Induced circular dichroism of incorporated fluorescent cholesteryl esters and polar lipids as a probe of human serum low density lipoprotein structure and melting.
AuthorsSklar LA, Craig IF, Pownall HJ
JournalJ Biol Chem
PubMed ID7217083
Two fluorescent cholesteryl esters, cholesteryl cis-parinarate and cholestatrienyl oleate, have been incorporated into human serum low density lipoprotein (LDL) by two alternative procedures. The core location of the incorporated cholesterol esters and the surface location of cis-parinaric acid and cholestatrienol are verified by fluorescence energy transfer. In these LDL preparations, ... More
Interactions between sarcoplasmic reticulum calcium adenosintriphosphatase and nonionic detergents.
AuthorsDean WL, Suárez CP
JournalBiochemistry
PubMed ID6452900
The interaction of Triton X-100 and other nonionic detergents with a delipidated preparation of the Ca2+ ATPase from sarcoplasmic reticulum has been studied. Binding of radiolabeled Triton X-100 was determined by column chromatography at 6 degrees C, and two classes of binding sites were observed. Below the critical micelle concentration ... More
Titrating the effects of mitochondrial complex I impairment in the cell physiology.
AuthorsBarrientos A, Moraes CT
JournalJ Biol Chem
PubMed ID10347173
'The mitochondrial oxidative phosphorylation system consists of five multimeric enzymes (complexes I-V). NADH dehydrogenase or complex I (CI) is affected in most of the mitochondrial diseases and in some neurodegenerative disorders. We have studied the physiological consequences of a partial CI inhibition at the cellular level. We used a genetic ... More
Oxidative susceptibility of low density lipoprotein subfractions is related to their ubiquinol-10 and alpha-tocopherol content.
AuthorsTribble DL, van den Berg JJ, Motchnik PA, Ames BN, Lewis DM, Chait A, Krauss RM
JournalProc Natl Acad Sci U S A
PubMed ID8302851
'The conjugated polyene fatty acid parinaric acid (PnA) undergoes a stoichiometric loss in fluorescence upon oxidation and can be used to directly monitor peroxidative stress within lipid environments. We evaluated the course of potentially atherogenic oxidative changes in low density lipoproteins (LDL) by monitoring the oxidation of PnA following its ... More
Lipid-phase structure in epithelial cell membranes: comparison of renal brush border and basolateral membranes.
AuthorsIllsley NP, Lin HY, Verkman AS
JournalBiochemistry
PubMed ID3378045
'The lipid-phase structures of brush border membrane vesicles (BBMV) and basolateral membrane vesicles (BLMV) isolated from rabbit renal cortex were compared by steady-state and phase-modulation measurements of diphenylhexatriene (DPH) and trans- and cis-parinaric acid (tPnA and cPnA) fluorescence. A temperature-scanning system was used which gave reproducible temperature profiles of steady-state ... More
Recombinant liver fatty acid binding protein interacts with fatty acyl-coenzyme A.
AuthorsHubbell T, Behnke WD, Woodford JK, Schroeder F
JournalBiochemistry
PubMed ID8136369
'Rat liver fatty acid binding protein (L-FABP) and rat intestine fatty acid binding protein (I-FABP) are homologous proteins which are both found in intestinal epithelial cells. It was once well accepted that liver fatty acid binding protein bound fatty acyl-CoAs, but the recent finding of a novel acyl-CoA binding protein ... More
Binding analyses between Human PPARgamma-LBD and ligands.
'The binding characteristics of a series of PPARgamma ligands (GW9662, GI 262570, cis-parinaric acid, 15-deoxy-Delta(12,14)-prostaglandin J(2), LY171883, indomethacin, linoleic acid, palmitic acid and troglitazone) to human PPARgamma ligand binding domain have been investigated for the first time by using surface plasmon resonance biosensor technology, CD spectroscopy and molecular docking simulation. ... More
Kinetics and site specificity of hydroperoxide-induced oxidative damage in red blood cells.
Authorsvan den Berg JJ, Op den Kamp JA, Lubin BH, Roelofsen B, Kuypers FA
JournalFree Radic Biol Med
PubMed ID1601324
'To provide a detailed description of the time course and the site specificity of hydroperoxide-induced oxidative stress in red blood cells (RBCs), we have characterized the action of a membrane-soluble (cumene hydroperoxide [cumOOH]) and a water-soluble (hydrogen peroxide [H2O2]) oxidant. The fluorescent polyunsaturated fatty acid (PUFA) parinaric acid (PnA) was ... More
Fluorescence depolarization of cis- and trans-parinaric acids in artificial and red cell membranes resolved by a double hindered rotational model.
AuthorsCalafut TM, Dix JA, Verkman AS
JournalBiochemistry
PubMed ID2765524
'Although steady-state anisotropy measurements of phase-sensitive probes provide a qualitative description of the phase behavior of biomembranes, there is little information about the physical state of lipid domains. We have developed a ground-state double hindered rotator model (DHR) for fluorescence anisotropy decay, in which probes possess separate rotational correlation times ... More
Estrogen and tamoxifen metabolites protect smooth muscle cell membrane phospholipids against peroxidation and inhibit cell growth.
AuthorsDubey RK, Tyurina YY, Tyurin VA, Gillespie DG, Branch RA, Jackson EK, Kagan VE
JournalCirc Res
PubMed ID9933255
'The goal of this study was to test the hypothesis that antioxidant estrogens, by a mechanism independent of the estrogen receptor, protect phospholipids residing in the plasma membrane of vascular smooth muscle cells from peroxidation and peroxidation-induced cell growth and migration. Peroxidation of membrane phospholipids was assessed by HPLC analysis ... More
An esterification protocol for cis-parinaric acid-determined lipid peroxidation in immune cells.
AuthorsMcGuire SO, James-Kracke MR, Sun GY, Fritsche KL
JournalLipids
PubMed ID9075214
'Loss of fluorescence from cis-parinaric acid (cPnA) is a sensitive indicator of lipid peroxidation. The purpose of this study was to utilize cPnA to determine, at the level of the intact immune cell, whether enrichment of membranes with polyunsaturated fatty acids (PUFA) increased lipid peroxidation. P388D1 macrophages were labeled by ... More
Glutathione propagates oxidative stress triggered by myeloperoxidase in HL-60 cells. Evidence for glutathionyl radical-induced peroxidation of phospholipids and cytotoxicity.
