Reinvestigation of the copper(II)–carcinine equilibrium system: “two-dimensional” EPR simulation and NMR relaxation studies for determining the formation constants and coordination modes

Árkosi, Zsuzsanna; Paksi, Z.; Korecz, L.; Gajda, Tamás; Henry, Bernard; Rockenbauer, Antal

doi:10.1016/j.jinorgbio.2004.09.002

Cited by 8 publications

(5 citation statements)

References 24 publications

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“…Both complexes produced a similar 50% inhibition (IC 50 ) 40.7 ± 3.7 lM and 34.7 ± 5.3 lM, for complex (2) and complex (1), respectively. Under the present experimental conditions the IC 50 value of SOD enzyme (from bovine erythrocytes) was 4 nM, similar to previously reported values [50].…”

Section: Superoxide Dismutase Activitysupporting

confidence: 92%

Molecular structure, bioavailability and bioactivity of [Cu(o-phen)2(cnge)](NO3)2·2H2O and [Cu(o-phen)(cnge)(H2O)(NO3)2] complexes

Ferrer¹,

Tévez²,

Baeza³

et al. 2007

Journal of Inorganic Biochemistry

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Section: Superoxide Dismutase Activitysupporting

confidence: 92%

Molecular structure, bioavailability and bioactivity of [Cu(o-phen)2(cnge)](NO3)2·2H2O and [Cu(o-phen)(cnge)(H2O)(NO3)2] complexes

Ferrer¹,

Tévez²,

Baeza³

et al. 2007

Journal of Inorganic Biochemistry

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“…In the pH range 6.2−9, the bis-complexes ML 2 and ML 2 H −1 are also formed. The close values of p K ML 2 ML 2 H −1 = log β 11−1 − log β 110 = 7.63 compared to Ni(II)-GlyHa (7.89) and Ni(II)-SarHa (7.94) suggests a similar deprotonation step as proposed earlier. − The species ML 2 can be denoted as MLH −1 (LH), where the water molecule in equatorial position of MLH −1 is replaced by another monodeprotonated ligand (N-amino or N-imidazole coordinated according to quantities of LH a or LH i , respectively). The species ML 2 H −1 (= MLH −1 (L)) is derived from the deprotonation of this monodentate ligand.…”

Section: Resultssupporting

confidence: 53%

“…The most characteristic feature of these short peptides is the formation of stable tetrameric M 4 L 4 H −8 complex with square-planar metal ion bridged by N 1 -imidazole nitrogens at alkaline pH. Such a cyclic tetramer has been proposed for copper(II), nickel(II), and palladium(II) containing di- or tripeptide − primarily on the basis of potentiometric and spectroscopic data in solution (UV−vis, NMR, EPR). Until now, the only crystal structure has been obtained for gold(III) glycyl- l -histidine, where the strong polarizing power of Au III (5d metal) favors the imidazole N 1 −H deprotonation at relatively low pH (6−7) and thus induces the cyclic tetramer formation …”

Section: Introductionmentioning

confidence: 99%

Nickel(II)-Dipeptidoamine-Based Tetrameric Complex: Structural Study in Solution and in Solid State

Selmeczi¹,

Gizzi²,

Champmartin³

et al. 2010

Inorg. Chem.

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The coordination structure of M(4)L(4)H(-8) macromolecules (M = Ni(II), Cu(II), Pd(II)) containing small peptidic ligands (L = Xaa-His or Xaa-His-Yaa) has been predicted primarily on the basis of spectroscopic and potentiometric data in the literature. In this work, the neutral tetranuclear nickel(II) complex 1 formed with four double-deprotonated ligands (L = α-methyl-alanyl-histamine) was prepared, and its crystal structure was determined (C(36)H(56)N(16)Ni(4)O(4)·4.5CH(3)OH·1.5H(2)O: a = 11.2645(4) A, b = 23.5003(8) A, c = 20.9007(7) A, β = 102.321(1)°, monoclinic, P2(1)/c, Z = 4). In complex 1, the metal ions have a square planar geometry with 4N donor set consisting of the N-terminal amino nitrogen, the deprotonated amide nitrogen, the imidazole N(3) atom, and the deprotonated imidazole N(1) atom of the adjacent ligand. The latter nitrogen atom provides the connection of the four NiLH(-2) units forming a C(1) symmetrical saddle-like shape. The complexation of L with Ni(II) ion has been studied by a potentiometric method combined with UV-visible spectrophotometric titration. At pH 8.0, the predominant species is M(4)L(4)H(-8) with pK(4)(oligomerization) = 5.73. The tetranuclear structure of complex 1 was also studied in solution by (1)H and (13)C NMR spectroscopy suggesting a structure of symmetry S(4). DFT calculations on optimized structure in symmetry C(1) and S(4) have been performed to explain the observed differences in solution and in solid state. The nuclearity was also confirmed in solution by ESI-HRMS analysis.

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“…His and Carc are bioligands in mammals with important physiological roles [42,43] and their copper complexes have been well characterized. [44][45][46] The CyD polymers can exploit the complexing ability of the moieties and form copper(II) complexes. We also studied the superoxide dismutase (SOD) activity of the new copper(II)polymer systems compared to His and Carc complexes.…”

Section: Introductionmentioning

confidence: 99%

“…In this context, we functionalized cross‐linked CyD polymers with histidine (His) or carcinine (Carc, β‐alanyl‐histamine) moieties (Figure 1) with high functionalization degree. His and Carc are bioligands in mammals with important physiological roles [42,43] and their copper complexes have been well characterized [44–46] …”

Section: Introductionmentioning

confidence: 99%

Cyclodextrin Polymers Functionalized with Histidine and Carcinine as Chelating Therapeutics for Copper Dyshomeostasis

Bognanni

Bellia²,

Vecchio

2023

ChemMedChem

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In recent years, cyclodextrin polymeric nanoparticles have been designed to introduce new properties and extend their medical applications. Based on the features of cyclodextrins, we derivatized cross‐linked cyclodextrin polymers with histidine or carcinine moieties. We found that amylases do not hydrolyze cyclodextrin polymers. The new polymers can form copper(II) complexes and may act as nanochelators to counteract copper(II) dyshomeostasis‐related diseases. Furthermore, the copper(II) complexes show superoxide dismutase activity, similar to free carcinine and histidine complexes. The antioxidant biological activity of the copper(II) complex formed in situ may protect cells from oxidative damage related to copper dyshomeostasis.

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Reinvestigation of the copper(II)–carcinine equilibrium system: “two-dimensional” EPR simulation and NMR relaxation studies for determining the formation constants and coordination modes

Cited by 8 publications

References 24 publications

Molecular structure, bioavailability and bioactivity of [Cu(o-phen)2(cnge)](NO3)2·2H2O and [Cu(o-phen)(cnge)(H2O)(NO3)2] complexes

Molecular structure, bioavailability and bioactivity of [Cu(o-phen)2(cnge)](NO3)2·2H2O and [Cu(o-phen)(cnge)(H2O)(NO3)2] complexes

Nickel(II)-Dipeptidoamine-Based Tetrameric Complex: Structural Study in Solution and in Solid State

Cyclodextrin Polymers Functionalized with Histidine and Carcinine as Chelating Therapeutics for Copper Dyshomeostasis

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