Metal Complexes as Alternative Base Pairs or Triplets in Natural and Synthetic Nucleic Acid Structures

Metallofoldamers: Supramolecular Architectures from Helicates to Biomimetics

Volumn , Issue , 2013, Pages 333-377

  De, Arnie ^a   Kong, Jing ^a   Achim, Catalina ^a  

^a CARNEGIE MELLON UNIVERSITY   (United States)

Author keywords

DNA; Molecular electronics; Nucleic acid duplexes; Nucleic acid triplexes; Nucleobase pair; Synthetic nucleic acid structures; Transition metal complexes; Watson Crick base pairing

Indexed keywords

EID: 84884571752     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9781118517413.ch10     Document Type: Chapter

References (159)

1. Derose, V.J., Burns, S., Kim, N.K., and Vogt, M. (2004) DNA and RNA as ligan. Compr. Coord. Chem. II, 8, 787-813.
2. Martin, R.B. (1996) Dichotomy of metal ion binding to N1 and N7 of purines. Met. Ions Biol. Syst., 32, 61-89.
3. Martin, R.B. (1985) Nucleoside sites for transition metal ion binding. Acc. Chem. Res., 18 (2), 32-38.
4. Schoenknecht, T. and Diebler, H. (1993) Spectrophotometric and kinetic studies of the binding of nickel, cobalt, and magnesium to poly(dG-dC).poly(dG-dC). Determination of the stoichiometry of the Ni2+-induced B-> Z transition. J. Inorg. Biochem., 50 (4), 283-298.
5. Gueron, M., Demaret, J.P., and Filoche, M. (2000) A unified theory of the B-Z transition of DNA in high and low concentrations of multivalent ions. Biophys. J., 78 (2), 1070-1083.
6. Van Steenwinkel, R., Campagnari, F., and Merlini, M. (1981) Interaction of manganese(2+) with DNA as studied by proton-relaxation enhancement of solvent water. Biopolymers, 20 (5), 915-923.
7. Zimmer, C., Luck, G., and Triebel, H. (1974) Conformation and reactivity of DNA. IV. Base binding ability of transition metal ions to native DNA and effect on helix conformation with special reference to DNA-Zn(II) complex. Biopolymers, 13 (3), 425-453.
8. Moldrheim, E., Andersen, B., Froystein, N.A., and Sletten, E. (1998) Interaction of manganese( II), cobalt(II) and nickel(II) with DNA oligomers studied by 1H NMR spectroscopy. Inorg. Chim. Acta, 273 (1, 2), 41-46.
9. Froeystein, N.A., Davis, J.T., Reid, B.R., and Sletten, E. (1993) Sequence-selective metal ion binding to DNA oligonucleotides. Acta Chem. Scand., 47 (7), 649-657.
10. Vinje, J., Parkinson, J.A., Sadler, P.J. et al. (2003) Sequence-selective metalation of double-helical oligodeoxyribonucleotides with PtII, MnII, and ZnII ions. Chem. Eur. J., 9 (7), 1620-1630.
11. Vinje, J. and Sletten, E. (2006) Internal versus terminal metalation of double-helical oligodeoxyribonucleotides. Chem. Eur. J., 12 (3), 676-688.
12. Jia, X., Zon, G., and Marzilli, L.G. (1991) Multinuclear NMR investigation of zinc(2+) binding to a dodecamer oligodeoxyribonucleotide: insights from carbon-13 NMR spectroscopy. Inorg. Chem., 30 (2), 228-239.
13. Pullman, A., Pullman, B., and Lavery, R. (1983) Molecular electrostatic potential versus field. Significance for DNA and its constituents. Theochemistry, 10, 85-91.
14. Abrescia, N.G.A., Malinina, L., Fernandez, L.G. et al. (1999) Structure of the oligonucleotide d(CGTATATACG) as a site-specific complex with nickel ions. Nucleic Acids Res., 27 (7), 1593-1599.
15. Abrescia, N.G.A., Tam, H.-D., and Subirana, J.A. (2002) Nickel-guanine interactions in DNA: crystal structure of nickel-d[CGTGTACACG]2. J. Biol. Inorg. Chem., 7 (1-2), 195-199.
16. Labiuk, S.L., Delbaere Louis, T.J., and Lee, J.S. (2003) Cobalt(II), nickel(II) and zinc(II) do not bind to intra-helical N(7) guanine positions in the B-form crystal structure of d (GGCGCC). J. Biol. Inorg. Chem., 8 (7), 715-720.
17. Soler-Lopez, M., Malinina, L., Tereshko, V. et al. (2002) Interaction of zinc ions with d(CGCAATTGCG) in a 2.9. ANG. resolution X-ray structure. J. Biol. Inorg. Chem., 7 (4-5), 533-538.
