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PubMed2006

Use of steady-state laurdan fluorescence to detect changes in liquid ordered phases in human erythrocyte membranes.

In artificial phospholipid bilayers, dual measurements of laurdan steady-state anisotropy and emission spectra can be used to identify the presence of liquid ordered phases. Human erythrocytes were used as a model to test whether similar measurements could be applied to biological samples. Specifically, laurdan anisotropy and emission spectra were obtained from native erythrocytes before and after treatment with calcium ionophore and from the microvesicles (known to be enriched in liquid ordered domains) shed from the cells during calcium entry. Spectral and anisotropy data were consistent with an increased order and reduced fluidity of erythrocyte membrane lipids upon ionophore treatment. Microvesicle membranes appeared more ordered than native erythrocytes and similar to ionophore-treated cells based on laurdan emission. In contrast, the anisotropy value was lower in microvesicles compared to ionophore-treated cells, suggesting greater probe mobility. Parallel measurements of diphenylhexatriene anisotropy corroborated the laurdan data. These results were consistent with the liquid ordered property of microvesicle membranes based on comparisons to behavior in artificial membranes. Two-photon microscopy was used to examine the distribution of laurdan fluorescence along the surface of erythrocyte membranes before and after ionophore treatment. A dual spatial analysis of laurdan anisotropy, as revealed by the distribution of laurdan emission spectra, and intensity excited by polarized light suggested that the plasma membranes of ionophore-treated erythrocytes may also exhibit elevated numbers of liquid ordered domains.

2-Naphthylamine↗
PubMed2001

The mechanism of the stabilization of the hexagonal II (HII) phase in phosphatidylethanolamine membranes in the presence of low concentrations of dimethyl sulfoxide.

Dimethyl sulfoxide (DMSO), a water-miscible organic solvent, has been used as a cryoprotectant for cells. It is known that DMSO stabilizes the HII phase of phosphatidylethanolamine (PE) membranes rather than the Lalpha phase, while most other water-miscible organic solvents such as acetone and ethanol destabilize the HII phase. To elucidate the mechanism for this stabilizing effect of DMSO on the HII phase, we have investigated its effects on the structures and physical properties of PE membranes. X-ray diffraction data indicated that dipalmitoleoylphosphatidylethanolamine (DPOPE) membranes in H2O at 20 degrees C were in the Lalpha phase and that an Lalpha to HII phase transition occurred at X=0.060 (mole fraction of DMSO) in water/DMSO mixtures. As the DMSO concentration increased, the basis vector length of the dioleoylphosphatidylethanolamine (DOPE)/ 16 wt% tetradecane membrane and also of the DPOPE/ 16 wt% tetradecane membrane in the HII phase decreased, suggesting that the spontaneous curvature of these membranes increased. We have also investigated the effects of DMSO on the physical properties of the PE membranes, and compared them with those of acetone. As the DMSO concentration increased, the excimer to monomer fluorescence intensities of pyrene-phosphatidylcholine in the PE membranes decreased, indicating that the membrane fluidity decreased, and also the generalized polarization value of the Laurdan fluorescent probe in the DPOPE membrane increased, indicating that the polarity of the membrane interface decreased. On the other hand, acetone had the opposite effects to DMSO. The interaction free energy between the membrane surface segments and solvent increased with an increase in DMSO concentration. It decreased the amount of solvent in the membrane interface, inducing an increase in the spontaneous curvature. This can reasonably explain the effects of DMSO on the phase stability and the physical properties of the membranes.

2-Naphthylamine↗
PubMed1998

In situ determination of intracellular membrane physical state heterogeneity in renal epithelial cells using fluorescence ratio microscopy.

6-Lauroyl-2-dimethylaminonaphtalene (laurdan) shows a spectral sensitivity to the lipid phase state with a 50 nm red shift of the emission maximum when passing from the gel to the liquid crystalline phase. This spectral sensitivity allows one to determine the membrane physical state using Generalized Polarization (GP). In the present experiments, we used fluorescence ratio imaging microscopy to determine the laurdan GP in living kidney cells. Two renal epithelial cells lines, MDCK and LLC-PK1 cells, and CV-1 cells, a fibroblast-like renal cell line were investigated. In these cells, laurdan labels both the plasma membrane and intracellular membranes. Comparison of spectrofluorimetry and fluorescence ratio imaging data obtained from liposomes and cells suspensions labeled with laurdan demonstrates that the GP can be accurately determined using common fluorescence microscopy equipment. The GP mean values determined from individual cells varied from 0.2 to 0.4 for the epithelial cells as compared to 0.0-0.1 for CV1 cells. Using living MDCK cells grown as a monolayer, the GP maps indicated that, within a single cell, the intracellular GP values varied from 0.0 to 0.6, i.e., from the equivalent of a liquid-crystalline state to a gel or a lipid-ordered state, and that there was a marked heterogeneity in the spatial distribution of the GP values. To further characterize this intracellular heterogeneity, co-localization experiments with specific organelle markers were undertaken. The results strongly suggest that in intact cells at physiological temperature, GP values decrease in the following order: plasma membranes > endosomes > mitochondria > Golgi apparatus.