AuthorsBorisenko GG, Martin I, Zhao Q, Amoscato AA, Tyurina YY, Kagan VE
JournalJ Biol Chem
PubMed ID15039448
'Glutathione acts as a universal scavenger of free radicals at the expense of the formation of the glutathionyl radicals (GS*). Here we demonstrated that GS* radicals specifically interact with a reporter molecule, paramagnetic and non-fluorescent 4-((9-acridinecarbonyl)-amino)-2,2,6,6-tetramethylpiperidine-1-oxyl (Ac-Tempo), and convert it into a non-paramagnetic fluorescent product, identified as 4-((9-acridinecarbonyl)amino)-2,2,6,6-tetramethylpiperidine (Ac-piperidine). Horseradish ... More
Effects of insulin on the lipid structure of liver plasma membrane measured with fluorescence and ESR spectroscopic methods.
AuthorsHyslop PA, York DA, Sauerheber RD
JournalBiochim Biophys Acta
PubMed ID6089886
'Insulin increased the lipid order of rat and mouse liver plasma membrane domains sampled by the hydrophobic fluorescent probe 1,6-diphenyl-1,3,5-hexatriene in a concentration-dependent saturable manner. The ordering is half maximal at 5.1 X 10(-11) M and fully saturated at 1.7 X 10(-10) M insulin. Membranes prepared from obese hyperglycemic (ob/ob) ... More
Effects of magnesium and iron on lipid peroxidation in cultured hepatocytes.
AuthorsGünther T, Vormann J, Höllriegl V
JournalMol Cell Biochem
PubMed ID7623785
'In primary cultures of rat hepatocytes, the effects of extracellular Mg2+ and Fe on lipid peroxidation (LPO) as measured by means of malondialdehyde (MDA) formation were investigated. Incubation of hepatocytes at decreasing extracellular Mg2+ concentration enhanced LPO, depending on extracellular Fe. About 96% of MDA accumulated in the culture medium. ... More
Lipid binding to amyloid beta-peptide aggregates: preferential binding of cholesterol as compared with phosphatidylcholine and fatty acids.
AuthorsAvdulov NA, Chochina SV, Igbavboa U, Warden CS, Vassiliev AV, Wood WG
JournalJ Neurochem
PubMed ID9326304
'Amyloid beta-peptide (A beta) aggregates are one of the key neuropathological characteristics of Alzheimer''s disease. A beta belongs to a group of proteins that aggregate and form beta-sheets, and some of these proteins bind cholesterol and other lipids. The purpose of the experiments reported here was to determine if cholesterol, ... More
Refinement of the structure of Escherichia coli-derived rat intestinal fatty acid binding protein with bound oleate to 1.75-A resolution. Correlation with the structures of the apoprotein and the protein with bound palmitate.
AuthorsSacchettini JC, Scapin G, Gopaul D, Gordon JI
JournalJ Biol Chem
PubMed ID1429698
'The structure of rat intestinal fatty acid binding protein (I-FABP) with bound oleate (C18:1) has been refined with x-ray diffraction data to a resolution of 1.75 A. The protein contains 10 anti-parallel beta strands composed of 99 residues and 2 short helices of 14 residues. Oleate is located in the ... More
Partition of parinaroylphosphatidylethanolamines and parinaroylphosphatidylglycerols in immiscible phospholipid mixtures.
AuthorsMartin LR, Avery RB, Welti R
JournalBiochim Biophys Acta
PubMed ID2185844
'Partitioning of two parinaroyl phosphatidylethanolamines and two parinaroyl phosphatidylglycerols between solid and fluid phase phospholipids was examined. Fluorescence quantum yields and fluorescence polarization measurements were used to calculate Ks/fp, the solid to fluid partition coefficient of each probe (Sklar, L.A., Miljanich, G.P. and Dratz, E.A. (1979) Biochemistry 18, 1707-1716). In ... More
Mechanism of protein-induced membrane fusion: fusion of phospholipid vesicles by clathrin associated with its membrane binding and conformational change.
AuthorsMaezawa S, Yoshimura T, Hong K, Düzgünes N, Papahadjopoulos D
JournalBiochemistry
PubMed ID2496757
'The clathrin-induced fusion of liposome membranes, the membrane binding of clathrin, and the conformational states of clathrin were investigated over a wide pH range using large unilamellar and multilamellar vesicles composed of phosphatidylserine (PS), phosphatidylcholine (PC), PS/PC (2:1), PS/PC (1:1), or PS/PC (1:2). The pH profiles of clathrin-induced fusion of ... More
A fluorescence anisotropy study on the phase behavior of dimyristoylphosphatidylcholine/cholesterol mixtures.
AuthorsSmutzer G, Yeagle PL
JournalBiochim Biophys Acta
PubMed ID3978104
'The phase behavior of L-alpha-dimyristoylphosphatidylcholine/cholesterol mixtures was studied in multilamellar vesicles by fluorescence polarization of the sterol molecule dehydroergosterol and of the polyene molecule alpha-parinaric acid. In the absence of cholesterol, dehydroergosterol exhibited an increase in polarization as DMPC vesicles were heated through the phase transition. This rise in polarization ... More
Interaction of trans-parinaric acid with phosphatidylcholine bilayers: comparison with the effect of other fluorophores.
AuthorsBen Yashar V, Menashe M, Biltonen RL, Johnson ML, Barenholz Y
JournalBiochim Biophys Acta
PubMed ID3663661
'The effect of the fluorophore trans-parinaric acid on the structure of lipid bilayer was studied and compared with the effect of other ''perturbants''. These include commonly used fluorophores (diphenylhexatriene, heptadecylhydroxycoumarin, cis-parinaric acid and two fatty acids, palmitic and oleic acids). Differential scanning calorimetry (DSC) and proton nuclear magnetic resonance techniques ... More
Fluorescence lifetime and time-resolved polarization anisotropy studies of acyl chain order and dynamics in lipid bilayers.
AuthorsWolber PK, Hudson BS
JournalBiochemistry
PubMed ID6894699
'The time-resolved fluorescence intensity and anisotropy decays of cis- and trans-parinaric acids and phosphatidylcholines labeled with trans-parinaric acid have been characterized in bilayers formed by several phosphatidylcholines and by dipalmitoylphosphatidylcholine-cholesterol mixtures, at several temperatures. Both a conventional free-running nitrogen flashlamp and the novel synchrotron source at the Stanford Linear Accelerator ... More
Incorporation of cis-parinaric acid, a fluorescent fatty acid, into synaptosomal phospholipids by an acyl-CoA acyltransferase.
