The chemistry of aqua ions, John Wiley & Sons, Inc.: Chichester, 1997.
23. Glusker, J. P. The binding of ions to proteins. In: Protein: A comprehensive treatise, vol. II, G. Allen, Ed.; Elsevier: Amsterdam, 1999, pp. 99-152.
24. Lindsey, J. S.; Woodford, J. N. A simple method for preparing magnesium porphyrins. Inorg. Chem., 1995, 34, 1063-1069.
25. Gao, Y. G.; Sriram, M.; Wang, A. H. J. Crystallographic studies of metal-ion DNA interactions different binding modes of cobalt(II), copper(II) and barium(II) to N-7 of guanines in Z-DNA and a drug DNA complex. Nucleic Acids Res., 1993, 21, 4093-4101.
26. Ohishi, H.; Kunisawa, S.; Vandermarel, G.; Vanboom, J. H.; Rich, A.; Wang, A. H. J.; Tomita, K.; Hakoshima, T. Interaction between the left-handed Z-DNA and polyamine the crystal-structure of the D(CG)3 and N-(2aminoethyl)-1,4-diamino-butane complex. Febs Lett., 1991, 284, 238-244.
27. Soler-Lopez, M.; Malinina, L.; Subirana, J. A. Interaction of zinc ions with d(CGCAATrGCG) in a 2.9 angstrom resolution X-ray structure. J. Biol. Chem., 2000, 275, 23034-23044.
28. Kielkopf, C. L.; Ding, S.; Kuhn, P.; Rees, D. C. Conformational flexibility of B-DNA at 0.74 angstrom resolution: d(CCAGTACTGG)(2). J. Mol. Biol., 2000, 296, 787-801.
29. Minasov, G.; Tereshko, V.; Egli, M. Atomic-resolution crystal structures of B-DNA reveal specific influences of divalent metal ions on conformation and packing. J. Mol. Biol., 1999, 291, 83-99.
30. Pavlov, M.; Siegbahn, P. E. M.; Sandstrom, M. Hydration of beryllium, magnesium, calcium, and zinc ions using density functional theory. J. Phys. Chem. A, 1998, 102, 219-228.
31. Abrescia, N. G. A.; Malinina, L.; Fernandez, L. G.; Huynh-Dinh, T.; Neidle, S.; Subirana, J. A. Structure of the oligonucleotide d(CGTATATACG) as a site-specific complex with nickel ions. Nucleic Acids Res., 1999, 27, 1593-1599.
32. Yang, X. L.; Robinson, H.; Gao, Y. G.; Wang, A. H. J. Binding of a macrocyclic bisacridine and ametantrone to CGTACG involves similar unusual intercalation platforms. Biochemistry, 2000, 39, 10950-10957.
33. Valls, N.; Uson, I.; Gouyette, C.; Subirana, J. A. A cubic arrangement of DNA double helices based on nickel-guanine interactions. J. Am. Chem. Soc., 2004, 126, 7812-7816.
34. Spink, N.; Nunn, C. M.; Vojtechovsky, J.; Berman, H. M.; Neidle, S. Crystal-structure of a DNA decamer showing a novel pseudo 4-way helix-helix junction. Proc. Nat. Acad. Sci. USA, 1995, 92, 10767-10771.
35. Millonig, H.; Pous, J.; Gouyette, C.; Subirana, J. A.; Campos, J. L. The interaction of manganese ions with DNA. J. Inorg. Biochem., 2009, 103, 876-880.
36. Harp, J. M.; Hanson, B. L.; Timm, D. E.; Bunick, G. J. Asymmetries in the nucleosome core particle at 2.5 angstrom resolution. Acta Crystallogr. D, 2000, 56, 1513-1534.
37. Soler-Lopez, M.; Malinina, L.; Tereshko, V.; Zarytova, V.; Subirana, J. A. Interaction of zinc ions with d(CGCAATrGCG) in a 2.9 angstrom resolution X-ray structure. J. Biol. Inorg. Chem., 2002, 7, 533-538.
38. Eichhorn, G. L.; Shin, Y. A. Interaction of metal ions with polynucleotides and related compounds. XII. The relative effect of various metal ions on DNA helicity. J. Am. Chem. Soc., 1968, 90, 7323-7328.
39. Harding, M. M. Metal-ligand geometry relevant to proteins and in proteins: sodium and potassium. Acta Crystallogr. D, 2002, 58, 872-874.
40. Komeda, S.; Moulaei, T.; Woods, K. K.; Chikuma, M.; Farrell, N. P.; Williams, L. D. A third mode of DNA binding: Phosphate clamps by a polynuclear platinum complex. J. Am. Chem. Soc., 2006, 128, 16092-16103.
41. Egli, M. DNA-cation interactions: Quo vadis?. Chem. Biol., 2002, 9, 277-286.
42. Hud, N. V.; Feigon, J. Localization of divalent metal ions in the minor groove of DNA A-tracts. J. Am. Chem. Soc., 1997, 119, 5756-5757.
43. Hud, N. V.; Sklenar, V.; Feigon, J. Localization of ammonium lone in the minor groove of DNA duplexes in solution and the origin of DNA A-tract bending. J. Mol. Biol., 1999, 286, 651-660.
44. Hud, N. V.; Polak, M. DNA-cation interactions: the major and minor grooves are flexible ionophores. Curr. Opin. Struc. Biol., 2001, 11, 293-301.
45. Hud, N. V.; Plavec, J. A unified model for the origin of DNA sequence-directed curvature. Biopolymers, 2003, 69, 144-159.
46. Drew, H. R.; Dickerson, R. E. Structure of a B-DNA dodecamer.2. Influence of base sequence on helix structure. J. Mol. Biol., 1981, 151, 535-556.
47. Shui, X. Q.; McFail-Isom, L.; Hu, G. G.; Williams, L. D. The B-DNA dodecamer at high resolution reveals a spine of water on sodium. Biochemistry, 1998, 37, 8341-8355.
48. Plavec, J. Metal ion coordination in G-quadruplexes. In: Metal complex DNA interactions, N. Hadjiliadis; E. Sletten, Eds.; John Wiley & Sons, Inc.: Chichester, 2009, pp. 55-94
49. Hud, N. V.; Engelhart, A. E. Sequence-specific DNA-metal ion interactions. In: Nucleic metal ion interactions, Hud, N.V., Ed.; RSC Publishing: Cambridge, 2009, pp. 75-117.
50. Howerton, S. B.; Sines, C. C.; VanDerveer, D.; Williams, L. D. Locating monovalent cations in the grooves of B-DNA. Biochemistry, 2001, 40, 10023-10031.
51. Sheehan, D. Ed. Physical Biochemistry, principles and applications, John Wiley & Sons, Inc.: Chichester, 2009.
52. Doerr, A. Together at last: crystallography and NMR. Nat. Methods, 2006, 3, 6-6.
53. Snyder, D. A.; Chen, Y.; Denissova, N. G.; Acton, T.; Aramini, J. M.; Ciano, M.; Karlin, R.; Liu, J. F.; Manor, P.; Rajan, P. A.; Rossi, P.; Swapna, G. V. T.; Xiao, R.; Rost, B.; Hunt, J.; Montelione, G. T. Comparisons of NMR spectral quality and success in crystallization demonstrate that NMR and X-ray crystallography are complementary methods for small protein structure determination. J. Am. Chem. Soc., 2005, 127, 16505-16511.
54. Yee, A. A.; Savchenko, A.; Ignachenko, A.; Lukin, J.; Xu, X. H.; Skarina, T.; Evdokimova, E.; Liu, C. S.; Semesi, A.; Guido, V.; Edwards, A. M.; Arrowsmith, C. H. NMR and X-ray crystallography, complementary tools in structural proteomics of small proteins. J. Am. Chem. Soc., 2005, 127, 16512-16517.
55. Lippert, B. Multiplicity of metal ion binding patterns to nucleobases. Coord. Chem. Rev., 2000, 200, 487-516.
56. Sanz Miguel, P. J.; Amo-Ochoa, P.; Castillo, O.; Houlton, A.; Zamora, F. Supramolecular chemistry of metal-nucleobase complexes. In: Metal complex DNA interactions, Hadjiliadis, N.; Sletten, E., Eds.; John Wiley & Sons, Inc.: Chichester, 2009, pp. 95-132.
57. Sletten, E. Crystal structure of a dinuclear 2:1 adenine-copper complex. Chem. Comm. (London), 1967, 1119-1120.
58. Kistenmacher, T. J.; Chiang, C. C.; Chalilpoyil, P.; Marzilli, L. G. Structural-properties of a nearly stoichiometric diamineplatinum(II) complex with inosine 5'-monophosphate. J. Am. Chem. Soc., 1979, 101, 1143-1148.
59. Chao, Y. Y. H.; Kearns, D. R. Magnetic-resonance studies of copper(II) interaction with nucleosides and nucleotides. J. Am. Chem. Soc., 1977, 99, 6425-6434.
60. Galy, J.; Mosset, A.; Grenthe, I.; Puigdomenech, I.; Sjoberg, B.; Hulten, F. An unusual copper uridine octamer existence in solution and structural study in its auto-built zeolitic network in the solid-state. J. Am. Chem. Soc., 1987, 109, 380-386.
61. Jancso, A.; Nagy, L.; Moldrheim, E.; Sletten, E. Potentiometric and spectroscopic evidence for co-ordination of dimethyltin(IV) to phosphate groups of DNA fragments and related ligands, J. Chem. Soc. Dalton Trans., 1999, 1587-1594.
62. Conn, J. F.; Kim, J. J.; Suddath, F. L.; Blattman P; Rich, A. Crystal and molecular-structure of an osmium bispyridine ester of adenosine. J. Am. Chem. Soc., 1974, 96, 7152-7153.
63. Topal, M. D.; Fresco, J. R. Complementary base-pairing and origin of substitution mutations. Nature, 1976, 263, 285-289.
64. Miles, H. T. Tautomeric forms in a polynucleotide helix and their bearing on the structure of DNA, Proc. Nat. Acad. Sci. USA, 1961, 47, 791-802.
65. Simpson, R. B. Association constants of methylmercuric and mercuric ions with nucleosides. J. Am. Chem. Soc., 1964, 86, 2059-2065.
