Interactions of d10 metal ions with hippuric acid and cytosine. X-ray structure of the first cadmium (II)–amino acid derivative–nucleobase ternary compound

Capllonch, Maria Concepció; Garcı́a-Raso, Ángel; Terrón, Àngel; Apella, María C.; Espinosa, Enrique; Molins, Elı́es

doi:10.1016/s0162-0134(01)00196-9

Cited by 39 publications

(19 citation statements)

References 29 publications

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“…Although several binary [6][7][8][9][10][11][12][13] and ternary [12,[14][15][16][17] complexes with hippuric acid and other related derivatives have been described in the literature, we have not found any structural information about transition metal complexes of I-hipH. For this reason we have studied the binary derivatives of o-iodohippuric acid with different divalent 3d transition metal ions: Zn(II), Cu(II), Co(II) and Ni(II) and their possible interaction with acyclovir (ACV) (Scheme 1) in order to know the general characteristics of this type of complexes.…”

Section: Introductionmentioning

confidence: 99%

Ternary complexes metal [Co(II), Ni(II), Cu(II) and Zn(II)] – ortho-iodohippurate (I-hip) – acyclovir. X-ray characterization of isostructural [(Co, Ni or Zn)(I-hip)2(ACV)(H2O)3] with stacking as a recognition factor

Barceló‐Oliver

Terrón

Garcı́a-Raso

et al. 2004

Journal of Inorganic Biochemistry

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Section: Introductionmentioning

confidence: 99%

Ternary complexes metal [Co(II), Ni(II), Cu(II) and Zn(II)] – ortho-iodohippurate (I-hip) – acyclovir. X-ray characterization of isostructural [(Co, Ni or Zn)(I-hip)2(ACV)(H2O)3] with stacking as a recognition factor

Barceló‐Oliver

Terrón

Garcı́a-Raso

et al. 2004

Journal of Inorganic Biochemistry

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“…The location of the hydrogen atom on the oxhydryl group attached to the 2-hydroxyhippuric acid phenyl ring in [Cu(Imz) 4 Cl 2 ][Cu(Imz) 4 Cl] 2 (2-OH-Hip) 2 was refined by rigid group rotation of the O-H bond around the corresponding (ph)C-O direction such as to maximize the electron density at the calculated position. The water Hatoms of [Co(2-OH-Hip)(Imz) 3 ] Á H 2 O were found in a difference Fourier map and refined with Ow-H and HÁ Á ÁH distances restrained to target values of 0.82(1) and 1.30 (1) A, respectively.…”

Section: X-ray Diffraction Datamentioning

confidence: 99%

“…Peptides are efficient metal ion binders in biological systems and their complexes can be used as models of their recognition [1]. In addition, some copper(II) complexes that contain these ligands where found to have a variety of pharmacological activities [2].…”

Section: Introductionmentioning

confidence: 99%

Model complexes with naturally occurring ligands (salicylglycine and imidazol) and the biometals copper and cobalt

Ferrer

Baró

Castellano

et al. 2004

Journal of Inorganic Biochemistry

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Two new complexes [Cu(Imz)(4)Cl(2)][Cu(Imz)(4)Cl] (2)(2-OH-Hip)(2) (1) and [Co(2-OH-Hip)(Imz)(3)].H(2)O (2) (with Imz=Imidazol and 2-OH-Hip=2-hydroxyhippuric acid) were prepared and characterized. The molecular structures and the solution and solid state behavior of the complexes were investigated. Complex 1 crystallizes in the monoclinic space group P2(1)/c with a=16.880(1), b=8.046(1), c=24.683(1) A, beta=107.88(1) degrees, and Z=2, while complex 2 crystallizes in the orthorhombic space group Pbca with a=11.712(2), b=15.741(4), c=22.254(4) A, and Z=8. The [Cu(Imz)(4)Cl(2)][Cu(Imz)(4)Cl](2)(2-OH-Hip)(2) solid consists in two distinct monomeric Cu(II) complexes: one of them is neutral octahedral [Cu(Imz)(4)Cl(2)] and the other, charged square basis pyramida [Cu(Imz)(4)Cl](+). The 2-hydroxyhippuric acid, which here acts as a counter ion, is deprotonated at its carboxylic group. Cobalt(III) ion in [Co(2-OH-Hip)(Imz)(3)].H(2)O is at the center of an octahedral environment, coordinated to three Imidazol ligands and to a triply deprotonated 2-hydroxyhippuric acid molecule acting as a tridentate ligand. Aqueous solution equilibrium of the quaternary system Cu(2+)/2-OH-Hip/Imz/H(+) was studied by potentiometric titrations.