AuthorsHarris WE, Stahl WL
JournalBiochim Biophys Acta
PubMed ID6580918
'The cis-isomer of parinaric acid, a naturally occurring C-18 polyene fatty acid, was incubated with brain subcellular fractions and the polarization of fluorescence increased in a time dependent manner. Greatest increases occurred in synaptosomal and microsomal membranes. This increase in polarization of fluorescence was found with the cis, but not ... More
Human serum albumin. Spectroscopic studies of binding and proximity relationships for fatty acids and bilirubin.
AuthorsBerde CB, Hudson BS, Simoni RD, Sklar LA
JournalJ Biol Chem
PubMed ID216673
'Binding and proximity relationships of hydrophobic ligands on human serum albumin have been studied using absorption, fluorescence, circular dichroism, and electron paramagnetic resonance spectroscopy. The ligands studied were bilirubin, two conjugated linear polyene fatty acids, cis-parinaric acid and cis-eleostearic acid, and three nitroxide derivatives of stearic acid with doxyl groups ... More
The interaction of N-oleylethanolamine with phospholipid bilayers.
AuthorsEpps DE, Cardin AD
JournalBiochim Biophys Acta
PubMed ID3663658
'Long chain acylamides of ethanolamine were previously found to increase in the infarcted canine myocardium. Subsequent in vitro experiments established a number of interesting biological and physiological properties of these compounds including alteration of rabbit skeletal sarcoplasmic reticulum function and inhibition of permeability dependent calcium release from heart mitochondria. These ... More
Measuring the adsorption of Fatty acids to phospholipid vesicles by multiple fluorescence probes.
AuthorsSimard JR, Kamp F, Hamilton JA,
JournalBiophys J
PubMed ID18296488
'Fatty acids (FA) are important nutrients that the body uses to regulate the storage and use of energy resources. The predominant mechanism by which long-chain fatty acids enter cells is still debated widely as it is unclear whether long-chain fatty acids require protein transporters to catalyze their transmembrane movement. We ... More
Enhanced lipid peroxidation by extracellular ATP in PC12 cells.
AuthorsCheng Y, Chen M, James-Kracke M, Wixom P, Sun AY
JournalNeurochem Res
PubMed ID8833220
'Recently we have demonstrated that extracellular ATP acts as an excitatory neurotransmitter and enhances cell death in the presence of ferrous ions. By using a newly developed cis-parinaric acid fluorescence technique, we demonstrated that ATP, in a dose dependent manner, enhanced the increased membrane lipid peroxidation in PC12 cells when ... More
Correlation of membrane lipid peroxidation with oxidation of hemoglobin variants: possibly related to the rates of hemin release.
AuthorsChiu DT, van den Berg J, Kuypers FA, Hung IJ, Wei JS, Liu TZ
JournalFree Radic Biol Med
PubMed ID8791096
'Experiments were performed to delineate the biochemical mechanism of hemoglobin (Hb)-catalyzed lipid peroxidation in human red blood cells (RBCs). Using a modified Langmuir trough lipid monolayer technique, we found that oxidized Hb induced an increase in lipid monolayer surface pressure, suggesting that oxidized Hb readily releases its heme moiety into ... More
Direct binding of ethanol to bovine serum albumin: a fluorescent and 13C NMR multiplet relaxation study.
AuthorsAvdulov NA, Chochina SV, Daragan VA, Schroeder F, Mayo KH, Wood WG
JournalBiochemistry
PubMed ID8555194
'Molecular mechanisms of ethanol interaction with proteins are not well-understood. In the present study, direct interaction of ethanol with hydrophobic binding sites on fatty acid free bovine serum albumin (BSA) was determined using the fluorescent probe 1-anilinonaphthalene-8-sulfonic acid (1,8-ANS), cis-parinaric acid, and 13C NMR. The affinity of ethanol for BSA ... More
An experimental model for the evaluation of lipid peroxidation in lens membranes.
AuthorsFernandes R, Pereira P, Ramalho JS, Mota MC, Oliveira CR
JournalCurr Eye Res
PubMed ID8670739
'Lipid peroxidation has been associated with a number of specific manifestations related both to lens aging and cataract development. The assessment of the effect of various naturally occurring prooxidants as well as the development of antioxidant strategies has often been limited by the lack of appropriate and simple experimental models. ... More
Hydrogen peroxide mediates amyloid beta protein toxicity.
AuthorsBehl C, Davis JB, Lesley R, Schubert D
JournalCell
PubMed ID8004671
'Amyloid beta protein (A beta) is a 40-43 amino acid peptide that is associated with plaques in the brains of Alzheimer''s patients and is cytotoxic to cultured neurons. Using both primary central nervous system cultures and clonal cell lines, it is shown that a number of anti-oxidants protect cells from ... More
Liver fatty acid-binding protein colocalizes with peroxisome proliferator activated receptor alpha and enhances ligand distribution to nuclei of living cells.
AuthorsHuang H, Starodub O, McIntosh A, Atshaves BP, Woldegiorgis G, Kier AB, Schroeder F
JournalBiochemistry
PubMed ID14992586
'Although it is hypothesized that long-chain fatty acyl CoAs (LCFA-CoAs) and long-chain fatty acids (LCFAs) regulate transcription in the nucleus, little is known regarding factors that determine the distribution of these ligands to nuclei of living cells. Immunofluorescence colocalization showed that liver fatty acid-binding protein (L-FABP; binds LCFA-CoA as well ... More
High-pressure effects on beta-lactoglobulin interactions with ligands studied by fluorescence.
AuthorsDufour E, Hoa GH, Haertlé T
JournalBiochim Biophys Acta
PubMed ID8003521
'The effects of pressure (0.1 MPa to 400 MPa) on intrinsic fluorescence of beta-lactoglobulin and on its binding of retinol and cis-parinaric acid have been studied at neutral and acid pHs. In neutral pH, fluorescence emission spectra of beta-lactoglobulin tryptophanes are characterized by an irreversible 14 nm red-shift indicating pressure-induced ... More
Fluorescent probes as markers of oxidative stress in keratinocyte cell lines following UVB exposure.