18. Kagawa, T.F., Geierstanger, B.H., Wang, A.H.J., and Ho, P.S. (1991) Covalent modification of guanine bases in doublestranded DNA. The 1. 2-. ANG. Z-DNA structure of d(CGCGCG) in the presence of copper(II) chloride. J. Biol. Chem., 266 (30), 20175-20184.
19. Braun, E., Eichen, Y., Sivan, U., and Ben-Yoseph, G. (1998) DNA-templated assembly and electrode attachment of a conducting silver wire. Nature, 391 (6669), 775-778.
20. Jayaraman, S., Tang, W., and Yongsunthon, R. (2011) Electrochemical Synthesis of M:DNA Nanohybrids. J. Electrochem. Soc., 158, K123-K126.
21. Keren, K., Krueger, M., Gilad, R. et al. (2002) Sequence-specific molecular lithography on single DNA molecule. Science, 297 (5578), 72-75.
22. Keren, K., Berman, R.S., and Braun, E. (2004) Patterned DNA metallization by sequence-specific localization of a reducing agent. Nano. Lett., 4 (2), 323-326.
23. Aich, P., Labiuk, S.L., Tari, L.W. et al. (1999) M-DNA: A Complex Between Divalent Metal Ions and DNA which Behaves as a Molecular . J. Mol. Biol., 294 (2), 477-485.
24. Wettig, S.D., Li, C.-Z., Long, Y.-T. et al. (2003) M-DNA: a self-assembling molecular wire for nanoelectronics and biosensing. Anal. Sci., 19 (1), 23-26.
25. Wettig, S.D., Wood, D.O., Aich, P., and Lee, J.S. (2005) M-DNA: A novel metal ion complex of DNA studied by fluorescence techniques. J. Inorg. Biochem., 99 (11), 2093-2101.
26. Wood, D.O., Dinsmore, M.J., Bare, G.A., and Lee, J.S. (2002) M-DNA is stabilized in G. C tracts or by incorporation of 5-fluorouracil. Nucleic Acids Res., 30 (10), 2244-2250
27. Wood, D.O. and Lee, J.S. (2005) Investigation of pH-dependent DNA-metal ion interactions by surface plasmon resonance. J. Inorg. Biochem., 99 (2), 566-574.
28. Alexandre, S.S., Murta, B.J., Soler, J.M., and Zamora, F. (2011) Stability and electronic structure of M-DNA: Role of metal positi. Phys. Rev. B Condens. Mat. Mater. Phys., 84, 045413/1-045413/7.
29. Brancolini, G. and Di, F.R. (2011) Combined effects of metal complexation and size expansion in the electronic structure of DNA base pairs. J. Chem. Phys., 134, 205102/1-205102/12.
30. Rubin, Y.V., Belous, L.F., and Yakuba, A.A. (2011) Electronic and molecular structure of M-DNA fragments. J. Mol. Model., 17, 997-1006.
31. Tanaka, K. and Shionoya, M. (1999) Synthesis of a novel nucleoside for alternative DNA base pairing through metal complexation. J. Org. Chem., 64 (14), 5002-5003.
32. Cao, H. Tanaka, K., and Shionoya, M. (2000) An alternative base-pairing of catecholbearing nucleosides by borate formation. Chem. Pharm. Bull. (Tokyo), 48 (11), 1745-1748.
33. Shionoya, M. and Tanaka, K. (2000) Synthetic incorporation of metal complexes into nucleic acids and peptides directed toward functionalized molecules. Bull. Chem. Soc. Jpn, 73 (9), 1945-1954.
34. Tanaka, K., Tasaka, M., Cao, H., and Shionoya, M. (2001) An approach to metal-assisted DNA base pairing: novel b-C-nucleosides with a 2-aminophenol or a catechol as the nucleobase. Eur. J. Pharm. Sci., 13 (1), 77-83.
35. Tasaka, M., Tanaka, K., Shiro, M., and Shionoya, M. (2001) A palladium-mediated DNA base pair of a b-C-nucleoside possessing a 2-aminophenol as the nucleobase. Supramol. Chem., 13 (6), 671-675.
36. Meggers, E., Holland, P.L., Tolman, W.B. et al. (2000) A novel copper-mediated DNA base pair. J. Am. Chem. Soc., 122 (43), 10714-10715.
37. Weizman, H. and Tor, Y. (2001) Oligo-ligandosides: a DNA mimetic approach to helicate formation. Chem. Commun., 2001 (5), 453-454.
