Ab initio insight on the interaction of ascorbate with Li+, Na+, K+, Be2+, Mg2+, and Ca2+metal cations

Allen, Reeshemah N.; Shukla, Manoj K.; Leszczyński, Jerzy

doi:10.1002/qua.20973

Cited by 14 publications

(7 citation statements)

References 17 publications

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“…What is more, it has also been successfully employed to investigate the relevant properties of Vc and its analogs [17][18][19][20]. In the present study, the popular Becke's three-parameter hybrid functional (B3LYP) method [21,22] has been employed as well as the 6-311?…”

Section: Computational Detailsmentioning

confidence: 99%

Explorations of the nature of the coupling interactions between vitamin C and methylglyoxal: a DFT study

Zhai

et al. 2011

Struct Chem

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As the first step toward understanding the augment role of vitamin C (Vc) for the anticancer effect of methylglyoxal (MG), the nature of the coupling interactions between Vc and MG has been systematically investigated at the B3LYP/6-311??G** level of theory in combination with the atoms in molecules (AIM) theory, natural bond orbital (NBO) method, and energy decomposition analysis (EDA). The possible stable complexes have been located on their potential energy surface (PES). Most of them are characterized by one or two intermolecular H-bonds with the binding energies varying from -11.1 to -2.0 kcal/mol. AIM analyses suggest that all the intermolecular H-bonds have been predominated by the electrostatic interaction. A good linear correlation between the intermolecular H-bond distance and the electron density as well as its Laplacian at the bond critical point of the intermolecular H-bond has been observed. Depending on the selected coupling modes between Vc and MG, the origin of the blue-shifts of the stretching vibrational frequencies of different C-H bonds has been elucidated. Additionally, the inherent reason for the positive role of Vc in the anticancer process for MG has been verified through the investigation of the one-electron oxidation behaviors of the most stable complex.

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Section: Computational Detailsmentioning

confidence: 99%

Explorations of the nature of the coupling interactions between vitamin C and methylglyoxal: a DFT study

Zhai

et al. 2011

Struct Chem

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“…The same approach has been used previously to determinate the interaction energy between metal cations and ligands. [6][7][8][9]11,[22][23][24][25][26][27] In Table 1 we list the interaction enthalpies for the phosphoryl, carbonyl, imino and thiocarbonyl complexes using the ab initio, DFT and semi-empirical methods. As a typical ionic bond, 15 the strength of the Li + -ligand interaction is strictly correlated to the distance between the interacting atoms (d 1 ), where the smallest distances lead to the strongest interaction enthalpy.…”

Section: Interaction Enthalpymentioning

confidence: 99%

“…This ligand affinity order was also found in previous studies with aminoacids [8][9][10] and other biological adducts. 6,7,24 Analysis of the interaction enthalpy in each set of ligands shows an interesting trend related to the nature of the para-substituted group. Figure 3 shows the correlation between the interaction enthalpy and the values of the s p Hammet parameter of the substituents for the para-substituted derivative in each set of phosphoryl, carbonyl, imino and thiocarbonyl compounds.…”

Section: Interaction Enthalpymentioning

confidence: 99%

“…5 In all these processes the Li + cation interacts with a wide range of biological molecules with several different organic functional groups. The most common types of interactions are with oxygen atoms of alcohols, 6 ketones, 7 carboxylic acids 8,9 and phosphates, 10 nitrogen atoms of amines, 9,11 amides 12 and imides 13 and sulfur atoms of thiols. 14 In the biological media the Li + cation is surrounded by different Vol.…”

Section: Introductionmentioning

confidence: 99%

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Ab Initio, DFT and semi-empirical studies on interactions of phosphoryl, carbonyl, imino and thiocarbonyl ligands with the li+ cation: affinity and associated parameters