AuthorsCarini M, Aldini G, Piccone M, Facino RM
JournalFarmaco
PubMed ID11132730
'In this work we describe the development of specific markers for determination of both the membrane and intracellular damage induced by free radicals generated by UVB radiation (5-150 mJ/cm2) in cultured keratinocytes. This using simple, specific and sensitive fluorescent probes: cis-parinaric acid (PNA) to monitor membrane lipid peroxidation and 2'',7''-dichloro-dihydrofluorescein ... More
Direct measurement of lipid peroxidation in submitochondrial particles.
Authorsde Hingh YC, Meyer J, Fischer JC, Berger R, Smeitink JA, Op den Kamp JA
JournalBiochemistry
PubMed ID7548029
'The susceptibility of the polyunsaturated fatty acid parinaric acid (cis-PnA) to peroxidative damage with concomitant loss of its fluorescent character can be used to detect lipid peroxidation in a direct and sensitive way. The procedure, originally developed to measure peroxidation in lipid vesicles and erythrocyte membranes, has been adapted for ... More
Hydrophobic probe binding of beta-lactoglobulin in the native and molten globule state induced by high pressure as affected by pH, KIO(3) and N-ethylmaleimide.
AuthorsYang J, Powers JR, Clark S, Dunker AK, Swanson BG
JournalJ Agric Food Chem
PubMed ID12188631
'High hydrostatic pressure (HHP) at 500 MPa and 50 degrees C induces beta-LG into the molten globule state. Retinol, cis-parinaric acid (CPA), and 1-anilino-naphthalene-8-sulfonate (ANS) fluorescence from pH 2.5 to 10.5 in the presence of the native and molten globule states of beta-LG indicate that retinol binds to beta-LG in ... More
Changes in chemical structure and function in Escherichia coli cell membranes caused by freeze-thawing. I. Change of lipid state in bilayer vesicles and in the original membrane fragments depending on rate of freezing.
AuthorsSouzu H
JournalBiochim Biophys Acta
PubMed ID2643992
'The effect of different rates of freezing on the character of lipids in unilamellar lipid bilayer vesicles and in the original membrane fragments of Escherichia coli B cells was investigated by measuring the temperature-dependent fluorescence polarization ratio changes of cis- and trans-parinaric acids. In lipid bilayer vesicles, both slow and ... More
Fatty acid binding protein: stimulation of microsomal phosphatidic acid formation.
AuthorsJolly CA, Hubbell T, Behnke WD, Schroeder F
JournalArch Biochem Biophys
PubMed ID9143360
'The effect of fatty acid binding proteins (FABPs) on two key steps of microsomal phosphatidic acid formation was examined. Rat liver microsomes were purified by size-exclusion chromatography to remove endogenous cytosolic fatty acid and fatty acyl-CoA binding proteins while recombinant FABPs were used to avoid cross-contamination with such proteins from ... More
Hydrophobic ligand binding by Zn-alpha 2-glycoprotein, a soluble fat-depleting factor related to major histocompatibility complex proteins.
AuthorsKennedy MW, Heikema AP, Cooper A, Bjorkman PJ, Sanchez LM
JournalJ Biol Chem
PubMed ID11425849
'Zn-alpha(2)-glycoprotein (ZAG) is a member of the major histocompatibility complex (MHC) class I family of proteins and is identical in amino acid sequence to a tumor-derived lipid-mobilizing factor associated with cachexia in cancer patients. ZAG is present in plasma and other body fluids, and its natural function, like leptin''s, probably ... More
Bcl-2 inhibits selective oxidation and externalization of phosphatidylserine during paraquat-induced apoptosis.
AuthorsFabisiak JP, Kagan VE, Ritov VB, Johnson DE, Lazo JS
JournalAm J Physiol
PubMed ID9124312
'Oxidative stress is a potential component of the final common pathway leading to apoptosis following many diverse stimuli. Here, we document that the oxidant paraquat caused apoptosis in mouse 32D cells. We examined early paraquat-induced lipid peroxidation after metabolic incorporation of the oxidant-sensitive fluorescent fatty acid cis-parinaric acid (cis-PA) into ... More
Influence of sterol structure on phospholipid phase behavior as detected by parinaric acid fluorescence spectroscopy.
AuthorsRujanavech C, Henderson PA, Silbert DF
JournalJ Biol Chem
PubMed ID3711085
'Phospholipid-sterol interactions were investigated using parinaric acid fluorescence spectroscopy. Cholesterol and cholesterol analogues which were modified in the sterol nucleus or side chain were added at 50 mol % to multilamellar vesicles of model phospholipids selected to be representative of major components in an LM cell plasma membrane. These included ... More
Mitochondrial effects of antiretroviral therapies in asymptomatic patients.
AuthorsLópez S, Miró O, Martínez E, Pedrol E, Rodríguez-Santiago B, Milinkovic A, Soler A, García-Viejo MA, Nunes V, Casademont J, Gatell JM, Cardellach F
JournalAntivir Ther
PubMed ID15040536
'BACKGROUND: A decrease in the mitochondrial (mt) DNA to nuclear DNA ratio has gained acceptance as a marker of mitochondrial toxicity in treated HIV-infected patients, but the functional meaning of this alteration is unclear. METHODS: We assessed mtDNA content, mitochondrial content and function in peripheral blood mononuclear cells (PBMCs) of ... More
Conjugated polyene fatty acids as membrane probes: preliminary characterization.
AuthorsSklar LA, Hudson BS, Simoni RD
JournalProc Natl Acad Sci U S A
PubMed ID1057769
'The use of fluorescent conjugated polyenoic fatty acids as probes of membrane structure is introduced. alpha- and beta-parinaric acid (cis, trans, trans, cis-, and all trans-9,11,13,15-octadecatetraenoic acid) and synthetic lecithins containing an alpha-parinaric acid chain in position 2 are prepared and their absorption and fluorescence properties are determined. Phase transitions ... More
Incorporation of the human erythrocyte sialoglycoprotein into recombined membranes containing cholesterol.
AuthorsYeagle PL
JournalJ Membr Biol
PubMed ID6726789
'Glycophorin, the major sialoglycoprotein from the human erythrocyte membrane, has been isolated and recombined with phosphatidylcholine and cholesterol. Sucrose density gradient analysis of the recombinants shows that it is possible not only to recombine this protein with phospholipid, but also with phospholipid-cholesterol mixtures. Surprisingly, by the same analysis, it was ... More
Tamoxifen and hydroxytamoxifen as intramembraneous inhibitors of lipid peroxidation. Evidence for peroxyl radical scavenging activity.