38. Weizman, H. and Tor, Y. (2001) 2,20-Bipyridine ligandoside: a novel building block for modifying DNA with intra-duplex metal complexes. J. Am. Chem. Soc., 123 (14), 3375-3376.
39. Tanaka, K., Tengeiji, A., Kato, T. et al. (2002) Efficient incorporation of a copper hydroxypyridone base pair in DNA. J. Am. Chem. Soc., 124 (42), 12494-12498.
40. Tanaka, K., Yamada, Y., and Shionoya, M. (2002) Formation of Silver(I)-mediated DNA duplex and triplex through an alternative base pair of pyridine nucleobases. J. Am. Chem. Soc., 124 (30), 8802-8803.
41. Switzer, C. and Shin, D. (2005) A pyrimidine-like nickel(II) DNA base pair. Chem. Commun., 2005 (10), 1342-1344.
42. Switzer, C., Sinha, S., Kim, P.H., and Heuberger, B.D. (2005) A purine-like nickel(II) base pair for DNA. Angew. Chem., Int. Ed., 44 (10), 1529-1532.
43. Shin, D. and Switzer, C. (2007) A metallo base-pair incorporating a terpyridyl-like motif: bipyridyl-pyrimidinoneág(I)-4-pyridine. Chem. Commun., 2007 (42), 4401-4403.
44. Heuberger, B.D., Shin, D., and Switzer, C. (2008) Two Watson-Crick-like metallo basepairs. Org. Lett., 10 (6), 1091-1094.
45. Boehme, D., Duepre, N., Megger, D.A., and Müller, J. (2007) Conformational change induced by metal-ion-binding to DNA containing the artificial 1,2,4-Triazole nucleoside. Inorg. Chem., 46 (24), 10114-10119.
46. Polonius, F.-A. and Müller, J. (2007) An artificial base pair, mediated by hydrogen bonding and metal-ion binding. Angew. Chem. Int. Ed., 46 (29), 5602-5604.
47. Megger, D.A. and Müller, J. (2010) Silver(I)-mediated cytosine self-pairing is preferred over hoogsteen-type base pairs with the artificial nucleobase 1,3-dideaza-6-nitropurine. Nucleosides Nucleotides Nucleic Acids, 29 (1), 27-38.
48. Megger, D.A., Fonseca Guerra, C., Bickelhaupt, F.M., and Müller, J. (2011) Silver(I)-mediated Hoogsteen-type base pairs. J. Inorg. Biochem., 105 (11), 1398-1404.
49. Megger, D.A., Guerra, C.F., Hoffmann, J. et al. (2011) Contiguous metal-mediated base pairs comprising two AgI ions. Chem. Eur. J., 17 (23), 6533-6544, S6533/1-S6533/21.
50. Clever, G.H. Polborn, K., and Carell, T. (2005) A highly DNA-duplex-stabilizing metalsalen base pair. Angew. Chem. Int. Ed., 44 (44), 7204-7208.
51. Clever, G.H., Soeltl, Y., Burks, H. et al. (2006) Metal-salen-base-pair complexes inside DNA: complexation overrides sequence information. Chem. Eur. J., 12 (34), 8708-8718.
52. Tanaka, K., Clever, G.H., Takezawa, Y. et al. (2006) Programmable self-assembly of metal ions inside artificial DNA duplexes. Nat. Nanotechnol., 1 (3), 190-194.
53. Clever, G.H. and Carell, T. (2007) Controlled stacking of 10 transition-metal ions inside a DNA duplex. Angew. Chem. Int. Ed., 46 (1/2), 250-253.
54. Clever, G.H., Kaul, C., and Carell, T. (2007) DNA-metal base pairs. Angew. Chem. Int. Ed., 46 (33), 6226-6236.
55. Tanaka, K., Clever, G.H., Takezawa, Y. et al. (2007) Programmable self-assembly of metal ions inside artificial DNA duplexes. [Erratum to document cited in CA147:380005]. Nat. Nanotechnol., 2 (1), 63.
56. Gaub, B.M., Kaul, C., Zimmermann, J.L. et al. (2009) Switching the mechanics of dsDNA by Cu salicylic aldehyde complexation. Nanotechnology, 20 (43), 434002/1-434002/8.
57. Clever, G.H., Reitmeier, S.J., Carell, T., and Schiemann, O. (2010) Antiferromagnetic coupling of stacked CuII-salen complexes in DNA. Angew. Chem. Int. Ed., 49 (29), 4927-4929.
58. Kaul, C., Mueller, M., Wagner, M. et al. (2011) Reversible bond formation enables the replication and amplification of a crosslinking salen complex as an orthogonal base pair. Nat. Chem., 3 (10), 794-800.