66. Gatenby, R. A.; Gillies, R. J. Why do cancers have high aerobic glycolysis?. Nat. Rev. Cancer, 2004, 4, 891-899.
67. Gillies, R. J.; Raghunand, N.; Karczmar, G. S.; Bhujwalla, Z. M. MRI of the tumor microenvironment. J. Magn. Reson. Imaging, 2002, 16, 430-450.
68. Raghunand, N.; Gatenby, R. A.; Gillies, R. J. Microenvironmental and cellular consequences of altered blood flow in tumours. Brit. J. Radiol., 2003, 76, S11-S22.
69. Gatenby, R. A.; Gawlinski, E. T. A reaction-diffusion model of cancer invasion. Cancer Res., 1996, 56, 5745-5753.
70. Turel, I.; Andersen, B.; Sletten, E.; White, A. J. P.; Williams, D. J. New studies in the copper(II) acyclovir (acv) system. NMR relaxation studies and the X-ray crystal structure of [Cu(acv)2(H2O)2](NO3)2. Polyhedron, 1998, 17, 4195-4201.
71. 5-cyclopentadienyl)(theophyllinato)titanium(III). Inorg. Chem., 1986, 25, 2600-2606.
72. 5-pentamethylcyclopentadienyl)rhodium aqua complexes. Angew. Chem. Int. Ed., 1995, 34, 1514-1517.
73. Chifotides, H. T.; Dunbar, K. R. Interactions of metal-metal-bonded antitumor active complexes with DNA fragments and DNA. Acc. Chem. Res., 2005, 38, 146-156.
74. Coll, M.; Solans, X.; Fontaltaba, M.; Subirana, J. A. Crystal and molecular-structure of the sodium-salt of the dinucleotide duplex D(CPG). J. Biomol. Struct. Dyn., 1987, 4, 797-811.
75. Pizarro, A. M.; Sadler, P. J. Unusual DNA binding modes for metal anticancer complexes. Biochimie, 2009, 91, 1198-1211.
76. Lippert, B. Ed. Cisplatin: Chemistry and biochemistry of a leading anticancer drug, John Wiley & Sons, Inc.: Amsterdam, 1999.
77. Hannon, M. J. Metal-based anticancer drugs: From a past anchored in platinum post-genomic future and biology. Pure Appl. Chem., 2007, 79, 2243-2261.
78. Rosenberg, B.; Vancamp, L.; Trosko, J. E.; Mansour, V. H. Platinum compounds: a new class of potent antitumour agents. Nature, 1969, 222, 385-386.
79. Dyson, P. J.; Sava, G. Metal-based antitumour drugs in the post genomic era. Dalton Trans., 2006, 1929-1933.
80. Centerwall, C. R.; Tacka, K. A.; Kerwood, D. J.; Goodisman, J.; Toms, B. B.; Dubowy, R. L.; Dabrowiak, J. C. Modification and uptake of a cisplatin carbonato complex by Jurkat cells. Mol. Pharmacol., 2006, 70, 348-355.
81. Eastman, A. Characterization of the adducts produced in DNA by cis-diamminedichloroplatinum(II) and cisdichloro(ethylenediamine)platinum(II). Biochemistry, 1983, 22, 3927-3933.
82. Eastman, A. Reevaluation of interaction of cisdichloro(ethylenediamine)platinum(II) with DNA. Biochemistry, 1986, 25, 3912-3915.
83. Caradonna, J. P.; Lippard, S. J.; Gait, M. J.; Singh, M. The antitumor drug cis-dichlorodiammineplatinum forms an intrastrand d(GpG) crosslink upon reaction with [d(ApGpGpCpCpT)]2. J. Am. Chem. Soc., 1982, 104, 5793-5795.
84. Filipski, J.; Kohn, K. W.; Bonner, W. M. The nature of inactivating lesions produced by platinum(II) complexes in phage-lambda DNA. Chem.-Biol. Interact., 1980, 32, 321-330.
85. Fichtingerschepman, A. M. J.; Vanderveer, J. L.; Denhartog, J. H. J.; Lohman, P. H. M.; Reedijk, J. Adducts of the antitumor drug cis-diamminedichloroplatinum(II) with DNA -formation, identification, and quantitation. Biochemistry, 1985, 24, 707-713.
86. Fichtingerschepman, A. M. J.; Vanoosterom, A. T.; Lohman, P. H. M.; Berends, F. Cis-diamminedichloroplatinum(II)-induced DNA adducts in peripheral leukocytes from 7 cancer-patients quantitative immunochemical detection of the adduct induction and removal after a single dose of cis-diamminedichloroplatinum(II). Cancer Res., 1987, 47, 3000-3004.
87. Poklar, N.; Pilch, D. S.; Lippard, S. J.; Redding, E. A.; Dunham, S. U.; Breslauer, K. J. Influence of cisplatin intrastrand crosslinking on the conformation, thermal stability, and energetics of a 20-mer DNA duplex. Proc. Nat. Acad. Sci. USA, 1996, 93, 7606-7611.
88. Pizarro, A. M.; Sadler, P. J. In: Metal ion nucleic acid interactions in disease medicine. Nucleic acid metal ions interaction, Hud, N.V. Ed.; RSC Publishing: Cambridge, 2009, pp. 350-416.
89. Takahara, P. M.; Rosenzweig, A. C.; Frederick, C. A.; Lippard, S. J. Crystal-structure of double-stranded DNA containing the major adduct of the anticancer drug cisplatin. Nature, 1995, 377, 649-652.
90. Gelasco, A.; Lippard, S. J. NMR solution structure of a DNA dodecamer duplex containing a cis-diammineplatinum(II) d(GpG) intrastrand cross-link, the major adduct of the anticancer drug cisplatin. Biochemistry, 1998, 37, 9230-9239.
91. Lummen, G.; Sperling, H.; Luboldt, H.; Otto, T.; Rubben, H. Phase II trial of titanocene dichloride in advanced renal-cell carcinoma. Cancer Chemoth. Pharm., 1998, 42, 415-417.
92. Stadler, W. M.; Kuzel, T. M.; Raghavan, D.; Levine, E.; Vogelzang, N. J.; Roth, B.; Dorr, F. A. Metastatic bladder cancer: Advances in treatment. Eur. J. Cancer, 1997, 33, S23-S26.
93. Jakupec, M. A.; Keppler, B. K. Gallium in cancer treatment. Curr. Top. Med. Chem., 2004, 4, 1575-1583.
94. Rademaker-Lakhai, J. M.; van den Bongard, D.; Pluim, D.; Beijnen, J. H.; Schellens, J. H. M. A phase I and pharmacological study with imidazolium-trans-DMSO-imidazoletetrachlororuthenate, a novel ruthenium anticancer agent. Clin. Cancer Res., 2004, 10, 3717-3727.
95. Hartinger, C. G.; Zorbas-Seifried, S.; Jakupec, M. A.; Kynast, B.; Zorbas, H.; Keppler, B. K. From bench to bedside preclinical and early clinical development of the anticancer agent indazolium trans-[tetrachlorobis(1H-indazole)ruthenate(III)] (KP1019 or FFC14A). J. Inorg. Biochem., 2006, 100, 891-904.
96. Reedijk, J. Metal-ligand exchange kinetics in platinum and ruthenium complexes: Significance for effectiveness as anticancer drugs. Platinum Met. Rev., 2008, 52, 2-11.
97. Fruhauf, S.; Zeller, W. J. New platinum, titanium, and ruthenium complexes with different patterns of DNA damage in rat ovarian tumor-cells. Cancer Res., 1991, 51, 2943-2948.
98. Morbidelli, L.; Donnini, S.; Filippi, S.; Messori, L.; Piccioli, F.; Orioli, P.; Sava, G.; Ziche, M. Antiangiogenic properties of selected ruthenium(III) complexes that are nitric oxide scavengers. Brit. J. Cancer, 2003, 88, 1484-1491.
99. Arion, V. B.; Jakupec, M. A.; Galanski, M.; Unfried, P.; Keppler, B. K. Synthesis, structure, spectroscopic and in vitro antitumour studies of a novel gallium(III) complex with 2-acetylpyridine N-4-dimethylthiosemicarbazone. J. Inorg. Biochem., 2002, 91, 298-305.
100. Sava, G.; Alessio, E.; Bergamo, A.; Mestroni, G. In: Sulphoxide Ruthenium Complexes: Non-Toxic Tools for the Selective Treatment of Solid Tumor Metastases. Topics in biological inorganic chemistry. Clarke, M. J.; Sadler, P. J., Eds.; Springer Verlag: Berlin, 1999, pp. 143-169.
101. Alessio, E.; Mestroni, G.; Bergamo, A.; Sava, G. Ruthenium antimetastatic agents. Curr. Top. Med. Chem., 2004, 4, 1525-1535.
102. Bergamo, A.; Sava, G. Ruthenium complexes can target determinants of tumour malignancy. Dalton Trans., 2007, 1267-1272.
103. Strekowski, L.; Wilson, B. Noncovalent interactions with DNA: An overview. Mutat. Res. Fund. Mol. M., 2007, 623, 3-13.
104. Lippard, S. J.; Jennette, K. W.; Vassilia G; Bauer, W. R. Metal-complexes that bind to DNA by intercalation. Abstr. Pap. Am. Chem. Soc., 1974, 2-2.
105. Erkkila, K. E.; Odom, D. T.; Barton, J. K. Recognition and reaction of metallointercalators with DNA. Chem. Rev., 1999, 99, 2777-2795.
106. Ruba, E.; Hart, J. R.; Barton, J. K. Ru(bpy)(2)(L) Cl-2: Luminescent metal complexes that bind DNA base mismatches. Inorg. Chem., 2004, 43, 4570-4578.
107. Angeles-Boza, A. M.; Bradley, P. M.; Fu, P. K. L.; Wicke, S. E.; Bacsa, J.; Dunbar, K. R.; Turro, C. DNA binding and photocleavage in vitro by new dirhodium(II) dppz complexes: Correlation to cytotoxicity and photocytotoxicity. Inorg. Chem., 2004, 43, 8510-8519.
108. Bradley, P. M.; Angeles-Boza, A. M.; Dunbar, K. R.; Turro, C. Direct DNA photocleavage by a new intercalating dirhodium(II/II) complex: Comparison to Rh-2(mu-O2CCH3)(4). Inorg. Chem., 2004, 43, 2450-2452.
