Fluorescent properties of pyrene bound at specific acylation sites of chicken liver fatty acid synthase.
AuthorsAnderson VE, Hammes GG
JournalBiochemistry
PubMed ID6871180
'The covalent modification of chicken liver fatty acid synthase by 4-(1-pyrenyl)butyryl-CoA (PBA-CoA), a fluorescent analogue of acetyl- and malonyl-CoA, has been studied. The binding isotherms and the kinetics of inactivation suggest 2 mol of PBA-CoA/mol of enzyme is specifically incorporated into the enzyme. Two classes of binding sites have been ... More
Variation of 1-pyrenebutyric acid fluorescence lifetime in single living cells treated with molecules increasing or decreasing reactive oxygen species levels.
AuthorsRharass T, Vigo J, Salmon JM, Ribou AC
JournalAnal Biochem
PubMed ID16920058
'1-Pyrenebutyric acid (PBA) is a fluorescent probe whose fluorescence lifetime depends on local oxygen and free radical concentrations. We propose to use PBA fluorescence lifetime to quantify reactive oxygen species (ROS) in biological samples. Time-resolved microfluorimetry was used to record the fluorescence decay of single living cells loaded with this ... More
Control of the erythrocyte membrane shape: recovery from the effect of crenating agents.
AuthorsAlhanaty E, Sheetz MP
JournalJ Cell Biol
PubMed ID7328127
'Intact erythrocytes become immediately crenated upon addition of 2,4-dinitrophenol (DNP) or pyrenebutyric acid (PBA). However, when cells are incubated at 37 degrees C in the presence of the crenating agents with glucose, they gradually (4--8 h) recover the normal biconcave disc form. The recovery process does not reflect a gradual ... More
(I-pyrenebutyryl)carnitine and 1-pyrenebutyryl coenzyme A: fluorescent probes for lipid metabolite studies in artificial and natural membranes.
AuthorsWolkowicz PE, Pownall HJ, McMillin-Wood JB
JournalBiochemistry
PubMed ID7104308
'Membrane properties of fatty acyl coenzyme A (CoA) and acylcarnitine have been studied with 1-pyrenebutyryl-CoA and (1-pyrenebutyryl) carnitine. These molecules have a spectroscopic properties of pyrene and its derivatives and exhibit biological and chemical characteristics related to acyl esters. (1-Pyrenebutyryl) carnitine (PBC) is more soluble in nonpolar solvents than 1-pyrenebutyryl-CoA ... More
C(60) and water-soluble fullerene derivatives as antioxidants against radical-initiated lipid peroxidation.
AuthorsWang IC, Tai LA, Lee DD, Kanakamma PP, Shen CK, Luh TY, Cheng CH, Hwang KC
JournalJ Med Chem
PubMed ID10579823
'C(60), vitamin E, and three C(60) derivatives (polar 1 and water-soluble C(3)/D(3)C(60)s) were examined for their antioxidant effects on prevention of lipid peroxidation induced by superoxide and hydroxyl radicals. The protection effect on lipid peroxidation was found to be in the sequence: C(60) >/= vitamin E > 1 > none, ... More
Interaction of the mitochondria-targeted antioxidant MitoQ with phospholipid bilayers and ubiquinone oxidoreductases.
'MitoQ(10) is a ubiquinone that accumulates within mitochondria driven by a conjugated lipophilic triphenylphosphonium cation (TPP(+)). Once there, MitoQ(10) is reduced to its active ubiquinol form, which has been used to prevent mitochondrial oxidative damage and to infer the involvement of reactive oxygen species in signaling pathways. Here we show ... More
Hydrolysis of fluorescent pyrene-acyl esters by human pancreatic carboxylic ester hydrolase and bile salt-stimulated lipase.
AuthorsNegre-Salvayre A, Abouakil N, Lombardo D, Salvayre R
JournalLipids
PubMed ID2215086
'Fluorescent esters containing pyrenedecanoic acid (P10) or pyrenebutanoic (P4) acid (P4cholesterol, P10cholesterol, P4- and P10-containing triacylglycerols) were synthesized and used as substrates for human pancreatic carboxylic ester hydrolase and bile salt-stimulated lipase from human milk. Both enzymes were purified by immunoaffinity chromatography. All fluorescent pyrene derivatives were hydrolyzed by pancreatic ... More
Affinity labeling of the active site of the Ca2+-ATPase of sarcoplasmic reticulum.
