Characteristics of quercetin interactions with liposomal and vacuolar membranes

Pawlikowska-Pawlęga, Bożena; Dziubińska, Halina; Król, Elżbieta; Trębacz, Kazimierz; Jarosz-Wilkołazka, Anna; Paduch, Roman; Gawron, Antoni; Gruszecki, Wiesław I.

doi:10.1016/j.bbamem.2013.08.014

Cited by 84 publications

(60 citation statements)

References 83 publications

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“…The spectral shift of band representing C=O stretching and broadening of P=O stretching vibrations relatively confirmed the binding of flavonoids to the polar head of the membrane through the oxygen groups of lipid and keto groups of flavonoids. Our results strongly support the previously reported study results, [53][54][55] where majority of the flavonoids bind to the polar heads (C-O-P-O-C stretching) of the PC via hydrogen bonding, thus indicating the localization of flavonoids. Thermal analysis behavior of PC alone (PC), flavonoids alone (QKA), physical mixture of flavonoids with carrier (QKA + PC), and M4 flavonosome (M4) was obtained by DSC and TGA ( Figure 7F).…”

supporting

confidence: 82%

Optimization, formulation, and characterization of multiflavonoids-loaded flavanosome by bulk or sequential technique

Karthivashan¹,

Kura²,

Abas³

et al. 2016

IJN

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This study involves adaptation of bulk or sequential technique to load multiple flavonoids in a single phytosome, which can be termed as “flavonosome”. Three widely established and therapeutically valuable flavonoids, such as quercetin (Q), kaempferol (K), and apigenin (A), were quantified in the ethyl acetate fraction of Moringa oleifera leaves extract and were commercially obtained and incorporated in a single flavonosome (QKA–phosphatidylcholine) through four different methods of synthesis – bulk (M1) and serialized (M2) co-sonication and bulk (M3) and sequential (M4) co-loading. The study also established an optimal formulation method based on screening the synthesized flavonosomes with respect to their size, charge, polydispersity index, morphology, drug–carrier interaction, antioxidant potential through in vitro 1,1-diphenyl-2-picrylhydrazyl kinetics, and cytotoxicity evaluation against human hepatoma cell line (HepaRG). Furthermore, entrapment and loading efficiency of flavonoids in the optimal flavonosome have been identified. Among the four synthesis methods, sequential loading technique has been optimized as the best method for the synthesis of QKA–phosphatidylcholine flavonosome, which revealed an average diameter of 375.93±33.61 nm, with a zeta potential of −39.07±3.55 mV, and the entrapment efficiency was >98% for all the flavonoids, whereas the drug-loading capacity of Q, K, and A was 31.63%±0.17%, 34.51%±2.07%, and 31.79%±0.01%, respectively. The in vitro 1,1-diphenyl-2-picrylhydrazyl kinetics of the flavonoids indirectly depicts the release kinetic behavior of the flavonoids from the carrier. The QKA-loaded flavonosome had no indication of toxicity toward human hepatoma cell line as shown by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide result, wherein even at the higher concentration of 200 µg/mL, the flavonosomes exert >85% of cell viability. These results suggest that sequential loading technique may be a promising nanodrug delivery system for loading multiflavonoids in a single entity with sustained activity as an antioxidant, hepatoprotective, and hepatosupplement candidate.

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supporting

confidence: 82%

Optimization, formulation, and characterization of multiflavonoids-loaded flavanosome by bulk or sequential technique

Karthivashan¹,

Kura²,

Abas³

et al. 2016

IJN

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“…The current view for the localization of the three 2 compounds correlates well with most other existing studies, which suggest localization of 3 flavonoids between the boundary of the lipid/water interface and the upper half of the 4 hydrocarbon chain region. 52,53,54,55,56,57 Notwithstanding this view, some studies suggest that the 5 flavonoids partition into the hydrophobic region of the membrane. 58,59 An NMR study has 6…”

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confidence: 99%

“…54 A FTIR study suggested the same explanation 8 for quercetin. 55 Movileanu et al, 53 proposed a pH dependent insertion of quercetin within 9 membranes. Quercetin molecules inserted between the polar head groups at alkaline pH, with 10 deeper localization at acidic pH, due to intercalation of quercetin molecules between the acyl 11 chains.…”

mentioning

confidence: 99%

Experimental Modeling of Flavonoid–Biomembrane Interactions

Sanver

Murray²,

Sadeghpour³

et al. 2016

Langmuir

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and visualization of the surface with BAM revealed a pronounced monolayer stabilization effect 10 with both quercetin and tiliroside, whereas rutin disrupted the monolayer structure rendering the 11 surface entirely smooth. SAXS showed a monotonous membrane thinning for all compounds 12 studied associated with an increase in the root mean square fluctuations of the membrane. Rutin, 13 quercetin and tiliroside decreased the bilayer thickness of DOPC by ~0.45 Å, 0.8 Å, and 1.1 Å at 14 6 mol %, respectively. In addition to the novelty of using lipid monolayers to systematically 15 characterize the structure activity relationship (SAR) of a variety of flavonoids; this is the first 16 report investigating the effect of tiliroside with biomimetic membrane models. All the flavonoids 17 studied are believed to be localized in the lipid/water interface region. Both this localization and 18 the membrane perturbations have implications for their therapeutic activity.

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“…Recent studies revealed that incorporation of quercetin into the phospholipid bilayer occurs via a hydrogen bonding between its own hydroxyl groups and lipid polar head groups in the C-O-P-O-C segment. Both FTIR and NMR techniques revealed that quercetin affects the lipid bilayer in the region corresponding to alkyl chains [21].…”

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confidence: 99%

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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Characteristics of quercetin interactions with liposomal and vacuolar membranes

Cited by 84 publications

References 83 publications

Optimization, formulation, and characterization of multiflavonoids-loaded flavanosome by bulk or sequential technique

Optimization, formulation, and characterization of multiflavonoids-loaded flavanosome by bulk or sequential technique

Experimental Modeling of Flavonoid–Biomembrane Interactions

Integration of Quercetin-Iron Complexes into Phosphatidylcholine or Phosphatidylethanolamine Liposomes

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