Interaction of a β-lactam calixarene derivative with a model eukaryotic membrane affects the activity of PLA2

Korchowiec, Beata; Gorczyca, M; Salem, Adel Ben; Vains, Jean-Bernard Regnouf de; Rogalska, Ewa

doi:10.1016/j.colsurfb.2012.10.045

Cited by 21 publications

(16 citation statements)

References 37 publications

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“…[1][2][3][4][5] With such properties, calixarenes have been used in detecting metallic ions, such as alkaline [6][7][8] and alkaline earth [8][9][10] metals, cadmium, [10][11][12] copper, 7,13,14 and for incorporating neutral molecules, [15][16][17][18][19][20] including dopamine, 15 volatile organic compounds 16 and aminoacids. 17 They have also been studied in biological membranes, [18][19][20] and in the formation of molecularly organized films using self-assembled monolayers [21][22][23] and LangmuirBlodgett (LB) [6][7][8][9][10][11][12][13][15][16][17][18][19][20] techniques. These organized films have been applied in metal ion sensors, biosensors, immunosensors and for encapsulating nanoparticles.…”

Section: Introductionmentioning

confidence: 99%

Interaction of para-tert-butylcalix[6]arene molecules in Langmuir films with cadmium ions and their effects on molecular conformation and surface potential

Wrobel

Santos

Lazzarotto

et al. 2014

Phys. Chem. Chem. Phys.

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In this paper, we employ the surface-specific polarization-modulated infrared reflection absorption spectroscopy (PM-IRRAS) and sum-frequency generation (SFG) methods with surface pressure and surface potential isotherms to determine the organization of p-tert-butylcalix[6]arene molecules and their interaction with Cd 2+ ions in Langmuir monolayers. The area per molecule was estimated to be 135 Å 2 , which corresponds to the Calix6 axis perpendicular to the air-water interface with most OH groups parallel to the interface. This area is larger than predicted by molecular modeling with quantum chemical calculations with a PM3 Hamiltonian (109 Å 2 ), which is ascribed to the repulsion between Calix6 molecules. The incorporation of Cd 2+ ions in the subphase leads to drastic changes in the dipole moment contribution of the monolayer surface potential. Rather than increasing with incorporation of Cd 2+ ions owing to a decrease in the negative double-layer potential, the measured surface potential decreased monotonically with increasing ion concentration. This unexpected result was ascribed to a strong interaction with Cd 2+ ions that induced the calyx of the molecule to adopt a more open conformation at the air/water interface and affected the orientation of hydration water molecules, according to the SFG data. This finding allows us to understand the reason why the Gouy-Chapman model fails to explain surface potential results for subphases containing divalent or trivalent ions, and may be relevant for the application of calixarenes in sensing.

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Section: Introductionmentioning

confidence: 99%

Interaction of para-tert-butylcalix[6]arene molecules in Langmuir films with cadmium ions and their effects on molecular conformation and surface potential

Wrobel

Santos

Lazzarotto

et al. 2014

Phys. Chem. Chem. Phys.

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“…The additive values of pure compounds are used as reference in the plots of MMA, MSP, and ΔG mix versus x calix ( Figure 11). 23,33 A comparison between the MMA of additive and experimental mixing as a function of the x calix mole fraction at an arbitrary chosen surface pressures of 24 mN m −1 is shown in Figure 11A. The experimental MMA values of DMPE/calix I films are close to the calculated additive values.…”

Section: Resultsmentioning

confidence: 65%

“…31, 32 We want to mention that thermodynamic terms used here were defined in our previous papers. 23,33 Namely, in accordance with the definition of Gibbs energy of mixing, ΔG mix = G − (x 1 G 1 + x 2 G 2 ), eq 2 gives ΔG mix instead of ΔG exc given by Goodrich 31 and Bacon et al 32 The morphology of the films was imaged with a computerinterfaced KSV 2000 Langmuir balance combined with a Brewster angle microscope (KSV Optrel BAM 300, Helsinki). The Teflon trough dimensions were 6.5 cm × 58 cm × 1 cm; other experimental conditions were as described above.…”

