Abstract
Metal-mediated base pairs are transition metal complexes formed from complementary nucleosides within nucleic acid double helices. Instead of relying on hydrogen bonds, they are stabilized by coordinative bonds. The nucleosides acting as ligands do not necessarily have to be artificial. In fact, several examples are known of naturally occurring nucleobases (e.g., thymine, cytosine) capable of forming stable metal-mediated base pairs that are highly selective towards certain metal ions. This chapter provides a comprehensive overview of metal-mediated base pairs formed from natural nucleosides or from closely related artificial nucleosides that are pyrimidine or purine derivatives. It addresses the different strategies that lead to the development of these base pairs. The article focuses on structural models for metal-mediated base pairs, their experimental characterization within a nucleic acid, and on their possible applications.
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References
J. Müller, Metallomics 2010, 2, 318–327.
G. L. Eichhorn, Y. A. Shin, J. Am. Chem. Soc. 1968, 90, 7323–7328.
G. L. Eichhorn, J. J. Butzow, P. Clark, E. Tarien, Biopolymers 1967, 5, 283–296.
R. M. Izatt, J. J. Christensen, J. H. Rytting, Chem. Rev. 1971, 71, 439–481.
R. H. Jensen, N. Davidson, Biopolymers 1966, 4, 17–32.
S. Katz, Nature 1962, 194, 569.
J. Müller, Eur. J. Inorg. Chem. 2008, 3749–3763.
G. H. Clever, C. Kaul, T. Carell, Angew. Chem. Int. Ed. 2007, 46, 6226–6236.
K. Tanaka, M. Shionoya, Coord. Chem. Rev. 2007, 251, 2732–2742.
S. Atwell, E. Meggers, G. Spraggon, P. G. Schultz, J. Am. Chem. Soc. 2001, 123, 12364–12367.
S. Johannsen, N. Megger, D. Böhme, R. K. O. Sigel, J. Müller, Nat. Chem. 2010, 2, 229–234.
G. H. Clever, M. Shionoya, Chapter 10 of this book.
J. S. Lee, L. J. P. Latimer, R. S. Reid, Biochem. Cell Biol. 1993, 71, 162–168.
P. Aich, S. L. Labiuk, L. W. Tari, L. J. T. Delbaere, W. J. Roesler, K. J. Falk, R. P. Steer, J. S. Lee, J. Mol. Biol. 1999, 294, 477–485.
B. Lippert, Prog. Inorg. Chem. 2005, 54, 385–447.
M. Fuentes-Cabrera, B. G. Sumpter, J. E. Šponer, J. Šponer, L. Petit, J. C. Wells, J. Phys. Chem. B 2007, 111, 870–879.
S. S. Alexandre, J. M. Soler, L. Seijo, F. Zamora, Phys. Rev. B 2006, 73, 205112.
E. C. Fusch, B. Lippert, J. Am. Chem. Soc. 1994, 116, 7204–7209.
S. L. Labiuk, L. T. J. Delbaere, J. S. Lee, J. Biol. Inorg. Chem. 2003, 8, 715–720.
A. Rakitin, P. Aich, C. Papadopoulos, Y. Kobzar, A. S. Vedeneev, J. S. Lee, J. M. Xu, Phys. Rev. Lett. 2001, 86, 3670–3673.
C.-Z. Li, Y.-T. Long, H.-B. Kraatz, J. S. Lee, J. Phys. Chem. B 2003, 107, 2291–2296.
M. J. Dinsmore, J. S. Lee, J. Electroanal. Chem. 2008, 617, 71–77.
X. Li, Y. Zhou, T. C. Sutherland, B. Baker, J. S. Lee, H.-B. Kraatz, Anal. Chem. 2005, 77, 5766–5769.
S. D. Wettig, D. O. Wood, P. Aich, J. S. Lee, J. Inorg. Biochem. 2005, 99, 2093–2101.
K. Mizoguchi, S. Tanaka, T. Ogawa, N. Shiobara, H. Sakamoto, Phys. Rev. B 2005, 72, 0033106.
F. Moreno-Herrero, P. Herrero, F. Moreno, J. Colchero, C. Gómez-Navarro, J. Gómez-Herrero, A. M. Baró, Nanotechnology 2003, 14, 128–133.