59. Popescu, D.-L., Parolin, T.J., and Achim, C. (2003) Metal incorporation in modified PNA duplexes. J. Am. Chem. Soc., 125 (21), 6354-6355.
60. Watson, R.M., Skorik, Y., Patra, G.K., and Achim, C. (2005) Influence of metal coordination on the mismatch tolerance of ligandmodified PNA duplexes. J. Am. Chem. Soc., 127, 14628-14639.
61. Franzini, R., Watson, R.M., Patra, G.K., and Achim, C. (2006) Metal binding to bipyridine-modified peptide nucleic acids. Inorg. Chem., 45 (24), 9798-9811.
62. Bezer, S., Rapireddy, S., Skorik, Y.A., Ly, D.H., and Achim, C. (2011) Coordination-driven inversion of handedness in ligand-modified PNA. Inorg. Chem., 50 (23), 11929-11937.
63. Ma, Z., Olechnowicz, F., Skorik, Y.A., and Achim, C. (2011) Metal binding to ligand-containing peptide nucleic acids. Inorg. Chem., 50 (13), 6083-6092.
64. Seubert, K., Guerra, C.F., Bickelhaupt, F.M., and Mueller, J. (2011) Chimeric GNA/DNA metal-mediated base pairs. Chem. Commun., 47 (39), 11041-11043.
65. Zhang, L., Peritz, A., and Meggers, E. (2005) A simple glycol nucleic acid. J. Am. Chem. Soc., 127 (12), 4174-4175.
66. Babu, B.R., Hrdlicka, P.J., McKenzie, C.J., and Wengel, J. (2005) Optimized DNA targeting using N,N-bis(2-pyridylmethyl)-b-alanyl 20-amino-LNA. Chem. Commun., 2005 (13), 1705-1707.
67. Kalek, M., Madsen, A.S., and Wengel, J. (2007) Effective modulation of DNA duplex stability by reversible transition metal complex formation in the minor groove. J. Am. Chem. Soc., 129 (30), 9392-9400.
68. Kuklenyik, Z. and Marzilli, L.G. (1996) Mercury(II) site-selective binding to a DNA hairpin. relationship of sequence-dependent intra-and interstrand crosslinking to the hairpin-duplex conformational transition. Inorg. Chem., 35 (19), 5654-5662.
69. Nielsen, P.E., Egholm, M., Berg, R.H., and Buchardt, O. (1991) Sequence-selective recognition of DNA by strand displacement with a thymine-substituted polyamide. Science, 254, 1497-1500.
70. Beck, F. (2002) Solid phase synthesis of PNA oligomers. Methods Mol. Biol., 208, 29-41.
71. Bahal, R., Sahu, B., Rapireddy, S. et al. (2012) Sequence-unrestricted, Watson-crick recognition of double helical B-DNA by (R)-MiniPEG-gPNAs. ChemBioChem, 13, 56-60.
72. Corradini, R., Sforza, S., Tedeschi, T. et al. (2007) Peptide nucleic acids with a structurally biased backbone: effects of conformational constraints and stereochemistry. Curr. Top. Med. Chem., 7, 681-775.
73. D'Costa, M., Kumar, V., and Ganesh, K. (1999) Aminoethylprolyl peptide nucleic acids (aepPNA): chiral PNA analogues that form highly stable DNA:aepPNA2 triplexes. Org. Lett., 1 (10), 1513-1516.
74. Dragulescu-Andrasi, A., Rapireddy, S., Frezza, B. et al. (2006) A simple gamma-backbone modification preorganizes peptide nucleic acid into a helical structure. J. Am. Chem. Soc., 128 (31), 10258-10267.
75. Ganesh, K.N. and Nielsen, P.E. (2000) Peptide nucleic acids analogs and derivatives. Curr. Org. Chem., 4 (9), 931-943.
76. Govindaraju, T., Kumar, V., and Ganesh, K. (2004) Synthesis and evaluation of (1S,2R/1R,2S)-aminocyclohexylglycyl PNAs as conformationally preorganized PNA analogues for DNA/RNA recognition. J. Org. Chem., 69 (6), 1858-1865.
77. Govindaraju, T., Kumar, V., and Ganesh, K. (2004) (1S,2R/1R,2S)-cis-cyclopentyl PNAs (cpPNAs) as constrained PNA analogues: synthesis and evaluation of aeg-cpPNA chimera and stereopreferences in hybridization with DNA/RNA. J. Org. Chem., 69 (17), 5725-5734.
78. Govindaraju, T., Kumar, V., and Ganesh, K. (2004) cis-Cyclopentyl PNA (cpPNA) as constrained chiral PNA analogues: stereochemical dependence of DNA/RNA hybridization. Chem. Commun., 2004, 860-861.