AuthorsCustódio JB, Dinis TC, Almeida LM, Madeira VM
JournalBiochem Pharmacol
PubMed ID8010983
'Tamoxifen (TAM) is the antiestrogen most widely used in the chemotherapy and chemoprevention of breast cancer. It has been reported that TAM and its more active metabolite 4-hydroxytamoxifen (OHTAM) induce multiple cellular effects, including antioxidant actions. Here sarcoplasmic reticulum membranes (SR) were used as a simple model of oxidation to ... More
Gel phase phospholipid in the plasma membrane of sterol-depleted mouse LM cells. Analysis by fluorescence polarization and x-ray diffraction.
AuthorsWelti R, Rintoul DA, Goodsaid-Zalduondo F, Felder S, Silbert DF
JournalJ Biol Chem
PubMed ID7251608
'Fluorescence polarization of cis- and trans-parinaric acid and high angle x-ray diffraction are used to examine the physical effects of in vitro sterol depletion of LM cell plasma membranes. Measurements on lipids isolated from the normal plasma membrane show that most of the lipid is fluid between 5 and 45 ... More
Detection of lipid peroxidation on erythrocytes using the excimer-forming property of a lipophilic BODIPY fluorescent dye.
AuthorsMakrigiorgos GM
JournalJ Biochem Biophys Methods
PubMed ID9310865
'Lipophilic analogues of dipyrrometheneboron (BODIPY-FL) dyes, used for membrane studies, normally fluoresce in the green wavelength region (approximately 516 nm), but at high local concentration, they shift their emission to the red region (approximately 540-600 nm) via excimer formation. A two-wavelength-based method is described that utilizes the excimer-forming property of ... More
Role of lipid peroxidation in dapsone-induced hemolytic anemia.
AuthorsMcMillan DC, Jensen CB, Jollow DJ
JournalJ Pharmacol Exp Ther
PubMed ID9864266
'Dapsone hydroxylamine (DDS-NOH) is a direct-acting hemolytic agent responsible for dapsone-induced hemolytic anemia in the rat. The hemolytic activity of DDS-NOH is associated with the formation of disulfide-linked hemoglobin adducts on membrane skeletal proteins. We have postulated that this membrane protein "damage" is a consequence of DDS-NOH-induced oxidative stress within ... More
Novel fluorescein-based flow-cytometric method for detection of lipid peroxidation.
AuthorsMakrigiorgos GM, Kassis AI, Mahmood A, Bump EA, Savvides P
JournalFree Radic Biol Med
PubMed ID8958133
'The novel property of fluorescein to detect peroxyl radicals is demonstrated. On the basis of this observation, a fluorescein-based, flow-cytometric method to directly and continuously detect free radicals generated in cell membranes during lipid peroxidation has been developed. 5- and 6-Carboxyfluorescein (5-/6-CF) free in solution and fluorescein-labeled polylysine lose their ... More
Direct and continuous measurement of hydroperoxide-induced oxidative stress on the membrane of intact erythrocytes.
Authorsvan den Berg JJ, Kuypers FA, Lubin BH, Roelofsen B, Op den Kamp JA
JournalFree Radic Biol Med
PubMed ID1937143
'Having minimized spectroscopic interference by hemoglobin (Hb), peroxidation processes in intact erythrocytes could be monitored in a continuous assay using the fluorescent polyunsaturated fatty acid, parinaric acid (PnA), as a peroxidation probe. Control experiments to establish the character of the method are described in detail. As a practical application, comparative ... More
Myeloperoxidase-catalyzed redox-cycling of phenol promotes lipid peroxidation and thiol oxidation in HL-60 cells.
AuthorsGoldman R, Claycamp GH, Sweetland MA, Sedlov AV, Tyurin VA, Kisin ER, Tyurina YY, Ritov VB, Wenger SL, Grant SG, Kagan VE
JournalFree Radic Biol Med
PubMed ID10569638
'Various types of cancer occur in peroxidase-rich target tissues of animals exposed to aryl alcohols and amines. Unlike biotransformation by cytochrome P450 enzymes, peroxidases activate most substrates by one-electron oxidation via radical intermediates. This work analyzed the peroxidase-dependent formation of phenoxyl radicals in HL-60 cells and its contribution to cytotoxicity ... More
Nonenzymatic glycosylation of human serum albumin alters its conformation and function.
AuthorsShaklai N, Garlick RL, Bunn HF
JournalJ Biol Chem
PubMed ID6706980
'Approximately 10% of the albumin in normal human serum is modified by nonenzymatic glycosylation, primarily at the epsilon-amino group of lysine residue 525. Incubation of albumin with glucose under physiological conditions in vitro resulted in glycosylation of the same residue. After separation of glycosylated human serum albumin from the nonglycosylated ... More
N-parinaroyl glycosphingolipids: synthesis and characterization of novel fluorescent probes of membrane structure.
AuthorsRintoul DA, Redd MB, Wendelburg B
JournalBiochemistry
PubMed ID3707895
'N-Parinaroylceramides and -glucocerebrosides were synthesized and characterized. These fluorescent glycolipids were found to be nonperturbing membrane lipid probes, which partitioned preferentially into fluid-phase phosphatidylcholine (PC) in liposomes containing both fluid and solid-phase PC. N-Parinaroylglucocerebroside, parinaroyl-PC, and free parinaric acid were used to analyze the motion and distribution of glucocerebroside and ... More
Mechanisms by which intracellular calcium induces susceptibility to secretory phospholipase A2 in human erythrocytes.
AuthorsSmith SK, Farnbach AR, Harris FM, Hawes AC, Jackson LR, Judd AM, Vest RS, Sanchez S, Bell JD
JournalJ Biol Chem
PubMed ID11294854
'Exposure of human erythrocytes to the calcium ionophore ionomycin rendered them susceptible to the action of secretory phospholipase A(2) (sPLA(2)). Analysis of erythrocyte phospholipid metabolism by thin-layer chromatography revealed significant hydrolysis of both phosphatidylcholine and phosphatidylethanolamine during incubation with ionomycin and sPLA(2). Several possible mechanisms for the effect of ionomycin ... More
Ascorbate 6-palmitate protects human erythrocytes from oxidative damage.
