Europium Coordination Complexes as Potential Anticancer Drugs: Their Partitioning and Permeation Into Lipid Bilayers as Revealed by Pyrene Fluorescence Quenching

Trusova, Valeriya; Yudintsev, Andrey; Limanskaya, L.A.; Gorbenko, Galyna; Deligeorgiev, Todor

doi:10.1007/s10895-012-1134-1

Cited by 11 publications

(7 citation statements)

References 48 publications

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“…The premise of these measurements is that pyrene, acting as an environmental probe, will partition into the more hydrophobic drug-rich phase created during the process of LLPS. The use of pyrene to characterize surfactant micelle formation, , as well as probe lipid bilayers, , is widely established. Based on this body of literature, as well as previous studies from our group using pyrene, a change in the ratio of two characteristic pyrene emission peaks ( I 1 at 373 nm, I 3 at 383 nm) was used to indicate a change in the probe environment and consequently the LLPS concentration.…”

Section: Methodsmentioning

confidence: 99%

Impact of Polymers on the Precipitation Behavior of Highly Supersaturated Aqueous Danazol Solutions

Jackson

Toth²,

Kestur

et al. 2014

Mol. Pharmaceutics

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The phase behavior of supersaturated solutions of a relatively hydrophobic drug, danazol, was studied in the absence and presence of polymeric additives. To differentiate between phase separation to a noncrystalline phase and phase separation to a crystalline phase, an environmentally sensitive fluorescent probe was employed. Induction times for crystallization in the presence and absence of polymeric additives were studied using a combination of ultraviolet and fluorescence spectroscopy. It was found that, when danazol was added to aqueous media at concentrations above the amorphous solubility, liquid-liquid phase separation was briefly observed prior to crystallization, resulting in a short-lived, drug-rich noncrystalline danazol phase with an initial size of around 500 nm. The addition of polymers was found to greatly extend the lifetime of the supersaturated two phase system, delaying the onset of crystallization from a few minutes to a few hours. Below a certain threshold danazol concentration, found to represent the amorphous solubility, only crystallization was observed. Thus, although the addition of polymers was unable to prevent danazol from precipitating once a threshold concentration was exceeded, they did inhibit crystallization, leading to a solution with prolonged supersaturation. This observation highlights the need to determine the structure of the precipitating phase, since it is linked to the resultant solution concentration time profile.

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Section: Methodsmentioning

confidence: 99%

Impact of Polymers on the Precipitation Behavior of Highly Supersaturated Aqueous Danazol Solutions

Jackson

Toth²,

Kestur

et al. 2014

Mol. Pharmaceutics

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“…This helps the penetration through the lipid membranes, disturbing the functioning of the bacterial/fungal cell. Moreover, the anticancer activity of lanthanides was also evaluated and several Eu(III) complexes were synthesized and tested, showing some promising results as new anticancer agents [ 28 , 29 , 30 ].…”

Section: Introductionmentioning

confidence: 99%

Caffeic Acid/Eu(III) Complexes: Solution Equilibrium Studies, Structure Characterization and Biological Activity

Arciszewska

Gama

Kalinowska

et al. 2022

IJMS

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Caffeic acid (CFA) is one of the various natural antioxidants and chemoprotective agents occurring in the human diet. In addition, its metal complexes play fundamental roles in biological systems. Nevertheless, research on the properties of CFA with lanthanide metals is very scarce, and little to no chemical or biological information is known about these particular systems. Most of their properties, including their biological activity and environmental impact, strictly depend on their structure, stability, and solution behaviour. In this work, a multi-analytical-technique approach was used to study these relationships for the Eu(III)/CFA complex. The synthesized metal complex was studied by FT-IR, FT-Raman, elemental, and thermal (TGA) analysis. In order to examine the chemical speciation of the Eu(III)/CFA system in an aqueous solution, several independent potentiometric and spectrophotometric UV-Vis titrations were performed at different M:L (metal:ligand) and pH ratios. The general molecular formula of the synthesized metal complex in the solid state was [Eu(CFA)3(H2O)3]∙2H2O (M:L ratio 1:3), while in aqueous solution the 1:1 species were observed at the optimum pH of 6 ≤ pH ≤ 10, ([Eu(CFA)] and [Eu(CFA)(OH)]−). These results were confirmed by 1H-NMR experiments and electrospray-ionization mass spectrometry (ESI-MS). To evaluate the interaction of Eu(III)/CFA and CFA alone with cell membranes, electrophoretic mobility assays were used. Various antioxidant tests have shown that Eu(III)/CFA exhibits lower antioxidant activity than the free CFA ligand. In addition, the antimicrobial properties of Eu(III)/CFA and CFA against Escherichia coli, Bacillus subtilis and Candida albicans were investigated by evaluation of the minimum inhibitory concentration (MIC). Eu(III)/CFA shows higher antibacterial activity against bacteria compared to CFA, which can be explained by the highly probable increased lipophilicity of the Eu(III) complex.

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“…However, this mechanism seems to be unlikely as the europium chelates under study were highly hydrophobic compounds. [ 4–6 ] Conversely, Tajmir‐Riahi reported that the association of a number of drugs with albumin was accompanied by a decrease in α‐helix content in favour of β‐sheet and turn structures, which may be indicative of partial protein unfolding. [ 20 ] The route by which a polypeptide chain changes its conformation is thought to be similar to protein unfolding upon heating and is related to alterations in the contribution of the T Δ S term into Gibbs free energy.…”

Section: Resultsmentioning

confidence: 99%

“…Our previous studies have focused on the interactions between a series of novel EC and the lipid bilayer, a major structural element of cellular membranes. [ 4–6 ] Analysis of the membrane‐associating and bilayer‐modifying properties of the europium chelates provided evidence for their accumulation in a lipid phase coupled with no significant effect on membrane integrity, thereby highlighting the possibility for development of EC liposomal formulations.…”

Section: Introductionmentioning

confidence: 99%

Probing the interactions of novel europium coordination complexes with serum albumin

et al. 2021

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Molecular interactions between novel europium coordination complexes (EC) possessing superior cytotoxic activity and bovine serum albumin (BSA), the most prominent representative of plasma proteins, were assessed using fluorescence spectroscopy and molecular docking techniques. Cumulative results from fluorescent probe binding, fluorescence quenching and Förster resonance energy transfer studies revealed that the europium complexes V4 and V8 do not perturb the BSA structure, while V3, V5, and V7 induce partial unfolding of the polypeptide chain. Molecular docking studies coupled with analysis of the three‐dimensional structure of the BSA–EC complexes showed that V4 and V8 reside in the vicinity of the protein IIA subdomain (Sudlow's site I), while V3, V5 and V5 were localized predominantly in the BSA IIIA subdomain (Sudlow's site II). Due to the intactness of the protein structure upon association with V4 and V8, these compounds may be recommended for further evaluation as potential antineoplastic agents.

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Europium Coordination Complexes as Potential Anticancer Drugs: Their Partitioning and Permeation Into Lipid Bilayers as Revealed by Pyrene Fluorescence Quenching

Cited by 11 publications

References 48 publications

Impact of Polymers on the Precipitation Behavior of Highly Supersaturated Aqueous Danazol Solutions

Impact of Polymers on the Precipitation Behavior of Highly Supersaturated Aqueous Danazol Solutions

Caffeic Acid/Eu(III) Complexes: Solution Equilibrium Studies, Structure Characterization and Biological Activity

Probing the interactions of novel europium coordination complexes with serum albumin

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