Structural and reactivity studies on 4,4′-dimethyl-2,2′-bipyridine acetylacetonate copper(II) nitrate (CASIOPEINA III-ia®) with methionine, by UV–visible and EPR techniques

Tovar‐Tovar, Araceli; Ruiz-Ramı̀rez, Lena; Campero, A.; Romerosa, Antonio; Moreno‐Esparza, Rafael; Rosales-Hoz, Marı́a J.

doi:10.1016/j.jinorgbio.2004.02.023

Cited by 42 publications

(27 citation statements)

References 26 publications

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“…were also conducted because of their various binding and bridging modes [26][27][28][29][30][31][32][33]. Not surprisingly, in a short course, biomolecules and natural products like amino acids [34][35][36][37][38][39][40][41][42][43][44][45][46], peptides [47], proteins [46], nucleobases [48], magnesium formates [49], carbohydrates [47], metal glutarates [50,51], γ-cyclodextrin [36] leaped into this mainstream as attractive precursors and soon tributaries like metal-peptide frameworks (MPFs) [47], metal-biomolecule frameworks (MBioFs) [46][47][48] surfaced out and established their niche.…”

Section: Introductionmentioning

confidence: 99%

“…Among them the perceptible appearance of amino acid derivatives in recent years, either as metal-based molecular entities or oligomeric scaffolds in MOFs or CPs, justify their inclusion in the synthon/tecton library [34][35][36][37][38][39][40][41][42][43][44][45][46][47][48]. In this frame, structure and reactivity of different amino acids in their natural or derivatized form were extensively studied.…”

Section: Introductionmentioning

confidence: 99%

“…In this frame, structure and reactivity of different amino acids in their natural or derivatized form were extensively studied. Relevant examples include proline [34,35], glycine [34], valine [36], alanine [37], aspartic acid [38], glutamic acid [36], phenyl alanine [39], histidine [40], methionine [41][42][43][44] and typtophan [36][37][38][39][40][41][42][43][44][45].…”

Section: Introductionmentioning

confidence: 99%

“…Advantages of amino acids are their natural framework with rich functional groups, which is amenable to derivatization thereby offering intriguing topologies when inserted as building blocks in supramolecular hierarchical self-assemblies [34][35][36][37][38][39][40][41][42][43][44][45][46][47][48][49][50][51]. Indeed, thanks to their genuine chirality (except glycine) and electronic asymmetry, amino acid derivatives are considered as a preeminent choice to introduce asymmetry in MOFs to direct the network construction.…”

Section: Introductionmentioning

confidence: 99%

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Coordination Polymers and Metal Organic Frameworks Derived from 1,2,4-Triazole Amino Acid Linkers

et al. 2011

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Abstract:The perceptible appearance of biomolecules as prospective building blocks in the architecture of coordination polymers (CPs) and metal-organic frameworks (MOFs) are redolent of their inclusion in the synthon/tecton library of reticular chemistry. In this frame, for the first time a synthetic strategy has been established for amine derivatization in amino acids into 1,2,4-triazoles. A set of novel 1,2,4-triazole derivatized amino acids were introduced as superlative precursors in the design of 1D coordination polymers, 2D chiral helicates and 3D metal-organic frameworks. Applications associated with these compounds are diverse and include gas adsorption-porosity partitioning, soft sacrificial matrix for morphology and phase selective cadmium oxide synthesis, Fe II spin crossover materials, zinc-β-lactamases inhibitors, logistics for generation of chiral/non-centrosymmetric networks; and thus led to a foundation of a new family of functional CPs and MOFs that are reviewed in this invited contribution.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Coordination Polymers and Metal Organic Frameworks Derived from 1,2,4-Triazole Amino Acid Linkers

et al. 2011

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“…[10][11][12][13][14][15] The X-ray structures of two complexes containing acac and phen (or 2,9-dimethyl-1,10-phenanthroline) and NO 3 − as counterion, show that in both complexes the copper atom has an approximate square pyramidal coordination geometry. 12 Another phen complex, in which the counterion is ClO 4 − , shows the same geometry, also with the anion occupying the axial position.…”

Section: Introductionmentioning

confidence: 99%

The solvation and redox behavior of mixed ligand copper(II) complexes of acetylacetonate and aromatic diimines in ionic liquids