AuthorsRoss D, Mendiratta S, Qu ZC, Cobb CE, May JM
JournalFree Radic Biol Med
PubMed ID9890643
'Lipid-soluble antioxidants, such as alpha-tocopherol, protect cell membranes from oxidant damage. In this work we sought to determine whether the amphipathic derivative of ascorbate, ascorbate 6-palmitate, is retained in the cell membrane of intact erythrocytes, and whether it helps to protect the cells against peroxidative damage. We found that ascorbate ... More
Fluorescence probes used for detection of reactive oxygen species.
AuthorsGomes A, Fernandes E, Lima JL,
JournalJ Biochem Biophys Methods
PubMed ID16297980
'Endogenously produced pro-oxidant reactive species are essential to life, being involved in several biological functions. However, when overproduced (e.g. due to exogenous stimulation), or when the levels of antioxidants become severely depleted, these reactive species become highly harmful, causing oxidative stress through the oxidation of biomolecules, leading to cellular damage ... More
Antioxidant properties of demethyldiisoeugenol.
AuthorsKo FN, Liao CH, Kuo YH, Lin YL
JournalBiochim Biophys Acta
PubMed ID7548177
'The antioxidant properties of demethyldiisoeugenol were investigated in this study using various models. Demethyldiisoeugenol inhibited Fe(2+)-induced lipid peroxidation in rat brain homogenate in a concentration-dependent manner with an IC50 1.8 +/- 0.1 microM. Demethyldiisoeugenol was more effective than alpha-tocopherol and BHT in reducing the stable free radical diphenyl-2-picrylhydrazyl (DPPH). It ... More
A fluorescence decay study of parinaroyl-phosphatidylinositol incorporated into artificial and natural membranes.
Authorsvan Paridon PA, Shute JK, Wirtz KW, Visser AJ
JournalEur Biophys J
PubMed ID3396518
'Phosphoinositide metabolism in the plasma membrane is linked to transmembrane signal transduction. In this study we have investigated some physical properties (e.g. molecular order and dynamics) of phosphatidylinositol (PI) in various membrane preparations by time-resolved fluorescence techniques, using a synthetic PI derivate with a cis-parinaroyl chain on the sn-2 position. ... More
Distributions of fluorescence decay times for parinaric acids in phospholipid membranes.
AuthorsJames DR, Turnbull JR, Wagner BD, Ware WR, Petersen NO
JournalBiochemistry
PubMed ID3689775
'Analysis of fluorescence decay data for probes incorporated into model or biological membranes invariably requires fitting to more than one decay time even though the same probe exhibits nearly single-exponential decay in solution. The parinaric acids (cis and trans) are examples of this. Data are presented for both parinaric acid ... More
Amphotericin B as an intracellular antioxidant: protection against 2,2'-azobis(2,4-dimethylvaleronitrile)-induced peroxidation of membrane phospholipids in rat aortic smooth muscle cells.
AuthorsOsaka K, Tyurina YY, Dubey RK, Tyurin VA, Ritov VB, Quinn PJ, Branch RA, Kagan VE
JournalBiochem Pharmacol
PubMed ID9354594
'The antifungal activity of amphotericin B (AmB) and its side-effects (e.g. nephrotoxicity and hemolytic action) are suggested to be associated with its prooxidant effects in target cells. To test this hypothesis, we have undertaken studies to examine the role of AmB in oxidative stress in cultured rat aortic smooth muscle ... More
Uptake, degradation, and release of fibrillar and soluble forms of Alzheimer's amyloid beta-peptide by microglial cells.
AuthorsChung H, Brazil MI, Soe TT, Maxfield FR
JournalJ Biol Chem
PubMed ID10542270
'Microglia are phagocytic cells that are the main inflammatory response cells of the central nervous system. In Alzheimer''s disease brain, activated microglia are concentrated in regions of compact amyloid deposits that contain the 39-43-amino acid Abeta peptide. We examined the uptake, degradation, and release of small aggregates of fibrillar Abeta ... More
Platelet aggregation inhibiting and anticoagulant effects of oligoamines, XXV: Interactions of the oligoamine RE 1492 with biomembranes.
AuthorsKesselhut A, Ebel H, von Bruchhausen F, Rehse K
JournalArch Pharm (Weinheim)
PubMed ID7695469
'The absorption of D-glucose by rat thymocytes is reduced to half of control by 30 mumol/L and decreased to 10% by 100 mumol/L of RE 1492. This is backed by the fact that the absorption of 2-deoxy-D-glucose is inhibited in the same extent. The more hydrophilic oligoamine RE 1888 had ... More
Chemical modification of the beta-subunit isolated from a membrane-bound Fo-F1-ATP synthase: modification by 4-chloro-7-nitrobenzofurazan does not inhibit restoration of ATP synthesis or hydrolysis.
AuthorsKhananshvili D, Gromet-Elhanan Z
JournalBiochem Biophys Res Commun
PubMed ID6184056
Human serum albumin: binding specificity and allosteric effect of parinarate and stearate. A dianionic spin label study.
AuthorsHsia JC, Kwan NH
JournalJ Biol Chem
PubMed ID6257712
Interaction of fatty acids with recombinant rat intestinal and liver fatty acid-binding proteins.
AuthorsNemecz G, Hubbell T, Jefferson JR, Lowe JB, Schroeder F
JournalArch Biochem Biophys
PubMed ID1897956
'Intestinal enterocytes contain two homologous fatty acid-binding proteins, intestinal fatty acid-binding protein (I-FABP)2 and liver fatty acid-binding protein (L-FABP). Since the functional basis for this multiplicity is not known, the fatty acid-binding specificity of recombinant forms of both rat I-FABP and rat L-FABP was examined. A systematic comparative analysis of ... More
Parinaric acid as a sensitive fluorescent probe for the determination of lipid peroxidation.
AuthorsKuypers FA, van den Berg JJ, Schalkwijk C, Roelofsen B, Op den Kamp JA
JournalBiochim Biophys Acta
PubMed ID3651488
'The decrease in fluorescence of conjugated polyenic acyl chains is used as a sensitive assay for lipid peroxidation. The fatty acid cis-trans-trans-cis-9,11,13, 15-octadecatetraenoic acid (cis-parinaric acid) is introduced into liposomal membranes as free fatty acid or, by using the PC specific transfer protein from bovine liver, as 1-palmitoyl-2-cis-parinaroyl-sn-glycero-3-phosphocholine. The peroxidation ... More
The use of cis-parinaric acid to determine lipid peroxidation in human erythrocyte membranes. Comparison of normal and sickle erythrocyte membranes.
