2-(9-anthroyloxy)stearic acid (2-AS) -"DISCONTINUED" - Citations

2-(9-anthroyloxy)stearic acid (2-AS) -"DISCONTINUED" - Citations

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Abstract
Mechanism and kinetics of merocyanine 540 binding to phospholipid membranes.
AuthorsVerkman AS
JournalBiochemistry
PubMed ID3651436
The physicochemical mechanism for merocyanine 540 (M540) binding to unilamellar phosphatidylcholine (PC) vesicles was examined by steady-state and dynamic fluorescence and fluorescence stopped-flow methods. At 530-nm excitation, aqueous M540 has an emission peak at 565 nm, which red shifts to 580 nm with formation of membrane-bound monomers (M); bound dimers ... More
Lipid dynamics and lipid-protein interactions in rat enterocyte basolateral and microvillus membranes.
AuthorsBrasitus TA, Schachter D
JournalBiochemistry
PubMed ID6249340
Study of a fatty acid binding site of interphotoreceptor retinoid-binding protein using fluorescent fatty acids.
AuthorsPutilina T, Sittenfeld D, Chader GJ, Wiggert B
JournalBiochemistry
PubMed ID8466918
'Interphotoreceptor retinoid-binding protein (IRBP) is a 140-kDa glycolipoprotein which constitutes about 70% of the soluble protein of the retinal interphotoreceptor matrix. Much is known concerning its role in the transport of retinoids between photoreceptor cells and pigment epithelium but little is known about its interactions with lipids. Here we have ... More
Capsaicin affects the structure and phase organization of phospholipid membranes.
AuthorsAranda FJ, Villalaín J, Gómez-Fernández JC
JournalBiochim Biophys Acta
PubMed ID7696298
'Capsaicin is a natural compound with pharmacological and toxicological effects, which given its hydrophobicity, can influence the structure of membranes. The interaction of capsaicin with model membranes of dipalmitoylphosphatidylcholine and dielaidoylphosphatidylethanolamine has been studied by using differential scanning calorimetry, fluorescent probe spectroscopy and 31P-nuclear magnetic resonance. Capsaicin remarkably affects the ... More
Determination of the location of fluorescent probes attached to fatty acids using parallax analysis of fluorescence quenching: effect of carboxyl ionization state and environment on depth.
AuthorsAbrams FS, Chattopadhyay A, London E
JournalBiochemistry
PubMed ID1606156
'In this report, parallax analysis of fluorescence quenching (see the preceding paper in this issue) was used to determine the location (depth) of anthroyloxy and carbazole probes attached to model membrane inserted fatty acids. A monotonic increase in depth was found as the number of carbon atoms between the attachment ... More
Dexamethasone influences the lipid fluidity, lipid composition and glycosphingolipid glycosyltransferase activities of rat proximal-small-intestinal Golgi membranes.
AuthorsDudeja PK, Dahiya R, Brown MD, Brasitus TA
JournalBiochem J
PubMed ID3140778
'Experiments were performed to examine the effects of subcutaneous administration of the synthetic glucocorticoid dexamethasone (100 micrograms/day per 100 g body wt.) on the lipid fluidity, lipid composition and glycosphingolipid glycosyltransferase activities of rat proximal-small-intestinal Golgi membranes. After 4 days of treatment, Golgi membranes and liposomes prepared from treated rats ... More
Stretch sensitivity of transmembrane mobility of hydrogen peroxide through voids in the bilayer. Role of cardiolipin.
AuthorsMathai JC, Sitaramam V
JournalJ Biol Chem
PubMed ID8027032
'Availability of voids for diffusion of quinone in the membrane was shown to be the rate-limiting step in electron transport in mitochondria and chloroplasts (Mathai, J. C., Sauna, Z. E., John, O., and Sitaramam, V (1993) J. Biol. Chem. 268, 15442-15454). The primary role of voids in these diffusion-controlled reactions ... More
Groups with polar characteristics can locate at both shallow and deep locations in membranes: the behavior of dansyl and related probes.
AuthorsAsuncion-Punzalan E, Kachel K, London E
JournalBiochemistry
PubMed ID9521780
'To understand the relationship between the chemical structure of polar molecules and their membrane location, the behavior of dansyl (dimethylaminonaphthalenesulfonyl) and related polar fluorescent probes was examined. The depth of these probes in lipid bilayers was determined by parallax analysis of fluorescence quenching [Chattopadhyay and London (1987) Biochemistry 26, 39-45; ... More
The cytosol-membrane interface of normal and sickle erythrocytes. Effect of hemoglobin deoxygenation and sickling.
AuthorsEisinger J, Flores J, Bookchin RM
JournalJ Biol Chem
PubMed ID6725285
'The effect of deoxygenation on the amount of hemoglobin (Hb) proximal to the membranes of intact, density-fractionated normal (AA) and sickle (SS) red cells was studied by estimating resonance energy transfer efficiencies from fluorescent probes, 12-(9-anthroyloxy)stearic acid or 2-(9-anthroyloxy)stearic acid, in the outer lipid layer to cytoplasmic hemes. For each ... More
Fatty acid transfer in taurodeoxycholate mixed micelles.
AuthorsNarayanan VS, Storch J
JournalBiochemistry
PubMed ID8652524
'Dietary triacylglycerol is acted upon by lipolytic enzymes in the stomach and the proximal small intestine, releasing fatty acids and monoacylglycerol as the ultimate products. These digestive products are solubilized by bile released from the gall bladder, resulting in the formation of two product phases-vesicles and micelles-depending upon the concentration ... More
Membrane lipid dynamics in human promyelocytic leukemia cells sensitive and resistant to 12-O-tetradecanoylphorbol-13-acetate induction of differentiation.
