Metal chelating ability and antioxidant properties of Curcumin-metal complexes – A DFT approach

Mary, Charline; Vijayakumar, S.; Shankar, Ravi

doi:10.1016/j.jmgm.2017.10.022

Cited by 108 publications

(63 citation statements)

References 70 publications

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“…is result is in accordance with previous observations done on 1,2,3-triazol derivatives [38], curcumin [24], and Hyperjovinol [36]. From Table 1, one could notice that the diminution of the electron transfer is more sensitive in acetonitrile.…”

Section: General Considerations On Isolatedsupporting

confidence: 92%

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Antioxidant Properties of Lapachol and Its Derivatives and Their Ability to Chelate Iron (II) Cation: DFT and QTAIM Studies

Pajoudoro

Lissouck

Amana

et al. 2020

Bioinorganic Chemistry and Applications

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The elucidation of the complexation of lapachol and its derivatives to Fe2+ cation has been done using the density functional theory (DFT). This complexation has been limited to bidentate and tridentate to Fe2+ cation. Geometry optimizations have been implemented in gas and solution phase (water, acetonitrile, chlorobenzene, benzene, and toluene) for ligands at B3LYP/6-311++G (d,p) level of theory using B3LYP/6-31+G(d,p) optimized data as starting point. But, the geometrical optimizations in solution phase of the 22 complexes analyzed of lapachol and its derivatives to Fe2+ cation were restricted to acetonitrile and benzene. The complexation energy and the metal ion affinity (MIA) have also been calculated using the B3LYP method. The results obtained indicated a proportionality between the MIA values and the retained charge on Fe2+ cation for k2-(O1,O2) modes. But, an inverse proportionality has been yielded between these two parameters for k3-(O2, C=C) tridentate modes. For k3-(O3,C=C) tridentate mode coordination, the higher stability has been obtained. In this latter tridentate coordination in gas phase, the topological analysis of complexes exhibits the fact that the electron density is concentrated between the O3 oxygen atom of the ligand attached to Fe2+ and this metal cation. Moreover, the hydrogen bond strength calculated for isolated ligands (situated between 23.92 and 30.15 kJ/mol) is in the range of normal HBs. Collectively, all the complexation processes have shown to be highly exothermic. Our results have also shown that the electron extraction from Fe2+...Lai complexes is more difficult compared to that from free ligands.

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Section: General Considerations On Isolatedsupporting

confidence: 92%

“…is last point must be helpful for the clarification of the properties of La n −Fe 2+ that may facilitate the selection of appropriate chelating and scavenging agent for the chelating therapy of Alzheimer [24].…”

Section: Introductionmentioning

confidence: 99%

Antioxidant Properties of Lapachol and Its Derivatives and Their Ability to Chelate Iron (II) Cation: DFT and QTAIM Studies

Pajoudoro

Lissouck

Amana

et al. 2020

Bioinorganic Chemistry and Applications

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“…The anti‐inflammatory and antioxidant activities of curcumin have been well documented (Gómez‐Estaca, Balaguer, López‐Carballo, Gavara, & Hernández‐Muñoz, ; Mary, Vijayakumar, & Shankar, ; Rauf, Imran, Orhan, & Bawazeer, ; Zhang et al, ); however, studies with nanocapsules containing curcumin showed that its potentiation promotes decreases in oxygen reactive species, DNA damage, and lipid peroxidation (Keskin‐Aktan et al, ; Soltani, Ghaemi, Sadeghizadeh, & Najafi, ), effects that are already known regarding the expression of Nrf2, an antioxidant regulator (Tapia et al, ) that influences in positive expression of target genes of antioxidant enzymes, including glutathione S‐transferase (GST), GPx, CAT, and SOD (Cardozo et al, ). All three of these are potent endogenous antioxidants.…”

Section: Discussionmentioning

confidence: 99%

“…The nanocapsules are formed by a polymer wall around an oily core, the active may be either dissolved in the core or adsorbed to the polymer wall. They are one of the most studied release systems nanostructured that can protect against degradation processes, increase the solubility and potentiate the biological absorption of the active, besides allowing a controlled release & Shankar, 2018;Rauf, Imran, Orhan, & Bawazeer, 2018;Zhang et al, 2018); however, studies with nanocapsules containing curcumin showed that its potentiation promotes decreases in oxygen reactive species, DNA damage, and lipid peroxidation (Keskin-Aktan et al, 2018;Soltani, Ghaemi, Sadeghizadeh, & Najafi, 2016), effects that are already known regarding the expression of Nrf2, an antioxidant regulator (Tapia et al, 2012) that influences in positive expression of target genes of antioxidant enzymes, including glutathione S-transferase (GST), GPx, CAT, and SOD (Cardozo et al, 2013). All three of these are potent endogenous antioxidants.…”