AuthorsVan den Berg JJ, Kuypers FA, Qju JH, Chiu D, Lubin B, Roelofsen B, Op den Kamp JA
JournalBiochim Biophys Acta
PubMed ID3415998
'The recently developed parinaric acid assay is shown to offer possibilities for studying peroxidation processes in biological membrane systems. Taking the human erythrocyte membrane as a model, several initiating systems were investigated, as well as the effect of residual hemoglobin in ghost membrane preparations. The effectivity of a radical generating ... More
Partition of amphiphilic molecules into phospholipid vesicles and human erythrocyte ghosts: measurements by ultraviolet difference spectroscopy.
'Molar partition coefficients for chlorpromazine and methochlorpromazine between phospholipid vesicles or human erythrocyte ghosts and buffer are determined by ultraviolet difference spectroscopy. The partition coefficients between small unilamellar egg phosphatidylcholine vesicles and buffer at pH 7.4 are 4.4 X 10(5) for chlorpromazine and 0.8 X 10(5) for methochlorpromazine, determined with ... More
Vitamin E recycling in human erythrocyte membranes.
AuthorsConstantinescu A, Han D, Packer L
JournalJ Biol Chem
PubMed ID8388377
'Vitamin E, the major lipid chain-breaking antioxidant in erythrocyte membranes, is present in low concentration, suggesting that mechanisms should exist to protect against its loss. Enzymatic pathways for the recycling of vitamin E from its tocopheroxyl radical have been observed previously in inner membranes of mitochondria and microsomes. These pathways ... More
Flow cytometric measurement of lipid peroxidation in vital cells using parinaric acid.
AuthorsHedley D, Chow S
JournalCytometry
PubMed ID1451599
'A method for measuring lipid peroxidation using time resolved flow cytometry is described. Because of its chemical nature, the naturally fluorescent fatty acid cis-parinaric acid is readily consumed in lipid peroxidation reactions. It could be loaded into Chinese hamster ovary cells in a time and concentration dependent manner at 37 ... More
Electrospray mass spectrometric investigation of the binding of cis-parinaric acid to bovine beta-lactoglobulin and study of the ligand-binding site of the protein using limited proteolysis.
AuthorsImre T, Zsila F, Szabó PT
JournalRapid Commun Mass Spectrom
PubMed ID14608614
'The binding property of parinaric acid, a polyunsaturated fatty acid, to bovine beta-lactoglobulin, has been studied by electrospray ionization mass spectrometry. Stable complexation was observed under acidic conditions in a molar ratio of 1:1. Competitive complexation experiments were performed using saturated and unsaturated fatty acid standards with different chain lengths ... More
Selective resistance of LDL core lipids to iron-mediated oxidation. Implications for the biological properties of iron-oxidized LDL.
AuthorsTribble DL, Chu BM, Levine GA, Krauss RM, Gong EL
JournalArterioscler Thromb Vasc Biol
PubMed ID8977465
'Although the nature and consequences of oxidative changes in the chemical constituents of low density lipoproteins (LDLs) have been extensively examined, the physical dynamics of LDL oxidation and the influence of physical organization on the biological effects of oxidized LDLs have remained relatively unexplored. To address these issues, in the ... More
Long chain fatty acids inhibit and medium chain fatty acids activate mammalian cardiac hexokinase.
AuthorsStewart JM, Blakely JA
JournalBiochim Biophys Acta
PubMed ID10760476
'We investigated the effect of non-esterified fatty acids (FAs) on bovine heart hexokinase (type I: ATP: D-hexose 6-phosphotransferase, EC 2.7.1.1). Long chain FAs (C14 to C20) inhibited the enzyme in a way that correlated positively with both the chain length and the degree of unsaturation. Medium chain FA with 12 ... More
Characterization of liposomes and other lipid assemblies by multiprobe fluorescence polarization.
AuthorsBorenstain V, Barenholz Y
JournalChem Phys Lipids
PubMed ID8242830
'This minireview describes the use of fluorescence polarization to characterize the dynamics and organization of biological membranes, lipoproteins, liposomes and other lipid-based assemblies. The advantages, disadvantages and limitations of this method are discussed. There is special emphasis on the multiprobe approach, which can monitor various parts of the lipid membrane ... More
Influence of follicular maturation on the susceptibility of chicken ovarian granulosa cells to free oxygen radicals.
AuthorsNemecz G, Asem EK
JournalComp Biochem Physiol C Pharmacol Toxicol Endocrinol
PubMed ID9185325
'The influence of ovarian follicular maturation on lipid peroxidation-induced changes in the fluidity of plasma membrane of granulosa cells was investigated using the fluorogenic polyunsaturated fatty acid cis-parinaric acid (cPNA). An increase in lipid peroxidation results in the decrease of fluorescence intensity of cPNA. A decrease in membrane fluidity results ... More
Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry for identifying the composition of labeled proteins.
AuthorsLu J, Zenobi R
JournalAnal Biochem
PubMed ID10222003
'Labeled proteins are extensively used in molecular biology and environmental science. The determination of the composition and label ratio is very important for monitoring the efficiency of their separation and purification. In this paper a novel method based on matrix-assisted laser desorption/ionization (MALDI) time-of-flight mass spectrometry was developed for this ... More
Apoptosis and increased generation of reactive oxygen species in Down's syndrome neurons in vitro.
AuthorsBusciglio J, Yankner BA
JournalNature
PubMed ID8524410
'Down''s syndrome (DS) or trisomy 21 is the most common genetic cause of mental retardation. Development of the DS brain is associated with decreased neuronal number and abnormal neuronal differentiation, and adults with DS develop Alzheimer''s disease. The cause of the neurodegenerative process in DS is unknown. Here we report ... More
The activation of porcine pancreatic lipase by cis-unsaturated fatty acids.
Authorsvan Kuiken BA, Behnke WD
JournalBiochim Biophys Acta
PubMed ID7918595
'In the presence of taurodeoxycholate, cis-unsaturated fatty acids increase porcine pancreatic lipase activity 15-fold at pH 7.5. This effect is saturable with a low proportion of fatty acid to substrate. The overall angle of the fatty acid, the position of its double bond and the presence of a carboxyl group ... More
Potentiation of murine astrocyte antioxidant defence by bcl-2: protection in part reflects elevated glutathione levels.