AuthorsFisher PB, Schachter D, Abbott RE, Callaham MF, Huberman E
JournalCancer Res
PubMed ID6594192
'A series of fluorescent probes was used to analyze membrane lipid dynamics in promyelocytic leukemic cells sensitive (HL-60) or resistant (R-55) to phorbol diester induction of cell differentiation. When examined with the probe 1,6-diphenyl-1,3,5-hexatriene, which can penetrate the plasma membrane and intercalate in the lipids of both leaflets of the ... More
Ethinylestradiol administration selectively alters liver sinusoidal membrane lipid fluidity and protein composition.
AuthorsRosario J, Sutherland E, Zaccaro L, Simon FR
JournalBiochemistry
PubMed ID3415965
'Administration of high-dose ethinylestradiol to rats decreases bile flow, Na,K-ATPase specific activity, and liver plasma membrane fluidity. By use of highly purified sinusoidal and bile canalicular membrane fractions, the effect of ethinylestradiol administration on the protein and lipid composition and fluidity of plasma membrane fractions was examined. In sinusoidal fractions, ... More
Lipid peroxidation of the brush-border membrane: membrane physical properties and glucose transport.
AuthorsJourd'Heuil D, Vaananen P, Meddings JB
JournalAm J Physiol
PubMed ID8333526
'During inflammatory conditions, peroxidation of biological membranes often takes place. Deleterious physiological consequences, in terms of membrane function, could theoretically be mediated by either direct oxidative attack upon integral membrane proteins or by indirectly altering the lipid environment surrounding these proteins. To address this issue, in vitro peroxidation of guinea ... More
Calibration of the parallax fluorescence quenching method for determination of membrane penetration depth: refinement and comparison of quenching by spin-labeled and brominated lipids.
AuthorsAbrams FS, London E
JournalBiochemistry
PubMed ID1606155
'We previously introduced the "parallax" method, which uses fluorescence quenching by spin-labeled lipids in order to measure the depth of molecules within a membrane [Chattopadhyay, A., & London, E. (1987) Biochemistry 26, 39-45]. In this report the accuracy of this method is established by comparison of spin-label quenching to that ... More
Lipid composition and fluidity of rat enterocyte basolateral membranes. Regional differences.
AuthorsBrasitus TA, Schachter D
JournalBiochim Biophys Acta
PubMed ID6329292
'The lipid composition and fluidity of basolateral membranes prepared from the mucosa of the proximal, middle and distal thirds of the rat small intestine were determined. Fluidity, as assessed by the fluorescence anisotropy of 1,6-diphenyl-1,3,5-hexatriene and a series of anthroyloxy fatty acid derivatives, is decreased in the distal third as ... More
Dibucaine interaction with phospholipid vesicles. A resonance energy-transfer study.
AuthorsCoutinho A, Costa J, Faria JL, Berberan-Santos MN, Prieto MJ
JournalEur J Biochem
PubMed ID2338082
'Resonance energy transfer between a local anaesthetic, dibucaine (donor) and a set of functionalized probes [n-(9-anthroyloxy)stearic acids, n = 2, 3, 6, 7, 9 and 12 and 16-(9-anthroyloxy)palmitic acid] (acceptors) was found to be an efficient process with a critical radius of transfer Ro = 2.1 nm, this interaction being ... More
Fatty acid transfer from liver and intestinal fatty acid-binding proteins to membranes occurs by different mechanisms.
AuthorsHsu KT, Storch J
JournalJ Biol Chem
PubMed ID8662836
'Intestinal absorptive cells contain high levels of expression of two homologous fatty acid-binding proteins (FABP), liver FABP (L-FABP), and intestinal FABP (I-FABP). Both bind long chain fatty acids with relatively high affinity. The functional distinction, if any, between these two proteins remains unknown. It is often hypothesized that FABP are ... More
Dexamethasone-induced alterations in lipid composition and fluidity of rat proximal-small-intestinal brush-border membranes.
AuthorsBrasitus TA, Dudeja PK, Dahiya R, Halline A
JournalBiochem J
PubMed ID3435460
'A series of experiments were conducted to examine the possible effects of subcutaneous administration of the synthetic glucocorticoid dexamethasone (100 micrograms/day per 100 g body wt.) on the lipid fluidity and lipid composition of rat proximal-small-intestinal brush-border membranes. After 4 days of treatment, membranes and their liposomes prepared from treated ... More
Asymmetry of lipid dynamics in human erythrocyte membranes studied with permanent fluorophores.
AuthorsSchachter D, Cogan U, Abbott RE
JournalBiochemistry
PubMed ID7093236
'The fluorescence anisotropy and mean excited-state lifetime of 1,6-diphenyl-1,3,5-hexatriene, 12-(9-anthroyloxy)stearate, 2-(9-anthroyloxy)stearate, and pyrenedecanoic acid in the membranes of intact human erythrocytes, lysate suspensions, and ghost membranes were compared. The excited-state lifetime of each lipid fluorophore, estimated by single photon counting, is significantly shorter in the intact erythrocytes as compared to ... More
Membrane studies in Huntington's disease: steady state and time-dependent fluorescence spectroscopy of intact lymphocytes.
AuthorsPettegrew JW, Nichols JS, Stewart RM
JournalJ Neurochem
PubMed ID6453955
'Recent evidence suggests that a membrane abnormality, expressed in peripheral tissues such as the lymphocyte, may be present in Huntington''s disease (HD). Both steady state and time-dependent fluorescence spectroscopic methods were performed on lymphocytes from patients with HD and from age- and sex-matched controls. Lymphocyte membrane dynamics were studied, using ... More
Tryptophan imaging of membrane proteins.
AuthorsKleinfeld AM
JournalBiochemistry
PubMed ID4016088
'A theoretical analysis of resonance energy transfer between protein tryptophan and the n-(9-anthroyloxy) (AO) fatty acid probes has been carried out to evaluate its potential use in determining the tryptophan distribution in membrane proteins. The Förster theory for two-dimensional energy transfer was formulated to calculate multiple donor (tryptophan) transfer efficiencies ... More
Barbiturates inhibit hexose transport in cultured mammalian cells and human erythrocytes and interact directly with purified GLUT-1.
