Erythrocyte lipids in triose-phosphate isomerase deficiency.
AuthorsHollán S, Dey I, Szollár L, Horányi M, Magócsi M, Harsányi V, Farkas T
JournalProc Natl Acad Sci U S A
PubMed ID7816830
Marked hypoalphalipoproteinemia was found together with relatively low serum cholesterol, triacylglycerol, and LDL levels in a triose-phosphate isomerase (TPI; D-glyceraldehyde-3-phosphate ketol-isomerase, EC 5.3.1.1)-deficient Hungarian family, especially in the two compound-heterozygote brothers. Apart from a slight increase in palmitic and stearic acids together with a slight decrease in oleic and linoleic ... More
Structure-activity relationships for antioxidant activities of a series of flavonoids in a liposomal system.
AuthorsArora A, Nair MG, Strasburg GM
JournalFree Radic Biol Med
PubMed ID9641252
'Structurally diverse plant phenolics were examined for their abilities to inhibit lipid peroxidation induced either by Fe(II) and Fe(III) metal ions or by azo-derived peroxyl radicals in a liposomal membrane system. The antioxidant abilities of flavonoids were compared with those of coumarin and tert-butylhydroquinone (TBHQ). The antioxidant efficacies of these ... More
Location of diphenylhexatriene (DPH) and its derivatives within membranes: comparison of different fluorescence quenching analyses of membrane depth.
AuthorsKaiser RD, London E
JournalBiochemistry
PubMed ID9609714
'The average membrane location of a series of diphenylhexatriene (DPH)-derived membrane probes was analyzed by measuring the quenching of DPH fluorescence with a series of nitroxide-labeled lipids in which the depth of the nitroxide group is varied. All DPH derivatives were located deeply within the bilayer. Some derivatives were anchored ... More
Advantages and limitations of 1-palmitoyl-2-[[2-[4- (6-phenyl-trans-1,3,5-hexatrienyl)phenyl]ethyl]carbonyl]-3- sn-phosphatidylcholine as a fluorescent membrane probe.
AuthorsParente RA, Lentz BR
JournalBiochemistry
PubMed ID4084512
'We have investigated the behavior of 1-palmitoyl-2-[[2-[4- (6-phenyl-trans-1,3,5-hexatrienyl)phenyl]ethyl]carbonyl]-3-sn -phosphatidylcholine (DPHpPC) in synthetic, multilamellar phosphatidylcholine vesicles. This fluorescent phospholipid has photophysical properties similar to its parent fluorophore, diphenylhexatriene (DPH). DPHpPC preferentially partitioned into fluid phase lipid (Kf/s = 3.3) and reported a lower phase transition temperature as detected by fluorescence anisotropy ... More
The active metabolite hydroxytamoxifen of the anticancer drug tamoxifen induces structural changes in membranes.
AuthorsCustódio JB, Almeida LM, Madeira VM
JournalBiochim Biophys Acta
PubMed ID8274502
'The effects of hydroxytamoxifen (OHTAM) on lipid organization of pure phospholipid liposomes, native sarcoplasmic reticulum (SR) membranes and liposomes of SR lipids were evaluated by intramolecular excimer formation of 1,3-di(1-pyrenyl)propane (Py(3)Py) and by fluorescence polarization of 1,6-diphenyl-1,3,5-hexatriene (DPH) and its derivative 3-[p-(6-phenyl)-1,3,5-hexatrienyl]phenylpropionic acid (DPH-PA). OHTAM promotes alterations in the thermotropic ... More
Partition coefficients of fluorescent probes with phospholipid membranes.
AuthorsHuang ZJ, Haugland RP
JournalBiochem Biophys Res Commun
PubMed ID1958185
'A method for determination of membrane partition coefficients of five fluorescent membrane probes, 1,6-diphenyl-1,3,5-hexatriene (DPH), p-((6-phenyl)-1,3,5-hexatrienyl) benzoic acid (DPH carboxylic acid), 3-(p-(6-phenyl)-1,3,5-hexatrienyl)phenylpropionic acid (DPH propionic acid), 1-(4-trimethylammoniumphenyl)-6-phenyl-1,3,5-hexatriene (TMA-DPH) and N-4-(4-didecylaminostyryl)-N-methylpyridinium iodide (4-di-10-ASP), was developed utilizing the fluorescence enhancement of a constant probe concentration by titration with excess phospholipid liposomes. The ... More
Effects of alcohols on fluorescence anisotropies of diphenylhexatriene and its derivatives in bovine blood platelets: relationships of the depth-dependent change in membrane fluidity by alcohols with their effects on platelet aggregation and adenylate cyclase activity.