AuthorsMurphy AJ
JournalBiochim Biophys Acta
PubMed ID2974728
'The inactivation of sarcoplasmic reticulum ATPase by fluorescein isothiocyanate (FITC) was shown to have a hyperbolic dependence on the concentration of FITC. The results were quantitatively accounted for by a model in which the reagent first binds reversibly (Kf = 70 microM) to the ATPase and then reacts irreversibly (kmax ... More
Molecular mechanism of lateral diffusion of py(10)-PC and free pyrene in fluid DMPC bilayers.
AuthorsMartins J, Melo E
JournalBiophys J
PubMed ID11159450
'From the study of the kinetics of the fluorescence self-quenching of pyrene in multilamellar vesicles of 1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC) in the fluid phase we obtain the molecular diffusion parameters, diffusion coefficients, and activation energies for lateral diffusion for three probes: 1-palmitoyl-2-(1-pyrenedecanoyl)-sn-glycero-3-phosphocholine (py(10)-PC), pyrene, and 1-pyrenebutanoic acid (py-but). The experiments are done ... More
Fluorescence studies of phosphatidylcholine micelle mixing: relevance to phospholipase kinetics.
AuthorsSoltys CE, Roberts MF
JournalBiochemistry
PubMed ID7918374
'Two fluorescent micellar phospholipid probes (1-hexanoyl-2-(1-pyrenebutyroyl)phosphatidylcholine and 1-octanoyl-2-(1-pyrenebutyroyl)phosphatidylcholine) have been synthesized, characterized, and used to monitor the dynamics of lipid/amphiphile exchange in a variety of detergents and phospholipid micelles using both steady-state and stopped-flow fluorescence techniques. The ratio of the pyrene monomer to excimer band is a good indicator of ... More
Specific fluorescent labeling of alpha 2-macroglobulin-bound proteases: accessibility and localization of their active site within the complex.
AuthorsTourbez M, Pochon F
JournalBiochimie
PubMed ID2430627
'Pyrenebutylmethylphosphonofluoridate reacts with trypsin and elastase to yield a conjugate with a stoichiometry of one fluorescent label per enzyme molecule as already observed with chymotrypsin. The kinetics of inactivation indicate that the serine active center of the proteases is involved in the labeling reaction. The binding of the proteases to ... More
Nondestructive detection of neutral glycosphingolipids with lipophilic anionic fluorochromes and their employment for preparative high-performance thin-layer chromatography.
AuthorsMüthing J, Kemminer SE
JournalAnal Biochem
PubMed ID8660611
'In this study a simple and effective procedure for the isolation of individual neutral glycosphingolipids (GSLs) by preparative thin-layer chromatography is described. The method is based on nondestructive visualization of neutral GSLs on silica gel precoated thin-layer chromatography plates with anionic lipophilic fluorochromes. After thin-layer chromatography, individual neutral GSLs were ... More
A dimerization hierarchy in the transmembrane domains of the HER receptor family.
AuthorsDuneau JP, Vegh AP, Sturgis JN
JournalBiochemistry
PubMed ID17253768
'Bitopic membrane proteins offer an opportunity for studying transmembrane domain interactions without the structural complexity inherent to multitopic integral membrane proteins. To date, only homomeric associations have been extensively studied quantitatively. Here we propose to assess the thermodynamics of heteromeric associations, which opens the way to investigating specificity and selectivity. ... More
Rates of sulfation and glucuronidation of 7-hydroxycoumarin in periportal and pericentral regions of the liver lobule.
AuthorsConway JG, Kauffman FC, Ji S, Thurman RG
JournalMol Pharmacol
PubMed ID7144740
Fluidity and oxygen penetration of lipid vesicles studied by fluorescence probes.
AuthorsGeiger MW, Turro NJ
JournalPhotochem Photobiol
PubMed ID918149
Fluorescence polarization of pyrenebutyric-bovine serum albumin and pyrenebutyric-human macroglobulin conjugates.
AuthorsKnopp JA, Weber G
JournalJ Biol Chem
PubMed ID4187702
Fluorescence decay times: proteins, coenzymes, and other compounds in water.
AuthorsChen RF, Vurek GG, Alexander N
JournalScience
PubMed ID6023261
'The fluorescence decay time (tau) was 2 to 5 nanoseconds for proteins and 4 to 5 nanoseconds for flavin, pyridine nucleotide, and vitamin B(6)coenzymes; tau varied widely in 48 compounds measured in water. Altholugh reported values of tau for a few of the soluttions studied were in excellenlt agreement. previously ... More
Kinetics of transfer of pyrene and rac-1-oleyl-2-[4-(3-pyrenyl)butanoyl]glycerol between human plasma lipoproteins.