Nunes

Nagy

Alegria

et al. 2014

Inorganica Chimica Acta

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The behavior of two cationic copper complexes of acetylacetonate and 2,2'-bipyridine or 1,10-phenanthroline, Cu(acac)(bipy)Cl (1) and Cu(acac)(phen)Cl (2), in organic solvents and ionic liquids, was studied by spectroscopic and electrochemical techniques. Both complexes showed solvatochromism in ionic liquids although no correlation with solvent parameters could be obtained. By EPR spectroscopy rhombic spectra with well-resolved superhyperfine structure were obtained in most ionic liquids. The spin Hamiltonian parameters suggest a square planar geometry with coordination of the ionic liquid anion. The redox properties of the complexes were investigated by cyclic voltammetry at a Pt electrode (d = 1 mm) in bmimBF 4 and bmimNTf 2 ionic liquids and showed that complexes 1 and 2 can be electrochemically reduced in these ionic media. The results show that both copper (II) complexes are reduced at more negative potentials when cyclic voltammetries are conducted in ionic liquids instead of organic solvents, thus being more difficult to reduce in these ionic solvents. This is in agreement with the EPR characterization, which shows lower A z and higher g z values for the complexes dissolved in ionic liquids, than in organic solvents, due to higher electron density at the Copper center.The anion basicity order obtained by EPR is NTf 2  , N(CN) 2  , MeSO 4  and Me 2 PO 4  , which agrees with previous determinations.

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The π‐Back‐Bonding Modulation and Its Impact in the Electronic Properties of Cu^II Antineoplastic Compounds: An Experimental and Theoretical Study

García‐Ramos

Galindo‐Murillo

Tovar‐Tovar

et al. 2014

Chemistry A European J

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A complete study of the electronic density distribution in antineoplastic mixed chelate complexes of the type [Cu(N-N)(glycinate)H2 O]NO3 (N-N=2,2'-bipyridine (bpy) (1), 4,4'-dimethyl-bpy (2), 5,5'-dimethyl-2,2'-bipyridine (3), 1,10-phenanthroline (phen) (4), 4-methyl-phen (5); 5-methyl-phen (6); 4,7-dimethyl-phen (7), 5,6-dimethyl-phen (8), and 3,4,7,8-tetramethyl-phen (9)), a family known as Casiopeínas, was carried out with cyclic voltammetry, EPR, and computational methods. Crystal structures of 1⋅H2 O, 2⋅H2 O, 3⋅H2 O, 6⋅H2 O, and 8⋅H2 O show the variability in the geometries adopted by the copper compounds in the solid state. Experimental properties are described employing electronic descriptors obtained from computational methods. The main descriptors found were: The total electronic population of the metal ion (N(Cu)), delocalization of the metal ion electrons over the donor atoms (Δ(Cu)), atomic dipolar moment (μ(Cu)), and the atomic quadrupole moment (Q(Cu)). It was found that π-back-bonding is the principal factor that modulates the distribution of the electron density around the metal ion. The electronic descriptors obtained from the computational approach can be used as electronic descriptors of inorganic compounds that have shown antiproliferative activities instead the experimental data, aiding the rational design of good candidates of metal-based drugs.

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Structural and reactivity studies on 4,4′-dimethyl-2,2′-bipyridine acetylacetonate copper(II) nitrate (CASIOPEINA III-ia®) with methionine, by UV–visible and EPR techniques

Cited by 42 publications

References 26 publications

Coordination Polymers and Metal Organic Frameworks Derived from 1,2,4-Triazole Amino Acid Linkers

Coordination Polymers and Metal Organic Frameworks Derived from 1,2,4-Triazole Amino Acid Linkers

The solvation and redox behavior of mixed ligand copper(II) complexes of acetylacetonate and aromatic diimines in ionic liquids

The π‐Back‐Bonding Modulation and Its Impact in the Electronic Properties of Cu^II Antineoplastic Compounds: An Experimental and Theoretical Study

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Structural and reactivity studies on 4,4′-dimethyl-2,2′-bipyridine acetylacetonate copper(II) nitrate (CASIOPEINA III-ia®) with methionine, by UV–visible and EPR techniques

Cited by 42 publications

References 26 publications

Coordination Polymers and Metal Organic Frameworks Derived from 1,2,4-Triazole Amino Acid Linkers

Coordination Polymers and Metal Organic Frameworks Derived from 1,2,4-Triazole Amino Acid Linkers

The solvation and redox behavior of mixed ligand copper(II) complexes of acetylacetonate and aromatic diimines in ionic liquids

The π‐Back‐Bonding Modulation and Its Impact in the Electronic Properties of CuII Antineoplastic Compounds: An Experimental and Theoretical Study

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The π‐Back‐Bonding Modulation and Its Impact in the Electronic Properties of Cu^II Antineoplastic Compounds: An Experimental and Theoretical Study