109. Angeles-Boza, A. M.; Bradley, P. M.; Fu, P. K. L.; Shatruk, M.; Hilfiger, M. G.; Dunbar, K. R.; Turro, C. Photocytotoxicity of a new Rh2(II,II) complex: Increase in cytotoxicity upon irradiation similar to that of PDT agent hematoporphyrin. Inorg. Chem., 2005, 44, 7262-7264.
110. Angeles-Boza, A. M.; Chifotides, H. T.; Aguirre, J. D.; Chouai, A.; Fu, P. K. L.; Dunbar, K. R.; Turro, C. Dirhodium(II,II) complexes: Molecular characteristics that affect in vitro activity. J. Med. Chem., 2006, 49, 6841-6847.
111. 2+ dimers. J. Am. Chem. Soc., 2001, 123, 3630-3637.
112. 4+: toxic effects and properties as a light emitting DNA probe in V79 Chinese hamster cells. Mutagenesis, 2002, 17, 317-320.
113. Harris, A. L.; Yang, X. H.; Hegmans, A.; Povirk, L.; Ryan, J. J.; Kelland, L.; Farrell, N. P. Synthesis, characterization, and cytotoxicity of a novel highly charged trinuclear platinum compound. Enhancement of cellular uptake with charge. Inorg. Chem., 2005, 44, 9598-9600.
114. Hannon, M. J.; Moreno, V.; Prieto, M. J.; Moldrheim, E.; Sletten, E.; Meistermann, I.; Isaac, C. J.; Sanders, K. J.; Rodger, Intramolecular DNA coiling mediated by a metallo-supramolecular cylinder. A. Angew. Chem. Int. Edit., 2001, 40, 880-884.
115. Meistermann, I.; Moreno, V.; Prieto, M. J.; Moldrheim, E.; Sletten, E.; Khalid, S.; Rodger, P. M.; Peberdy, J. C.; Isaac, C. J.; Rodger, A.; Hannon, M. J. Intramolecular DNA coiling mediated by metallosupramolecular cylinders: Differential binding of P and M helical enantiomers. Proc. Nat. Acad. Sci. USA, 2002, 99, 5069-5074.
116. Sinden, R. R. Ed. DNA structure and function, Academic press: London, 1994.
117. Dickerson, R. E. DNA bending: The prevalence of kinkiness and the virtues of normality. Nucleic Acids Res., 1998, 26, 1906-1926.
118. Branden, C.; Tooze, J. Eds. Introduction to protein structure, Garland: New York, 1999.
119. Cerasino, L.; Hannon, M. J.; Sletten, E. DNA three-way junction with a dinuclear iron(II) supramolecular helicate at the center: A NMR structural study. Inorg. Chem., 2007, 46, 6245-6251.
120. Baguley, B. C. Non-intercalative DNA-binding anti-tumor compounds. Mol. Cell. Biochem., 1982, 43, 167-181.
121. Denny, W. A. DNA-intercalating ligands as anti-cancer drugs prospects for future design. Anti-Cancer Drug Des., 1989, 4, 241-263.
122. Uerpmann, C.; Malina, J.; Pascu, M.; Clarkson, G. J.; Moreno, V.; Rodger, A.; Grandas, A.; Hannon, M. J. Design and DNA binding of an extended triple-stranded metallo-supramolecular cylinder. Chem. Eur. J., 2005, 11, 1750-1756.
123. Oleksi, A.; Blanco, A. G.; Boer, R.; Uson, I.; Aymami, 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.
124. Muller, J.; Lippert, B. Imposing a three-way junction on DNA or recognizing one: A metal triple helicate meets double helix. Angew. Chem. Int. Ed., 2006, 45, 2503-2505.
125. Malina, J.; Hannon, M. J.; Brabec, V. Interaction of dinuclear ruthenium(II) supramolecular cylinders with DNA: Sequence specific binding, unwinding, and photocleavage. Chem. Eur. J., 2008, 14, 10408-10414.
126. Williams, D. A.; Lemke, T. L. Eds. Foye's principles of medicinal chemistry, Lippincott Williams & Wilkins: Philadelphia, PA, 2002. 268.
127. Peters, G. J.; van der Wilt, C. L.; van Moorsel, C. J. A.; Kroep, J. R.; Bergman, A. M.; Ackland, S. P. Basis for effective combination cancer chemotherapy with antimetabolites. Pharmacol. Therapeut., 2000, 87, 227-253.
128. Burchenal, J. H.; Murphy, M. L.; Ellison, R. R.; Sykes, M. P.; Tan, T. C.; Leone, L. A.; Karnofsky, D. A.; Craver, L. F.; Dargeon, H. W.; Rhoads, C. P. Clinical evaluation of a new antimetabolite, 6-mercaptopurine, in the treatment of leukemia and allied diseases. Blood, 1953, VIII, 965-999.
129. Lukens, L. N.; Herrnigton, K. A. Enzymic formation of 6-mercaptopurine ribotide. Biochim. Biophys. Acta, 1957, 24, 432-433.
130. Elion, G. B.; Furman, P. A.; Fyfe, J. A.; Demiranda, P.; Beauchamp, L.; Schaeffer, H. J. Selectivity of action of an anti-herpetic agent, 9-(2-hydroxyethoxymethyl)guanine. Proc. Nat. Acad. Sci. USA, 1977, 74, 5716-5720.
131. Yamanari, K.; Fukuda, I.; Kawamoto, T.; Kushi, Y.; Fuyuhiro, A.; Kubota, N.; Fukuo, T.; Arakawa, R. Self-assembling synthesis of cyclic tri and tetranuclear cobalt(III) complexes bridged by purine 6-thione and their characterization by electrospray mass spectrometry and X-ray crystal analysis. Inorg. Chem., 1998, 37, 5611-5618.
132. Yamanari, K.; Ito, R.; Yamamoto, S.; Konno, T.; Fuyuhiro, A.; Fujioka, K.; Arakawa, R. Cyclic tetramers composed of rhodium(III), iridium(III), or ruthenium(II) half-sandwich and 6-purinethiones. Inorg. Chem., 2002, 41, 6824-6830.
133. Yamanari, K.; Nozaki, T.; Fuyuhiro, A.; Kaizaki, S. Crystal structure of bis(2,2'-bipyridine)(purine-6-thione)ruthenium(II) complex. Bull. Chem. Soc. Jpn., 2002, 75, 109-110.
134. Lakomska, I. Molecular structure and antitumor activity of platinum(II) complexes containing purine analogs. Inorg. Chim. Acta, 2009, 362, 669-681.
135. Das, M.; Livingstone, S. E. Metal-chelates as anti-cancer agents.2. Cytotoxic action of palladium and platinum complexes of 6-mercaptopurine and thioguanine. Brit. J. Canc., 1978, 38, 325-328.
136. Nazimova, N. V.; Tischenko, G. N.; Nikitina, I. V.; Ershov, A.; Kazmina, E. M. Kristallografiya, 1987, 32, 1404.
137. Amagai, T.; Miyamoto, T. K.; Ichida, H.; Sasaki, Y. Preparation and crystal-structure of new gold(I) complexes linked to pyrimidines. Bull. Chem. Soc. Jpn., 1989, 62, 1078-1080.
138. Lukevics, E.; Ignatovich, L.; Shilina, N.; Kemme, A.; Sjakste, N. Synthesis, structure and biological activity of 6-R3Si(Ge,Sn) substituted 5-fluorouracils. Metal-based drugs, 1994, 1, 65-72.
139. 5-C5H5Fe(CO)2 complex of deprotonated 5-fluoro-1-(tetrahydro-2-furyl) uracil (Ftorafur). J. Organomet. Chem., 1995, 495, 83-90.
140. Blazic, B.; Turel, I.; Bukovec, N.; Bukovec, P.; Lazarini, F. Synthesis and structure of diaquadichlorobis(9-(2-hydroxyethoxy) methyl guanine) copper(II). J. Inorg. Biochem., 1993, 51, 737-744.
141. Turel, I.; Bukovec, N.; Goodgame, M.; Williams, D. J. Synthesis and characterization of copper(II) coordination compounds with acyclovir: Crystal structure of triaquabis 9-{(2-hydroxyethoxy) methyl}guanine copper(II) nitrate(V) hydrate. Polyhedron, 1997, 16, 1701-1706.
142. Sinur, A.; Grabner, S. A platinum(II) diammine complex cis-[Pt(C8H11N5O3)2(NH3)2]Cl2·2H2O. Acta Crystallogr. C, 1995, 51, 1769-1772.
143. Grabner, S.; Plavec, J.; Bukovec, N.; Di Leo, D.; Cini, R.; Natile, G. Synthesis and structural characterization of platinum(II) acyclovir complexes. J. Chem. Soc., Dalton Trans., 1998, 1447-1451.
144. Cini, R.; Grabner, S.; Bukovec, N.; Cerasino, L.; Natile, G. Synthesis and structural characterisation of a new form of bis(acyclovir)(ethylenediamine)platinum(II) Correlation between the puckering of the carrier ligand and the canting of the nucleobases. Eur. J. Inorg. Chem., 2000, 1601-1607.
145. Garcia-Raso, A.; Fiol, J. J.; Badenas, F.; Cons, R.; Terron, A.; Quiros, M. Synthesis and structural characteristics of metal acyclovir (ACV) complexes: [Ni(or Co)(ACV)2(H2O)4]Cl2·2ACV, [Zn(ACV)Cl2(H2O)], [Cd(ACV)Cl2]·H2O and [{Hg(ACV)Cl2}(x)]. Recognition of acyclovir by Ni-ACV. J. Chem. Soc., Dalton Trans., 1999, 167-173.
146. Turel, I.; Pecanac, M.; Golobic, A.; Alessio, E.; Serli, B. Novel Ru-III-DMSO complexes of the antiherpes drug acyclovir. Eur. J. Inorg. Chem., 2002, 1928-1931.
147. Turel, I.; Pecanac, M.; Golobic, A.; Alessio, E.; Serli, B.; Bergamo, A.; Sava, G. Solution, solid state and biological characterization of ruthenium(III)-DMSO complexes with purine base derivatives. J. Inorg. Biochem., 2004, 98, 393-401.