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“…[35][36][37][38][39][40] In many cases, the copper ions form dimers with identical symmetry around the paramagnetic ions and with a shared ligand mediating exchange interaction between those ions. In this case, there is a greater possibility of formation of antiferromagnetically (AFM) coupled dimers, where the singlet (S = 0) state is the ground state and the triplet is thermally populated, than the ferromagnetic (FM) interaction at different site symmetries in bimetallic systems, [41][42][43][44][45][46] as here reported.…”

Section: Introductionmentioning

confidence: 99%

“…[35][36][37][38][39][40] In many cases, the copper ions form dimers with identical symmetry around the paramagnetic ions and with a shared ligand mediating Vieira et al 1615 Vol. 19, No.…”

mentioning

confidence: 99%

Exchange interactions in the copper(II)-N-benzoylglycine (hippuric acid) complex

Vieira¹,

Facchin²,

Torre³

et al. 2008

J. Braz. Chem. Soc.

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O complexo Cu II -N-benzoilglicina provê um sistema conveniente para se estudar interações de troca fracas entre elétrons desemparelhados que são transmitidas por caminhos químicos de interesse biológico. A molécula existe como um dímero onde cada Cu II está coordenado a cinco ligantes, formando uma pirâmide de base quadrada distorcida. O único caminho químico entre íons Cu II magneticamente não-equivalentes envolve 17 átomos diamagnéticos e uma fraca ligação de hidrogênio putativa. Esta interação foi estudada por Ressonância Paramagnética Eletrônica de amostras monocristalinas a 9,5 e 34,5 GHz, tendo sua magnitude sido calculada em 4(1) mK. Esse valor é discutido em termos de valores obtidos para caminhos similares em outros compostosmodelo e proteínas.The complex Cu II -N-benzoylglycine provides a convenient system to study weak exchange interactions between unpaired spins transmitted through a biologically relevant long chemical bridge.The molecule exists as a dimer with each Cu II ion coordinated to five ligands, forming a distorted square-based pyramid. The only chemical connection between magnetically non-equivalent copper ions is a very long path comprising 17 diamagnetic atoms and a weak putative hydrogen bond. This interaction was studied using Electron Paramagnetic Resonance in single-crystal samples at 9.5 and 34.5 GHz and its magnitude was calculated as 4(1) mK. This value is discussed in terms of values obtained for similar paths in other model compounds and in proteins.Keywords: electron paramagnetic resonance, exchange interactions, model systems IntroductionToluene and other volatile organic compounds (VOCs) 1 are widely used as organic solvents in pharmacological, plastic and rubber industries, as well as in various materials such as paints, adhesives and combustion materials.2 The exposure to high concentration of toluene and other VOCs causes adverse health effects in nervous system, 3 mucous and dermal irritations, 4 and chromosome aberrations. 5,6 Toluene is metabolized in human liver microsomes 7,8 or in rat hepatic microsomes 9,10 by the hepatic cytochrome P450-mediated mixed function oxidase system to benzyl alcohol, to benzoic acid and finally to hippuric acid, by conjugation with glycine to yield hippuric acid or N-benzoylglycine, which is then excreted in urine. 11Copper is a bioessential element with relevant oxidation states. 12,13 Due to the complexity of metalobiomolecules and the associated problems, a very useful way of gaining information is examining the behavior of simpler model compounds. The study of ion complexes of copper-amino acids 14-26 (or peptides) 27-31 and copper-nucleoside (or related bases) 32,33 has been a topic of increasing interest in the last few years, manly due to their relevance in the development of new reagents for biotechnology and medicine. 34 N-benzoylglycine is structurally similar to a dipeptide except for the absence of the N-terminal group. Due to its high affinity for Cu II , the dimeric complex Cu II -N-benzoylglycine could form in vivo, especia...

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Interactions of d10 metal ions with hippuric acid and cytosine. X-ray structure of the first cadmium (II)–amino acid derivative–nucleobase ternary compound

Cited by 39 publications

References 29 publications

Ternary complexes metal [Co(II), Ni(II), Cu(II) and Zn(II)] – ortho-iodohippurate (I-hip) – acyclovir. X-ray characterization of isostructural [(Co, Ni or Zn)(I-hip)2(ACV)(H2O)3] with stacking as a recognition factor

Ternary complexes metal [Co(II), Ni(II), Cu(II) and Zn(II)] – ortho-iodohippurate (I-hip) – acyclovir. X-ray characterization of isostructural [(Co, Ni or Zn)(I-hip)2(ACV)(H2O)3] with stacking as a recognition factor

Model complexes with naturally occurring ligands (salicylglycine and imidazol) and the biometals copper and cobalt

Exchange interactions in the copper(II)-N-benzoylglycine (hippuric acid) complex

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