AuthorsCharlton SC, Smith LC
JournalBiochemistry
PubMed ID7126530
Time-resolved detection of energy transfer: theory and application to immunoassays.
AuthorsMorrison LE
JournalAnal Biochem
PubMed ID3218725
'Energy-transfer measurements based upon acceptor fluorophore emission are plagued with background fluorescence resulting from absorption of the excitation light by the acceptor fluorophore. The present work examines the use of a long-lifetime donor fluorophore and a short-lifetime acceptor fluorophore, combined with pulsed-laser excitation and electronic gating of detector signals, to ... More
Influence of fructose 2,6-bisphosphate on the aggregation properties of rat liver phosphofructokinase.
AuthorsReinhart GD
JournalJ Biol Chem
PubMed ID6224792
'The influence that fructose 2,6-bisphosphate (Fru-2,6-BP) has on the aggregation properties of rat liver phosphofructokinase has been studied by observing the fluorescence polarization of the enzyme covalently bound to the fluorescent probe pyrenebutyric acid. Fru-2,6-BP dramatically slows the dissociation of the high molecular weight aggregate forms of the enzyme when ... More
Acyl-chain specificity and properties of cholesterol esterases from normal and Wolman lymphoid cell lines.
AuthorsNègre A, Salvayre R, Rogalle P, Dang QQ, Douste-Blazy L
JournalBiochim Biophys Acta
PubMed ID3030438
'Cholesteryl esters with various chain lengths of fatty acid, radioactive (C2-C18:1) and fluorescent (pyrene butanoic and decanoic acid, P4 and P10, respectively) were synthesized and their hydrolysis was investigated in lymphoid cell lines from normal subjects and from Wolman''s disease patients. The comparison of their hydrolysis showed that three cholesterol ... More
In vivo comparison of cerebral tissue PO2 and cytochrome aa3 reduction-oxidation state in cats during hemorrhagic shock.
AuthorsKariman K, Hempel FG, Jöbsis FF, Burns SR, Saltzman HA
JournalJ Clin Invest
PubMed ID6265497
'To assess the adequacy of oxygen availability and utilization within the cerebral cortex in vivo, we have measured the partial pressure of oxygen in tissue (PtO2), as well as the reduction oxidation state of cytochrome c oxidase (cyt aa3) during shock induced by slow or rapid hemorrhage in anesthetized cats. ... More
Perturbation of the quaternary structure and allosteric behavior of rat liver phosphofructokinase by polyethylene glycol.
AuthorsReinhart GD, Hartleip SB
JournalArch Biochem Biophys
PubMed ID2959201
'The effect that polyethylene glycol (PEG) has on the aggregation of rat liver phosphofructokinase (PFK) has been directly assessed by measuring the fluorescence polarization of pyrenebutyrate covalently attached to the enzyme. After correcting for the changes in bulk viscosity that accompany PEG addition, the results confirm that PEG causes a ... More
Characterization of yeast strains of the genera candida, Hansenula, Kluyveromyces, Pichia, Rhodotorula, and Saccharomyces by mixed-dye fluorometry.
AuthorsGeyer W, Brueggemann L, Flemming I, Nagel B
JournalInt J Syst Bacteriol
PubMed ID1854639
'An analytical method in which we used the selective adsorption of several fluorophores by yeast cells is described. The suitability of using binary mixtures of 1-pyrene butyric acid, 3,6-dimethylamino acridine, 4-acetamido-4''-isothiocyanatostilbene-2,2''-disulfonic acid, and rhodamine B isothiocyanate for the characterization and identification of microorganisms was tested with 98 yeast strains belonging ... More
Intracellular oxygen measurements of mouse liver cells using quantitative fluorescence video microscopy.
AuthorsBenson DM, Knopp JA, Longmuir IS
JournalBiochim Biophys Acta
PubMed ID7388014
'Our currently developed fluorescence video microscope can measure fluorescence intensities with an error of +/- 1.5% of full scale in 65536 different positions of a microscope field. With a video frame freeze acquisition time of 33 ms, time-dependent changes of this order of time or slower can be followed. Using ... More
Joint determination by Brownian dynamics and fluorescence quenching of the in-depth location profile of biomolecules in membranes.