148. Golobic, A.; Saric, D.; Turel, I.; Serli, B. Crystal structure of ionic compound between antiviral drug acyclovir and complex ruthenate(II). Acta Chim. Slov., 2008, 55, 973-977.
149. Varadinova, T.; Vilhelmova, N.; Badenas, F.; Terron, A.; Fiol, J.; Garcia-Raso, A.; Genova, P. Effect of metal complexes of acyclovir and its acetylated derivative on Herpes simplex virus 1 and Herpes simplex virus 2 replication. Acta Virol., 2005, 49, 251-260.
150. Gomez-Segura, J.; Caballero, S.; Moreno, V.; Prieto, M. J.; Bosch, A. Palladium(II) binding to N(7) of acyclovir: DNA interaction and herpes simplex virus (HSV-1) inhibitory activity. J. Inorg. Biochem., 2009, 103, 128-134.
151. Coluccia, M.; Boccarelli, A.; Cermelli, C.; Portolani, M.; Natile, G. Platinum(II)-acyclovir complexes: synthesis, antiviral and antitumour activity. Metal-based drugs, 1995, 2, 249-256.
152. Balcarova, Z.; Kasparkova, J.; Zakovska, A.; Novakova, O.; Sivo, M. F.; Natile, G.; Brabec, V. DNA interactions of a novel platinum drug, cis-[PtCl(NH3)2(N7-acyclovir)]. Mol. Pharmacol., 1998, 53, 846-855.
153. Grabner, S.; Cemazar, M.; Bukovec, N.; Sersa, G. Syntheses and cytotoxicity of Pt(II) complexes with acyclovir. Acta Chim. Slov., 2006, 53, 153-158.
154. Margiotta, N.; Fanizzi, F. P.; Kobe, J.; Natile, G. Synthesis, characterisation and antiviral activity of platinum(II) complexes with 1,10-phenanthrolines and the antiviral agents acyclovir and penciclovir. Eur. J. Inorg. Chem., 2001, 1303-1310.
155. Papadia, P.; Margiotta, N.; Bergamo, A.; Sava, G.; Natile, G. Platinum(II) complexes with antitumoral/antiviral aromatic heterocycles: Effect of glutathione upon in vitro cell growth inhibition. J. Med. Chem., 2005, 48, 3364-3371.
156. Nicola, M. A.; Alberta, B. B.; Gianni, S. B.; Giacomo, P. D.; de Clercq, E.; Natile, G. Antiviral properties and cytotoxic activity of platinum(II) complexes with 1,10-phenanthrolines and acyclovir or penciclovir. J. Inorg. Biochem., 2004, 98, 1385-1390.
157. Carraher, C. E.; Sabir, T. S.; Roner, M. R.; Shahi, K.; Bleicher, R. E.; Roehr, J. L.; Bassett, K. D. Synthesis of organotin polyamine ethers containing acyclovir and their preliminary anticancer and antiviral activity. J. Inorg. Organomet. Polym. Mater., 2006, 16, 249-257.
158. Shionoya, M.; Kimura, E.; Shiro, M. A new ternary zinc(II) complex with [12]aneN4 (=1,4,7,10-tetraazacyclododecane) and AZT (=3'-azido-3'-deoxythymidine). Highly selective recognition of thymidine and its related nucleosides by a zinc(II) macrocyclic tetraamine complex with novel complementary associations. J. Am. Chem. Soc., 1993, 115, 6730-6737.
159. Szlyk, E.; Lakomska, I.; Kobe, J.; Surdykowski, A.; Glowiak, T.; Sitkowski, J. The bonding of ribavirin to platinum(II) ion. The X-ray and spectroscopy of Pt(II) complexes with 1-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxamide and dimethylsulfoxide. Polyhedron, 2002, 21, 2001-2007.
160. Bukovec, P.; Golic, L.; Orel, B.; Kobe, J. The molecular and crystal-structure of ribavirin (1-XI-D-ribofuranosyl-1,2,4-triazole-3-carboxamide)-CuCl2 complex. J. Carb. Nucleos. Nucl., 1981, 8, 1-17.
161. Pagano, J. S.; Blaser, M.; Buendia, M. A.; Damania, B.; Khalili, K.; Raab-Traub, N.; Roizman, B. Infectious agents and cancer: criteria for a causal relation. Semin. in Cancer Biol., 2004, 14, 453-471.
162. Parsonnet, J. Bacterial infection as a cause of cancer. Environ. Health Persp., 1995, 103, 263-268.
163. Ming, L. J. Structure and function of "metalloantibiotics". Med. Res. Rev., 2003, 23, 697-762.
164. Takeshita, M.; Horwitz, S. B.; Grollman, A. P. Mechanism of antiviral action of bleomycin. Ann. NY Acad. Sci., 1977, 284, 367-374.
165. Mir, L. M.; Tounekti, O.; Orlowski, S. Bleomycin: Revival of an old drug. Gen. Pharmacol., 1996, 27, 745-748.
166. Sersa, G.; Cemazar, M.; Miklavcic, D. Antitumor effectiveness of electrochemotherapy with cis-diamminedichloroplatinum(II) in mice. Cancer Res., 1995, 55, 3450-3455.
167. Bicek, A.; Turel, I.; Kanduser, M.; Miklavcic, D. Combined therapy of the antimetastatic compound NAMI-A and electroporation on B16F1 tumour cells in vitro. Bioelectrochemistry, 2007, 71, 113-117.
168. Mitscher, L. A. Bacterial topolsomerase inhibitors: Quinolone and pyridone antibacterial agents. Chem. Rev., 2005, 105, 559-592.
169. Drevensek, P.; Kosmrlj, J.; Giester, G.; Skauge, T.; Sletten, E.; Sepcic, K.; Turel, I. X-ray crystallographic, NMR and antimicrobial activity studies of magnesium complexes of fluoroquinolones racemic ofloxacin and its S-form, levofloxacin. J. Inorg. Biochem., 2006, 100, 1755-1763.
170. Palumbo, M.; Gatto, B.; Zagotto, G.; Palù, G. On the mechanism of action of quinolone drugs. Trends Microbiol., 1993, 1, 232-235.
171. Noble, C. G.; Barnard, F. M.; Maxwell, A. Quinolone-DNA interaction: Sequence-dependent binding to single-stranded DNA reflects the interaction within the gyrase-DNA complex. Antimicrob. Agents Ch., 2003, 47, 854-862.
172. Llorente, B.; Leclerc, F.; Cedergren, R. Using SAR and QSAR analysis to model the activity and structure of the quinolone-DNA complex. Bioorg. Med. Chem., 1996, 4, 61-71.
173. 2+ self-assembly model formed in the presence of topoisomerase II. J. Biol. Chem., 1999, 274, 17226-17235.
174. Drevensek, P.; Ulrih, N. P.; Majerle, A.; Turel, I. Synthesis, characterization and DNA binding of magnesium-ciprofloxacin (cfH) complex [Mg(cf)2]·2.5H2O. J. Inorg. Biochem., 2006, 100, 1705-1713.
175. Turel, I.; Zivec, P.; Pevec, A.; Tempelaar, S.; Psomas, G. Compounds of antibacterial agent ciprofloxacin and magnesium Crystal structures and molecular modeling calculations. Eur. J. Inorg. Chem., 2008, 3718-3727.
176. Turel, I. The interactions of metal ions with quinolone antibacterial agents. Coord. Chem. Rev., 2002, 232, 27-47.
177. 2+ complex on DNA a new paradigm for the structure of a drug-DNA complex and implications for the structure of the quinolone bacterial gyrase DNA complex. J. Med. Chem., 1995, 38, 408-424.
178. Zeng, Q. P.; Kwok, Y.; Kerwin, S. M.; Mangold, G.; Hurley, L. H. Design of new topoisomerase II inhibitors based upon a quinobenzoxazine self-assembly model. J. Med. Chem., 1998, 41, 4273-4278.
179. Bloomfield, V. A. DNA condensation by multivalent cations. Biopolymers, 1997, 44, 269-282.
180. Duguid, J. G.; Bloomfield, V. A. Aggregation of melted DNA by divalent metal ion-mediated cross-linking. Biophys. J., 1995, 69, 2642-2648.
181. Garcia-Raso, A.; Fiol, J. J.; Tasada, A.; Prieto, M. J.; Moreno, V.; Mata, I.; Molins, E.; Bunic, T.; Golobic, A.; Turel, I. Ruthenium complexes with purine derivatives: Syntheses, structural characterization and preliminary studies with plasmidic DNA. Inorg. Chem. Commun., 2005, 8, 800-804.
182. Clark, G. R.; Squire, C. J.; Baker, L. J.; Martin, R. F.; White, J. Intermolecular interactions and water structure in a condensed phase B-DNA crystal. Nucleic Acids Res., 2000, 28, 1259-1265.
183. Ghosh, A.; Bansal, M. A glossary of DNA structures from A to Z. Acta Crystallogr. D, 2003, 59, 620-626.
184. Voet, D. Ed. Biochemistry, John Wiley & Sons, Inc.: Hoboken, 2004.
185. Berg, J. M.; Tymoczko, J. L.; Stryer, L. Eds. Biochemistry, W.H. Freeman & Co. Ltd.: New York, 2007.
186. Fuertes, M. A.; Cepeda, V.; Alonso, C.; Perez, J. M. Molecular mechanisms for the B-Z transition in the example of poly d(G-C)·d(G-C) polymers. A critical review. Chem. Rev., 2006, 106, 2045-2064.
187. Howell, M. L.; Schroth, G. P.; Ho, P. S. Sequence-dependent effects of spermine on the thermodynamics of the B-DNA to Z-DNA transition. Biochemistry, 1996, 35, 15373-15382.
188. Thomas, T. J.; Gunnia, U. B.; Thomas, T. Polyamine-induced B-DNA to Z-DNA conformational transition of a plasmid DNA with (DG-DC)N insert. J. Biol. Chem., 1991, 266, 6137-6141.
189. Spingler, B. Anions or cations: Who is in charge of inhibiting the nickel(II) promoted B-to Z-DNA transition?. Inorg. Chem., 2005, 44, 831-833.
190. Spingler, B.; Da Pieve, C. Induction of B-to Z-DNA transition by copper and zinc complexes with C(15) substituted macrocyclic pentaaza ligands. Dalton Trans., 2005, 1637-1643.