Paes

Carneiro²,

São

et al. 2012

J. Braz. Chem. Soc.

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A afinidade do cátion Li + para uma série de ligantes fosforila, carbonila, imino e tiocarbonila substituídos na posição para de um anel aromático foi calculada com os métodos ab initio MP2/6-311+G(d,p), DFT B3LYP/6-311+G(d,p) e semi-empírico PM6. Cada série de ligante é constituída pelos seguintes grupos substituídos na posição para: NH 2 , OCH 3 , CH 3 , H, Cl, CN and NO 2 . A entalpia de interação foi calculada para quantificar a afinidade dos ligantes para o cátion Li + . Parâmetros geométricos e eletrônicos foram correlacionados com a força da interação metal-ligante. A natureza eletrônica dos grupos substituintes é o principal parâmetro que modula a intensidade da ligação metal-ligante. Grupos doadores de elétrons tornam a entalpia de interação mais exotérmica, enquanto grupos aceptores de elétrons tornam a entalpia de interação menos exotérmica. Análise da decomposição da energia mostra que os grupos substituintes modulam a intensidade da componente eletrostática da interação sem afetar a componente covalente.The affinity of the Li + cation for a set of para-substituted phosphoryl, carbonyl, imino and thiocarbonyl ligands was calculated with the ab initio MP2/6-311+G(d,p), DFT B3LYP/6-311+G(d,p) and semi-empirical PM6 methods. Each set of ligand is constituted by the following para-substituted groups: NH 2 , OCH 3 , CH 3 , H, Cl, CN and NO 2 . The interaction enthalpy was calculated to quantify the affinity of the ligands for the Li + cation. Geometric and electronic parameters were correlated with the strength of the metal-ligand interaction. The electronic nature of the para-substituted group is the main parameter that modulates the intensity of the metalligand binding energy. Electron donor groups make the interaction enthalpy more exothermic, whereas electron acceptor groups make the interaction enthalpy less exothermic. The energy decomposition analysis shows that the para-substituted groups modulate the intensity of the electrostatic component of the interaction without affecting the covalent component. Keywords: lithium cation, substituent effect, interaction enthalpy, EDA, ligand interactionAb Initio, DFT and Semi-Empirical Studies on Interactions of Ligands J. Braz. Chem. Soc. 650

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“…In case of vitamin-C, oxygen of enediol group may take part in bond formation with Cd II , formed a five membered ring [29].…”

Section: Trend Of Stability Constants Of CD (Ii) Complexesmentioning

confidence: 99%

Study of complexes of cadmium with some L-amino acids and vitamin-C by voltammetric technique

Khan

Khanam

2008

Eclet. Quim.

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Voltammetric technique was used to study the binary and ternary complexes of cadmium with L-amino acids and vitamin-C (L-ascorbic acid) at pH =7.30 ± 0.01, μ = 1.0M KNO3 at 25ºC and 35ºC. Cd (II) formed 1:1:1, 1:1:2 and 1:2:1 complexes with L-lysine, L-ornithine, L-threonine, L-serine, L-phenylglycine, L-phenylalanine, L-glutamic acid and L-aspartic acid used as primary ligands and L-ascorbic acid used as secondary ligand. The trend of stability constant of complexes was Llysine < L-ornithine < L-threonine < L-serine < L-phenylglycine < L-phenylalanine < L-glutamic acid < L-aspartic acid which can be explained on the basis of size, basicity and steric hindrance of ligands. The values of stability constant (log β) varied from 2.23 to11.33 confirm that these drugs i.e. L-aminoacids or in combination with L-ascorbic acid or their complexes could be used against Cd (II) toxicity. The study has been carried out at 35ºC also to determine the thermodynamic parameters such asenthalpy change (ΔH), Free energy change (ΔG) and entropy change (ΔS) respectively.

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Ab initio insight on the interaction of ascorbate with Li⁺, Na⁺, K⁺, Be²⁺, Mg²⁺, and Ca²⁺metal cations

Cited by 14 publications

References 17 publications

Explorations of the nature of the coupling interactions between vitamin C and methylglyoxal: a DFT study

Explorations of the nature of the coupling interactions between vitamin C and methylglyoxal: a DFT study

Ab Initio, DFT and semi-empirical studies on interactions of phosphoryl, carbonyl, imino and thiocarbonyl ligands with the li+ cation: affinity and associated parameters

Study of complexes of cadmium with some L-amino acids and vitamin-C by voltammetric technique

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