AuthorsHonkanen RA, McBath H, Kushmerick C, Callender GE, Scarlata SF, Fenstermacher JD, Haspel HC
JournalBiochemistry
PubMed ID7819247
'Barbiturates reduce cerebral blood flow, metabolism, and Glc transfer across the blood-brain barrier. The effect of barbiturates on hexose transport in cultured mammalian cell lines and human erythrocytes was studied. Pentobarbital inhibits [3H]-2-dGlc uptake in 3T3-C2 murine fibroblasts by approximately 95% and approximately 50% at 10 and 0.5 mM, respectively. ... More
Contribution of electrostatic and hydrophobic interactions of bitter substances with taste receptor membranes to generation of receptor potentials.
AuthorsKumazawa T, Kashiwayanagi M, Kurihara K
JournalBiochim Biophys Acta
PubMed ID3488763
'The effects of changed ionic environments on the frog taste nerve responses to the bitter substances were examined. The responses to quinine and strychnine carrying a positive charge were suppressed by an increase in ionic strength of stimulating solutions. It was concluded that electrostatic interaction of these positive bitter substances ... More
Effects of ethanol on the Escherichia coli plasma membrane.
AuthorsDombek KM, Ingram LO
JournalJ Bacteriol
PubMed ID6360997
'The effects of ethanol on the fluidity of Escherichia coli plasma membranes were examined by using a variety of fluorescent probes: 1,6-diphenyl-1,3,5-hexatriene, perylene, and a set of n-(9-anthroyloxy) fatty acids. The anthroyloxy fatty acid probes were used to examine the fluidity gradient across the width of the plasma membrane and ... More
Effects of benzyl alcohol on erythrocyte shape, membrane hemileaflet fluidity and membrane viscoelasticity.
AuthorsChabanel A, Abbott RE, Chien S, Schachter D
JournalBiochim Biophys Acta
PubMed ID4005233
'The effects of benzyl alcohol on cell shape, hemileaflet lipid fluidity and membrane rheology of human red blood cells were studied. Membrane fluidity was assessed by determining the fluorescence anisotropy of permeant probes (1,6-diphenyl-1,3,5-hexatriene,12-(9-anthroyloxy)stearate, 2-(9-anthroyloxy)stearate) and a new impermeant probe (N-stachyosylsuccinic acid dihydrazide-2-(9-anthroyloxy)stearate). Measurements made on intact red blood cells ... More
Decreased membrane deformability in Melanesian ovalocytes from Papua New Guinea.
AuthorsSaul A, Lamont G, Sawyer WH, Kidson C
JournalJ Cell Biol
PubMed ID6715408
'We examined the ability of Melanesian ovalocytes from Papua New Guinea to be deformed in order to probe the resistance of these cells to invasion by several species of malaria parasite. We found ovalocytes were refractile to drug-induced endocytosis, that they formed abnormal rouleaux, showed reduced deformability when aspirated into ... More
Fluorescent probe studies of the interactions of 1-alkyl-2-pyrrolidones with stratum corneum lipid liposomes.
AuthorsYoneto K, Li SK, Higuchi WI, Jiskoot W, Herron JN
JournalJ Pharm Sci
PubMed ID8742943
'Previously, the effects of a series of 1-alkyl-2-pyrrolidones (APs; C2-C8) on the lipoidal pathway of hairless mouse skin (HMS) were studied with a parallel pathway skin model. At their isoenhancement concentrations, these 1-alkyl-2-pyrrolidones induce the same transport enhancement (isoenhancement factor, EHMS) on the lipoidal pathway of the stratum comeum for ... More
Fluorescence anisotropy decays of n-(9-anthroyloxy) fatty acids in dipalmitoyl phosphatidylcholine vesicles. Localization of the effects of cholesterol addition.
AuthorsVincent M, de Foresta B, Gallay J, Alfsen A
JournalBiochem Biophys Res Commun
PubMed ID6897188
Effects of the cannabinoids on physical properties of brain membranes and phospholipid vesicles: fluorescence studies.
AuthorsHillard CJ, Harris RA, Bloom AS
JournalJ Pharmacol Exp Ther
PubMed ID2983062
'The effects of four cannabinoids on the physical properties of brain synaptic plasma membranes (SPM), lipid extracts of SPM and phospholipid vesicles were evaluated using fluorescence probes. In vitro, the psychoactive cannabinoids, delta 9-tetrahydrocannabinol (delta 9-THC) and 11-hydroxyl-delta 9-tetrahydrocannabinol (11-OH-delta 9-THC) at concentrations of 1 and 3 microM decreased polarization ... More
3-[p-(6-phenyl)-1,3,5-hexatrienyl]phenylpropionic acid (PA-DPH): characterization as a fluorescent membrane probe and binding to fatty acid binding proteins.
AuthorsTrotter PJ, Storch J
JournalBiochim Biophys Acta
PubMed ID2742883
'The negatively charged fluorophore 3-[p-(6-phenyl)-1,3,5-hexatrienyl]phenylpropionic acid (PA-DPH) was characterized by comparison with its parent compound DPH, and with cationic trimethylammonium-DPH (TMA-DPH). The molar absorption coefficient of PA-DPH (60,000 cm-1.mol-1) as well as its quantum yield (0.7) and fluorescence lifetime (5 ns) in fluid phase membranes are intermediate between DPH and ... More
The interaction of local anaesthetics with synthetic phospholipid bilayers.
AuthorsSikaris KA, Sawyer WH
JournalBiochem Pharmacol
PubMed ID7138557
'The preferred position and orientation of two local anaesthetics in lipid bilayers has been determined using fluorescence quenching techniques. The aromatic amine of tetracaine and butesin quenches the fluorescence of a series of n-(9-anthroyloxy) fatty acids (n = 2,6,9,12,16) which place a fluorophore at a graded series of depths from ... More
Alteration in rat liver microsomal membranes induced by acetaminophen.
