Sphingomyelin ability to act as chiral selector using nanodisc electrokinetic chromatography

Penny, William M.; Palmer, Christopher P.

doi:10.1016/j.chemphyslip.2018.05.002

Cited by 5 publications

(2 citation statements)

References 39 publications

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“…Meanwhile, the different, and often opposite activity of drug enantiomers is a big problem for pharmacology, since most chiral drugs are still used in the form of racemates [ 2 , 3 , 4 , 5 ]. Note that stereoselectivity is well established for drug-receptor binding and enzyme catalysis, but has been scarcely investigated for carrier-mediated membrane transport [ 6 , 7 , 8 , 9 ].…”

Section: Introductionmentioning

confidence: 99%

Stereoselectivity of Interaction of Nonsteroidal Anti-Inflammatory Drug S-Ketoprofen with L/D-Tryptophan in Phospholipid Membranes

2022

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The mechanisms of stereoselectivity of the interaction of chiral drugs with active sites of enzymes and cell receptors attract significant attention. The first reason is the difference in therapeutic activity of the enantiomers of the common drugs. Another reason is the interest in the role of chiral inversion of amino acids involved in various peptides in the development of many diseases including Alzheimer’s, Parkinson’s, type II diabetes, and a number of other pathological conditions. In our study we use elementary chemical process—electron transfer (ET) to simulate individual stages of ligand–receptor and enzyme–substrate interactions. In particular, previous studies of photoinduced ET in chiral donor-acceptor dyads consisting of the nonsteroidal anti-inflammatory drug (R/S)-ketoprofen and (L)-tryptophan show the stereo and spin selectivity of ET in diastereomers. The present study is devoted to the interaction of (S)-ketoprofen with L- and D-enantiomers of tryptophan in homogeneous aqueous solution and in phospholipid membranes. The study was done using the NMR technique and molecular modeling. These approaches confirm efficient penetration of ketoprofen into the lipid bilayer and binding with tryptophan molecule. The short-lived paramagnetic intermediates formed during the photoinduced ET from electron donor tryptophan to ketoprofen have been detected using the chemically induced dynamic nuclear polarization (CIDNP) technique. It was found that S-ketoprofen interacts stereoselectively with tryptophan enantiomers in the lipid membrane. The formation of the ketyl radical of ketoprofen under irradiation leads to the oxidation of membrane lipids and may be the cause of ketoprofen phototoxicity. However, in contrast to a homogeneous solution in phosphate buffer saline, where the amino acid tryptophan accelerates the photodecomposition of KP due to intramolecular hydrogen transfer, tryptophan in a lipid membrane significantly reduces the rate of photodegradation due to a reversible electron (or hydrogen) transfer reaction. The stereoselectivity in the rate of KP and lipids decomposition under UV irradiation of S-ketoprofen in the presence of tryptophan enantiomers in lipid bilayer has been detected.

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Section: Introductionmentioning

confidence: 99%

Stereoselectivity of Interaction of Nonsteroidal Anti-Inflammatory Drug S-Ketoprofen with L/D-Tryptophan in Phospholipid Membranes

2022

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“…[68] Similarly, SPM nanodisks have been used for chiral separation chromatography of naphthol, a fluorescent organic compound. [71] These studies show the potential of lipids to be used as chiral selectors in separations chemistry.…”

Section: Small Biomoleculesmentioning

confidence: 94%

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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Preferential adsorption of L-tryptophan by L-phospholipid coated porous polymer particles

Takase

Suga

Matsune

et al. 2022

Colloids and Surfaces B: Biointerfaces

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Sphingomyelin ability to act as chiral selector using nanodisc electrokinetic chromatography

Cited by 5 publications

References 39 publications

Stereoselectivity of Interaction of Nonsteroidal Anti-Inflammatory Drug S-Ketoprofen with L/D-Tryptophan in Phospholipid Membranes

Stereoselectivity of Interaction of Nonsteroidal Anti-Inflammatory Drug S-Ketoprofen with L/D-Tryptophan in Phospholipid Membranes

Probing the Role of Chirality in Phospholipid Membranes

Preferential adsorption of L-tryptophan by L-phospholipid coated porous polymer particles

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