Section: Methodsmentioning

confidence: 99%

“…This technique was used before for studying new calixarene derivatives with biologically relevant properties upon interaction with model membranes. 23 The fact that the two derivatives used in this work differ by the number of the grafted nalidixic acid moieties permits estimating the contribution of the pendant arms to the properties of the mixed calixarene-lipid films. DMPE was used as a model membrane lipid because, first, it plays a particular role in the transport of quinolones across membranes and, second, it is useful for Brewster angle microscopy (BAM) studies because it forms characteristic domains in the liquid expanded-liquid condensed phase transition region.…”

Section: Introductionmentioning

confidence: 99%

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Molecular Organization of Nalidixate Conjugated Calixarenes in Bacterial Model Membranes Probed by Molecular Dynamics Simulation and Langmuir Monolayer Studies

Korchowiec

Gorczyca

et al. 2015

J. Phys. Chem. B

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Two p-tert-butylcalix[4]arene derivatives bearing one or two nalidixic acid groups connected to the lower rim of p-tert-butylcalix[4]arene through the propylenic spacer were studied upon interaction with model bacterial membranes. Indeed, these derivatives were developed recently as new macrocyclic antibiotic carriers for antibacterial therapy. To obtain molecular level information about the interaction between the calixarene conjugates and a membrane lipid, atomistic molecular dynamics simulation, as well as surface pressure, surface potential, polarization modulation infrared reflection-absorption spectroscopy, and Brewster angle microscopy studies of 1,2-dimyristoyl-sn-glycero-3-phosphoethanolamine (DMPE)-calixarene derivative films were performed. The results obtained indicate that the interaction between the calixarene derivatives and DMPE occurs via the phosphate and carbonyl groups present in the lipid. Although both calixarene derivatives increase the chain tilt and conformational disordering of the DMPE molecules, these effects are more important in the case of the monosubstituted derivative. Importantly, the two derivatives have an opposite impact on hydration of the phosphoglyceride polar head.

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“…33, 34 We want to mention that thermodynamic terms used here were defined in our previous papers. 35,36 Namely, in accordance with the definition of Gibbs energy of mixing, ΔG mix = G − (x 1 G 1 + x 2 G 2 ), eq 2 gives ΔG mix instead of ΔG exc given by Goodrich at al. 33 and Bacon et al 34 Polarization-Modulation Infrared Reflection−Absorption Spectroscopy (PM-IRRAS).…”

Section: ■ Experimental Sectionmentioning

confidence: 94%

A Study of the Interaction between a Family of Gemini Amphiphilic Pseudopeptides and Model Monomolecular Film Membranes Formed with a Cardiolipin

Gorczyca

Korchowiec

et al. 2015

J. Phys. Chem. B

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The interaction between five gemini amphiphilic pseudopeptides (GAPs) differing by the length of the central spacer and a model membrane lipid, 1,3-bis[1,2-dimyristoyl-sn-glycero-3-phospho]-sn-glycerol (cardiolipin) were studied with the aim to evaluate their possible antimicrobial properties. To this end, monomolecular films were formed at the air/water interface with pure cardiolipin or cardiolipin/GAPs mixtures; film properties were determined using surface pressure and surface potential measurements, as well as polarization-modulation infrared reflection–absorption spectroscopy. Moreover, to better understand the GAPs-phospholipid interaction at the molecular level, molecular dynamics simulations were performed. The results obtained indicate that the length of the central spacer has an effect on the interaction of GAPs with cardiolipin and on the properties of the lipid film. The GAPs with the longer linkers can be expected to be useful for biological membrane modification and for possible antimicrobial applications.

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Interaction of a β-lactam calixarene derivative with a model eukaryotic membrane affects the activity of PLA2

Cited by 21 publications

References 37 publications

Interaction of para-tert-butylcalix[6]arene molecules in Langmuir films with cadmium ions and their effects on molecular conformation and surface potential

Interaction of para-tert-butylcalix[6]arene molecules in Langmuir films with cadmium ions and their effects on molecular conformation and surface potential

Molecular Organization of Nalidixate Conjugated Calixarenes in Bacterial Model Membranes Probed by Molecular Dynamics Simulation and Langmuir Monolayer Studies

A Study of the Interaction between a Family of Gemini Amphiphilic Pseudopeptides and Model Monomolecular Film Membranes Formed with a Cardiolipin

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