AuthorsAraya H, Horie T, Hayashi M, Awazu S
JournalJ Pharmacobiodyn
PubMed ID3694422
'Acetaminophen caused a reversible change in the fluorescence polarization of eosin maleimide and dansyl chloride labeled to rat liver microsomes, indicating that acetaminophen acts on microsomal membrane proteins. Acetaminophen in the presence of nicotinamide adenine dinucleotide phosphate (NADPH), brought about an irreversible change in the fluorescence polarization of the probes. ... More
Properties of phosphatidylcholine bilayers as revealed by mixed-acyl phospholipid fluorescent probes containing n-(9-anthroyloxy) fatty acids.
AuthorsMason JT
JournalBiochim Biophys Acta
PubMed ID8075146
'A series of five mixed-acyl phosphatidylcholine (PC) fluorescent probes having the structure 1-caproyl-2-(n-(9-anthroyloxy)-acyl)-sn-glycero-3-phosphocholine, where the sn-2 anthroyloxy-labeled acyl chain is stearic acid (n = 2,6,9,12) or palmitic acid (n = 16), have been prepared. These probes have been used to study the thermal behavior and transbilayer organization of 1,2-distearoyl-PC (C(18)C(18)PC), ... More
Steady-state fluorescence polarization data in membranes. Resolution into physical parameters by an extended Perrin equation for restricted rotation of fluorophores.
Authorsvan der Meer BW, van Hoeven RP, van Blitterswijk WJ
JournalBiochim Biophys Acta
PubMed ID3942718
'An extended Perrin equation is derived applicable to the restricted rotation of fluorophores. The equation results in a relation between time-resolved (r infinity) and steady-state fluorescence anisotropy (rs) data. This relation contains a parameter m, which expresses the difference between rotational diffusion in a lipid membrane and that in an ... More
Effects of cholesterol on acyl chain dynamics in multilamellar vesicles of various phosphatidylcholines.
AuthorsKutchai H, Chandler LH, Zavoico GB
JournalBiochim Biophys Acta
PubMed ID6652079
'Phase modulation fluorescence spectroscopy was used to investigate the influence of cholesterol (0 to 50 mol%) on acyl chain dynamics in multilamellar vesicles of phosphatidylcholine. Four different phosphatidylcholines (DPPC, DOPC, POPC, and egg PC) and six different fluorescent probes (diphenylhexatriene and five anthroyloxy fatty acids) were employed. We found that: ... More
Rat proximal small intestinal Golgi membranes: lipid composition and fluidity.
AuthorsBrasitus TA, Dahiya R, Dudeja PK
JournalBiochim Biophys Acta
PubMed ID3337837
'The present studies were conducted to examine and characterize the lipid composition and physical state of the membrane lipids of rat proximal small intestinal Golgi membranes. Golgi membranes were purified from isolated enterocytes; lipids were extracted from these membranes and analyzed by thin-layer and gas-liquid chromatography. The ''static'' and ''dynamic'' ... More
Cytosol-membrane interface of human erythrocytes. A resonance energy transfer study.
AuthorsEisinger J, Flores J
JournalBiophys J
PubMed ID6838975
A comment on the localization of cyanine dye binding to brush-border membranes by the fluorescence quenching of n-(9-anthroyloxy) fatty acid probes.
AuthorsFaria JL, Berberan-Santos M, Prieto MJ
JournalBiochim Biophys Acta
PubMed ID2378877
This work comments on the location and orientation of 3,3'-dipropylthiodicarbocyanine (diS-C3-(5)) in renal brush-border membrane vesicles (RBBMV) (Cabrini, G. and Verkman, A.S. (1986) Biochim. Biophys. Acta 862, 285-293) evaluated from collisional quenching of n-(9-anthroyloxy)stearic acid (n-AS) fluorescence. At variance with these authors, it is concluded that the quenching is due ... More
Vertical fluctuations of phospholipid acyl chains in bilayers.
AuthorsWardlaw JR, Sawyer WH, Ghiggino KP
JournalFEBS Lett
PubMed ID3666138
The possibility of vertical displacement of acyl chains in lipid bilayers has been examined by quenching the fluorescence of 2-(9-anthroyloxy)palmitic acid with 5- and 16-doxylstearates in dipalmitoylphosphatidylcholine unilamellar vesicles. Measurement of lifetime and steady-state quenching showed that the dynamic component of quenching was independent of the transverse position of the ... More
Fluorescence quenching of a series of membrane probes measured in living cells by flow cytometry.
AuthorsCollins JM, Grogan WM
JournalCytometry
PubMed ID2036918
The transverse location normal to the bilayer surface of a series of n-(9-anthroyloxy) fatty acid probes, where n = 2, 3, 6, 7, 9, 12, and 16, was determined by fluorescence quenching measurements with a flow cytometer. We show that the anthroyloxy moieties of the probes locate at a graded ... More
Further characterization of mitochondrial contact sites: effect of short-chain alcohols on membrane fluidity and activity.
AuthorsArdail D, Lermé F, Louisot P
JournalBiochem Biophys Res Commun
PubMed ID2176492
Two mitochondrial contact site-enriched fractions were further characterized by freeze-fracture electron microscopy. Examination of the replicas revealed that these two fractions are in the form of vesicles with membrane sheets attached to the vesicles. The physical state of these fractions has been investigated by means of steady-state fluorescence polarization to ... More
The activation energy of incorporation of extrinsic probes in model vesicles.
AuthorsRockley MG, Najjar DS
JournalBiochim Biophys Acta
PubMed ID6894862
Time dependence of fluorescence enhancement of probes after addition to lipid vesicles has been used to investigate the position of chromophores in the lipid bilayer. Incorporation studies of a series of n-(9-anthroyloxy) fatty acids (n = 2, 2, 12 and 16) and 1,6-diphenylhexatriene in dipalmitoyl phosphatidylcholine vesicles are described. The ... More
The transverse organisation of ubiquinones in mitochondrial membranes as determined by fluorescence quenching. Evidence for a two-site model.
