Three new modes of adenine-copper(II) coordination: interligand interactions controlling the selective N3-, N7- and bridging μ-N3,N7-metal-bonding of adenine to different N-substituted iminodiacetato-copper(II) chelates

Bugella-Altamirano, E; Choquesillo-Lazarte, Duane; González‐Pérez, Josefa María; Sánchez‐Moreno, Manuel; Marı́n-Sánchez, R; Martı́n-Ramos, J. D.; Covelo, Berta; Carballo, Rosa; Castiñeiras, Alfonso; Niclós‐Gutiérrez, Juan

doi:10.1016/s0020-1693(02)00920-9

Cited by 90 publications

(48 citation statements)

References 20 publications

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“…Hence, one may conclude that the 2'-OH group is not involved in metal ion binding and that an interaction with N3 is responsible for the stability enhancement. It should be added here that it is becoming increasingly clear from solution [152][153][154] as well as X-ray crystal structure studies that the N3 site of a purine may bind metal ions [155][156][157][158][159][160]. For example, Pt 2+ [155] and Cd 2+ [156] bind via N3 to adenine derivatives, Pd 2+ to N6',N6',N9-trimethyladenine [157], Pt 2+ to a guanine derivative [158], as well as Cu 2+ [159] and Ni 2+ [160] to neutral adenine.…”

Section: Nucleoside 2'-and 3'-monophosphatesmentioning

confidence: 99%

Complex Formation of Cadmium with Sugar Residues, Nucleobases, Phosphates, Nucleotides, and Nucleic Acids

Sigel

Skilandat

Sigel

et al. 2012

Metal Ions in Life Sciences

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Cadmium(II), commonly classified as a relatively soft metal ion, prefers indeed aromaticnitrogen sites (e.g., N7 of purines) over oxygen sites (like sugar-hydroxyl groups). However, matters are not that simple, though it is true that the affinity of Cd(2+) towards ribose-hydroxyl groups is very small; yet, a correct orientation brought about by a suitable primary binding site and a reduced solvent polarity, as it is expected to occur in a folded nucleic acid, may facilitate metal ion-hydroxyl group binding very effectively. Cd(2+) prefers the guanine(N7) over the adenine(N7), mainly because of the steric hindrance of the (C6)NH(2) group in the adenine residue. This Cd(2+)-(N7) interaction in a guanine moiety leads to a significant acidification of the (N1)H meaning that the deprotonation reaction occurs now in the physiological pH range. N3 of the cytosine residue, together with the neighboring (C2)O, is also a remarkable Cd(2+) binding site, though replacement of (C2)O by (C2)S enhances the affinity towards Cd(2+) dramatically, giving in addition rise to the deprotonation of the (C4)NH(2) group. The phosphodiester bridge is only a weak binding site but the affinity increases further from the mono-to the di-and the triphosphate. The same also holds for the corresponding nucleotides. Complex stability of the pyrimidine-nucleotides is solely determined by the coordination tendency of the phosphate group(s), whereas in the case of purine-nucleotides macrochelate formation takes place by the interaction of the phosphate-coordinated Cd(2+) with N7. The extents of the formation degrees of these chelates are summarized and the effect of a non-bridging sulfur atom in a thiophosphate group (versus a normal phosphate group) is considered. Mixed ligand complexes containing a nucleotide and a further mono-or bidentate ligand are covered and it is concluded that in these species N7 is released from the coordination sphere of Cd(2+). In the case that the other ligand contains an aromatic residue (e.g., 2,2'-bipyridine or the indole ring of tryptophanate) intramolecular stack formation takes place. With buffers like Tris or Bistris mixed ligand complexes are formed. Cd(2+) coordination to dinucleotides and to dinucleoside monophosphates provides some insights regarding the interaction between Cd(2+) and nucleic acids. Cd(2+) binding to oligonucleotides follows the principles of coordination to its units. The available crystal studies reveal that N7 of purines is the prominent binding site followed by phosphate oxygens and other heteroatoms in nucleic acids. Due to its high thiophilicity, Cd(2+) is regularly used in so-called thiorescue experiments, which lead to the identification of a direct involvement of divalent metal ions in ribozyme catalysis.

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Section: Nucleoside 2'-and 3'-monophosphatesmentioning

confidence: 99%

Complex Formation of Cadmium with Sugar Residues, Nucleobases, Phosphates, Nucleotides, and Nucleic Acids

Sigel

Skilandat

Sigel

et al. 2012

Metal Ions in Life Sciences

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show abstract

“…[33][34][35][36][37] the strategies of the synthesis here reported are designed on the basis of obtaining suitable copper (II) chelates by reactions of the basic copper(II) carbonate and the corresponding chelating ligand in their free-acid forms. Reactions (a) and (b) yield the copper(II) chelates of IDA and glygly respectively.…”

Section: Synthesis and Formulas Of Novel Compoundsmentioning

confidence: 99%

“…As it is well known, the origin of these bands is the overlapping of d-d transitions more o less probable according to the selection rules in the slipping diagram related to the chromophores CuN 2 O 2 + O(apical) of 1 and CuN 3 Osquare planar of 2 [33]. Polycrystalline samples of novel compounds give RSE spectra of isotropic (1, g iso 2.13) or axial (2, g // 2.17 N g ⊥ 2.06) type according to the alignment or misalignment of the chromophores in the crystals of 1 and 2 respectively [44].…”

Section: Other Physical Properties Of Novel Compoundsmentioning

confidence: 99%

Metal ion binding patterns of acyclovir: Molecular recognition between this antiviral agent and copper(II) chelates with iminodiacetate or glycylglycinate

Brandi-Blanco

Choquesillo-Lazarte

Domínguez‐Martín

et al. 2011

Journal of Inorganic Biochemistry

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“…Hence, one may conclude that the 2Ј-OH group is not involved in metal ion binding. It should be added here that it is becoming increasingly clear from solution [134,135] as well as X-ray crystal structure studies that the N3 site of a purine may bind metal ions [136][137][138][139][140][141]. For example, Pt 2ϩ binds via N3 to guanine [136] and adenine [137] derivatives, Pd 2ϩ to N6Ј,N6Ј,N9-trimethyladenine [138], Rh ϩ to 8-azaadenine [139] as well as Cu 2ϩ [140] and Ni 2ϩ [141] to neutral adenine.…”

Section: Complexes Of 2ј-and 3ј-nucleoside Monophosphatesmentioning

confidence: 99%

Complex Formation of Nickel(II) with Sugar Residues, Nucleobases, Phosphates, Nucleotides, and Nucleic Acids

Sigel¹,

Sigel²

2007

Nickel and Its Surprising Impact in Nature

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Three new modes of adenine-copper(II) coordination: interligand interactions controlling the selective N3-, N7- and bridging μ-N3,N7-metal-bonding of adenine to different N-substituted iminodiacetato-copper(II) chelates

Cited by 90 publications

References 20 publications

Complex Formation of Cadmium with Sugar Residues, Nucleobases, Phosphates, Nucleotides, and Nucleic Acids

Complex Formation of Cadmium with Sugar Residues, Nucleobases, Phosphates, Nucleotides, and Nucleic Acids

Metal ion binding patterns of acyclovir: Molecular recognition between this antiviral agent and copper(II) chelates with iminodiacetate or glycylglycinate

Complex Formation of Nickel(II) with Sugar Residues, Nucleobases, Phosphates, Nucleotides, and Nucleic Acids

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