AuthorsPapadopoulos MC, Koumenis IL, Xu L, Giffard RG
JournalEur J Neurosci
PubMed ID9749779
'Overexpression of the proto-oncogene bcl-2 has been shown to protect a variety of cell types from oxidative and non-oxidative injury, blocking apoptotic and necrotic types of cell death. Retroviral vectors were used to stably overexpress bcl-2 in primary murine astrocyte cultures with more than 95% efficiency. Compared to beta-galactosidase-expressing and ... More
Effects of thyroid status on the structure of the very low density lipoprotein secreted by the perfused liver.
AuthorsSchroeder F, Wilcox HG, Keyes WG, Heimberg M
JournalEndocrinology
PubMed ID7056212
'To determine whether hyperthyroidism or hypothyroidism affected the structure of the very low density lipoprotein (VLDL) secreted by the perfused rat liver, rats were pretreated with 0.9% NaCl, T3, or propylthiouracil. The livers were perfused with 0-332 mumol bovine serum albumin-oleate/h for 4 h. The structure of the secreted VLDL ... More
Transition of lipid phase in aqueous dispersions of diacylglyceryltrimethylhomoserine.
AuthorsSato N, Murata N
JournalBiochim Biophys Acta
PubMed ID2009297
'The phase transition in the lipid phase of aqueous dispersions of diacylglyceryltrimethylhomoserine (DGTS) was measured by fluorescence depolarization of parinaric acid and differential scanning calorimetry. In both techniques, the phase transition temperatures (Tm) of 1-palmitoyl-2-stearoyl DGTS and of 1,2-distearoyl DGTS were 53 and 59 degrees C, respectively. Each of these ... More
Parinaroyl and pyrenyl phospholipids as probes for the lipid surface layer of human low density lipoproteins.
AuthorsVauhkonen M, Somerharju P
JournalBiochim Biophys Acta
PubMed ID2765542
'A simple protocol employing lipid transfer proteins was developed to label human low density lipoprotein (LDL) in a controlled manner with parinaroyl and pyrenyl phosphatidylcholines. In order to study the lipid fluidity in the surface lipid layer of LDL, the temperature-dependence of both polarization (parinaroyl probes) and excimer to monomer ... More
Evaluation of hydrophobicity versus chaperonelike activity of bovine alphaA- and alphaB-crystallin.
AuthorsBhattacharyya J, Srinivas V, Sharma KK
JournalJ Protein Chem
PubMed ID11902669
'Calf lens alphaA-crystallin isolated by reversed-phase HPLC demonstrates a slightly more hydrophobic profile than alphaB-crystallin. Fluorescent probes in addition to bis-ANS, like cis-parinaric acid (PA) and pyrene, show higher quantum yields or Ham ratios when bound to alphaA-crystallin than to alphaB-crystallin at room temperature. Bis-ANS binding to both alphaA- and ... More
Acyl coenzyme A binding protein. Conformational sensitivity to long chain fatty acyl-CoA.
AuthorsFrolov A, Schroeder F
JournalJ Biol Chem
PubMed ID9556588
'Cellular unbound long chain fatty acyl-CoAs (>14 carbon) are potent regulators of gene transcription and intracellular signaling. Although the cytosolic acyl-CoA binding protein (ACBP) has high affinity for medium chain fatty acyl-CoAs, direct interaction of ACBP with >14-carbon fatty acyl-CoAs has not been established. Steady state, photon counting fluorescence spectroscopy ... More
Increased susceptibility to membrane lipid peroxidation in renal failure.
AuthorsAnderton JG, Thomas TH, Wilkinson R
JournalNephron
PubMed ID8893158
'The susceptibility of membrane lipids to peroxidation in renal failure was investigated. A fluorescent polyunsaturated fatty acid probe, cis-parinaric acid, showed that mononuclear leucocytes from both chronic renal failure and haemodialysis patients had increased susceptibility to membrane lipid peroxidation compared with normal controls. The effect of oxidant stress on the ... More
Human alpha-fetoprotein. Fluorescence studies on binding and proximity relationships for fatty acids and bilirubin.
AuthorsBerde CB, Nagai M, Deutsch HF
JournalJ Biol Chem
PubMed ID91613
'The binding of bilirubin and the polyene fatty acids cis-parinaric acid and cis-eleostearic acid to human alpha-fetoprotein was studied using fluorescence quenching and fluorescence enhancement techniques. alpha-Fetoprotein has three fatty acid binding sites of decreasing affinity (association constants 2.1 x 10(7) M-1 9.1 X 10(5) M-1, and 1.4 x 10(5) ... More
Use of beta-parinaric acid, a novel fouorimetric probe, to determine characteristic temperatures of membranes and membrane lipids from cultured animal cells.
AuthorsSchroeder F, Holland JF, Vagelos PR
JournalJ Biol Chem
PubMed ID977594
'A naturally occurring fluorescent compound, beta-parinaric acid, was employed as a probe to measure the effects of temperature changes on plasma membrenes, microsomes, and mitochondria and on their respective lipids after isolation form LM cells grown in suspension culture. A computer-centered spectrofluorimenter simultaneously measured the absorbance, absorbance-corrected fluorescence, and relative ... More
Comparison of three methods for measuring LDL resistance against copper-induced oxidation.
A comparison of the effects of calcium on the structure of bovine retinal rod outer segment membranes, phospholipids, and bovine brain phosphatidylserine.
AuthorsSklar LA, Miljanich GP, Dratz EA
JournalJ Biol Chem
PubMed ID489553
Thermal lateral phase separations in bovine retinal rod outer segment membranes and phospholipids as evidenced by parinaric acid fluorescence polarization and energy transfer.
AuthorsSklar LA, Miljanich GP, Bursten SL, Dratz EA
JournalJ Biol Chem
PubMed ID489552
Ligand-binding properties of albumin Parklands: Asp365----His.
AuthorsReed RG
JournalBiochim Biophys Acta
PubMed ID3365447
An albumin variant, isolated from the plasma of a patient with bisalbuminemia, was compared with albumin A from the same patient for binding of long-chain fatty acids and bilirubin. No differences in binding of [14C]palmitate, cis-parinaric acid or bilirubin could be detected for the variant form. These results suggest that ... More