?-Mimosine, an amino acid with maltol-type binding properties toward copper(II), oxovanadium(IV) and other metal ions

Chruscinska, Elzbieta

doi:10.1016/s0162-0134(99)80003-8

Cited by 27 publications

(11 citation statements)

References 10 publications

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“…The position of the metal species bands is in quite good accordance with the absorption maxima obtained by Buglyó et al [18] for the ka-oxovanadium(IV) species, and with those obtained by Chruscinska et al [20] for the coordination compounds of the cation with maltol and L-mimosine (see Table 2). In the case of L-mimosine (α-amino-β-(3-hydroxy-4-oxo-1,4-dihydropyridin-1-yl)-propanoic acid), the participation of the amino groups in coordination was excluded [20]. These findings support the hypothesis that only the oxygenated functions of the ligands participate to the oxocation coordination.…”

Section: Resultssupporting

confidence: 90%

Oxovanadium(IV) Coordination Compounds with Kojic Acid Derivatives in Aqueous Solution

et al. 2019

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Hydroxypyrone derivatives have a good bioavailability in rats and mice and have been used in drug development. Moreover, they show chelating properties towards vanadyl cation that could be used in insulin-mimetic compound development. In this work, the formation of coordination compounds of oxovanadium(IV) with four kojic acid (5-hydroxy-2-(hydroxymethyl)-4-pyrone) derivatives was studied. The synthetized studied ligands (S2, S3, S4, and SC) have two or three kojic acid units linked through diamines or tris(2-aminoethyl)amine chains, respectively. The chemical systems were studied by potentiometry (25 °C, ionic strength 0.1 mol L−1 with KCl), and UV-visible and EPR spectroscopy. The experimental data were analyzed by a thermodynamic and a chemometric (Multivariate Curve Resolution–Alternating Least Squares) approach. Chemical coordination models were proposed, together with the species formation constants and the pure estimated UV-vis and EPR spectra. In all systems, the coordination of the oxovanadium(IV) starts already under acidic conditions (the cation is totally bound at pH higher than 3–4) and the metal species remain stable even at pH 8. Ligands S3, S4, and SC form three coordination species. Two of them are probably due to the successive insertion of the kojate units in the coordination shell, whereas the third is most likely a hydrolytic species.

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Section: Resultssupporting

confidence: 90%

Oxovanadium(IV) Coordination Compounds with Kojic Acid Derivatives in Aqueous Solution

et al. 2019

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“…The comparison of the present results with those reported for progressively stronger ligands, like kojic acid, maltol, l -mimosine, Hdmpp, catechol, and 3,4-dihydroxybenzoic acid (3,4-DHB), allows us to infer some general features about the effect of the basicity and electronic structure on the thermodynamic (stability constants of the complexes) and spectroscopic ( 51 V hyperfine coupling constant) properties of V IV O species. Given the insulin-mimetic properties displayed by many of such systems, this could be useful for analyzing their biological behavior.…”

Section: Discussionsupporting

confidence: 55%

Spectroscopic and Potentiometric Characterization of Oxovanadium(IV) Complexes Formed by 3-Hydroxy-4-Pyridinones. Rationalization of the Influence of Basicity and Electronic Structure of the Ligand on the Properties of V^IVO Species in Aqueous Solution

Rangel¹,

Leite²,

Amorim³

et al. 2006

Inorg. Chem.

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Aqueous solution studies regarding the identification and characterization of complexes formed by the VIVO ion and 11 3-hydroxy-4-pyridinone derivatives have been performed using EPR and UV/vis spectroscopic techniques. For the three ligands (HL) adequately soluble in water (1-methyl-3-hydroxy-4-pyridinone, 1-methyl-2-ethyl-3-hydroxy-4-pyridinone, and 1,2-diethyl-3-hydroxy-4-pyridinone), potentiometric titrations were performed; the results are consistent with the formation of [V(IV)OL]+, [V(IV)OL2], [V(IV)OL2H(-1)]-, [(V(IV)O)2L2H(-2)], and [V(IV)L3]+ species. Bis chelated complexes are characterized by a cis-trans isomerism, the trans isomer being strongly favored with respect to the cis arrangement. Tris chelated non-oxo V(IV) species were prepared in CH3COOH; their spectroscopic features point to a d(z2) ground state and a geometry intermediate between an octahedron and a trigonal prism, related to the steric requirements of the substituent on the carbon atom in position 2 of the pyridinone ring. Four new solid derivatives, [V(IV)O(1,2-diethyl-3-hydroxy-4-pyridinonato)2], [V(IV)O(1-(p-tolyl)-2-ethyl-3-hydroxy-4-pyridinonato)2], [V(IV)O(1-(p-(n-butyl)phenyl)-2-ethyl-3-hydroxy-4-pyridinonato)2], and [V(IV)O(1-(p-(n-hexyl)phenyl)-2-ethyl-3-hydroxy-4-pyridinonato)2], were isolated and characterized; they exhibited a five-coordinate geometry close to square-pyramid. A criterion for establishing the degree of distortion toward the trigonal-bipyramid on the basis of the electronic absorption spectra is provided. Relationships between the pKa of the -OH group in position 3 of the ring and (i) log K of mono and bis chelated complexes, (ii) pK of the water molecule in cis-[V(IV)OL2(H2O)], (iii) log K of tris chelated species [V(IV)L3]+, and (iv) 51V hyperfine coupling constant (Az) have been established and discussed for a number of pyrone, pyridinone, and catechol ligands. The results are rationalized by assuming for pyridinones an electronic structure intermediate between that of pyrones and catechols. The relationships are valuable to the understanding of the behavior of VIVO species in aqueous solution.