191. Kasyanenko, N. A.; Zanina, A. V.; Nazarova, O. V.; Panarin, E. F. DNA interaction with complex ions in solution. Langmuir, 1999, 15, 7912-7917.
192. Rich, A.; Zhang, S. G. Z-DNA: the long road to biological function. Nat. Rev. Genet., 2003, 4, 566-572.
193. Suram, A.; Rao, L. K. S.; Latha, K. S.; Viswamitra, M. A. First evidence to show the topological change of DNA from B-DNA to Z-DNA conformation in the hippocampus of Alzheimer's brain. Neuromol. Med., 2002, 2, 289-297.
194. Wettig, S. D.; Wood, D. O.; Aich, P.; Lee, J. S. M-DNA: A novel metal ion complex of DNA studied by fluorescence techniques. J. Inorg. Biochem., 2005, 99, 2093-2101.
195. 2+ and other divalent metal-ions. Biochem. Cell. Biol., 1993, 71, 162-168.
196. Wettig, S. D.; Wood, D. O.; Lee, J. S. Thermodynamic investigation of M-DNA: a novel metal ion-DNA complex. J. Inorg. Biochem., 2003, 94, 94-99.
197. Aich, P.; Kraatz, H. B.; Lee, J. S. M-DNA: pH stability, nuclease resistance and signal transmission. J. Biomol. Struct. Dyn., 2000, 297-301.
198. Aich, P.; Labiuk, S. L.; Tari, L. W.; Delbaere, L. J. T.; Roesler, W. J.; Falk, K. J.; Steer, R. P.; Lee, J. S. M-DNA: A complex between divalent metal ions and DNA which behaves as a molecular wire. J. Mol. Biol., 1999, 294, 477-485.
199. Spring, B. Q.; Clegg, R. M. Fluorescence measurements of duplex DNA oligomers under conditions conducive for forming M-DNA (a metal-DNA complex). J. Phys. Chem. B, 2007, 111, 10040-10052.
200. Wettig, S. D.; Li, C. Z.; Long, Y. T.; Kraatz, H. B.; Lee, J. S. M-DNA: a self-assembling molecular wire for nanoelectronics and biosensing. Anal. Sci., 2003, 19, 23-26.
201. Wettig, S. D.; Bare, G. A.; Skinner, R. J. S.; Lee, J. S. Signal transduction through dye-labeled M-DNA Y-branched junctions: Switching modulated by chemical reduction of anthraquinone. Nano Lett., 2003, 3, 617-622.
202. Rakitin, A.; Aich, P.; Papadopoulos, C.; Kobzar, Y.; Vedeneev, A. S.; Lee, J. S.; Xu, J. M. Metallic conduction through engineered DNA: DNA nanoelectronic building blocks. Phys. Rev. Lett., 2001, 86, 3670-3673.
203. Li, C. Z.; Long, Y. T.; Kraatz, H. B.; Lee, J. S. Electrochemical investigations of M-DNA self-assembled monolayers on gold electrodes. J. Phys. Chem. B, 2003, 107, 2291-2296.
204. Eichhorn, G. L. Metal Ions as Stabilizers or Destabilizers of the Deoxyribonucleic Acid Structure. Nature, 1962, 194, 474-475.
205. 4+(1-MeC=1-Methylcytosine): Structural model for DNA cross-linking and DNA rewinding bx Zn(II)?. J. Am. Chem. Soc., 1994, 116, 7204-7209.
206. Liu, B.; Bard, A. J.; Li, C. Z.; Kraatz, H. B. Scanning electrochemical microscopy. 51. Studies of self-assembled monolayers of DNA in the absence and presence of metal ions. J. Phys. Chem. B, 2005, 109, 5193-5198.
207. Moreno-Herrero, F.; Herrero, P.; Moreno, F.; Colchero, J.; Gomez-Navarro, C.; Gomez-Herrero, J.; Baro, A. M. Topographic characterization and electrostatic response of M-DNA studied by atomic force microscopy. Nanotechnology, 2003, 14, 128-133.
208. Mizoguchi, K.; Tanaka, S.; Ogawa, T.; Shiobara, N.; Sakamoto, H. Magnetic study of the electronic states of B-DNA and M-DNA doped with metal ions. Phys. Rev. B, 2005, 72, 033106
209. Bustamante, C.; Bryant, Z.; Smith, S. B. Ten years of tension: single-molecule DNA mechanics. Nature, 2003, 421, 423-427.
210. Hagerman, P. J. Flexibility of DNA. Annu. Rev. Biophys. Bio., 1988, 17, 265-286.
211. Sanchez, S. A.; Chen, Y.; Muller, J. D.; Gratton, E.; Hazlett, T. L. Solution and interface aggregation states of Crotalus atrox venom phospholipase A2 by two-photon excitation fluorescence correlation spectroscopy. Biochemistry, 2001, 40, 6903-6911.
212. Omerzu, A.; Mihailovic, D.; Anzelak, B.; Turel, I. Optical spectra of wet and dry M-DNA. Phys. Rev. B, 2007, 75, 121103.
213. Omerzu, A.; Anzelak, B.; Turel, I.; Strancar, J.; Potocnik, A.; Arcon, D.; Arcon, I.; Mihailovic, D.; Matsui, H. Strong correlations in highly electron-doped Zn(II)-DNA complexes. Phys. Rev. Lett., 2010, 104, 156804.
214. Fuentes-Cabrera, M.; Sumpter, B. G.; Sponer, J. E.; Sponer, J.; Petit, L.; Wells, J. C. Theoretical study on the structure, stability, and electronic properties of the guanine-Zn-cytosine base pair in M-DNA. J. Phys. Chem. B, 2007, 111, 870-879.
215. Phillips, K.; Dauter, Z.; Murchie, A. I. H.; Lilley, D. M. J.; Luisi, B. The crystal structure of a parallel-stranded guanine tetraplex at 0.95 angstrom resolution. J. Mol. Biol., 1997, 273, 171-182.
216. Clark, G. R.; Pytel, P. D.; Squire, C. J.; Neidle, S. Structure of the first parallel DNA quadruplex-drug complex. J. Am. Chem. Soc., 2003, 125, 4066-4067.
217. Schultze, P.; Smith, F. W.; Feigon, J. Refined solution structure of the dimeric quadruplex formed from the Oxytrichia telomeric oligonucleotide D(GGGGTTTTGGGG). Structure, 1994, 2, 221-233.
218. Smith, F. W.; Feigon, J. Quadruplex structure of Oxytrichia telomeric DNA oligonucleotides. Nature, 1992, 356, 164-168.
219. Parkinson, G. N.; Lee, M. P. H.; Neidle, S. Crystal structure of parallel quadruplexes from human telomeric DNA. Nature, 2002, 417, 876-880.
220. Haider, S.; Parkinson, G. N.; Neidle, S. Structure of a G-quadruplex-ligand complex. J. Mol. Biol., 2002, 320, 189-200.
221. + ions. Nucleic Acids Res., 2004, 32, 1097-1102.
222. Gill, M. L.; Strobel, S. A.; Loria, J. P. Crystallization and characterization of the thallium form of the Oxytricha nova G-quadruplex. Nucleic Acids Res., 2006, 34, 4506-4514.
223. 31P NMR-studies of the self-assembly of the 5'-guanosine monophosphate dianion in neutral aqueous-solution in the presence of sodium-cations. J. Am. Chem. Soc., 1980, 102, 1124-1134.
224. Lee, M. P. H.; Parkinson, G. N.; Hazel, P.; Neidle, S. Observation of the coexistence of sodium and calcium ions in a DNA G-quadruplex ion channel. J. Am. Chem. Soc., 2007, 129, 10106-10107.
225. Yu, H. Q.; Miyoshi, D.; Sugimoto, N. Characterization of structure and stability of long telomeric DNA G-quadruplexes. J. Am. Chem. Soc.2006., vol 128;15461-15468
226. Zakian, V. A. Telomeres -beginning to understand the end. Science, 1995, 270, 1601-1607.
227. Allsopp, R. C.; Vaziri, H.; Patterson, C.; Goldstein, S.; Younglai, E. V.; Futcher, A. B.; Greider, C. W.; Harley, C. B. Telomere length predicts replicative capacity of human fibroblasts. Proc. Nat. Acad. Sci. USA, 1992, 89, 10114-10118.
228. Vaziri, H.; Benchimol, S. Reconstitution of telomerase activity in normal human cells leads to elongation of telomeres and extended replicative life span. Curr. Biol., 1998, 8, 279-282.
229. II complex Ru2(obip)L4. Inorg. Chem., 2008, 47, 2910-2912.
230. Haider, S. M.; Parkinson, G. N.; Neidle, S. Structure of a G-quadruplex-ligand complex. J. Mol. Biol., 2003, 326, 117-125.
231. Rezler, E. M.; Bearss, D. J.; Hurley, L. H. Telomere inhibition and telomere disruption as processes for drug targeting. Annu. Rev. Pharmacol., 2003, 43, 359-379.
232. Arola-Arnal, A.; Benet-Buchholz, J.; Neidle, S.; Vilar, R. Effects of metal coordination geometry on stabilization of human telomeric quadruplex DNA by square-planar and square-pyramidal metal complexes. Inorg. Chem., 2008, 47, 11910-11919.
233. Ma, D. L.; Che, C. M.; Yan, S. C. Platinum(II) complexes with dipyridophenazine ligands as human telomerase inhibitors and luminescent probes for G-quadruplex DNA. J. Am. Chem. Soc., 2009, 131, 1835-1846.
234. Kim, N. W.; Piatyszek, M. A.; Prowse, K. R.; Harley, C. B.; West, M. D.; Ho, P. L. C.; Coviello, G. M.; Wright, W. E.; Weinrich, S. L.; Shay, J. W. Specific association of human telomerase activity with immortal cells and cancer. Science, 1994, 266, 2011-2015.
235. Kerwin, S. M. G-quadruplex DNA as a target for drug design. Curr. Pharm. Design, 2000, 6, 441-471.
236. White, L. K.; Wright, W. E.; Shay, J. W. Telomerase inhibitors. Trends Biotechnol., 2001, 19, 114-120.
237. Pisano, S.; Marchioni, E.; Galati, A.; Mechelli, R.; Savino, M.; Cacchione, S. Telomeric nucleosomes are intrinsically mobile. J. Mol. Biol., 2007, 369, 1153-1162.