AuthorsKitagawa S, Hirata H
JournalBiochim Biophys Acta
PubMed ID1329963
'The effects of three short-chain alkyl alcohols and benzyl alcohol on the membrane fluidity of bovine blood platelets were investigated by studies on the fluorescence anisotropies of diphenylhexatriene (DPH), its cationic trimethylammonium derivative (TMA-DPH) and its anionic propionic acid derivative (DPH-PA). These alcohols decreased the fluorescence anisotropy of DPH, which ... More
A dimerization model for the concentration dependent photophysical properties of diphenylhexatriene and its phospholipid derivatives. DPHpPC and DPHpPA.
AuthorsLentz BR, Burgess SW
JournalBiophys J
PubMed ID2819236
'We have investigated the reason for the sensitivity of the fluorescence excited-state lifetime of 1,6-diphenyl-1,3,5-hexatriene (DPH) and its phospholipid derivatives, 1-palmitoyl-2-[2-[4-(6-phenyl-trans-1,3,5- hexatrienyl)phenyl]ethyl)carbonyl)-3-sn-phosphatidylcholine (DPHpPC) and 1-palmitoyl-2-[2-[4-(6-phenyl-trans-1,3,5- hexatrienyl)phenyl]ethyl)carbonyl)-3-sn-phosphatidic acid (DPHpPA), to the concentration of these probes in dipalmitoylphosphatidylcholine (DPPC) multilamellar membranes (Barrow, D. A., and B. R. Lentz, 1985. Biophys. J. 48:221-234; ... More
Structure and polarity of mouse brain synaptic plasma membrane: effects of ethanol in vitro and in vivo.
AuthorsColles S, Wood WG, Myers-Payne SC, Igbavboa U, Avdulov NA, Joseph J, Schroeder F
JournalBiochemistry
PubMed ID7727452
'Structural and dielectric alteration by ethanol in vitro and chronic ethanol consumption were examined in synaptic plasma membranes (SPM) using diphenylhexatriene and charged diphenylhexatriene derivatives. These fluorophores, in combination with multifrequency phase and modulation fluorometry, allowed the examination of the surface and interior core of SPM. Limiting anisotropy and rotational ... 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
Differential effect of aging on cholesterol modulation of carbachol-stimulated low-K(m) GTPase in striatal synaptosomes.
AuthorsDenisova NA, Erat SA, Kelly JF, Roth GS
JournalExp Gerontol
PubMed ID9615923
'Previous research has suggested that age-related decline in physiological functions may be the result of substantial alterations in membrane molecular structure. The purpose of the present experiments was to elucidate the role of cholesterol domains in the age-related decline in receptor-G-protein interactions in striatal synaptosomes. We observed a significant age-related ... More
Partitioning of exchangeable fluorescent phospholipids and sphingolipids between different lipid bilayer environments.
AuthorsGardam MA, Itovitch JJ, Silvius JR
JournalBiochemistry
PubMed ID2713353
'Exchangeable phospho- and sphingolipid probes (phosphatidylcholine, -ethanolamine, -serine, and -glycerol, phosphatidic acid, sphingomyelin, cerebroside, and sulfatide) have been synthesized in which one acyl chain is substituted with a fluorescent bimanyl, 7-(dimethylamino)coumarin-3-yl, or diphenyl-hexatrienyl group. The distribution of these probes between two different populations of lipid vesicles can be readily monitored ... More
Membranotropic effects of the antibacterial agent Triclosan.