79. Govindaraju, T., Kumar, V., and Ganesh, K. (2005) (SR/RS)-cyclohexanyl PNAs: conformationally preorganized PNA analogues with unprecedented preference for duplex formation with RNA. J. Am. Chem. Soc., 127 (12), 4144-4145.
80. Govindaraju, T., Madhuri, V., Kumar, V., and Ganesh, K. (2006) Cyclohexanyl peptide nucleic acids (chPNAs) for preferential RNA binding: effective tuning of dihedral angle beta in PNAs for DNA/RNA discrimination. J. Org. Chem., 71 (1), 14-21.
81. Haaima, G., Hansen, H., Christensen, L. et al. (1997) Increased DNA binding and sequence discrimination of PNA oligomers containing 2,6-diaminopurine. Nucleic Acids Res., 25 (22), 4639-4643.
82. Kumar, R., Singh, S.K., Koshkin, A.A. et al. (1998) The first analogs of LNA (locked nucleic acids): phosphorothioate-LNA and 20-thio-LNA. Bioorg. Med. Chem. Lett., 8 (16), 2219-2222.
83. Lagriffoule, P., Eriksson, M., Jensen, K.K. et al. (1997) Peptide nucleic acids with a conformationally constrained chiral cyclohexyl derived backbone. Chem. Eur. J., 3 (6), 912-919.
84. Pokorski, J., Witschi, M., Purnell, B., and Appella, D. (2004) (S,S)-transcyclopentane-constrained peptide nucleic acids. a general backbone modification that improves binding affinity and sequence specificity. J. Am. Chem. Soc., 126 (46), 15067-15073.
85. Rapireddy, S., He, G., Roy, S. et al. (2007) Strand invasion of mixed-sequence B-DNA by acridinelinked, gamma-peptide nucleic acid (gamma-PNA). J. Am. Chem. Soc., 129 (50), 15596-15600.
86. Diederichsen, U. (1996) Pairing properties of alanyl peptide nucleic acids containing an amino acid backbone with alternating configuration. Angew. Chem. Int. Ed., 35 (4), 445-448.
87. Nielsen, P.E. (ed.) (2004) Peptide Nucleic Acids: Protocols and Applications, 3nd edn, Horizon Bioscience, Wymondham, p. 318.
88. Wolak, M.A., Balaeff, A., Gutmann, S. et al. (2011) Electronic structure of self-assembled peptide nucleic acid thin films. J. Phys. Chem. C, 115 (34), 17123-17135.
89. Paul, A., Watson, R.M., Lund, P. et al. (2008) Charge transfer through single-stranded peptide nucleic acid composed of thymine nucleotides. J. Phys. Chem. C, 112 (18), 7233-7240.
90. Wittung, P., Eriksson, M., Lyng, R. et al. (1995) Induced chirality in PNA-PNA duplexes. J. Am. Chem. Soc., 117 (41), 10167-10173.
91. Rasmussen, H., Kastrup, J.S., Nielsen, J.N. et al. (1997) Crystal structure of a peptide nucleic acid (PNA) duplex at 1.7 A resolution. Nat. Struct. Biol., 4 (2), 98-101.
92. Yeh, J.I., Pohl, E., Truan, D. et al. (2010) The crystal structure of non-modified and bipyridinemodified PNA duplexes. Chem. Eur. J., 16 (39), 11867-11875.
93. Yeh Joanne, I., Pohl, E., Truan, D. et al. (2011) The crystal structure of non-modified and bipyridine-modified PNA duplexes. [Erratum to document cited in CA154:046259]. Chem. Eur. J., 17 (44), 12227.
94. Sforza, S., Tedeschi, T., Corradini, R., and Marchelli, R. (2007) Induction of helical handedness and DNA binding properties of peptide nucleic acids (PNAs) with two stereogenic centers. Eur. J. Org. Chem., 2007 (35), 5879-5885.
95. Sforza, S., Haaima, G., Marchelli, R., and Nielsen, P.E. (1999) Chiral peptide nucleic acids (PNAs). Helix handedness and DNA recognition. Eur. J. Org. Chem., 1999 (1), 197-204.
96. Pensato, S., Saviano, M., Bianchi, N. et al. (2010) g-Hydroxymethyl PNAs: Synthesis, interaction with DNA and inhibition of protein/DNA interactions. Bioorg. Chem., 38 (5), 196-201.
97. He, W., Hatcher, E., Balaeff, A. et al. (2008) Solution structure of a peptide nucleic acid duplex from NMR data: Features and limitations. J. Am. Chem. Soc., 130 (40), 13264-13273.