238. Reed, J. E.; Arnal, A. A.; Neidle, S.; Vilar, R. Stabilization of G-quadruplex DNA and inhibition of telomerase activity by square-planar nickel(II) complexes. J. Am. Chem. Soc., 2006, 128, 5992-5993.
239. Reed, J. E.; Neidle, S.; Vilar, R. Stabilisation of human telomeric quadruplex DNA and inhibition of telomerase by a platinum-phenanthroline complex. Chem. Commun., 2007, 4366-4368.
240. Bertrand, H.; Bombard, S.; Monchaud, D.; Teulade-Fichou, M. P. A platinum-quinacridine hybrid as a G-quadruplex ligand. J. Biol. Inorg. Chem., 2007, 12, 1003-1014.
241. Bertrand, H.; Monchaud, D.; De Cian, A.; Guillot, R.; Mergny, J. L.; Teulade-Fichou, M. P. The importance of metal geometry in the recognition of G-quadruplex-DNA by metal-terpyridine complexes. Org. Biomol. Chem., 2007, 5, 2555-2559.
242. Evans, S. E.; Mendez, M. A.; Turner, K. B.; Keating, L. R.; Grimes, R. T.; Melchoir, S.; Szalai, V. A. End-stacking of copper cationic porphyrins on parallel-stranded guanine quadruplexes. J. Biol. Inorg. Chem., 2007, 12, 1235-1249.
243. Kieltyka, R.; Fakhoury, J.; Moitessier, N.; Sleiman, H. F. Platinum phenanthroimidazole complexes as G-quadruplex DNA selective binders. Chem. Eur. J., 2008, 14, 1145-1154.
244. Dixon, I. M.; Lopez, F.; Tejera, A. M.; Esteve, J. P.; Blasco, M. A.; Pratviel, G.; Meunier, B. A G-quadruplex ligand with 10000-fold selectivity over duplex DNA. J. Am. Chem. Soc., 2007, 129, 1502-1503.
245. Ourliac-Garnier, I.; Charif, R.; Bombard, S. In: Telomeres and telomerase: Potential targets for platinum complexes. Metal complex -DNA interactions, Hadjiliadis, N.; Sletten, E., Eds.; John Wiley & Sons, Inc.: Chichester, 2009, pp. 209-234.
246. Copeland, K. D.; Fitzsimons, M. P.; Houser, R. P.; Barton, J. K. DNA hydrolysis and oxidative cleavage by metal-binding peptides tethered to rhodium intercalators. Biochemistry, 2002, 41, 343-356.
247. Baik, M. H.; Friesner, R. A.; Lippard, S. J. Theoretical study on the stability of N-glycosyl bonds: Why does N7-platination not promote depurination?. J. Am. Chem. Soc., 2002, 124, 4495-4503.
248. Lindahl, T. Instability and decay of the primary structure of DNA. Nature, 1993, 362, 709-715.
249. Arpalahti, J.; Kappi, R.; Hovinen, J.; Lonnberg, H.; Chattopadhyaya, J. The effect of metal-ion complex-formation on acidic depurination of 2'-deoxyadenosine and 2'-deoxyguanosine. Tetrahedron, 1989, 45, 3945-3954.
250. Arpalahti, J.; Jokilammi, A.; Hakala, H.; Lonnberg, H. Depurination of (dien)Pt(II) complexes of purine deoxy-ribonucleotides comparison with the effects of (dien)Pd(II) ion complexing. J. Phys. Org. Chem., 1991, 4, 301-309.
251. Sigman, D. S.; Mazumder, A.; Perrin, D. M. Chemical nucleases. Chem. Rev., 1993, 93, 2295-2316.
252. Drevensek, P.; Zupancic, T.; Pihlar, B.; Jerala, R.; Kolitsch, U.; Plader, A.; Turel, I. Mixed-valence Cu(II)/Cu(I) complex of quinolone ciprofloxacin isolated by a hydrothermal reaction in the presence of L-histidine: comparison of biological activities of various copper-ciprofloxacin compounds. J. Inorg. Biochem., 2005, 99, 432-442.
253. He, J.; Hu, P.; Wang, Y. J.; Tong, M. L.; Sun, H. Z.; Mao, Z. W.; Ji, L. N. Double-strand DNA cleavage by copper complexes of 2,2 '-dipyridyl with guanidinium/ammonium pendants. Dalton Trans., 2008, 3207-3214.
254. Bower, J. J.; Leonard, S. S.; Shi, X. L. Conference overview: Molecular mechanisms of metal toxicity and carcinogenesis. Mol. Cell. Biochem., 2005, 279, 3-15.
255. Churg, A.; Brauer, M.; Avila-Casado, M. D.; Fortoul, T. I.; Wright, J. L. Chronic exposure to high levels of particulate air pollution and small airway remodeling. Environ. Health Persp., 2003, 111, 714-718.
256. Gambelunghe, A.; Piccinini, R.; Ambrogi, M.; Villarini, M.; Moretti, M.; Marchetti, C.; Abbritti, G.; Muzi, G. Primary DNA damage in chrome-plating workers. Toxicology, 2003, 188, 187-195.
257. 109Cd accumulation in the calcified parts of rat bones. Toxicology, 2001, 159, 1-10.
258. Tsai, S. M.; Wang, T. N.; Ko, Y. C. Mortality for certain diseases in areas with high levels of arsenic in drinking water. Arch. Environ. Health, 1999, 54, 186-193.
259. Roat-Malone, R. M. Ed. Bioinorganic chemistry: A short course, John Wiley & Sons, Inc.: Chichester, 2002.
260. Finney, L. A.; O'Halloran, T. V. Transition metal speciation in the cell: Insights from the chemistry of metal ion receptors. Science, 2003, 300, 931-936.
261. Outten, C. E.; O'Halloran, T. V. Femtomolar sensitivity of metalloregulatory proteins controlling zinc homeostasis. Science, 2001, 292, 2488-2492.
262. Pedersen, S.; Bloch, P. L.; Reeh, S.; Neidhardt, F. C. Patterns of protein-synthesis in Escherichia Coli catalog of amount of 140 individual proteins at different growth-rates. Cell, 1978, 14, 179-190.
263. Huffman, D. L.; O'Halloran, T. V. Energetics of copper trafficking between the Atx1 metallochaperone and the intracellular copper transporter, Ccc2. J. Biol. Chem., 2000, 275, 18611-18614.
264. Leonard, S. S.; Roberts, J. R.; Antonini, J. M.; Castranova, V.; Shi, X. L. PbCrO4 mediates cellular responses via reactive oxygen species. Mol. Cell. Biochem., 2004, 255, 171-179.
265. Shi, X. L.; Flynn, D. C.; Porter, D. W.; Leonard, S. S.; Valllyathan, V.; Castranova, V. Efficacy of taurine based compounds as hydroxyl radical scavengers in silica induced peroxidation. Ann. Clin. Lab. Sci., 1997, 27, 365-374.
266. Wang, Y. D.; Fang, J.; Leonard, S. S.; Rao, K. M. K. Cadmium inhibits the electron transfer chain and induces reactive oxygen species. Free Radical Bio. Med., 2004, 36, 1434-1443.
267. Leonard, S.; Gannett, P. M.; Rojanasakul, Y.; Schwegler-Berry, D.; Castranova, V.; Vallyathan, V.; Shi, X. L. Cobalt-mediated generation of reactive oxygen species and its possible mechanism. J. Inorg. Biochem., 1998, 70, 239-244.
268. Hei, T. K.; Filipic, M. Role of oxidative damage in the genotoxicity of arsenic. Free Radical Bio. Med., 2004, 37, 574-581.
269. Bagchi, D.; Bagchi, M.; Stohs, S. J. Chromium(VI)-induced oxidative stress, apoptotic cell death and modulation of p53 tumor suppressor gene. Mol. Cell. Biochem., 2001, 222, 149-158.
270. Wang, S. W.; Leonard, S. S.; Ye, J. P.; Gao, N.; Wang, L. Y.; Shi, X. L. Role of reactive oxygen species and Cr(VI) in Ras-mediated signal transduction. Mol. Cell. Biochem., 2004, 255, 119-127.
271. Lefebvre, Y.; Pezerat, H. R. Eactive oxygen species produced from chromate pigments and ascorbate. Environ. Health Persp., 1994, 102, 243-245.
272. Wang, S. W.; Leonard, S. S.; Ye, J. P.; Ding, M.; Shi, X. L. The role of hydroxyl radical as a messenger in Cr(VI)-induced p53 activation. Am. J. Physiol. Cell Physiol., 2000, 279, C868-C875.
273. Balamurugan, K.; Rajaram, R.; Ramasami, T.; Narayanan, S. Chromium(III)-induced apoptosis of lymphocytes: Death decision by ROS and Src-family tyrosine kinases. Free Radical Bio. Med., 2002, 33, 1622-1640.
274. Petit, A.; Mwale, F.; Tkaczyk, C.; Antoniou, J.; Zukor, D. J.; Huk, O. L. Induction of protein oxidation by cobalt and chromium ions in human U937 macrophages. Biomaterials, 2005, 26, 4416-4422.
275. Chakrabarti, S. K.; Bai, C. J.; Subramanian, K. S. DNA-protein crosslinks induced by nickel compounds in isolated rat lymphocytes: Role of reactive oxygen species and specific amino acids. Toxicol. Appl. Pharm., 2001, 170, 153-165.
276. Kang, J.; Zhang, Y. T.; Chen, J.; Chen, H. F.; Lin, C. J.; Wang, Q.; Ou, Y. X. Nickel-induced histone hypoacetylation: The role of reactive oxygen species. Toxicol. Sci., 2003, 74, 279-286.
277. Lin, C. J.; Kang, J. H.; Zheng, R. L. Oxidative stress is involved in inhibition of copper on histone acetylation in cells. Chem. Biol. Interact., 2005, 151, 167-176.
278. Little, L. G.; Sugden, K. D. Chromium-induced DNA damage and repair. In: Metal complex DNA interactions, Sletten, N.; Hadjiliadis, E., Eds.; John Wiley & Sons, Inc.: Chichester, 2009, pp. 463-49.
