The effect of propoxycaine·HCl on the physical properties of neuronal membranes

Lee, Jong Hwa; Kim, Dong Il; Mun, Hun; Lee, Sung Key; Kim, Jong Ho; Lee, Jang Hoon; Park, Yi Hoon; Jeon, Young Chan; Yoon, Ung Chan; Bae, Moon Kyung; Jang, Hye Ock; Wood, W. Gibson; Yun, Il Dong

doi:10.1016/j.chemphyslip.2008.03.009

Cited by 6 publications

(13 citation statements)

References 39 publications

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“…These features can influence the bilayer permeability and optimal activity of membrane bound proteins 194. It is worth noting that the term ‘fluidity’ and what it encompasses remains under debate 28,229,230. A number of studies fall into this category: B1.…”

Section: Fluorescent Analogs Of Phospholipids and Fatty Acidsmentioning

confidence: 99%

Fluorescent Analogs of Biomolecular Building Blocks: Design, Properties, and Applications

2010

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Section: Fluorescent Analogs Of Phospholipids and Fatty Acidsmentioning

confidence: 99%

Fluorescent Analogs of Biomolecular Building Blocks: Design, Properties, and Applications

2010

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“…Despite repulsions against the membrane lipid interaction concept, data have been suggesting the action of local anesthetics on lipid bilayers (Yun et al 2002; Högberg et al 2007; Lee et al 2008). Although the ionic analogues of local anesthetics had been recognized to be devoid of the pharmacological activity because of their membrane-impermeability, the extracellular application of quaternary lidocaine derivatives was found to affect action potentials and produce anesthesia, challenging the conventional notion that charged molecular species are ineffective when administered from the external side of cells (Štolc et al 1989; Lim et al 2007).…”

Section: Introductionmentioning

confidence: 99%

Membrane interactivity of charged local anesthetic derivative and stereoselectivity in membrane interaction of local anesthetic enantiomers

Tsuchiya¹

2008

LRA

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With respect to the membrane lipid theory as a molecular mechanism for local anesthetics, two critical subjects, the negligible effects of charged drugs when applied extracellularly and the stereoselective effects of enantiomers, were verified by paying particular attention to membrane components, phospholipids with the anionic property, and cholesterol with several chiral carbons. The membrane interactivities of structurally-different anesthetics were determined by their induced fluidity changes of liposomal membranes. Lidocaine (3.0 μmol/mL) fluidized phosphatidylcholine membranes, but not its quaternary derivative QX-314 (3.0 μmol/mL). Similarly to the mother molecule lidocaine, however, QX-314 fluidized phosphatidylserine-containing nerve cell model membranes and acidic phospholipids-constituting membranes depending on the acidity of membrane lipids. Positively charged local anesthetics are able to act on lipid bilayers by ion-pairing with anionic (acidic) phospholipids. Bupivacaine (0.75 mol/mL) and ropivacaine (0.75 and 1.0 μmol/mL) fluidized nerve cell model membranes with the potency being S(−)-enantiomer < racemate < R(+)-enantiomer (P < 0.01, vs antipode and racemate) and cardiac cell model membranes with the potency being S(−)-ropivacaine < S(−)-bupivacaine < R(+)-bupivacaine (P < 0.01). However, their membrane effects were not different when removing cholesterol from the model membranes. Stereoselectivity is producible by cholesterol which increases the chirality of lipid bilayers and enables to discriminate anesthetic enantiomers. The membrane lipid interaction should be reevaluated as the mode of action of local anesthetics.

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“…SPMV was isolated using the procedure reported earlier [3,4,14,16-20]. Their protein concentration was determined using the method reported by Lowry et al [21] with BSA as the standard.…”

Section: Methodsmentioning

confidence: 99%

“…The first considers the direct binding of local anesthetic molecules to the specific receptors on the sodium channels [1-4], and the second proposes the general perturbation of the bulk membrane structure by anesthetics and its consequences on the channel function [3-9]. A significant amount of evidence supports the specific receptor hypothesis [10].…”

Section: Introductionmentioning

confidence: 99%

“…This is due to the interest in biological membranes as well as the unique information on the intermolecular interactions that can be derived from an investigation of the volume changes. The potency of an anesthetic increases roughly in proportion to its lipid/water partition coefficient, strongly suggesting an amphiphilic site for anesthetic molecules [3,4,8,13-15]. Yun et al [8] reported that local anesthetics decreased the microviscosity of synaptosomal plasma membrane vesicles isolated from the bovine cerebral cortex (SPMV).…”

Section: Introductionmentioning

confidence: 99%

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Decreasing Effect of Lidocaine·HCl on the Thickness of the Neuronal and Model Membrane

Park

Kim

et al. 2013

Korean J Physiol Pharmacol

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This study examined the mechanism of action of a local anesthetic, lidocaine·HCl. Energy transfer between the surface fluorescent probe, 1-anilinonaphthalene-8-sulfonic acid, and the hydrophobic fluorescent probe, 1,3-di(1-pyrenyl) propane, was used to determine the effect of lidocaine·HCl on the thickness (D) of the synaptosomal plasma membrane vesicles (SPMV) isolated from the bovine cerebral cortex, and liposomes of the total lipids (SPMVTL) and phospholipids (SPMVPL) extracted from the SPMV. The thickness (D) of the intact SPMV, SPMVTL and SPMVPL were 1.044±0.008, 0.914±0.005 and 0.890±0.003 (arbitrary units, n=5) at 37℃ (pH 7.4), respectively. Lidocaine·HCl decreased the thickness of the neuronal and model membrane lipid bilayers in a dose-dependent manner with a significant decrease in the thickness, even at 0.1 mM. The decreasing effect of lidocaine·HCl on the membrane thickness might be responsible for some, but not all of its anesthetic action.

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The effect of propoxycaine·HCl on the physical properties of neuronal membranes

Cited by 6 publications

References 39 publications

Fluorescent Analogs of Biomolecular Building Blocks: Design, Properties, and Applications

Fluorescent Analogs of Biomolecular Building Blocks: Design, Properties, and Applications

Membrane interactivity of charged local anesthetic derivative and stereoselectivity in membrane interaction of local anesthetic enantiomers

Decreasing Effect of Lidocaine·HCl on the Thickness of the Neuronal and Model Membrane

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