Section: Discussionmentioning

confidence: 99%

Low‐dose curcumin‐loaded Eudragit L‐100‐nanocapsules in the diet of dairy sheep increases antioxidant levels and reduces lipid peroxidation in milk

et al. 2019

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The main objective of this study was to evaluate whether the addition of curcumin‐loaded nanocapsules (prepared and characterized) in the diets of dairy sheep improved milk quality. The nanocapsules were prepared using two polymers: poly‐ε‐caprolactone (PCL) and Eudragit L‐100. The nanocapsules contained 0.25 mg/ml (Nano‐Eudragit L‐100) and 2 mg/ml (Nano‐PCL) of curcumin. Dairy sheep were divided into four groups: A (control), B (30 mg free curcumin/kg concentrate), C (3 mg Nano‐PCL/kg concentrate), and D (3 mg Nano‐Eudragit/kg concentrate). We observed that the number of total leukocytes and serum globulin levels were lower in Group D than in the control (Group A) (p < 0.05). Antioxidant capacity against peroxyl radicals (ACAP) and catalase enzymes was elevated in Group D, with consequently reduced lipid peroxidation (LPO; p < 0.05). In milk, there were no differences in production and composition between groups during the experimental period (p > 0.05); however, ACAP increased and LPO decreased in milk. Practical applications Curcumin is a functional molecule with potent antioxidant, anti‐inflammatory, and antimicrobial actions, used frequently and with medical indications in human food. Free curcumin in sheep diets improves milk quality and increases its shelf life. This study showed that curcumin nanocapsules produced from the Eudragit L‐100 polymer potentiated the anti‐inflammatory and antioxidant actions of dairy sheep when used in the diet daily, at doses 10 times lower than that of free curcumin. These positive effects were reflected in higher total antioxidant capacity and lower lipid peroxidation in milk in sheep‐fed curcumin‐loaded Eudragit L‐100 nanocapsules, generating desirable milk properties. In practice, the use of nanotechnology enhances the beneficial effects of curcumin in milk, possibly creating a nutraceutical food desirable to consumers.

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“…Zinc prevents lipid peroxidation and thus plays an essential role in protecting the cells from oxidative stress . In addition, it was reported that metal chelation of curcumin with Fe 2+ , Mn 2+ , and Zn 2+ enhanced the antioxidant activity of curcumin . Superoxide dismutase (SOD) is one of the important enzymes for scavenging reactive oxygen species (ROS) by converting the superoxide into less‐toxic hydrogen peroxide and oxygen .…”

Section: Antioxidant Activitymentioning

confidence: 99%

Biological properties of metal complexes of curcumin

et al. 2019

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Curcumin, a naturally occurring phenolic compound isolated from Curcuma longa, has different pharmacological effects, including antiinflammatory, antimicrobial, antioxidant, and anticancer properties. However, curcumin has been found to have a limited bioavailability because of its hydrophobic nature, low-intestinal absorption, and rapid metabolism. Therefore, there is a need for enhancing the bioavailability and its solubility in water in order to increase the pharmacological effects of this bioactive compound. One strategy is curcumin complexation with transition metals to circumvent the abovementioned problems. Curcumin can undergo chelation with various metal ions to form metallo-complexes of curcumin, which may show greater effects as compared with curcumin alone. Promising results with metal curcumin complexes have been observed with regard to antioxidant, anticancer, and antimicrobial activity, as well as in treatment of Alzheimer's disease. The present review provides a concise summary of the characterization and biological properties of curcumin-metal complexes. © 2019 BioFactors, 45(3):304-317, 2019

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Metal chelating ability and antioxidant properties of Curcumin-metal complexes – A DFT approach

Cited by 108 publications

References 70 publications

Antioxidant Properties of Lapachol and Its Derivatives and Their Ability to Chelate Iron (II) Cation: DFT and QTAIM Studies

Antioxidant Properties of Lapachol and Its Derivatives and Their Ability to Chelate Iron (II) Cation: DFT and QTAIM Studies

Low‐dose curcumin‐loaded Eudragit L‐100‐nanocapsules in the diet of dairy sheep increases antioxidant levels and reduces lipid peroxidation in milk

Biological properties of metal complexes of curcumin

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