279. t 20 years (1968-1988). Free Radical Bio. Med., 1988, 5, 363-369.
280. Brewer, G. J. Achromatic regiond of tetrazolium stained starch gels: inherited electrophoretic variation. Am. J. Hum. Genet., 1967, 19, 674-680.
281. Tainer, J. A.; Getzoff, E. D.; Richardson, J. S.; Richardson, D. C. Structure and mechanism of copper, zinc superoxide-dismutase. Nature, 1983, 306, 284-287.
282. Borgstahl, G. E. O.; Parge, H. E.; Hickey, M. J.; Beyer, W. F.; Hallewell, R. A.; Tainer, J. A. The structure of human mitochondrial manganese superoxide-dismutase reveals a novel tetrameric interface of 2 4-helix bundles. Cell, 1992, 71, 107-118.
283. Barondeau, D. P.; Kassmann, C. J.; Bruns, C. K.; Tainer, J. A.; Getzoff, E. D. Nickel superoxide dismutase structure and mechanism. Biochemistry, 2004, 43, 8038-8047.
284. Wuerges, J.; Lee, J. W.; Yim, Y. I.; Yim, H. S.; Kang, S. O.; Carugo, K. D. Crystal structure of nickel-containing superoxide dismutase reveals another type of active site. Proc. Nat. Acad. Sci. USA, 2004, 101, 8569-8574.
285. Cousins, R. J. A role of zinc in the regulation of gene expression. P. Nutr. Soc., 1998, 57, 307-311.
286. Pavletich, N. P.; Pabo, C. O. Zinc finger-DNA recognition: Crystal structure of a Zif268-DNA complex at 2.1 A. Science, 1991, 252, 809-817.
287. Schwabe, J. W. R.; Rhodes, D. Beyond zinc fingers steroid hormone receptors have a novel structural motif for DNA recognition. Trends Biochem. Sci., 1991, 16, 291-297.
288. Lohrmann, R.; Bridson, P. K.; Orgel, L. E. Efficient metal-ion catalyzed template-directed oligonucleotide synthesis. Science, 1980, 208, 1464-1465.
289. Basile, L. A.; Barton, J. K. Metallonucleases Real and artificial. In: Metal ions in biological systems: Interrelations among metal ions, enzymes and gene expression, vol. 25, Sigel, H.; Sigel, A., Eds., Marcel Dekker: New York, 1989, pp. 31-103.
290. Joerger, A. C.; Ang, H. C.; Fersht, A. R. Structural basis for understanding oncogenic p53 mutations and designing rescue drugs. Proc. Nat. Acad. Sci. USA, 2006, 103, 15056-15061.
291. Ho, E. Zinc deficiency, DNA damage and cancer risk. J. Nutr. Biochem., 2004, 15, 572-578.
292. Bertram, J. S. The molecular biology of cancer. Mol. Aspects Med., 2000, 21, 167-223.
293. Ames, B. N.; Shigenaga, M. K.; Gold, L. S. DNA lesions, inducible DNA-repair, and cell-division -3 key factors in mutagenesis and carcinogenesis. Environ. Health Persp., 1993, 101, 35-44.
294. Roulston, A.; Marcellus, R. C.; Branton, P. E. Viruses and apoptosis. Annu. Rev. Microbiol., 1999, 53, 577-628.
295. Cadet, J.; Douki, T.; Ravanat, J. L. One-electron oxidation of DNA and inflammation processes. Nat. Chem. Biol., 2006, 2, 348-349.
296. Bjelland, S.; Seeberg, E. Mutagenicity, toxicity and repair of DNA base damage induced by oxidation. Mutat. Res., 2003, 531, 37-80.
297. Henderson, P. T.; Delaney, J. C.; Muller, J. G.; Neeley, W. L.; Tannenbaum, S. R.; Burrows, C. J.; Essigmann, J. M. The hydantoin lesions formed from oxidation of 7,8-dihydro-8-oxoguanine are potent sources of replication errors in vivo.Biochemistry, 2003, 42, 9257-9262.
298. Leipold, M. D.; Muller, J. G.; Burrows, C. J.; David, S. S. Removal of hydantoin products of 8-oxoguanine oxidation by the Escherichia coli DNA repair enzyme, FPG. Biochemistry, 2000, 39, 14984-14992.
299. Henderson, P. T.; Delaney, J. C.; Gu, F.; Tannenbaum, S. R.; Essigmann, J. M. Oxidation of 7,8-dihydro-8-oxoguanine affords lesions that are potent sources of replication errors in vivo. Biochemistry, 2002, 41, 914-921.
300. Muller, J. G.; Duarte, V.; Hickerson, R. P.; Burrows, C. J. Gel electrophoretic detection of 7,8-dihydro-8-oxoguanine and 7,8-dihydro-8-oxoadenine via oxidation by Ir(IV). Nucleic Acids Res., 1998, 26, 2247-2249.
301. Mateuca, R.; Aka, P. V.; De Boeck, M.; Hauspie, R.; Kirsch-Volders, M.; Lison, D. Influence of hOGG1, XRCC1 and XRCC3 genotypes on biomarkers of genotoxicity in workers exposed to cobalt or hard metal dusts. Toxicol. Lett., 2005, 156, 277-288.
302. Kim, Y. D.; An, S. C.; Oyama, T.; Kawamoto, T.; Kim, H. Oxidative stress, hogg1 expression and NF-B activity in cells exposed to low level chromium. J. Occup. Health, 2003, 45, 271-277.
303. Zharkov, D. O.; Rosenquist, T. A. Inactivation of mammalian 8-oxoguanine-DNA glycosylase by cadmium(II): implications for cadmium genotoxicity. DNA Repair, 2002, 1, 661-670.
304. Hartwig, A. Recent advances in metal carcinogenicity. Pure Appl. Chem., 2000, 72, 1007-1014.
305. Bal, W.; Kasprzak, K. S. Induction of oxidative DNA damage by carcinogenic metals. Toxicol. Lett., 2002, 127, 55-62.
306. Kasprzak, K. S.; Buzard, G. S. In: The role of metals in oxidative damage and redox cell signaling derangement. Molecular Biology and Toxicology of Metals, Koropatnick, J.; Zalups, R., Eds.; Taylor and Francis: London, 2000, pp. 477-527.
307. Haber, F.; Weiss, J. The catalytic decomposition of hydrogen peroxide by iron salts. Proc. R. Soc. Lon. Ser.-A, 1934, 147, 332-351.
308. Kligerman, A. D.; Tennant, A. H. Insights into the carcinogenic mode of action of arsenic. Toxicol. Appl. Pharm., 2007, 222, 281-288.
309. Hartwig, A.; Schwerdtle, T. Arsenic-induced carcinogenicity: New insights in molecular mechanism. In: Metal complex DNA interactions, Hadjiliadis, N.; Sletten, E., Eds.; John Wiley & Sons, Inc.: Chichester, 2009, pp. 491-510.
310. Onyido, I.; Norris, A. R.; Buncel, E. Biomolecule-mercury interactions: Modalities of DNA base-mercury binding mechanisms. Remediation strategies. Chem. Rev., 2004, 104, 5929.
311. Nriagu, J.O. Ed. The biogeochemistry of mercury in the environment, Elsevier: Amsterdam, 1979.
312. Lippard, S. J.; Berg, M. In: Principles of bioinorganic chemistry; University science books: Mill Valley, CA, 1994, pp. 15 and 148.
313. van Loon, G. W., Duffy, S.J. In: Environmental chemistry; Oxford university press: Oxford, 2000, pp. 272.
314. Neville, G. A.; Berlin, M. Identification and biotransformation of organomercurial compounds in living systems review of current understanding. Environ. Res., 1974, 7, 75-82.
315. Katz, S. The reversible reaction of sodium thymonucleate and mercuric chloride. J. Am. Chem. Soc., 1952, 74, 2238-2245.
316. Katz, S. The reversible reaction of Hg (II) and double-stranded polynucleotides a step-function theory and its significance. Biochim. Biophys. Acta, 1963, 68, 240-253.
317. II mediated T-T base-pair using NMR spectroscopy. In: Metal DNA interactions, Hadjiliadis, N.; Sletten, E., Eds.; John Wiley & Sons, Inc.: Chichester, 2009, pp. 439-462.
318. Miyake, Y.; Togashi, H.; Tashiro, M.; Yamaguchi, H.; Oda, S.; Kudo, M.; Tanaka, Y.; Kondo, Y.; Sawa, R.; Fujimoto, T.; Machinami, T.; Ono, A. Mercury(II)-mediated formation of thymine-Hg-II-thymine base pairs in DNA duplexes. J. Am. Chem. Soc., 2006, 128, 2172-2173.
319. Silbergeld, E. K.; Waalkes, M.; Rice, J. M. Lead as a carcinogen: Experimental evidence and mechanisms of action. Am. J. Ind. Med., 2000, 38, 316-323.
320. Hengstler, J. G.; Bolm-Audorff, U.; Faldum, A.; Janssen, K.; Reifenrath, M.; Gotte, W.; Jung, D. L.; Mayer-Popken, O.; Fuchs, J.; Gebhard, S.; Bienfait, H. G.; Schlink, K.; Dietrich, C.; Faust, D.; Epe, B.; Oesch, F. Occupational exposure to heavy metals: DNA damage induction and DNA repair inhibition prove co-exposures to cadmium, cobalt and lead as more dangerous than hitherto expected. Carcinogenesis, 2003, 24, 63-73.
321. Schuetzle, D. Sampling of vehicle emissions for chemical-analysis and biological testing. Environ. Health Persp., 1983, 47, 65-80.
322. Ichinose, T.; Furuyama, A.; Sagai, M. Biological affects of diesel exhaust particles (DEP).2. Acute toxicity of DEP introduced into lung by intratracheal instillation. Toxicology, 1995, 99, 153-167.
323. Han, J. Y.; Takeshita, K.; Utsumi, H. Noninvasive detection of hydroxyl radical generation in lung by diesel exhaust particles. Free Radical Bio. Med., 2001, 30, 516-525.
324. Casillas, A. M.; Hiura, T.; Li, N.; Nel, A. E. Enhancement of allergic inflammation by diesel exhaust particles: permissive role of reactive oxygen species. Ann. Allerg. Asthma Im., 1999, 83, 624-629.