98. Sosniak, A.M., Gasser, G., and Metzler-Nolte, N. (2009) Thermal melting studies of alkyneand ferrocene-containing PNA bioconjugates. Org. Biomol. Chem., 7 (23), 4992-5000.
99. Kise, K.J. Jr and Bowler, B.E. (2002) A Ruthenium(II) Tris(bipyridyl) Amino Acid: Synthesis and Direct Incorporation into an a-Helical Peptide by Solid-Phase Synthesis. Inorg. Chem., 41 (2), 379-386.
100. Nickita, N., Gasser, G., Bond, A.M., and Spiccia, L. (2009) Synthesis, spectroscopic properties and electrochemical oxidation of ruii-polypyridyl complexes attached to a peptide nucleic acid monomer backbone. Eur. J. Inorg. Chem., 2009, 2179-2186.
101. Singh, S.K., Nielsen, P., Koshkin, A.A., and Wengel, J. (1998) LNA (locked nucleic acids): synthesis and high-affinity nucleic acid recognition. Chem. Commun., 1998 (4), 455-456.
102. Obika, S., Nanbu, D., Hari, Y. et al. (1998) Stability and structural features of the duplexes containing nucleoside analogs with a fixed N-type conformation, 20-O,40-C-methyleneribonucleosides. Tetrahedron Lett., 39 (30), 5401-5404.
103. Wengel, J., Petersen, M., Frieden, M., and Koch, T. (2004) Chemistry of locked nucleic acids (LNA): Design, synthesis, and bio-physical properties. Lett. Pept. Sci., 10 (3/4), 237-253.
104. Doessing, H. and Vester, B. (2011) Locked and unlocked nucleosides in functional nucleic acids. Molecules, 16 (6), 4511-4526.
105. Nielsen, K.E., Rasmussen, J., Kumar, R. et al. (2004) NMR studies of fully modified locked nucleic acid (LNA) hybrids: solution structure of an LNA:RNA hybrid and characterization of an LNA:DNA hybrid. Bioconjugate Chem., 15 (3), 449-457.
106. Meggers, E. and Zhang, L. (2010) Synthesis and properties of the simplified nucleic acid glycol nucleic acid. Acc. Chem. Res., 43 (8), 1092-1102.
107. Zhang, L. and Meggers, E. (2005) An extremely stable and orthogonal DNA base pair with a simplified three-carbon backbone. J. Am. Chem. Soc., 127 (1), 74-75.
108. Schlegel, M.K., Essen, L.-O., and Meggers, E. (2010) Atomic resolution duplex structure of the simplified nucleic acid GNA. Chem. Commun., 46 (7), 1094-1096.
109. Johnson, A.T., Schlegel, M.K., Meggers, E. et al. (2011) On the structure and dynamics of duplex GNA. J. Org. Chem., 76 (19), 7964-7974.
110. Shionoya, M. and Tanaka, K. (2004) Artificial metallo-DNA: a bio-inspired approach to metal array programming. Curr. Opin. Chem. Biol., 8 (6), 592-597.
111. Wagenknecht, H.-A. (2003) Metal-mediated DNA base pairing and metal arrays in artificial DNA: Towards new nanodevices. Angew. Chem. Int. Ed., 42 (28), 3204-3206.
112. Henry, A.A. and Romesberg, F.E. (2003) Beyond A, C, G and T: augmenting nature's alphabet. Curr. Opin. Chem. Biol., 7 (6), 727-733.
113. Kool, E.T. (2002) Replacing the nucleobases in DNAwith designer molecules. Acc. Chem. Res., 35 (11), 936-943.
114. Park, K.S. Jung, C., and Park, H.G. (2010) "Illusionary" polymerase activity triggered by metal ions: use for molecular logic-gate operations. Angew. Chem. Int. Ed., 49 (50), 9757-9760.
115. Urata, H., Yamaguchi, E., Funai, T. et al. (2010) Incorporation of thymine nucleotides by DNA polymerases through T-HgII-T base pairing. Angew. Chem. Int. Ed., 49 (37), 6516-6519.
116. Brotschi, C. and Leumann, C.J. (2003) Transition metal ligands as novel DNA-base substitutes. Nucleosides Nucleotides Nucleic Acids, 22 (5/8), 1195-1197.
117. Megger, D., Megger, N., and Müller, J. (2012) Metal-mediated base pairs in nucleic acids with purine-and pyrimidine-derived nucleosides. Metal Ions Life Sci., 10, 295-317.
118. Müller, J., Boehme, D., Lax, P. et al. (2005) Metal ion coordination to azole nucleosides. Chem. Eur. J., 11 (21), 6246-6253.