2-Naphthylamine↗
PubMed2005

Minimum inhibitory concentrations of herbal essential oils and monolaurin for gram-positive and gram-negative bacteria.

New, safe antimicrobial agents are needed to prevent and overcome severe bacterial, viral, and fungal infections. Based on our previous experience and that of others, we postulated that herbal essential oils, such as those of origanum, and monolaurin offer such possibilities. We examined in vitro the cidal and/or static effects of oil of origanum, several other essential oils, and monolaurin on Staphylococcus aureus, Bacillus anthracis Sterne, Escherichia coli, Klebsiella pneumoniae, Helicobacter pylori, and Mycobacterium terrae. Origanum proved cidal to all tested organisms with the exception of B. anthracis Sterne in which it was static. Monolaurin was cidal to S. aureus and M. terrae but not to E. coli and K. pneumoniae. Unlike the other two gram-negative organisms, H. pylori were extremely sensitive to monolaurin. Similar to origanum, monolaurin was static to B. anthracis Sterne. Because of their longstanding safety record, origanum and/or monolaurin, alone or combined with antibiotics, might prove useful in the prevention and treatment of severe bacterial infections, especially those that are difficult to treat and/or are antibiotic resistant.

Anti-Bacterial Agents↗
PubMed2000

Kinetic properties of Penicillium cyclopium lipases studied with vinyl esters.

Penicillium cyclopium produces two lipases with different substrate specificities. Lipase I is predominantly active on triacylglycerols whereas lipase II hydrolyzes mono- and diacylglycerols but not triacylglycerols. In this study, we compared the kinetic properties of P. cyclopium lipases and human pancreatic lipase, a classical triacylglycerol lipase, by using vinyl esters as substrates. Results indicate that P. cyclopium lipases I and II and human pancreatic lipase hydrolyze solutions of vinyl propionate or vinyl butyrate at high relative rates compared with emulsions of the same esters, although, in all cases, maximal activity is reached in the presence of emulsified particles, at substrate concentrations above the solubility limit. It appears that partially water-soluble short-chain vinyl esters are suitable substrates for comparing the activity of lipolytic enzymes of different origin and specificity toward esters in solution and in emulsion.

Biochemistry↗
PubMed2005

Synthesis of a novel series of 2-methylsulfanyl fatty acids and their toxicity on the human K-562 and U-937 leukemia cell lines.

The hitherto unknown 2-methylsulfanyldecanoic acid and 2-methylsulfanyldodecanoic acid were synthesized from methyl decanoate and methyl dodecanoate, respectively, through the reaction of lithium diisopropylamide and dimethyldisulfide in THF followed by saponification with potassium hydroxide in ethanol. Both alpha-methylsulfanylated FA were cytotoxic to the human chronic myelogenous leukemia K-562 and the human histiocytic lymphoma U-937 cell lines with EC50 values in the 200-300 microM range, which makes them more cytotoxic to these cell lines than decanoic and/or dodecanoic acid. The cytotoxicity of the studied FA toward K-562 followed the order 2-SCH3-12:0 > 2-SCH3-10:0 > 10:0 > 12:0 > 2-OCH3-12:0, whereas toward U-937 the cytotoxicity was 2-SCH3-10:0 > 2-SCH3-12:0 > 12:0 > 10:0 > 2-OCH3-12:0. These results indicate that the alpha-methylsulfanyl substitution increases the cytotoxicity of the C10 and C12 FA toward the studied leukemia cell lines.

Amsacrine↗
PubMed2001

Effect of glycation of high density lipoproteins on their physicochemical properties and on paraoxonase activity.