B. Liu, A. J. Bard, C.-Z. Li, H.-B. Kraatz, J. Phys. Chem. B 2005, 109, 5193–5198.
B. Q. Spring, R. M. Clegg, J. Phys. Chem. B 2007, 111, 10040–10052.
G. H. Clever, M. Shionoya, Coord. Chem. Rev. 2010, 254, 2391–2402.
S. Katz, J. Am. Chem. Soc. 1952, 74, 2238–2245.
C. A. Thomas, J. Am. Chem. Soc. 1954, 76, 6032–6034.
S. Katz, Biochim. Biophys. Acta 1963, 68, 240–253.
L. D. Kosturko, C. Folzer, R. F. Stewart, Biochemistry 1974, 13, 3949–3952.
Z. Kuklenyik, L. G. Marzilli, Inorg. Chem. 1996, 35, 5654–5662.
Y. Miyake, H. Togashi, M. Tashiro, H. Yamaguchi, S. Oda, M. Kudo, Y. Tanaka, Y. Kondo, R. Sawa, T. Fujimoto, T. Machinami, A. Ono, J. Am. Chem. Soc. 2006, 128, 2172–2173.
H. Torigoe, A. Ono, T. Kozasa, Chem. Eur. J. 2010, 16, 13218–13225.
Y. Tanaka, S. Oda, H. Yamaguchi, Y. Kondo, C. Kojima, A. Ono, J. Am. Chem. Soc. 2007, 129, 244–245.
A. Ono, H. Togashi, Angew. Chem. Int. Ed. 2004, 43, 4300–4302.
R.-M. Kong, X.-B. Zhang, L.-L. Zhang, X.-Y. Jin, S.-Y. Huan, G.-L. Shen, R.-Q. Yu, Chem. Commun. 2009, 5633–5635.
C.-X. Tang, Y. Zhao, X.-W. He, X.-B. Yin, Chem. Commun. 2010, 46, 9022–9024.
Y. Miyake, A. Ono, Tetrahedron Lett. 2005, 46, 2441–2443.
E. Ennifar, P. Walter, P. Dumas, Nucleic Acids Res. 2003, 31, 2671–2682.
S. Johannsen, S. Paulus, N. Düpre, J. Müller, R. K. O. Sigel, J. Inorg. Biochem. 2008, 102, 1141–1151.
T. Yamane, N. Davidson, Biochim. Biophys. Acta 1962, 55, 609–621.
L. G. Marzilli, T. J. Kistenmacher, M. Rossi, J. Am. Chem. Soc. 1977, 99, 2797–2798.
T. J. Kistenmacher, M. Rossi, L. G. Marzilli, Inorg. Chem. 1979, 18, 240–244.
A. Ono, S. Cao, H. Togashi, M. Tashiro, T. Fujimoto, T. Machinami, S. Oda, Y. Miyake, I. Okamoto, Y. Tanaka, Chem. Commun. 2008, 4825–4827.