119. Boehme, D., Duepre, N., Megger, D.A., and Mueller, J. (2007) Conformational change induced by metal-ion-binding to DNA containing the artificial 1,2,4-Triazole nucleoside. Inorg. Chem., 46 (24), 10114-10119.
120. Johannsen, S., Megger, N., Boehme, D. et al. (2010) Solution structure of a DNA double helix with consecutive metal-mediated base pairs. Nat. Chem., 2 (3), 229-234.
121. Smith, A.P. and Fraser, C.L. (2004) Bipyridine ligands. Compr. Coord. Chem. II, 1, 1-23.
122. Zimmermann, N., Meggers, E., and Schultz, P.G. (2002) A novel Silver(I)-Mediated DNA base pair. J. Am. Chem. Soc., 124 (46), 13684-13685.
123. Constable, E.C. (1989) Homoleptic complexes of 2,20-bipyridine. Adv. Inorg. Chem., 34, 1-63.
124. Brotschi, C., Haberli, A., and Leumann, C.J. (2001) A stable DNA duplex containing a nonhydrogen-bonding and non-shape-complementary base couple: Interstrand stacking as the stability determining factor. Angew. Chem. Int. Ed., 40 (16), 3012-3014.
125. Franzini, R., Watson, R.M., Popescu, D.-L. et al. (2004) Metal-containing modified peptide nucleic acids. Polymer Preprints, 45 (1), 337-338.
126. Wierzbinski, E., de Leon, A., Davis, K.L. et al. (2012) Charge transfer through modified peptide nucleic acids. Langmuir, 28 (4), 1971-1981.
127. Milani, B., Anzilutti, A., Vicentini, L. et al. (1997) Bis-chelated Palladium(II) complexes with nitrogen-donor chelating ligands are efficient catalyst precursors for the CO/Styrene copolymerization reaction. Organometallics, 16 (23), 5064-5075.
128. Schlegel, M.K., Zhang, L., Pagano, N., and Meggers, E. (2009) Metal-mediated base pairing within the simplified nucleic acid GNA. Org. Biomol. Chem., 7 (3), 476-482.
129. Tanaka, K., Tasaka, M., Cao, H., and Shionoya, M. (2002) Toward nano-assembly of metals through engineered DNAs. Supramol. Chem., 14 (2-3), 255-261.
130. Zhan, Z.-Y.J. and Lynn, D.G. (1997) Chemical amplification through template-directed synthesis. J. Am. Chem. Soc., 119 (50), 12420-12421.
131. Czlapinski, J.L. and Sheppard, T.L. (2004) Template-directed assembly of metallosalen-DNA hairpin conjugates. ChemBioChem, 5 (1), 127-129.
132. El-Jammal, A., Howell, P.L., Turner, M.A. et al. (1994) Copper complexation by 3-Hydroxypyridin-4-one Iron chelators: structural and iron competition studies. J. Med. Chem., 37 (4), 461-466.
133. Ahmed, S.I., Burgess, J., Fawcett, J. et al. (2000) The structures of bis-maltolato-zinc(II) and of bis(3-hydroxy-1,2-dimethyl-4-pyridinonato)zinc(II) and-lead(II). Polyhedron, 19 (2), 129-135.
134. Griffith, W.P. and Mostafa, S.I. (1992) Complexes of 3-hydroxypyridin-2-one and 1,2-dimethyl-3-hydroxypyridin-4-one with second and third row elements of groups 6, 7 and 8. Polyhedron, 11 (23), 2997-3005.
135. Schlegel, M.K., Essen, L.-O., and Meggers, E. (2008) Duplex structure of a minimal nucleic acid. J. Am. Chem. Soc., 130 (26), 8158-8159.
136. Liu, S., Clever, G.H., Takezawa, Y. et al. (2011) Direct conductance measurement of individual metallo-DNA duplexes within single-molecule break junctions. Angew. Chem. Int. Ed., 50 (38), 8886-8890, S8886/1-S8886/12.
137. Heuberger, B.D. and Switzer, C. (2008) An alternative nucleobase code: characterization of purine-purine DNA double helices bearing guanine-isoguanine and diaminopurine 7-deaza-xanthine base pairs. ChemBioChem, 9 (17), 2779-2783.
138. Karlsen, K.K., Jensen, T.B., and Wengel, J. (2009) Synthesis of an unlocked nucleic acid terpyridine monomer and binding of divalent metal ion in nucleic acid duplexes. J. Org. Chem., 74 (22), 8838-8841.
139. Yang, H., Rys, A.Z., McLaughlin, C.K., and Sleiman, H.F. (2009) Templated ligand environments for the selective incorporation of different metals into DNA. Angew. Chem. Int. Ed., 48 (52), 9919-9923.
