Molecular recognition modes between adenine or adeniniun(1+) ion and binary MII(pdc) chelates (MCoZn; pdc=pyridine-2,6-dicarboxylate(2-) ion)

Brandi-Blanco, María del Pilar; Choquesillo-Lazarte, Duane; Domínguez‐Martín, Alicia; Matilla, Ángel J.; González‐Pérez, Josefa María; Castiñeiras, Alfonso; Niclós‐Gutiérrez, Juan

doi:10.1016/j.jinorgbio.2013.06.008

Cited by 11 publications

(7 citation statements)

References 24 publications

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“…The observed N7 -Ade coordination mode is reinforced by an intramolecular hydrogen bond, involving the Ade N6 exocyclic amino group as a donor and one carboxylate group of mcheld as an acceptor (N6···O2 2.846(6) Å) (Figure ). This molecular recognition pattern has been previously observed in related aromatic amine analogues ,, and reasonably influences the low value of the angle between the rms planes of mcheld and the nucleobase (23.98(12)°).…”

Section: Resultssupporting

confidence: 83%

“…To the best of our knowledge, only the crystal structure of the Cheld-Cu-adenine ternary complex and the interaction of other iminodiacetic acid based copper(II) complexes toward adenine derivatives have been reported. Though the molecular structure of Cheld-Cu-nucleoside systems could be foretold in principle on the basis of these previously described systems, detailed, experimentally derived structural information at the molecular and crystal-packing level is still needed to accurately understand the structural implications that the Cheld-Cu-nucleoside systems can have in DNA molecules.…”

Section: Introductionmentioning

confidence: 99%

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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: Resultssupporting

confidence: 83%

Section: Introductionmentioning

confidence: 99%

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

et al. 2020

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“…This coordination mode is very similar to the one observed by Stylianou et al In contrast, adenine exhibits a rare coordination mode through the N 3 and N 7 sites in 2 (Figure g). To the best of our knowledge, this coordination mode was only observed in two previous discrete Cu(II)-based complexes. , Through this [N 3 , N 7 ] coordination mode, adenine participates in the formation of infinite Co(II)-adenine chains that are 3D linked by BTeC 4– linkers.…”

Section: Resultsmentioning

confidence: 78%

Two New Adenine-Based Co(II) Coordination Polymers: Synthesis, Crystal Structure, Coordination Modes, and Reversible Hydrochromic Behavior

Burneo

Stylianou

Rodríguez‐Hermida

et al. 2015

Crystal Growth & Design

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We report the synthesis of two new 3D coordination polymers (CPs) based on Co(II), adenine and aromatic tetracarboxylate linkers. Adenine exhibits bidentate binding modes in both CPs, coordinating through the N3 and N 9 sites in a first compact CP and through the more rare N 3 and N7 sites in a second open, flexible and H2O-responsive CP. These differences together with an analysis of the extended coordination structures made of adenine reported in Cambridge Structural Database illustrate the rich coordination versatility of adenine as a building block for CPs. Although the latter CP is non-porous to N2 or CO2, it shows a reversible and detectable colour change from pinkto purple, and vice versa, upon hydration and dehydration, respectively.

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“…Diffuse reflectance (electronic) spectra were recorded in a Varian Cary-5E spectrophotometer. reported [21]. In this case, the Cu-N7(Hade) bond is also reinforced by an N6-H···O(coordinated carboxylate) interligand interaction [21].…”

Section: Other Physical Methodsmentioning

confidence: 85%

“…reported [21]. In this case, the Cu-N7(Hade) bond is also reinforced by an N6-H···O(coordinated carboxylate) interligand interaction [21]. In contrast, neither Cu(BCBC) nor Cu(pheida) chelates have proved to be able to yield the corresponding mononuclear complexes with general formula Cu(chelator)(Hade) [20].…”

Section: Other Physical Methodsmentioning

confidence: 99%

Molecular recognition between adenine or 2,6-diaminopurine and copper(II) chelates with N,O2,S-tripodal tetradentate chelators having thioether or disulfide donor groups

González‐Pérez

Choquesillo-Lazarte

Domínguez‐Martín

et al. 2015

Journal of Inorganic Biochemistry

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Molecular recognition modes between adenine or adeniniun(1+) ion and binary MII(pdc) chelates (MCoZn; pdc=pyridine-2,6-dicarboxylate(2-) ion)

Cited by 11 publications

References 24 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

Two New Adenine-Based Co(II) Coordination Polymers: Synthesis, Crystal Structure, Coordination Modes, and Reversible Hydrochromic Behavior

Molecular recognition between adenine or 2,6-diaminopurine and copper(II) chelates with N,O2,S-tripodal tetradentate chelators having thioether or disulfide donor groups

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