Metal–base pairing in DNA

Clever, Guido H.; Shionoya, Mitsuhiko

doi:10.1016/j.ccr.2010.04.014

Cited by 233 publications

(125 citation statements)

References 97 publications

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“…[5][6][7][8][9][10][11][12] The most important metal-ion binding sites in B-form duplexes include the N3 and N7 positions of purine residues and the phosphodiester backbone. [13] The binding of Pt II to proximal guanine residues through N7 coordination is thought to be responsible for the antitumor activity of cisplatin, [14,15] but cisplatin treatment of genomic DNA results in a heterogeneous mixture of monoadducts, intra-and interstrand cross-links.…”

Section: Introductionmentioning

confidence: 99%

Site‐Specific Control of N7–Metal Coordination in DNA by a Fluorescent Purine Derivative

Dumas

Luedtke

2011

Chemistry A European J

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A synthetic strategy that utilizes O6-protected 8-bromoguanosine gives broad access to C8-guanine derivatives with phenyl, pyridine, thiophene, and furan substituents. The resulting 8-substituted 2'-deoxyguanosines are push-pull fluorophores that can exhibit environmentally sensitive quantum yields (Φ=0.001-0.72) due to excited-state proton-transfer reactions with bulk solvent. Changes in nucleoside fluorescence were used to characterize metal-binding affinity and specificity of 8-substituted 2'-deoxyguanosines. One derivative, 8-(2-pyridyl)-2'-deoxyguanosine (2PyG), exhibits selective binding of Cu(II), Ni(II), Cd(II), and Zn(II) through a bidentate effect provided by the N7 position of guanine and the 2-pyridyl nitrogen atom. Upon incorporation into DNA, 2-pyridine-modified guanine residues selectively bind to Cu(II) and Ni(II) with equilibrium dissociation constants (K(d)) that range from 25 to 850 nM; the affinities depend on the folded state of the oligonucleotide (duplex>G-quadruplex) as well as the identity of the metal ion (Cu>Ni≫Cd). These binding affinities are approximately 10 to 1 000 times higher than for unmodified metal binding sites in DNA, thereby providing site-specific control of metal localization in alternatively folded nucleic acids. Temperature-dependent circular-dichroism studies reveal metal-dependent stabilization of duplexes, but destabilization of G-quadruplex structures upon adding Cu(II) to 2PyG-modified oligonucleotides. These results demonstrate how the addition of a single pyridine group to the C8 position of guanine provides a powerful new tool for studying the effects of N7 metalation on the structure, stability, and electronic properties of nucleic acids.

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Section: Introductionmentioning

confidence: 99%

Site‐Specific Control of N7–Metal Coordination in DNA by a Fluorescent Purine Derivative

Dumas

Luedtke

2011

Chemistry A European J

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“…The prospect of self-assembling nanoscale electronic architectures based on DNA is certainly a fascinating one [ 29 ] . At present, it is not clear whether this goal can be achieved with M-DNA.…”

Section: Physical Propertiesmentioning

confidence: 99%

Metal-Mediated Base Pairs in Nucleic Acids with Purine- and Pyrimidine-Derived Nucleosides

Megger

Müller

2011

Metal Ions in Life Sciences

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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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“…Incorporation of metallo-base pairs into DNA structures allows us to enhance their thermal stability and to regulate their folding structures [2,3,7]. Natural pyrimidine nucleobases (i.e.…”

Section: Introductionmentioning

confidence: 99%

“…Unnatural metal-mediated DNA base pairs, formed through metal coordination between two ligand-type nucleobases and a metal ion, have been widely explored as functional building blocks of DNA-based supermolecules [1][2][3][4][5][6][7]. Incorporation of metallo-base pairs into DNA structures allows us to enhance their thermal stability and to regulate their folding structures [2,3,7].…”

Section: Introductionmentioning

confidence: 99%

pH-Dependence of the thermal stability of metallo-DNA duplexes containing ligand-type 5-hydroxyuracil nucleobases

Nishiyama

Takezawa

Shionoya

2016

Inorganica Chimica Acta

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Metal–base pairing in DNA

Cited by 233 publications

References 97 publications

Site‐Specific Control of N7–Metal Coordination in DNA by a Fluorescent Purine Derivative

Site‐Specific Control of N7–Metal Coordination in DNA by a Fluorescent Purine Derivative

Metal-Mediated Base Pairs in Nucleic Acids with Purine- and Pyrimidine-Derived Nucleosides

pH-Dependence of the thermal stability of metallo-DNA duplexes containing ligand-type 5-hydroxyuracil nucleobases

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