We investigated the effect of incubation of high density lipoprotein (HDL) under hyperglycaemic conditions on lipid composition, physicochemical properties and activity of paraoxonase (PON), a calcium-dependent enzyme associated with HDL that contributes to the antiatherogenicity of this lipoprotein. HDL incubated for three days with various glucose concentrations (0-100 mM) had significant increases in thiobarbituric acid-reactive substances (TBARS) and conjugated dienes with respect to control HDL. These results suggest that lipid peroxidation accompanies HDL glycation in vitro. The susceptibility to lipid peroxidation was higher in HDL isolated from subjects with low HDL-paraxonase activity with respect to subjects with higher HDL-PON activity. The lipid compositional changes were associated with modifications of apoprotein conformation as shown by the red-shifted position of the maximum emission of tryptophan in treated HDL. The decrease in the Gp (generalized polarization) value and the red-shifted position of the maximum emission of Laurdan incorporated in treated HDL demonstrate modifications of order and polarity with respect to control HDL. The negative correlation established between the Gp value and TBARS demonstrates that the modifications in molecular order are likely related to the increase in lipid peroxidation products. The activity of paraoxonase was significantly decreased in HDL incubated at 37 degrees C; a greater decrease occurred in the presence of 50 mM and 100 mM glucose. This study demonstrates modifications of lipid composition, apoprotein conformation and physicochemical properties of HDL incubated in the presence of glucose. These modifications affect the activity of HDL-associated paraoxonase. The physicochemical properties of lipoproteins play a regulatory role in lipoprotein function. The modification of order and polarity of glycated HDL and the alterations in paraoxonase activity could potentially contribute to the accelerated atherosclerosis in diabetic patients.

2-Naphthylamine↗
PubMed1982

Influence of selected fatty acids upon plaque formation and caries in the rat.

Weanling rats were given high-sucrose cariogenic diets containing 2 per cent lauric acid, linoleic acid, nonanoic acid or monolaurin. Plaque accumulation was determined on the incisors of half the animals during only the last 3 days of the study and on the remaining animals at the conclusion of a 21-day test period when both sulcal and smooth-surface caries were assessed. No significant differences between the test groups in food consumption were observed nor were there any differences in body weight gain. The least amount of plaque was observed in the animals given monolaurin; the other fatty acids exerted no significant effect upon plaque accumulation. The smooth-surface caries data indicated that the least number of lesions occurred in the animals on the diet containing monolaurin. Nonanoic acid was significantly more effective in limiting sulcal caries than any of the other fatty acids studied. Thus both monolaurin and nonanoic acid have significant cariostatic activity in the rat.

Animals↗
PubMed1993

Interactions of Laurdan with phosphatidylcholine liposomes: a high pressure FTIR study.

The interactions of 6-lauroyl-2-dimethylaminonaphthalene (Laurdan) with L-alpha-dimyristoylphosphatidylcholine (DMPC) have been studied isothermally at 28 degrees C by Fourier-transform infrared spectroscopy (FTIR) at two pH values (6.8 and 3.0) and over the pressure range of 0.001-25 kbar. The results obtained with Laurdan are compared with those previously obtained with 6-propionyl-2-dimethylaminonaphthalene (Prodan) (Chong et al. (1989) Biochemistry 28, 8358-8363). The objective of this study is to delineate the differential interactions of Prodan and Laurdan with lipid membranes. The Laurdan carbonyl and naphthalene vibrational bands as well as the correlation field splitting of the methylene scissoring mode all indicate that in phospholipid model membrane systems, Laurdan behaves differently from Prodan. The data suggest that the chromophore of Laurdan is embedded somewhat deeper in the membrane than that of Prodan. The correlation field splitting pressure suggests that Laurdan causes more perturbation to DMPC vesicles than Prodan. Instead of being relocated to the exterior of the membrane as is the case of Prodan, Laurdan is found to remain in the membrane even when it is partially positively charged at pH 3. Apparently the stabilizing forces come from the strong van der Waals and hydrophobic interactions between the lauroyl chain and its neighboring lipid molecules. Laurdan seems to remain in the membrane at high pressures (up to 25 kbar). Using deuterated DMPC (d-DMPC) and deuterated L-alpha-dipalmitoylphosphatidylcholine (d-DPPC), we have demonstrated that, at 1 atm, there is a void space between the lauroyl chain of Laurdan and the acyl chain of the matrix lipid, regardless of the physical state of the matrix lipid. This void space, probably caused by the bulky naphthalene ring, is eventually diminished by elevated pressures.

