Synthesis, structure, solution and DFT studies of a pyrazine-bridged binuclear Cu(II) complex: On the importance of noncovalent interactions in the formation of crystalline network

Mirzaei, Masoud; Eshtiagh‐Hosseini, Hossein; Karrabi, Zahra; Notash, Behrouz; Bauzá, Antonio; Habibi, M.; Ardalani, Mehdi; Shamsipur, Mojtaba

doi:10.1016/j.molstruc.2014.09.019

Cited by 7 publications

(2 citation statements)

References 38 publications

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“…Overall, these interactions bring about the formation of a 3D supramolecular network. The methylation of the hydroxyl group of mcheld avoids the formation of intermolecular hydrogen bonds via this position. , As shown below, this feature is important regarding the coordination of the [Cu(mcheld)] fragment to nucleobases and nucleosides, since it favors the formation of hydrogen bonds exclusively between the carboxylic groups of mcheld and the donor or acceptor groups of the nucleobase moiety…”

Section: Resultsmentioning

confidence: 99%

Comparative Structural Study of Metal-Mediated Base Pairs Formed outside and inside DNA Molecules

et al. 2020

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The formation of copper(II)-mediated base pairs involving pyridine-2,6-dicarboxylate derivatives and canonical nucleosides has proven to be a smart approach to introduce copper(II) ions at specific locations of DNA duplexes. However, the structural characteristics of these metalized base pairs have not yet been revealed, and their effect on DNA structures is difficult to assess. Herein, for the first time, we report on the different structural details of copper-mediated base pairs formed by themselves and in DNA duplexes. The individual base pairs [Cu(mcheldwere obtained from the reaction of the metal complex [Cu(mcheld)(H 2 O) 2 ] (1Cu) (mcheld = 4-methoxypyridine-2,6-dicarboxylic acid) with model nucleosides (Cyt = N1-methylcytosine, Ade = N9-ethyladenine, Gua = N9-propylguanine, 7C Ade = N9-propyl-7-deazaadenine). The crystal structure of the five complexes was determined by means of single-crystal X-ray diffraction. Furthermore, the formation of the 1Cu_Cyt and 1Cu_Gua base pairs in the middle of DNA duplexes, duplex DNA 15 (917 atoms) and DNA 10 (649 atoms), respectively, was studied using highly demanding ab initio computational calculations. These theoretical studies aimed to validate, from a structural point of view, whether base pairs of the kind 1Cu_nucleosides can be included in a DNA double helix and how this situation affects the double-helical structure. The results indicate that the 1Cu_Cyt and 1Cu_Gua base pairs can be formed in a DNA molecule without significant structural constraints. In addition, the double-helix DNA structure remains virtually unchanged when it contains these Cu(II)-mediated base pairs.

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Section: Resultsmentioning

confidence: 99%

Comparative Structural Study of Metal-Mediated Base Pairs Formed outside and inside DNA Molecules

et al. 2020

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“…Under a particular set of equilibrium conditions, the ∆ G 0 value dictates the direction of the equilibrium. The Gibbs energy is a balance between enthalpy and entropy of an equilibrium [45][46][47][48][49][50][51]. The change in the Gibbs free energy for the dissociation equilibria of the ligands (-log 10 K a = pK a ) investigated can be calculated by Eq.…”

Section: The Standard Gibbs Free Energy Change Parameter (∆ G 0 )mentioning

confidence: 99%

Complexation Equilibria and Determination of Stability Constants of Some Divalent Metal Ion Complexes of L-Cysteine and Diphenylamine in Aqueous Media

Radalla¹

2022

AJCHE

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Background. Metal complexes of biologically active ligands had considerable interests. L-cysteinate residue, L-Cys, is a biologically abundant and important versatile binding site of proteins. Diphenylamine, DPA, is an important aromatic amine containing two phenyl groups. Complexation equilibria of the divalent metal ions, Ca 2+ and Zn 2+ with the bio-relevant α-amino acid, L-cysteine and the nitrogen-containing diphenylamine ligand were investigated by means of the potentiometric technique at 25.0 ± 0.1°C and constant ionic strength of 0.200 ± 0.001 mol•dm -3 NaNO 3 . Objective. The stability constants and standard free energy changes of the α-amino acid, L-cysteine and diphenylamine complex species were determined at 0.200 ± 0.001 mol•dm -3 ionic strength. Methods. The formation of the different 1:1 and 1:2 binary complexes and 1:1:1 ternary complexes were inferred from the potentiometric titrations. Results. The concentration distribution of L-cysteine species formed in solution was evaluated. The dissociation constants of the α-amino acid and diphenylamine were determined at different ionic strength. The stability constants of these binary and ternary systems were calculated. The values of ∆ log 10 K, percent relative stabilization, %R.S. and log 10 X for the ternary systems were evaluated and discussed. Concussion. The ternary complex formation occurred in a stepwise manner with L-cysteine acting as the primary ligand. The obtained values of ∆ G 0 indicated that Complex formation reactions are spontaneous. Also, for all systems studied, the ternary complexes formed are more thermodynamically stable than the binary complexes.

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Syntheses and crystal structure of copper (II) and cobalt (II) complexes containing N-heterocyclic compounds

Luo

Guo

et al. 2017

J IRAN CHEM SOC

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Synthesis, structure, solution and DFT studies of a pyrazine-bridged binuclear Cu(II) complex: On the importance of noncovalent interactions in the formation of crystalline network

Cited by 7 publications

References 38 publications

Comparative Structural Study of Metal-Mediated Base Pairs Formed outside and inside DNA Molecules

Comparative Structural Study of Metal-Mediated Base Pairs Formed outside and inside DNA Molecules

Complexation Equilibria and Determination of Stability Constants of Some Divalent Metal Ion Complexes of L-Cysteine and Diphenylamine in Aqueous Media

Syntheses and crystal structure of copper (II) and cobalt (II) complexes containing N-heterocyclic compounds

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