Lipophilicity of flavonoid complexes with iron(II) and their interaction with liposomes

Kim, Yu. A.; Tarahovsky, Yury S.; Yagolnik, Elena A.; Кузнецова, С.М.; Muzafarov, Eugeny N.

doi:10.1016/j.bbrc.2013.01.060

Cited by 29 publications

(17 citation statements)

References 39 publications

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“…Changes in T h transition were considerably stronger when quercetin and iron were added sequentially. Similar data were presented earlier [31]. The complex of quercetin with iron is not soluble in water and produces particles that could be analyzed with photon correlation spectroscopy.…”

Section: Resultssupporting

confidence: 70%

“…The effect could be observed only when quercetin was added to liposomes before and about 30 min after adding iron cations. As we have reported earlier [31], in the case when the compounds were added in the reverse order or when a preliminarily prepared complex of quercetin-iron was added to liposomes, we did not observe any influence of the complex on lipid melting (Fig. 2e).…”

Section: Resultssupporting

confidence: 61%

“…As we demonstrated earlier on liposomal models, complexes of flavonoids with iron exibited аn increased hydrophobicity and readily interacted with the lipid bilayer [31]. Here, we studied the influence of quercetin and the quercetin-iron complex on liposomes composed of phosphatidylcholine or phosphatidylethanolamine, which are extensively used for drug and gene delivery [32][33][34][35].…”

Section: Introductionmentioning

confidence: 93%

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Integration of Quercetin-Iron Complexes into Phosphatidylcholine or Phosphatidylethanolamine Liposomes

Kim

Tarahovsky

Yagolnik

et al. 2015

Appl Biochem Biotechnol

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It is well known that flavonoids can chelate transition metals. Flavonoid-metal complexes exhibit a high antioxidative and therapeutic potential. However, the complexes are frequently hydrophobic ones and low soluble in water, which restricts their medical applications. Integration of these complexes into liposomes may increase their bioavailability and therapeutic effect. Here, we studied the interaction of quercetin-iron complexes with dimyristoylphosphatidylcholine (DMPC) or palmitoyl-oleoyl phosphatidylethanolamine (POPE) multilamellar liposomes. Differential scanning calorimetry (DSC) and freeze-fracture electron microscopy revealed that quercetin-iron complexes did not interact with liposomes. Quercetin however could penetrate lipid bilayers, when added to liposomes at a temperature above lipid melting. Iron cations added later penetrated into the lipid bilayers and produced complexes with quercetin in the liposomes. The quercetin-iron entry in POPE liposomes was improved when the suspension was heated above the temperature of the bilayer-hexagonal HII phase transition of the lipid. The approach proposed facilitates the integration of quercetin-iron complexes into liposomes and may promote their use in medicine.

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Section: Resultssupporting

confidence: 70%

Section: Resultssupporting

confidence: 61%

Section: Introductionmentioning

confidence: 93%

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Integration of Quercetin-Iron Complexes into Phosphatidylcholine or Phosphatidylethanolamine Liposomes

Kim

Tarahovsky

Yagolnik

et al. 2015

Appl Biochem Biotechnol

Self Cite

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“…and Fe 2+ ) (Kim et al, 2013;Pekal et al, 2011) one may speculate that quercetin and catechol can bind Ca 2+ and thus diminish the Ca 2+ -dependent signal from Fura 2. Nevertheless, a supposed chelation of extracellular and intracellular Ca 2+ by both these compounds would be negligible considering the 200-fold higher Ca 2+ level to polyphenol concentration in the buffer used for the preparation of experimental cell suspensions.…”

Section: +mentioning

confidence: 99%

Inhibitory effect of plant phenolics on fMLP-induced intracellular calcium rise and chemiluminescence of human polymorphonuclear leukocytes and their chemotactic activityin vitro

Nowak

Zasowska-Nowak

Białasiewicz

et al. 2015

Pharmaceutical Biology

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Context: Polymorphonuclear leukocytes (PMNs) produce oxidants, contributing to systemic oxidative stress. Diets rich in plant polyphenols seem to decrease the risk of oxidative stressinduced disorders including cardiovascular disease. Objective: The objective of this study was to examine the in vitro effect of each of the 14 polyphenols on PMNs chemotaxis, intracellular calcium response, oxidants production. Materials and methods: Blood samples and PMNs suspensions were obtained from 60 healthy non-smoking donors and incubated with a selected polyphenol (0.5-10 mM) or a control solvent. We assessed resting and fMLP-dependent changes of intracellular calcium concentration ([Ca 2+ ] i ) in PMNs with the Fura-2AM method and measured fMLP-induced luminol enhanced whole blood chemiluminescence (fMLP-LBCL). Polyphenol chemoattractant activity for PMNs was tested with Boyden chambers. Results: Polyphenols had no effect on resting [Ca 2+ ] i . Unaffected by other compounds, fMLPdependent increase of [Ca 2+ ] i was inhibited by quercetin and catechol (5 mM) by 32 ± 14 and 12 ± 10% (p50.04), respectively. Seven of the 14 tested substances (5 mM) influenced fMLP-LBCL by decreasing it. Catechol, quercetin, and gallic acid acted most potently reducing fMLP-LBCL by 49 ± 5, 42 ± 15, and 28 ± 18% (p50.05), respectively. 3,4-Dihydroxyhydrocinnamic, 3,4-dihydroxyphenylacetic, 4-hydroxybenzoic acid, and catechin (5 mM) revealed distinct (p50.02) chemoattractant activity with a chemotactic index of 1.9 ± 0.8, 1.8 ± 0.7, 1.6 ± 0.6, 1.4 ± 0.2, respectively. Conclusion and discussion: Catechol, quercetin, and gallic acid at concentrations commensurate in human plasma strongly suppressed the oxidative response of PMNs. Regarding quercetin and catechol, this could result from an inhibition of [Ca 2+ ] i response.

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“…Thus, after chelating the metal ion, the polarity of flavonoid molecules generally decreased, while the iron atom becomes the most polar and hence hydrophilic part of the molecule. Overall, the lipophilicity of the complexes is considerably larger than that of the corresponding free flavonoids [113,114].…”

Section: Liposomal Systemsmentioning

confidence: 99%

Flavonoid Complexes as Promising Anticancer Metallodrugs

Uivaroşi¹,

Arbănași²

2017

Flavonoids - From Biosynthesis to Human Health

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Flavonoid metal complexes commonly exhibit an improvement of biological activity compared to the parent ligands. This chapter is focused on the antioxidant and anticanccer properties of flavonoid metal complexes, in correlation with their binding ability to vital macromolecules such as nucleic acids and serum proteins. Perspectives for an adequate formulation of these complexes were also discussed.

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Lipophilicity of flavonoid complexes with iron(II) and their interaction with liposomes

Cited by 29 publications

References 39 publications

Integration of Quercetin-Iron Complexes into Phosphatidylcholine or Phosphatidylethanolamine Liposomes

Integration of Quercetin-Iron Complexes into Phosphatidylcholine or Phosphatidylethanolamine Liposomes

Inhibitory effect of plant phenolics on fMLP-induced intracellular calcium rise and chemiluminescence of human polymorphonuclear leukocytes and their chemotactic activityin vitro

Flavonoid Complexes as Promising Anticancer Metallodrugs

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