1,2-Dipalmitoylphosphatidylcholine↗
PubMed1993

Perturbation of the chain melting transition of DPPC by galactose, agarose and Laurdan as determined by differential scanning calorimetry.

Differential scanning calorimetry was used to determine the effects of agarose hydrogel, galactose and the fluorophore Laurdan on the thermal behavior of multilamellar liposomes of DPPC. Although the effect of agarose on the phase transition was found to be negligible at low concentrations (< or = 2.5%), higher concentrations result in an endotherm that broadens and splits into two calorimetric events, one of which is at a higher temperature than that of hydrated DPPC. Equal weight fractions of galactose produce similar effects, although both fractions have raised melting temperatures. The higher melting components may be produced by osmotically-driven dehydration of the inner liposomal monolayers, a physical interaction between the carbohydrates and lipid headgroups, or a combination of both. Laurdan has little effect on the phase transition of DPPC vesicles at the concentration used in the sensor (0.67 mol%); concentrations up to 5.4 mol% only slightly lowered the melting temperature.

1,2-Dipalmitoylphosphatidylcholine↗
PubMed1993

Absence of lipid gel-phase domains in seven mammalian cell lines and in four primary cell types.

Fluorescence properties of 6-lauroyl-2-dimethylaminonaphthalene (Laurdan) are used to explore gel and liquid-crystalline phase domains coexistence in membranes of various cell types and in erythrocyte ghosts. Experiments and simulations were performed using liposomes composed of equimolar gel and liquid-crystalline phases in the absence and in the presence of 30 mol% cholesterol. In this model system two distinct coexisting phases can be easily recognized in the absence of cholesterol. When cholesterol is added to this phospholipid mixture, Laurdan parameters characteristic of the gel and of the liquid-crystalline phase are no longer resolvable. Coexisting domains of gel and liquid-crystalline phase were not detected in any of the examined cell membranes as judged by Laurdan excitation and emission Generalized Polarization (GP) spectra. Both in liposomes and in cell membranes, the behaviour of GP values as a function of excitation and emission wavelength corresponds to a homogeneous liquid-crystalline phase, despite the absolute GP values being relatively high, closer to the values observed in gel phase phospholipids. The presence of cholesterol appears to be the major cause for the homogeneity of phospholipids' dynamical properties in natural membranes, properties that appear close to the liquid-ordered phase state, defined to describe model systems with cholesterol concentration > or = 30 mol%.

2-Naphthylamine↗
PubMed1996

Laurdan fluorescence spectroscopy reveals a single liquid-crystalline lipid phase and lack of thermotropic phase transitions in the plasma membrane of living human sperm.

Membrane lipid phase(s), phase coexistence, and thermotropic phase transitions have been investigated in viable human spermatozoa using Laurdan fluorescence spectroscopy. Generalized polarization (GP) values derived from Laurdan excitation and emission spectra confirm that the sperm plasma membrane is a low polar, highly rigid (liquid-ordered) structure, and give evidence that, in the range from 10 degrees C to 42 degrees C, membrane lipids are in a single liquid-crystalline phase. The absence of phase transitions in the same thermal range argues against the hypothesis that the lipid domains previously detected on the sperm surface are produced by lipid lateral phase separation. The above findings are likely accounted for by the high cholesterol to phospholipid molar ratio found in the human sperm membrane. This is the first time that membrane lipid phase and polarity have been detected and quantified in living mammalian spermatozoa.

2-Naphthylamine↗
PubMed1996

Role of membrane fluidity in Epstein Barr virus (EBV) infectivity on Akata cell line.

Infection of Epstein Barr virus (EBV) to its host cells is initiated by the attachment of the glycoprotein gp 350/220 to the CR2 molecule. We used the sensitivity at the polar environment of the fluorescent probe Laurdan to study the membrane viscosity distribution from single leaving cells on two lymphoid cell lines Raji and Akata. Lipid analysis on both cells line demonstrated a lower cholesterol to phospholipid molar ratio on Akata than Raji cells. Cell fluidity analysis by Laurdan generalized emission polarization (GP) or by DPH polarization, indicated that membrane viscosity of Akata was lower than Raji cells. This difference was correlated to the increased susceptibility of Akata cells in expressing EBV early antigens (EA) after EBV superinfection.

2-Naphthylamine↗
PubMed1980

The influence of bile salts and bile lipoprotein complex on pancreatic lipase hydrolysis of monomolecular films.