AuthorsChatelier RC, Sawyer WH
JournalEur Biophys J
PubMed ID3987642
The transverse organisation of ubiquinone in mitochondrial membranes was investigated by quenching a set of fluorescent fatty acids. We show that the fluorescent moiety of the probes is located at a graded series of depths in the mitochondrial membrane. The probes sense the characteristics of the lipid phase and do ... More
Fluorescence study of the membrane-perturbing action of sodium caprylate as related to promotion of drug absorption.
AuthorsKajii H, Horie T, Hayashi M, Awazu S
JournalJ Pharm Sci
PubMed ID3411458
The medium-chain fatty acid sodium caprylate released 6-carboxyfluorescein (CF), a model compound of water-soluble drugs, from the rat small intestinal brush border membrane (BBM) vesicles and liposomes containing CF. Caprylate caused a decrease in the fluorescence polarization of dansyl chloride, fluorescein isothiocyanate, and eosin maleimide covalently labeled to BBM. This ... More
Calcium alters the acyl chain composition and lipid fluidity of rat hepatocyte plasma membranes in vitro.
AuthorsStorch J, Schachter D
JournalBiochim Biophys Acta
PubMed ID3917683
Calcium ion decreases the lipid fluidity of isolated rat hepatocyte plasma membranes by modulating the activity of membrane enzymes which alter the lipid composition. To explore the mechanism of the effect of the cation, eight fluorophores were used to assess lipid fluidity via estimations of either steady-state fluorescence polarization or ... More
Perturbation of phospholipid bilayers by DDT.
AuthorsChefurka W, Chatelier RC, Sawyer WH
JournalBiochim Biophys Acta
PubMed ID3801467
The localization of the effects of DDT (5-50 mol%) addition on the acyl chain dynamics in unilamellar vesicles of two phosphatidylcholines (DPPC and egg PC) has been investigated by steady-state fluorescence polarization of a series of n-(9-anthroyloxy) fatty acids (n = 2, 6, 9, 12 and 16) whose fluorophore is ... More
A change in the lipid fluidity of the porcine intestinal brush-border membranes by lipid peroxidation. Studies using pyrene and fluorescent stearic acid derivatives.
AuthorsOhyashiki T, Ohtsuka T, Mohri T
JournalBiochim Biophys Acta
PubMed ID3756162
The effect of lipid peroxidation on the lipid fluidity of porcine intestinal brush-border membranes was examined by measuring the rotational mobility and the accessibility to fluorescence quenchers (CH3COOT1, CuSO4 and KI) of pyrene or n-(9-anthroyloxy)stearic acid (n = 2 or 12) in the membranes. The harmonic mean of the rotational ... More
Spectroscopic investigations on the binding site of bovine hepatic fatty acid binding protein. Evidence for the existence of a single binding site for two fatty acid molecules.
AuthorsKeuper HJ, Klein RA, Spener F
JournalChem Phys Lipids
PubMed ID4064218
The hydrophobic region of the binding site of a bovine fatty acid binding protein (pI 7.0-FABP) has been characterized using fluorescence and circular dichroism (CD) spectroscopy. Blue-shifts of fluorescence emission maxima and increased lifetimes of naphthylamine dyes, anthroyloxy-fatty acids, pyrene nonanoic acid and trans-parinaric acid indicated a hydrophobic interaction with ... More
pH-induced reorganization of synaptic membrane as revealed by fluorescence anisotropy and energy transfer.
AuthorsBurgun C, Waksman A, Crémel G
JournalArch Biochem Biophys
PubMed ID1897965
Two fluorescent probes, 2-(9-anthroyloxy)stearate and 12-(9-anthroyloxy)stearate, were used to investigate the effects of the neutralization of membrane charges on the organization of synaptic plasma membrane. Steady state fluorescence anisotropy measurements showed that a pH decrease provoked a rigidification of the synaptic membrane surface, whereas the bilayer core remained unaffected. The ... More
Membrane studies in Huntington's disease: steady-state fluorescence studies of intact erythrocytes.
AuthorsPettegrew JW, Nichols JS, Stewart RM
JournalAnn Neurol
PubMed ID6449174
Recent evidence suggests that a membrane abnormality may be present in Huntington's disease (HD), including peripheral tissues such as erythrocytes. Steady-state fluorescence spectroscopy was performed on intact erythrocytes from patients with HD and from normal age- and sex-matched controls. Fluorescent probes with known specificity for certain membrane areas were used ... More
Transfer of fluorescent fatty acids from liver and heart fatty acid-binding proteins to model membranes.
AuthorsStorch J, Bass NM
JournalJ Biol Chem
PubMed ID2335507
Fatty acid binding proteins (FABP) are a family of 14-15 kDa proteins found in high abundance in many mammalian cell types. The physiological functions of the FABP remain unknown. It is also not known whether each FABP has a unique function, or whether all FABP function in a similar manner ... More
Fluorescence polarization of six membrane probes in embryonal carcinoma cells after differentiation as measured on a FACS II cell sorter.
AuthorsSchaap GH, de Josselin de Jong JE, Jongkind JF
JournalCytometry
PubMed ID6201328
Fluorescence polarization measurements on a FACS II cell sorter were compared with static measurements on a spectrofluorimeter using calibration solutions and Hoechst 33258-labeled cells. For the flow cytometric measurements on the FACS we used a pseudodepolarizer for normalization of the output of the two photomultipliers. The results showed that fluorescein ... More
Energy-transfer study of cytochrome b5 using the anthroyloxy fatty acid membrane probes.