AuthorsVillalaín J, Mateo CR, Aranda FJ, Shapiro S, Micol V
JournalArch Biochem Biophys
PubMed ID11368524
'Triclosan is a broad-spectrum hydrophobic antibacterial agent used in dermatological preparations and oral hygiene products. To gain further insight into the mode of action of Triclosan we examined its effects on membranes by performing leakage titrations of different oral bacteria and studying its interaction with model membranes through the use ... More
Detection of protein mediated glycosphingolipid clustering by the use of resonance energy transfer between fluorescent labelled lipids. A method established by applying the system ganglioside GM1 and cholera toxin B subunit.
AuthorsAntes P, Schwarzmann G, Sandhoff K
JournalChem Phys Lipids
PubMed ID1468126
'Glycosphingolipids labelled in the ceramide moiety with 3-(p-(6-phenyl)-1,3,5-hexatrienyl)phenylpropionic acid (DPH) or 6-(4-nitrobenz-2-oxa-1,3-diazole-7-yl)aminohexanoic acid (NBD) were incorporated into small unilamellar lecithin liposomes. They were used in resonance energy transfer (RET) experiments between the donor fluorophore DPH and the acceptor NBD to study glycosphingolipid distribution. In pure lecithin liposomes the fluorescent derivatives ... More
Asymmetry of plasma membrane lipid order in Madin-Darby Canine Kidney cells.
AuthorsLe Grimellec C, Friedlander G, Giocondi MC
JournalAm J Physiol
PubMed ID3134820
Fluorescence anisotropy experiments have been done to estimate, in situ, the lipid order of the plasma membrane of polarized Madin-Darby Canine Kidney cells (MDCK) grown on glass cover slips and labeled by 1-[4-(trimethylamino)phenyl]-6-phenylhexa-1,3,5-triene (TMA-DPH), a specific marker of the plasma membrane of living cells. Fluorescence microscopy, back-exchange, and quenching experiments ... More
High-throughput fluorescence screening of antioxidative capacity in human serum.
AuthorsMayer B, Schumacher M, Brandstätter H, Wagner FS, Hermetter A
JournalAnal Biochem
PubMed ID11673881
Diphenylhexatriene-labeled phosphatidylcholine and propionic acid have been established as selective fluorescence markers for the continuous determination of oxidation processes in the lipid and aqueous phases of unfractionated human serum. Oxidation of the respective fluorophores leads to a decrease in fluorescence intensity from which the time-dependent degradation of the marker molecule ... More
The dynamics of lipid motion in sarcoplasmic reticulum membranes determined by steady-state and time-resolved fluorescence measurements on 1,6-diphenyl-1,3,5-hexatriene and related molecules.
AuthorsStubbs CD, Kinosita K, Munkonge F, Quinn PJ, Ikegami A
JournalBiochim Biophys Acta
PubMed ID6466678
Steady-state and time-resolved fluorescence anisotropy measurements were made on 1,6-diphenyl-1,3,5-hexatriene (DPH), 1-(4-trimethylammoniumphenyl)-6-phenyl-1,3,5-hexatriene (TMA-DPH) and 1-acyl-2-(DPH)-phosphatidylcholine (DPH-PC) incorporated into sarcoplasmic reticulum membranes. The results were analysed in terms of the 'wobbling-in-cone' model. Considerable differences in the fluorescence parameters were found. In particular TMA-DPH and DPH-PC showed a smaller cone angle, relating ... More
Use of fluorescent probes to monitor molecular order and motions within liposome bilayers.
AuthorsLentz BR
JournalChem Phys Lipids
PubMed ID8242843
This article reviews the use of fluorescent probes to monitor the order and dynamics within the acyl chain region of liposome lipid bilayers. Fluorescence anisotropy is first defined and the theoretical framework that allows interpretation of steady-state or dynamic measurements in terms of molecular details is reviewed. The general advantages ... More
Dynamics of the bilayer-water interface of phospholipid vesicles and the effect of cholesterol: a picosecond fluorescence anisotropy study.