140. Zimmermann, N., Meggers, E., and Schultz, P.G. (2004) A second-generation copper(II)-mediated metallo-DNA-base pair. Bioorg. Chem., 32 (1), 13-25.
141. Conley, H.L. Jr and Martin, R.B. (1965) Cupric ion catalyzed hydrolyses of glycine ethyl ester, glycinamide, and picolinamide. J. Phys. Chem., 69 (9), 2914-2923.
142. Nawata, Y., Iwasaki, H., and Saito, Y. (1967) Crystal structure of bis(pyridine-2-carboxamido)nickel(II) dihydrate. Bull. Chem. Soc. Jpn, 40 (3), 515-521.
143. Bonomo, R.P., Cucinotta, V., and Riggi, F. (1980) EPR solution studies of copper(II) mixed complexes containing iminodiacetic or pyridine-2,6-dicarboxylic acids and pyridine, ethylenediamine or diethylenetriamine. J. Mol. Struct., 69, 295-300.
144. Atwell, S., Meggers, E., Spraggon, G., and Schultz, P.G. (2001) Structure of a copper-mediated base pair in DNA. J. Am. Chem. Soc., 123 (49), 12364-12367.
145. Mokhir, A., Stiebing, R., and Krämer, R. (2003) Peptide nucleic acid-metal complex conjugates: facile modulation of PNA-DNA duplex stability. Bioorg. Med. Chem. Lett., 13 (8), 1399-1401.
146. Hrdlicka, P.J., Babu, B.R., Sorensen, M.D., and Wengel, J. (2004) Interstrand communication between 20-N-(pyren-1-yl)methyl-20-amino-LNA monomers in nucleic acid duplexes: directional control and signalling of full complementarity. Chem. Commun., 2004 (13), 1478-1479.
147. Hirva, P., Nielsen, A., Bond, A.D., and McKenzie, C.J. (2010) Potential cross-linking transition metal complexes (M=Ni, Cu, Zn) in the ligand-modified LNA duplexes. J. Phys. Chem. B, 114 (36), 11942-11948.
148. Brotschi, C. and Leumann, C.J. (2003) DNA with hydrophobic base substitutes: a stable, zipperlike recognition motif based on interstrand-stacking interactions. Angew. Chem. Int. Ed., 42 (14), 1655-1658.
149. Brotschi, C., Mathis, G., and Leumann, C.J. (2005) Bipyridyl-and biphenyl-DNA: a recognition motif based on interstrand aromatic stacking. Chem. Eur. J., 11 (6), 1911-1923.
150. Johar, Z., Zahn, A., Leumann, C.J., and Jaun, B. (2008) Solution structure of a DNA duplex containing a biphenyl pair. Chem. Eur. J., 14 (4), 1080-1086.
151. Mees, A., Klar, T., Gnau, P. et al. (2004) Crystal structure of a photolyase bound to a CPD-Like DNA lesion after in situ repair. Science, 306 (5702), 1789-1793.
152. Tanaka, K., Tengeiji, A., Kato, T. et al. (2003) A discrete self-assembled metal array in artificial DNA. Science, 299 (5610), 1212-1213.
153. Zhang, H.Y., Calzolari, A., and Di Felice, R. (2005) On the magnetic alignment of metal ions in a DNA-Mimic Helix. J. Phys. Chem. B, 109, 15345-15348.
154. Jishi, R.A. and Bragin, J. (2007) Symmetry selection in artificial DNA base pairs. J. Phys. Chem. B, 111 (19), 5357-5361.
155. Nakanishi, Y., Kitagawa, Y., Shigeta, Y. et al. (2009) Theoretical studies on magnetic interactions between Cu(II) ions in hydroxypyridone nucleobases. Polyhedron, 28 (9-10), 1714-1717.
156. Mallajosyula, S.S. and Pati, S.K. (2009) Conformational Tuning of Magnetic Interactions in Metal-DNA Complexes. Angew. Chem. Int. Ed., 48 (27), 4977-4981, S4977/1-S4977/8.
157. Takezawa, Y., Maeda, W., Tanaka, K., and Shinoya, M. (2009) Discrete self-assembly of iron (III) ions inside triple-stranded artificial DNA. Angew. Chem. Int. Ed., 48 (6), 1081-1084.
158. Kalachova, L., Pohl, R., and Hocek, M. (2012) Synthesis of nucleoside mono-and triphosphates bearing oligo-pyridine ligands, their incorporation into DNA and complexation with transition metals. Org. Biomol. Chem., 10 (1), 49-55.
159. Megger, D.A., Guerra, C.F., Hoffmann, J. et al. (2011) Contiguous metal-mediated base pairs comprising two AgI ions. Chem. Eur. J., 17 (23), 6533-6544.