AuthorsKleinfeld AM, Lukacovic MF
JournalBiochemistry
PubMed ID4016089
Resonance energy transfer was used to study the structure of cytochrome b5 and its nonpolar segment reconstituted into sonicated vesicles of dimyristoylphosphatidylcholine. The n-(9-anthroyloxy) (AO) fatty acid probes were added to these vesicles, and energy-transfer measurements were carried out between tryptophan and AO, tryptophan and the heme moiety of cytochrome ... More
Lipid permeability of the intestinal microvillus membrane may be modulated by membrane fluidity in the rat.
AuthorsMeddings JB
JournalBiochim Biophys Acta
PubMed ID2765545
Fatty acids and cholesterol permeate across the intestinal microvillus membrane at rates dictated by the hydrophobicity of the permeating lipid and the permeability properties of the microvillus membrane. A theory has evolved suggesting that the chemical composition and physical properties of the microvillus membrane are important in determining microvillus membrane ... More
Consequences of omega -6-oleate desaturase deficiency on lipid dynamics and functional properties of mitochondrial membranes of Arabidopsis thaliana.
AuthorsCaiveau O, Fortune D, Cantrel C, Zachowski A, Moreau F
JournalJ Biol Chem
PubMed ID11104757
We probed the role of the polyunsaturated fatty acids on the dynamic and functional properties of mitochondrial membranes using the fad2 mutant of Arabidopsis thaliana, deficient in omega-6-oleate desaturase. In mitochondria of this mutant, the oleic acid content exceeded 70% of the total fatty acids, and the lipid/protein ratio was ... More
Developmental changes in hepatic basolateral membrane lipid composition and fluidity.
AuthorsNovak D, Ray W, Carver J, Grossman S
JournalBiochim Biophys Acta
PubMed ID1390865
Membrane fluidity and lipid composition influence the activity of a variety of membrane proteins. Decreased rates of hepatic ion clearance are associated with the neonatal period. We postulated that hepatic basolateral membranes derived from suckling animals might be less fluid than those from adult animals. Basolateral membrane vesicles were prepared ... More
Perturbations to lipid bilayers by spectroscopic probes as determined by dielectric measurements.
AuthorsAshcroft RG, Thulborn KR, Smith JR, Coster HG, Sawyer WH
JournalBiochim Biophys Acta
PubMed ID7426652
Dielectric measurements on lecithin/cholesterol bimolecular lipid membranes have indicated that the series of extrinsic fluorescent probe molecules, the n-(9-anthroyloxy) fatty acids, cause significant perturbation to the bilayer structure at concentrations equivalent to those used in fluorescence experiments (0.1 mol%). Perturbations were observed in the capacitance and conductance of the electrically ... More
Effect of cholesterol and protein content on membrane fluidity and 3 beta-hydroxysteroid dehydrogenase activity in mitochondrial inner membranes of bovine adrenal cortex.
AuthorsDe Paillerets C, Gallay J, Alfsen A
JournalBiochim Biophys Acta
PubMed ID6586204
The steroid biosynthetic enzymes in the adrenal cortex are localised in endoplasmic reticulum and mitochondrial membranes. For some of the enzymes in endoplasmic reticulum the activity appears to be modulated by lipid fluidity, (21-hydroxysteroid hydroxylase and 3 beta-hydroxysteroid dehydrogenase). A mechanism for the regulation of corticosteroid biosynthesis mediated by the ... More
Mechanism of fluorescent fatty acid transfer from adipocyte fatty acid binding protein to membranes.
AuthorsWootan MG, Bernlohr DA, Storch J
JournalBiochemistry
PubMed ID8357805
Adipocyte fatty acid binding protein (A-FABP) is a 15-kDa protein found in high abundance in the cytosol of adipose cells. To better understand the role of this protein in intracellular free fatty acid (ffa) transport, the mechanism of ffa transfer from A-FABP to model membranes was examined by monitoring the ... More
Lipid dynamics and lipid-protein interactions in rat hepatocyte plasma membranes.
AuthorsLivingstone CJ, Schachter D
JournalJ Biol Chem
PubMed ID7430161
Rat hepatocyte plasma membranes were isolated and examined by differential scanning calorimetry and by steady state fluorescence polarization of 1,6-diphenyl-1,3,5-hexatriene, 12-anthroyl stearate, and 2-anthroyl stearate. Calorimetry of the intact membranes revealed a reversible lipid thermotropic transition with lower and upper critical temperatures of 18 degrees and 31 degrees C, respectively. ... More
Shape of the fluidity gradient in the plasma membrane of living HeLa cells.
AuthorsCollins JM, Dominey RN, Grogan WM
JournalJ Lipid Res
PubMed ID2324646
The shape of the fluidity gradient of the outer hemi-leaflet of the plasma membrane of living HeLa cells was determined using a series of n-(9-anthroyloxy) fatty acid probes where n = 2, 3, 6, 7, 9, 10, 11, 12, and 16. Fluorescence uptake and steady-state anisotropy values were obtained with ... More
Dietary induction of acyl chain desaturases alters the lipid composition and fluidity of rat hepatocyte plasma membranes.
AuthorsStorch J, Schachter D
JournalBiochemistry
PubMed ID6324863
Rats were maintained on a regimen of intermittent starvation followed by refeeding a fat-free diet in order to induce hepatic acyl desaturase activities and other enzymes involved in lipid synthesis. The effects of the dietary regimen on the lipid composition and fluidity of isolated hepatocyte plasma membranes were compared to ... More
Interaction of alpha-tocopherol with fatty acids in membranes and ethanol.
AuthorsStillwell W, Ehringer W, Wassall SR
JournalBiochim Biophys Acta
PubMed ID1586661
The techniques of fluorescence polarization, ultraviolet light absorbance and fluorescence quenching by acrylamide are used to probe the structural role of alpha-tocopherol in phospholipid bilayers. Using 1,6-diphenyl-1,3,5-hexatriene (DPH) and a series of (anthroyloxy)stearic acid (AS) fluorescence probes, alpha-tocopherol is shown to increase fluidity and decrease order of gel state bilayers, ... More
Transport of fluorescent derivatives of fatty acids into cultured human leukemic myeloid cells and their subsequent metabolic utilization.