AuthorsSaito H, Araiso T, Shirahama H, Koyama T
JournalJ Biochem (Tokyo)
PubMed ID1869508
The motion of the head group of phospholipid molecules in the bilayer structure was investigated by a picosecond fluorescence anisotropy technique using a newly synthesized fluorescent phospholipid, dipalmitoyl-L-alpha-phosphatidyl-(3-p-methoxyphenyl)umbelliferone (DPPU). In this phospholipid, a coumarin derivative is attached covalently to the phosphate moiety. The motion of the acyl chain of the ... More
Asymmetry of membrane fluidity in the lipid bilayer of blood platelets: fluorescence study with diphenylhexatriene and analogs.
AuthorsKitagawa S, Matsubayashi M, Kotani K, Usui K, Kametani F
JournalJ Membr Biol
PubMed ID2056522
Membrane fluidity of bovine platelets was examined with diphenylhexatriene (DPH), its cationic trimethylammonium derivative (TMA-DPH) and anionic propionic acid derivative (DPH-PA). After addition of these probes to platelet suspensions at 37 degrees C, the fluorescence intensity of DPH-PA reached equilibrium within 2 min, whereas those of DPH and TMA-DPH increased ... More
Different sphingolipids show differential partitioning into sphingolipid/cholesterol-rich domains in lipid bilayers.
AuthorsWang TY, Silvius JR
JournalBiophys J
PubMed ID10969009
Two fluorescence-based approaches have been applied to examine the differential partitioning of fluorescent phospho- and sphingolipid molecules into sphingolipid-enriched domains modeling membrane "lipid rafts." Fluorescence-quenching measurements reveal that N-(diphenylhexatrienyl)propionyl- (DPH3:0-)-labeled gluco- and galactocerebroside partition into sphingolipid-enriched domains in sphingolipid/phosphatidylcholine/cholesterol bilayers with substantially higher affinity than do analogous sphingomyelin, ceramide, or ... More
Effects of fluorophore structure and hydrophobicity on the uptake and metabolism of fluorescent lipid analogs.
AuthorsNaylor BL, Picardo M, Homan R, Pownall HJ
JournalChem Phys Lipids
PubMed ID1934193
Cellular transport and metabolism of fatty acids are integral components of lipid metabolism, but the mechanisms and regulation involved are poorly understood. A variety of commercially available fluorescent analogs of fatty acids, are potentially useful probes for the study of lipid metabolism by such techniques as cell sorting and fluorescence ... More
The use of fluorescence energy transfer to distinguish between poly(ethylene glycol)-induced aggregation and fusion of phospholipid vesicles.
AuthorsMorgan CG, Thomas EW, Yianni YP
JournalBiochim Biophys Acta
PubMed ID6687434
Two fluorescence energy transfer assays for phospholipid vesicle-vesicle fusion have been developed, one of which is also sensitive to vesicle aggregation. Using a combination of these assays it was possible to distinguish between vesicle aggregation and fusion as induced by poly(ethylene glycol) PEG 8000. The chromophores used were 1-(4'-carboxyethyl)-6-diphenyl-trans-1,3,5-hexatriene as ... More
A comparison of heart and liver fatty acid-binding proteins: interactions with fatty acids and possible functional differences studied with fluorescent fatty acid analogues.
AuthorsStorch J
JournalMol Cell Biochem
PubMed ID2266956
Fatty acid-binding proteins (FABP) are distinct but related gene products which are found in many mammalian cell types. They are generally present in high abundance, and are found in those tissues where free fatty acid (ffa) flux is high. The function(s) of FABP is unknown. Also not known is whether ... More
Calmodulin-dependent enzymes undergo a protein-induced conformational change that is associated with their interactions with calmodulin.
AuthorsHuang S, Carlson GM, Cheung WY
JournalJ Biol Chem
PubMed ID8125988
The anionic hydrophobic (amphipathic) fluorescent probe 2-(p-toluidinyl)-naphthalene-6-sulfonate was used to investigate the surface hydrophobic properties of calmodulin (CaM)-dependent enzymes as follows: calcineurin, myosin light chain kinase, cyclic nucleotide phosphodiesterase, CaM-dependent protein kinase II, and the gamma-subunit of phosphorylase kinase. We found that certain domains of these enzymes that interacted with ... More
Disclosure of discrete sites for phospholipid and sterols at the protein-lipid interface in native acetylcholine receptor-rich membrane.