H. Torigoe, Y. Miyakawa, A. Ono, T. Kozasa, Nucleosides Nucleotides Nucleic Acids 2011, 30, 149–167.
D. A. Megger, J. Müller, Nucleosides Nucleotides Nucleic Acids 2010, 29, 27–38.
H. Urata, E. Yamaguchi, Y. Nakamura, S.-i. Wada, Chem. Commun. 2011, 47, 941–943.
T. Ono, K. Yoshida, Y. Saotome, R. Sakabe, I. Okamoto, A. Ono, Chem. Commun. 2011, 47, 1542–1544.
D. A. Megger, C. Fonseca Guerra, F. M. Bickelhaupt, J. Müller, J. Inorg. Biochem. 2011, 105, 1398–1404.
Y. Wen, F. Xing, S. He, S. Song, L. Wang, Y. Long, D. Li, C. Fan, Chem. Commun. 2010, 46, 2596–2598.
I. Okamoto, K. Iwamoto, Y. Watanabe, Y. Miyake, A. Ono, Angew. Chem. Int. Ed. 2009, 48, 1648–1651.
K. Aoki, W. Saenger, Acta Cryst. 1984, C40, 775–778.
B. Lippert, Coord. Chem. Rev. 2000, 200–202, 487–516.
J. Ruiz, M. D. Villa, V. Rodríguez, N. Cutillas, C. Vicente, G. López, D. Bautista, Inorg. Chem. 2007, 46, 5448–5449.
C. Switzer, D. Shin, Chem. Commun. 2005, 1342–1344.
D. Shin, C. Switzer, Chem. Commun. 2007, 4401–4403.
F.-A. Polonius, J. Müller, Angew. Chem. Int. Ed. 2007, 46, 5602–5604.
T. Ihara, T. Ishii, N. Araki, A. W. Wilson, A. Jyo, J. Am. Chem. Soc. 2009, 131, 3826–3827.
M. G. Santangelo, P. M. Antoni, B. Spingler, G. Jeschke, ChemPhysChem 2010, 11, 599–606.
F. Seela, T. Wenzel, Helv. Chim. Acta 1994, 77, 1485–1499.
D. A. Megger, C. Fonseca Guerra, J. Hoffmann, B. Brutschy, F. M. Bickelhaupt, J. Müller, Chem. Eur. J. 2011, 17, 6533–6544.
F. Seela, T. Wenzel, Helv. Chim. Acta 1995, 78, 833–846.
L. E. Kapinos, A. Holý, J. Günter, H. Sigel, Inorg. Chem. 2001, 40, 2500–2508.
C. Switzer, S. Sinha, P. H. Kim, B. D. Heuberger, Angew. Chem. Int. Ed. 2005, 44, 1529–1532.
B. D. Heuberger, D. Shin, C. Switzer, Org. Lett. 2008, 10, 1091–1094.
H. Urata, E. Yamaguchi, T. Funai, Y. Matsumura, S.-i. Wada, Angew. Chem. Int. Ed. 2010, 49, 6516–6519.
K. S. Park, C. Jung, H. G. Park, Angew. Chem. Int. Ed. 2010, 49, 9757–9760.
R. Freeman, T. Finder, I. Willner, Angew. Chem. Int. Ed. 2009, 48, 7818–7821.
N. Kanayama, T. Takarada, M. Maeda, Chem. Commun. 2011, 47, 2077–2079.
H. Torigoe, T. Kozasa, A. Ono, Nucleic Acids Symp. Ser. 2006, 50, 89–90.
J. Joseph, G. B. Schuster, Org. Lett. 2007, 9, 1843–1846.
Z.-G. Wang, J. Elbaz, I. Willner, Nano Lett. 2011, 11, 304–309.
J. Müller, D. Böhme, P. Lax, M. Morell Cerdà, M. Roitzsch, Chem. Eur. J. 2005, 11, 6246–6253.
L. Benda, M. Straka, Y. Tanaka, V. Sychrovský, Phys. Chem. Chem. Phys. 2011, 13, 100–103.
M. K. Schlegel, L. Zhang, N. Pagano, E. Meggers, Org. Biomol. Chem. 2009, 7, 476–482.
R. M. Franzini, R. M. Watson, G. K. Patra, R. M. Breece, D. L. Tierney, M. P. Hendrich, C. Achim, Inorg. Chem. 2006, 45, 9798–9811.
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Financial support of our research by the Deutsche Forschungsgemeinschaft is gratefully acknowledged.
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Megger, D.A., Megger, N., Müller, J. (2012). Metal-Mediated Base Pairs in Nucleic Acids with Purine- and Pyrimidine-Derived Nucleosides. In: Sigel, A., Sigel, H., Sigel, R. (eds) Interplay between Metal Ions and Nucleic Acids. Metal Ions in Life Sciences, vol 10. Springer, Dordrecht. https://doi.org/10.1007/978-94-007-2172-2_11
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