AuthorsMorand O, Fibach E, Dagan A, Gatt S
JournalBiochim Biophys Acta
PubMed ID6954994
Transport of fluorescent derivatives of fatty acids across the cell membrane of cultured human leukemic myeloid cells (HL 60) and their subsequent metabolic utilization were studied. The rates of uptake of these derivatives and their incorporation into cellular lipids wer compared with that of radioactively labelled palmitic acid. Three groups ... More
Ursodeoxycholate stimulates Na+-H+ exchange in rat liver basolateral plasma membrane vesicles.
AuthorsMoseley RH, Ballatori N, Smith DJ, Boyer JL
JournalJ Clin Invest
PubMed ID3040805
Na+:H+ and Cl-:HCO3- exchange are localized, respectively, to basolateral (blLPM) and canalicular (cLPM) rat liver plasma membranes. To determine whether these exchangers play a role in bile formation, we examined the effect of a choleretic agent, ursodeoxycholate (UDCA), on these exchange mechanisms. 22Na (1 mM) and 36Cl (5 mM) uptake ... More
Fluorescence resonance energy transfer analysis of lipopolysaccharide in detergent micelles.
AuthorsWiström CA, Jones GM, Tobias PS, Sklar LA
JournalBiophys J
PubMed ID8789116
Bacterial endotoxins or lipopolysaccharides (LPS), cell wall components of gram-negative bacteria, are involved in septic shock. LPS consists of a lipid A tail attached to core and O-antigen polysaccharides, but little is known about the supramolecular structure of LPS in blood. We have developed an approach to locate donor and ... More
Fatty acid binding sites of rodent adipocyte and heart fatty acid binding proteins: characterization using fluorescent fatty acids.
AuthorsWootan MG, Bass NM, Bernlohr DA, Storch J
JournalBiochemistry
PubMed ID2248947
Murine adipocyte and rat heart fatty acid binding proteins (FABP) are closely related members of a family of cytosolic proteins which bind long-chain free fatty acids (ffa). The physical and chemical characteristics of the fatty acid binding sites of these proteins were studied using a series of fluorescent analogues of ... More
Static and dynamic components of renal cortical brush border and basolateral membrane fluidity: role of cholesterol.
AuthorsMolitoris BA, Hoilien C
JournalJ Membr Biol
PubMed ID3694671
Static polarization and differential polarized phase fluorimetry studies on rat renal cortical brush border (BBM) and basolateral membranes (BLM) were undertaken to determine the membrane components responsible for differences in BBM and BLM fluidity, whether these differences were due to the order or dynamic components of membrane fluidity and if ... More
Extension of the parallax analysis of membrane penetration depth to the polar region of model membranes: use of fluorescence quenching by a spin-label attached to the phospholipid polar headgroup.
AuthorsAbrams FS, London E
JournalBiochemistry
PubMed ID8399232
The parallax method is a method by which the depth of fluorescent molecules within a membrane is calculated from the ratio of quenching induced by two spin-labeled phospholipids at different depths. In this report, the method is extended to measurements of depth in the polar headgroup region of the membrane ... More
Effect of diethylstilbestrol and related compounds on the Ca(2+)-transporting ATPase of sarcoplasmic reticulum.
AuthorsMartinez-Azorin F, Teruel JA, Fernandez-Belda F, Gomez-Fernandez JC
JournalJ Biol Chem
PubMed ID1318306
Diethylstilbestrol is a potent inhibitory agent of the Ca(2+)-ATPase activity of sarcoplasmic reticulum membranes. Other structurally related molecules, such as dienestrol or hexestrol having hydroxyl groups at para positions of the two benzene rings produce similar effects. The absence or derivatization of the hydroxyl groups as occurs with trans-stilbene or ... More
Localization of cyanine dye binding to brush-border membranes by quenching of n-(9-anthroyloxy) fatty acid probes.
AuthorsCabrini G, Verkman AS
JournalBiochim Biophys Acta
PubMed ID3778893
The location and orientation of 3,3'-dipropylthiodicarbocyanine (diS-C3-(5)) binding sites in renal brush-border membrane vesicles was examined from the quenching of n-(9-anthroyloxy) fatty acid (n-AS) fluorescence. Based on previous kinetic studies (Cabrini, G. and Verkman, A.S. (1986) J. Membrane Biol. 90, 163-175) monomeric aqueous diS-C3-(5) binds to brush-border membrane vesicles (BBMV) ... More
Lipid chain order and dynamics at different bilayer depths in liposomes of several phosphatidylcholines studied by differential polarized phase fluorescence.
AuthorsTricerri MA, Garda HA, Brenner RR
JournalChem Phys Lipids
PubMed ID8039258
The influence of acyl chain length, double bond number and position on the structural and dynamic properties of phosphatidylcholine bilayers in the liquid crystalline state was studied. The range and rate of the rotation of 1,6-diphenyl-1,3,5-hexatriene and a set of n-(9-anthroyloxy)stearates(n = 2, 7 and 12), which are located at ... More
Plasma membrane fluidity gradients of human peripheral blood leukocytes.
AuthorsCollins JM, Scott RB, Grogan WM
JournalJ Cell Physiol
PubMed ID2365745
The shape of the fluidity gradient of the outer hemileaflet of the plasma membrane of normal, living, human white blood cells was determined using a series of n-(9-anthroyloxy) fatty acid probes where n = 2, 3, 6, 7, 9, 11, 12, and 16, to establish a baseline for future studies ... More
Effect of phospholipid headgroup composition on the transfer of fluorescent long-chain free fatty acids between membranes.