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“…EPR and potentiometric data suggest that L-mimosine forms a stable bischelated species with the V IV O 2+ ion at physiological pH with a coordination mode similar to that of maltol and a cisoctahedral geometry, its composition being [VO-(mim) 2 (H 2 O)] 2− with the carboxylic group of the amino acid in the deprotonated form (Scheme 1). 69 EPR spectra of the ternary system containing V IV O 2+ , mim, and Ub at pH 7.4 and ratio V IV O/Ub of 1/1, 2/1, and 4/1 are reported in Figure S12. Three species were revealed: III and IV denote the two adducts VO(mim) 2 (His-N) and VO-(mim) 2 (Asp/Glu-COO), analogous to those observed for dhp, and I the unbound binary species cis-[VO(mim) 2 (H 2 O)] 2− .…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Interaction of Vanadium(IV) Species with Ubiquitin: A Combined Instrumental and Computational Approach

et al. 2019

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The interaction of VIVO2+ ion and five VIVOL2 compounds with potential pharmacological application, where L indicates maltolate (ma), kojate (koj), acetylacetonate (acac), 1,2-dimethyl-3-hydroxy-4(1H)-pyridinonate (dhp), and l-mimosinate (mim), with ubiquitin (Ub) was studied by EPR, ESI-MS, and computational (docking and DFT) methods. The free metal ion VIVO2+ interacts with Glu, Asp, His, Thr, and Leu residues, but the most stable sites (named 1 and 2) involve the coordination of (Glu16, Glu18) and (Glu24, Asp52). In the system with VIVOL2 compounds, the type of binding depends on the vanadium concentration. When the concentration is in the mM range, the binding occurs with cis-VOL2(H2O), L = ma, koj, dhp, and mim, or with VO(acac)2: in the first case, the equatorial coordination of His68, Glu16, Glu18, or Asp21 residues yields species with formula n[VOL2]–Ub where n = 2–3, while with VO(acac)2 only noncovalent surface interactions are revealed. When the concentration of V is on the order of micromolar, the mono-chelated species VOL(H2O)2 + with L = ma, koj, acac, dhp, and mim, favored by the hydrolysis, interact with Ub, and adducts with composition n[VOL]–Ub (n = 1–2) are observed with the contemporaneous coordination of (Glu18, Asp21) or (Glu16, Glu18), and (Glu24, Asp52) or (Glu51, Asp52) donors. The results of this work suggest that the combined application of spectroscopic, spectrometric, and computational techniques allow the complete characterization of the ternary systems formed by a V compound and a model protein such as ubiquitin. The same approach can be applied, eventually changing the spectroscopic/spectrometric techniques, to study the interaction of other metal species with other proteins.

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?-Mimosine, an amino acid with maltol-type binding properties toward copper(II), oxovanadium(IV) and other metal ions

Cited by 27 publications

References 10 publications

Oxovanadium(IV) Coordination Compounds with Kojic Acid Derivatives in Aqueous Solution

Oxovanadium(IV) Coordination Compounds with Kojic Acid Derivatives in Aqueous Solution

Spectroscopic and Potentiometric Characterization of Oxovanadium(IV) Complexes Formed by 3-Hydroxy-4-Pyridinones. Rationalization of the Influence of Basicity and Electronic Structure of the Ligand on the Properties of V^IVO Species in Aqueous Solution

Interaction of Vanadium(IV) Species with Ubiquitin: A Combined Instrumental and Computational Approach

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?-Mimosine, an amino acid with maltol-type binding properties toward copper(II), oxovanadium(IV) and other metal ions

Cited by 27 publications

References 10 publications

Oxovanadium(IV) Coordination Compounds with Kojic Acid Derivatives in Aqueous Solution

Oxovanadium(IV) Coordination Compounds with Kojic Acid Derivatives in Aqueous Solution

Spectroscopic and Potentiometric Characterization of Oxovanadium(IV) Complexes Formed by 3-Hydroxy-4-Pyridinones. Rationalization of the Influence of Basicity and Electronic Structure of the Ligand on the Properties of VIVO Species in Aqueous Solution

Interaction of Vanadium(IV) Species with Ubiquitin: A Combined Instrumental and Computational Approach

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Spectroscopic and Potentiometric Characterization of Oxovanadium(IV) Complexes Formed by 3-Hydroxy-4-Pyridinones. Rationalization of the Influence of Basicity and Electronic Structure of the Ligand on the Properties of V^IVO Species in Aqueous Solution