Association of ibuprofen at the polar/apolar interface of lipid membranes

Aloi, Erika; Rizzuti, Bruno; Guzzi, Rita; Bartucci, Rosa

doi:10.1016/j.abb.2018.07.013

Cited by 19 publications

(12 citation statements)

References 39 publications

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“…This statement is to be compared with the results of MD simulations for ibuprofen embedded in lipid bilayers [28,51,52] which indicate that ibuprofen molecules prefer to be located in the hydrophobic interior. This is not surprising because, although a hydrophilic carboxylate group of ibuprofen interacts with lipid hydrophilic heads, its large non-polar residue is indeed expected to be located in the hydrophobic interior.…”

Section: Pulsed Epr: Location In the Popc Membranementioning

confidence: 99%

“…In this regard, new data on the processes of interaction of ibuprofen with lipid membranes and with proteins, previously inaccessible for detection and description, could be extremely useful. Different methods, such as X-ray diffraction/scattering [17,18], differential scanning calorimetry [19], quasielastic neutron scattering [20], fluorescence [21], neutron spin echo [22], electrochemical impedance [23], Raman microspectroscopy [24], vibrational sum frequency spectroscopy [25], powder NMR [26] and electron paramagnetic resonance (EPR) spectroscopy [27,28] are used to study ibuprofen-mediated changes in model lipid membranes.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Spin-Labeled Ibuprofen and Its Interaction with Lipid Membranes

2022

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Ibuprofen is a non-steroidal anti-inflammatory drug possessing analgesic and antipyretic activity. Electron paramagnetic resonance (EPR) spectroscopy could be applied to study its interaction with biological membranes and proteins if its spin-labeled analogs were synthesized. Here, a simple sequence of ibuprofen transformations—nitration, esterification, reduction, Sandmeyer reaction, Sonogashira cross-coupling, oxidation and saponification—was developed to attain this goal. The synthesis resulted in spin-labeled ibuprofen (ibuprofen-SL) in which the spin label TEMPOL is attached to the benzene ring. EPR spectra confirmed interaction of ibuprofen-SL with 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC) bilayers. Using 2H electron spin echo envelope modulation (ESEEM) spectroscopy, ibuprofen-SL was found to be embedded into the hydrophobic bilayer interior.

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Section: Pulsed Epr: Location In the Popc Membranementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of Spin-Labeled Ibuprofen and Its Interaction with Lipid Membranes

2022

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“…The inner membrane fluidity of the lipid nanovesicles was evaluated as described previously 22 , 23 . The fluorescent probe DPH was added to the lipid nanovesicle suspension at a molar ratio of 250:1, lipid:DPH; the final concentrations of lipid and DPH were 100 and 0.4 μM, respectively.…”

Section: Methodsmentioning

confidence: 99%

Controlled rate slow freezing with lyoprotective agent to retain the integrity of lipid nanovesicles during lyophilization

Yang

Choi

et al. 2021

Sci Rep

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We designed a novel lyophilization method using controlled rate slow freezing (CSF) with lyoprotective agent (LPA) to achieve intact lipid nanovesicles after lyophilization. During the freezing step, LPA prevented water supercooling, and the freezing rate was controlled by CSF. Regulating the freezing rate by various liquid media was a crucial determinant of membrane disruption, and isopropanol (freezing rate of 0.933 °C/min) was the optimal medium for the CSF system. Lyophilized lipid nanovesicle using both CSF and LPA retained 92.9% of the core material and had uniform size distributions (Z-average diameter = 133.4 nm, polydispersity index = 0.144), similar to intact vesicles (120.7 nm and 0.159, respectively), after rehydration. Only lyophilized lipid nanovesicle using both CSF and LPA showed no changes in membrane fluidity and polarity. This lyophilization method can be applied to improve storage stability of lipid nanocarriers encapsulating drugs while retaining their original activity.

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“…[73] It is known that IBU affects characteristics such as fluidity and hydration of DMPC membranes. [74] It is unclear if these effects are only due to one enantiomer of IBU. The Umakoshi group found that DOPC liposomes showed limited chiral discrimination between the two enantiomers of IBU, even though IBU inserts into the liposomes and reaches the chiral glycerol moiety.…”

Section: Bioactive Small Moleculesmentioning

confidence: 99%

Probing the Role of Chirality in Phospholipid Membranes

2021

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Nucleotides, amino acids, sugars, and lipids are almost ubiquitously homochiral within individual cells on Earth. While oligonucleotides and proteins exist as one natural chirality throughout the tree of life, two stereoisomers of phospholipids have separately emerged in archaea and bacteria, an evolutionary divergence known as "the lipid divide". Within this review, we focus on the emergence of phospholipid homochirality and compare the stability of synthetic homochiral and heterochiral membranes in vitro. We discuss chemical probes designed to study the stereospecific interactions of lipid membranes in vitro. Overall, we aim to highlight studies that help elucidate the determinants of stereospecific interactions between lipids, peptides, and small molecule ligands. Continued work in understanding the drivers of favorable interactions between chiral molecules and biological membranes will lead to the design of increasingly selective chemical tools for bioorthogonal labeling of lipid membranes and safer membrane-associating pharmaceuticals.

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Association of ibuprofen at the polar/apolar interface of lipid membranes

Cited by 19 publications

References 39 publications

Synthesis of Spin-Labeled Ibuprofen and Its Interaction with Lipid Membranes

Synthesis of Spin-Labeled Ibuprofen and Its Interaction with Lipid Membranes

Controlled rate slow freezing with lyoprotective agent to retain the integrity of lipid nanovesicles during lyophilization

Probing the Role of Chirality in Phospholipid Membranes

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