AuthorsSunderland JE, Storch J
JournalBiochim Biophys Acta
PubMed ID8323971
The transfer of long-chain anthroyloxy-labeled-free fatty acids (AOffa) between small unilamellar vesicles (SUV) was studied using a fluorescence energy transfer assay. Donor SUV were labeled with AOffa, and acceptor SUV contained the nonexchangeable quencher NBD-phosphatidylethanolamine. Donor and acceptor membranes were mixed using a stopped-flow apparatus, and intermembrane transfer was monitored ... More
Inhibition of phospholipase C-delta 1 catalytic activity by sphingomyelin.
AuthorsScarlata S, Gupta R, Garcia P, Keach H, Shah S, Kasireddy CR, Bittman R, Rebecchi MJ
JournalBiochemistry
PubMed ID8942652
We measured the ability of sphingomyelin (SPM) to inhibit phosphatidylinositol 4,5-bisphosphate [PI(4,5)P2] hydrolysis catalyzed by human phospholipase C-delta 1 (PLC-delta 1) in model membranes and detergent phospholipid mixed micelles. SPM strongly inhibited PLC-delta 1 catalytic activity measured in large unilamellar vesicles (LUVs) composed of egg phosphatidylcholine (PC), PI(4,5)P2, and SPM ... More
Nanosecond fluorescence anisotropy decays of n-(9-anthroyloxy) fatty acids in dipalmitoylphosphatidylcholine vesicles with regard to isotropic solvents.
AuthorsVincent M, de Foresta B, Gallay J, Alfsen A
JournalBiochemistry
PubMed ID6896158
A set of n-(9-anthroyloxy) fatty acids [2-, 7-, 9-, and 12-(9-anthroyloxy)stearic acid (AS) and 16-(9-anthroyloxy)palmitic acid (16-AP)] has been studied by time-resolved and steady-state fluorescence anisotropy measurements in isotropic media (i.e., propylene glycol and a liquid paraffinic oil, Primol 342) and in vesicles of dipalmitoylphosphatidylcholine. The two modes of rotation, ... More
Comparisons of steady-state anisotropy of the plasma membrane of living cells with different probes.
AuthorsCollins JM, Grogan WM
JournalBiochim Biophys Acta
PubMed ID1878371
We have used an extended Perrin equation which was in agreement with literature data for steady-state anisotropy (rSS) for a wide variety of artificial and isolated biological membranes labeled with various probes (Van der Meer et al. (1986) Biochim. Biophys. Acta 854, 38-44 to obtain the static component (r infinity) ... More
Fluorescence spectroscopy of 9-anthroyloxy fatty acids in solvents.
AuthorsGarrison MD, Doh LM, Potts RO, Abraham W
JournalChem Phys Lipids
PubMed ID8033287
A series of anthroyloxy fatty acid (AF) fluorescent probes, with the anthroyloxy group covalently linked at various positions along the alkyl chain, were studied in solvents exhibiting a wide range of polarity and hydrogen-bond donor (Hd) and acceptor (Ha) ability. These probes were sensitive to the solvent polarity as reflected ... More
Association of cytosol hemoglobin with the membrane in intact erythrocytes.
AuthorsEisinger J, Flores J, Salhany JM
JournalProc Natl Acad Sci U S A
PubMed ID6804940
The problem of demonstrating hemoglobin binding to the erythrocyte membrane in intact cells was approached by observing the quenching of fluorescent membrane probes by hemoglobin as a function of pH. This quenching was studied by measuring fluorescence intensities and decay rates of membrane-bound donors by both right-angle and front-face fluorometry. ... More
Nonpolar environment of tryptophans in erythrocyte water channel CHIP28 determined by fluorescence quenching.
AuthorsFarinas J, Van Hoek AN, Shi LB, Erickson C, Verkman AS
JournalBiochemistry
PubMed ID8218257
CHIP28 is an abundant water-transporting protein in erythrocytes, kidney proximal tubule, and other fluid-transporting tissues. To determine the environment of the four tryptophans in CHIP28, fluorescence spectra and quenching by polar and nonpolar compounds were measured in stripped human erythrocyte membranes containing CHIP28 and in proteoliposomes reconstituted with purified CHIP28; ... More
Effect of lipid packing on the conformational states of purified GLUT-1 hexose transporter.
AuthorsScarlata S, McBath H, Haspel HC
JournalBiochemistry
PubMed ID7779817
The purpose of this study was to determine the effect of increased lipid packing on the conformational states of the GLUT-1 hexose transporter purified in endogenous lipids. The binding of glucose results in a conformational change that can be followed by a decrease in fluorescence intensity. Lipid packing was increased ... More
Free fatty acid transfer from rat liver fatty acid-binding protein to phospholipid vesicles. Effect of ligand and solution properties.
AuthorsKim HK, Storch J
JournalJ Biol Chem
PubMed ID1730626
Fatty acid binding proteins (FABP) are a family of 14-15-kDa proteins found in many mammalian cell types in high abundance. Although their precise physiological role remains hypothetical, the transfer of free fatty acids (ffa) to intracellular membrane sites is believed to be an important function of FABP. To better understand ... More
Perturbation of egg phosphatidylcholine and dipalmitoylphosphatidylcholine multilamellar vesicles by n-alkanols. A fluorescent probe study.
AuthorsZavoico GB, Chandler L, Kutchai H
JournalBiochim Biophys Acta
PubMed ID3838141
The perturbing effects of n-alkanols (pentanol, decanol and tetradecanol) in egg phosphatidylcholine and dipalmitoylphosphatidylcholine multilamellar vesicles were studied with five fluorescent probes, 1-(4'-trimethylaminophenyl)-6-phenylhexa-1,3,5-triene (TMA-DPH), 1,6-diphenyl-1,3,5-hexatriene, and 2-, 7-, and 12-(9-anthroxyloxy)stearic acid (2-, 7-, and 12-AS). These probes localize at various depths in the membrane, enabling study of the membrane-order gradient. ... More