AuthorsAntollini SS, Barrantes FJ
JournalBiochemistry
PubMed ID9843433
There is an increasing body of evidence to support the notion that the function of the nicotinic acetylcholine receptor (AChR) is influenced by its lipid microenvironment [see Barrantes, F. J. (1993) FASEB J. 7, 1460-1467]. We have recently made use of the so-called generalized polarization (GP) of the fluorescent probe ... More
Distribution and metabolism of fluorescent sphingosines and corresponding ceramides bearing the diphenylhexatrienyl (DPH) fluorophore in cultured human fibroblasts.
AuthorsAntes P, Schwarzmann G, Sandhoff K
JournalEur J Cell Biol
PubMed ID1468445
Fluorescent D-erythro-sphingosines bearing the diphenyl-1,3,5-hexatrienyl group (DPH) as fluorophore were synthesized for the first time. Two isomers, the DPH-4(E)- and DPH-4(Z)-sphingosine [(2S,3R)-2-amino-6-(p-(18-phenyl)-13,15,17(E,E,E)-hexatrienyl)phenylh ex- 4(E/Z)-en-1,3-diol], and the N-hexanoyl derivative of DPH-4(E)-sphingosine (C6-DPH-ceramide) were studied for their distribution and metabolism in cultured human skin fibroblasts. Both DPH-sphingosines (4-trans and 4-cis) were not ... More
Molecular order and fluidity of the plasma membrane of human platelets from time-resolved fluorescence depolarization.
AuthorsMateo CR, Lillo MP, González-Rodríguez J, Acuña AU
JournalEur Biophys J
PubMed ID1935812
The ability of seven fluorescence polarization probes (1,6-diphenyl-1,3,5-hexatriene, 1-[(4-trimethyl- amino)phenyl]-6-phenyl-1,3,5-hexatriene, (2-carboxy- ethyl)-1,6-diphenyl-1,3,5-hexatriene, 16(9-anthroyloxy)-palmitic acid, CIS-parinaric acid, trans-parinaric acid and perylene) to report changes induced by temperature and Ca2+ in the plasma membrane of human platelets has been examined. The steady-state fluorescence anisotropy of the probes was compared after being incorporated ... More
Modulation of pig kidney Na+/K+-ATPase activity by cholesterol: role of hydration.
Cholesterol is known to affect the activity of membrane-bound enzymes, including Na(+)/K(+)-ATPase. To gain insight into the mechanism of cholesterol's effect, we have used various hydrophobic fluorescent probes which insert into different regions of the membrane bilayer and report on the degree of hydration of their environment. Specifially, we have ... 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 quenching in model membranes: phospholipid acyl chain distributions around small fluorophores.
AuthorsYeager MD, Feigenson GW
JournalBiochemistry
PubMed ID2161684
Fluorescence quenching in lipid bilayers is treated by a new approach based on calculation of the probability distribution of quenching and nonquenching acyl chains around a fluorophore. The effect of acyl lattice site dependence (i.e., correlations of phospholipid sister chain occupancy of neighbor sites) was modeled by use of Monte ... More
Fluorescence dynamics of diphenyl-1,3,5-hexatriene-labeled phospholipids in bilayer membranes.
AuthorsPap EH, ter Horst JJ, van Hoek A, Visser AJ
JournalBiophys Chem
PubMed ID8110960
A comparative study of the dynamical fluorescence properties of three phosphatidylcholines having a diphenyl-1,3,5-hexatriene (DPH) group attached at different depths from the head group incorporated into membrane vesicles has been carried out. The probes were covalently attached to the sn-2 position of the glycerol part of the phosphatidylcholine via either ... More
The interfacial region of dipalmitoylphosphatidylcholine bilayers is perturbed by fusogenic amphipaths.
AuthorsLentz BR, Wu JR, Zheng L, Prevrátil J
JournalBiophys J
PubMed ID8968599
Several structural methods were used to probe the influence of three fusogenic and four nonfusogenic amphipaths on large, unilamellar dipalmitoylphosphatidylcholine (DPPC) vesicles. For four of these structural measurements there was a correlation observed between the ability of an amphipath to favor poly(ethylene glycol) (PEG)-induced fusion and the structural perturbation reported ... More