We report a new technique which allows us to follow the lipolysis of monomolecular films in the presence of bile salts by using a 'zero-order' trough (Verger, R. and de Haas, G.H. (1973) Chem. Phys. Lipids 10, 127). The effects of bile salts, the bile lipoprotein complex and colipase on pancreatic lipase hydrolysis of rac-1,2-didodecanoylglycerol films were studied at different surface pressures. Taking into account previous studies, lipase activity was interpreted as a function of its degree of binding to the bile lipoprotein complex.

Animals↗
PubMed1988

In vivo studies on stereospecificity of the monoglyceride kinase, lysophosphatidic acid acyltransferase, phosphatidic acid phosphatase and CDP-diglyceride synthase of Streptococcus mutans BHT using the stereoisomers of the ether lipid, dodecylglycerol.

Streptococcus mutans BHT metabolizes radioactive 3-dodecyl-sn-glycerol (sn-3-DDG) almost exclusively to lysophosphatidic acid, phosphatidic acid and 1,3-diradyl-sn-glycerol, whereas the cells of this organism metabolize 1-dodecyl-sn-glycerol (sn-1-DDG) to all of the glycerol lipids of S. mutans BHT, with the largest amounts incorporated into phosphatidylglycerol and diradylglycerol (mostly the 1,2- but also the 1,3-isomer). (The common names of lipids, such as phosphatidic acid, are used in the broader sense to mean that the lipid may contain alkyl as well as acyl groups.) The addition of an equivalent amount of nonradioactive sn-3-DDG to radioactive sn-1-DDG causes more of the radioactivity to accumulate at phosphatidic acid. These results indicate that the monoglyceride kinase (EC 2.7.1.94), lysophosphatidic acid acyltransferase (EC 2.3.1.40) and the monoglyceride acyltransferase (EC 2.3.1.22) enzymatic reactions are not stereospecific, and that the CDP-diglyceride synthase (EC 2.7.7.41) and phosphatidic acid phosphatase (EC 3.1.3.4) metabolic steps are stereospecific in S. mutans BHT. The synthesis of phosphatidic acid and lysophosphatidic acid from sn-3-DDG provides a unique method for synthesizing these glycerol lipids with the uncommon stereochemical configuration in which the phosphate moiety is in the sn-1 position.

Acyltransferases↗
PubMed1995

Inhibition of phorbol ester-stimulated arachidonic acid release by alkylglycerols.

Although synthetic analogs of alkylglycerol (AG), such as dodecylglycerol, possess potent biological activities, their mechanism of action has not been determined. We recently detected substantial amounts of AG in unstimulated MDCK cells (Warne, T.R. and Robinson, M. (1991) Anal. Biochem. 198, 302-307) raising the possibility that the endogenous compound may act as a biological mediator. In this study, we examined the effects of synthetic AG on the release of arachidonic acid and arachidonate metabolites (AA) from Madin Darby canine kidney (MDCK) cells in response to 12-O-tetradecanoylphorbol-13-acetate (TPA) in order to characterize its effects on this signalling pathway. Treatment of MDCK with AG potently inhibited the release of AA during subsequent stimulation with TPA. Dodecylglycerol, the most effective of a series of alkyglycerols tested, was active at concentrations as low as 3 microM. The sn-1 and sn-3 forms of AG were found to be equally potent inhibitors. The effects of AG on AA release were not the result of arachidonic acid redistribution among cellular lipids and were independent of the phospholipid source of the released AA. AG did not inhibit the release of AA from MDCK cells when bradykinin was used as a stimulus, indicating selectivity for the effects produced by phorbol esters. These results show that AG can function as a potent and specific inhibitor of TPA-mediated AA release. The ability of AG to regulate this signalling pathway in intact MDCK cells, together with its natural occurrence, suggests a potential bioregulatory role for the endogenous compound as an inhibitor of protein kinase C.

Animals↗
PubMed1978

Studies on cephalopod rhodopsin. Fatty acid esters of sucrose as effective detergents.

Squid rhodopsin was extracted with solutions of fatty acid esters of sucrose (monolaurate and monostearate) and purified by DEAE-cellulose and concanavalin A-Sepharose affinity chromatography. The purified rhodopsin (A280/A480 = 2.5) contained 2.3 mol of glucosamine and 1.2 mol of phospholipid per mol of rhodopsin. The photoproduct metarhodopsin was also stable in these detergent solutions as in digitonin solution. Concanavalin A had no affinity for retinochrome.

Animals↗