325. Tsurudome, Y.; Hirano, T.; Yamato, H.; Tanaka, I.; Sagai, M.; Hirano, H.; Nagata, N.; Itoh, H.; Kasai, H. Changes in levels of 8-hydroxyguanine in DNA, its repair and OGG1 mRNA in rat lungs after intratracheal administration of diesel exhaust particles Carcinogenesis, 1999, 20, 1573-1576.
326. Baulig, A.; Garlatti, M.; Bonvallot, V.; Marchand, A.; Barouki, R.; Marano, F.; Baeza-Squiban, A. Involvement of reactive oxygen species in the metabolic pathways triggered by diesel exhaust particles in human airway epithelial cells. Am. J. Physiol.-Lung C., 2003, 285, L671-L679.
327. Siegel, P. D.; Saxena, R. K.; Saxena, Q. B.; Ma, J. K. H.; Ma, J. Y. C.; Yin, X. J.; Castranova, V.; Al-Humadi, N.; Lewis, D. M. Effect of diesel exhaust particulate (DEP) on immune responses: Contributions of particulate versus organic soluble components. J. Toxicol. Env. Heal. A, 2004, 67, 221-231
328. Bunger, J.; Muller, M. M.; Krahl, J.; Baum, K.; Weigel, A.; Hallier, E.; Schulz, T. G. Mutagenicity of diesel exhaust particles from two fossil and two plant oil fuels. Mutagenesis, 2000, 15, 391-397.
329. Thompson, K. H.; Orvig, C. Boon and bane of metal ions in medicine. Science, 2003, 300, 936-939.
330. Dobi, A. L.; Matsumoto, K.; Santha, E.; Vonagoston, D. Guanine specific chemical sequencing of DNA by osmium-tetroxide. Nucleic Acids Res., 1994, 22, 4846-4847.
331. Hnatowich, D. J.; Winnard, P.; Virzi, F.; Fogarasi, M.; Sano, T.; Smith, C. L.; Cantor, C. R.; Rusckowski, M. Technetium-99m labelling of DNA nucleotides. J. Nucl. Med., 1995, 36, 2306-2314.
332. Yuan, J.; Wang, G. Lanthanide-based luminescence probes and time-resolved luminescence bioassays. TrAC, Trends Anal. Chem., 2006, 25, 490-500.
333. Tsien, R. Y.; Ernst, L.; Waggoner, A. Handbook of biological confocal microscopy, Springer: Berlin, 2006.
334. Martin, R. M.; Leonhardt, H.; Cardoso, M. C. DNA labeling in living cells. Cytom. Part A, 2005, 67A, 45-52.
335. Pfeifer, G. P.; You, Y. H.; Besaratinia, A. Mutations induced by ultraviolet light. Mutat. Res.-Fund. Mol. M., 2005, 571, 19-31.
336. Pandya, S.; Yu, J. H.; Parker, D. Engineering emissive europium and terbium complexes for molecular imaging and sensing. Dalton Trans., 2006, 2757-2766.
337. Botchway, S. W.; Charnley, M.; Haycock, J. W.; Parker, A. W.; Rochester, D. L.; Weinstein, J. A.; Williams, J. A. G. Time-resolved and two-photon emission imaging microscopy of live cells with inert platinum complexes. Proc. Nat. Acad. Sci. USA, 2008, 105, 16071-16076.
338. 2+. J. Am. Chem. Soc., 1990, 112, 4960-4962.
339. Jimenez-Hernandez, M. E.; Orellana, G.; Montero, F.; Portoles, M. T. A ruthenium probe for cell viability measurement using flow cytometry, confocal microscopy and time-resolved luminescence. Photochem. Photobiol., 2000, 72, 28-34.
340. Amoroso, A. J.; Coogan, M. P.; Dunne, J. E.; Fernandez-Moreira, V.; Hess, J. B.; Hayes, A. J.; Lloyd, D.; Millet, C.; Pope, S. J. A.; Williams, C. Rhenium fac tricarbonyl bisimine complexes: biologically useful fluorochromes for cell imaging applications. Chem. Commun., 2007, 3066-3068.
341. Puckett, C. A.; Barton, J. K. Methods to explore cellular uptake of ruthenium complexes. J. Am. Chem. Soc., 2007, 129, 46-47.
342. Puckett, C. A.; Barton, J. K. Mechanism of cellular uptake of a ruthenium polypyridyl complex. Biochemistry, 2008, 47, 11711-11716.
343. Lo, K. K. W.; Lee, T. K. M.; Lau, J. S. Y.; Poon, W. L.; Cheng, S. H. Luminescent biological probes derived from ruthenium(II) estradiol polypyridine complexes. Inorg. Chem., 2008, 47, 200-208.
344. Neugebauer, U.; Pellegrin, Y.; Devocelle, M.; Forster, R. J.; Signac, W.; Morand, N.; Keyes, T. E. Ruthenium polypyridyl peptide conjugates: membrane permeable probes for cellular imaging. Chem. Commun., 2008, 5307-5309.
345. Gill, M. R.; Garcia-Lara, J.; Foster, S. J.; Smythe, C.; Battaglia, G.; Thomas, J. A. A ruthenium(II) polypyridyl complex for direct imaging of DNA structure in living cells. Nat. Chem., 2009, 1, 662-667.
346. Service, R. F. Nanotechnology takes aim at cancer. Science, 2005, 310, 1132-1134.
347. Alivisatos, A. P. Semiconductor clusters, nanocrystals, and quantum dots. Science, 1996, 271, 933-937.
348. Feldheim, D. L.; Keating, C. D. Self-assembly of single electron transistors and related devices. Chem. Soc. Rev., 1998, 27, 1-12.
349. Shipway, A. N.; Katz, E.; Willner, I. Nanoparticle arrays on surfaces for electronic, optical, and sensor applications. ChemPhysChem, 2000, 1, 18-52.
350. Mirkin, C. A.; Letsinger, R. L.; Mucic, R. C.; Storhoff, J. J. A DNA-based method for rationally assembling nanoparticles into macroscopic materials. Nature, 1996, 382, 607-609.
351. Park, S. J.; Lazarides, A. A.; Mirkin, C. A.; Brazis, P. W.; Kannewurf, C. R.; Letsinger, R. L. The electrical properties of gold nanoparticle assemblies linked by DNA. Angew. Chem. Int. Ed., 2000, 39, 3845-3848.
352. Bardea, A.; Dagan, A.; Ben-Dov, I.; Amit, B.; Willner, I. Amplified microgravimetric quartz crystal-microbalance analyses of oligonucleotide complexes: a route to a Tay-Sachs biosensor device. Chem. Commun., 1998, 839-840.
353. Patolsky, F.; Ranjit, K. T.; Lichtenstein, A.; Willner, I. Dendritic amplification of DNA analysis by oligonucleotide-functionalized Au-nanoparticles.Chem. Commun., 2000, 1025-1026.
354. Mahtab, R.; Rogers, J. P.; Murphy, C. J. Protein-sized quantum-dot luminescence can distinguish between straight, bent, and kinked oligonucleotides. J. Am. Chem. Soc., 1995, 117, 9099-9100.
355. Mahtab, R.; Harden, H. H.; Murphy, C. J. Temperature and salt dependent binding of long DNA to protein-sized quantum dots: Thermodynamics of "inorganic protein"-DNA interactions. J. Am. Chem. Soc., 2000, 122, 14-17.
356. Mitchell, G. P.; Mirkin, C. A.; Letsinger, R. L. Programmed assembly of DNA functionalized quantum dots. J. Am. Chem. Soc., 1999, 121, 8122-8123.
357. Storhoff, J. J.; Mirkin, C. A. Programmed materials synthesis with DNA. Chem. Rev., 1999, 99, 1849-1862.
358. Lin, L.; Zhao, H. Q.; Li, J. R.; Tang, J. A.; Duan, M. X.; Jiang, L. Study on colloidal Au-enhanced DNA sensing by quartz crystal microbalance. Biochem. Biophys. Res. Commun., 2000, 274, 817-820.
359. Han, S. B.; Lin, J. Q.; Satjapipat, M.; Baca, A. J.; Zhou, F. M. A three-dimensional heterogeneous DNA sensing surface formed by attaching oligodeoxynucleotide-capped gold nanoparticles onto a gold-coated quartz crystal. Chem. Commun., 2001, 609-610.
360. Su, X. D.; Li, S. F. Y.; O'Shea, S. J. Au nanoparticle and silver enhancement reaction-amplified microgravimetric biosensor. Chem. Commun., 2001, 755-756.
361. Willner, I.; Patolsky, F.; Wasserman, J. Photoelectrochemistry with controlled DNA-cross-linked CdS nanoparticle arrays. Angew. Chem. Int. Ed., 2001, 40, 1861-1864.
362. Kang, B.; Mackey, M. A.; El-Sayed, M. A. Nuclear targeting of gold nanoparticles in cancer cells induces DNA damage, causing cytokinesis arrest and apoptosis. J. Am. Chem. Soc., 2010, 132, 1517-1519.
363. Niemeyer, C. M. Nanoparticles, proteins, and nucleic acids: Biotechnology meets materials science. Angew. Chem. Int. Ed., 2001, 40, 4128-4158.
364. Dhar, S.; Daniel, W. L.; Giljohann, D. A.; Mirkin, C. A.; Lippard, S. J. Polyvalent oligonucleotide gold nanoparticle conjugates as delivery vehicles for platinum(IV) warheads. J. Am. Chem. Soc., 2009, 131, 14652-14653.
365. Giljohann, D. A.; Seferos, D. S.; Patel, P. C.; Millstone, J. E.; Rosi, N. L.; Mirkin, C. A. Oligonucleotide loading determines cellular uptake of DNA-modified gold nanoparticles. Nano Lett., 2007, 7, 3818-3821.
366. Rosi, N. L.; Giljohann, D. A.; Thaxton, C. S.; Lytton-Jean, A. K. R.; Han, M. S.; Mirkin, C. A. Oligonucleotide-modified gold nanoparticles for intracellular gene regulation. Science, 2006, 312, 1027-1030.
367. Seferos, D. S.; Prigodich, A. E.; Giljohann, D. A.; Patel, P. C.; Mirkin, C. A. Polyvalent DNA nanoparticle conjugates stabilize nucleic acids. Nano Lett., 2009, 9, 308-311.