AuthorsFernandes MX, García de la Torre J, Castanho MA
JournalAnal Biochem
PubMed ID12137772
'The in-depth molar distribution function of fluorophores is revealed by a new methodology for fluorescence quenching data analysis in membranes. Brownian dynamics simulation was used to study the in-depth location profile of quenchers. A Lorentzian profile was reached. Since the Stern-Volmer equation is valid at every depth in the membrane ... More
Oxygen quenching of pyrenebutyric acid fluorescence in water. A dynamic probe of the microenvironment.
AuthorsVaughan WM, Weber G
JournalBiochemistry
PubMed ID5461215
Intracellular measurement of oxygen by quenching of fluorescence of pyrenebutyric acid.
AuthorsKnopp JA, Longmuir IS
JournalBiochim Biophys Acta
PubMed ID5082508
Fluorescence lifetime reference standards for the range 0.189 to 115 nanoseconds.
AuthorsChen RF
JournalAnal Biochem
PubMed ID4819745
Fluorescence depolarization studies of conformation changes in pyrene-butyryl-fumarase.
AuthorsMcIntosh RP, Johnson P
JournalBiopolymers
PubMed ID708849
N-(2-Naphthyl)-23,24-dinor-5-cholen-22-amin-3beta-ol, a fluorescent cholesterol analogue.
AuthorsKao YJ, Soutar AK, Hong KY, Pownall HJ, Smith LC
JournalBiochemistry
PubMed ID678537
Microspectrofluorometric evaluation of the oxygen probe 1-pyrene butyric acid in single living cells.
AuthorsKohen E, Salmon JM, Kohen C, Bengtsson G
JournalExp Cell Res
PubMed ID4154863
Fluorescence polarization studies of the self-association of beef liver glutamate dehydrogenase.
AuthorsMalencik DA, Anderson SR
JournalBiochemistry
PubMed ID4114417
Effect of tissue absorption and microscope optical parameters on the depth of penetration for fluorescence and reflectance measurements of tissue samples.
AuthorsBenson DM, Knopp JA
JournalPhotochem Photobiol
PubMed ID6728921
Continuous fluorometric assay of phospholipase A2 with pyrene-labeled lecithin as a substrate.
AuthorsHendrickson HS, Rauk PN
JournalAnal Biochem
PubMed ID7316183
The rotational diffusion of thyroglobulin. A study of thyroglobulin conjugated with pyrenebutyrate and with dimethyl-aminonaphthalenesulfonate.
AuthorsRawitch AB, Hudson E, Weber G
JournalJ Biol Chem
PubMed ID4187703
Structural and mechanistic studies of the alpha-ketoglutarate dehydrogenase multienzyme complex from Escherichia coli.
AuthorsAngelides KJ, Hammes GG
JournalBiochemistry
PubMed ID391269
Fluorescent probe studies of normal, persistently infected, Rous sarcoma virus-transformed, and trypsinized rat cells.
AuthorsBurleson GR, Kulpa CF, Edwards HE, Thomas JK
JournalExp Cell Res
PubMed ID213301
Optical activity of dye-apohemoglobin complexes.
AuthorsHsu MC, Woody RW
JournalBiopolymers
PubMed ID5094580
Fluorophores as visualization aides in agar growth media.
AuthorsLepp CA, Nowlan ED, Mason RD, Ramsey WS
JournalExperientia
PubMed ID383493
A survey of 26 fluorophores revealed 5 which were non-inhibitory to Staphylococcus aureus and Escherichia coli and produced low background and high colony fluorescence.
A cell nanoinjector based on carbon nanotubes.
AuthorsChen X, Kis A, Zettl A, Bertozzi CR,
JournalProc Natl Acad Sci U S A
PubMed ID17485677
Technologies for introducing molecules into living cells are vital for probing the physical properties and biochemical interactions that govern the cell's behavior. Here, we report the development of a nanoscale cell injection system (termed the nanoinjector) that uses carbon nanotubes to deliver cargo into cells. A single multiwalled carbon nanotube ... More
Reagent for introducing pyrene residues in oligonucleotides.
AuthorsKorshun VA, Pestov NB, Birikh KR, Berlin YA
JournalBioconjug Chem
PubMed ID1463786
A novel pyrenyl-containing phosphoramidite reagent, N-[4-(1-pyrenyl)butyryl]-O1-(4,4'-dimethoxytrityl)-O2- [(diisopropylamino)(2-cyanoethoxy)phosphino]-3-amino-1 ,2-propanediol (5), has been synthesized from 4-(1-pyrenyl)butanoic acid in four steps with the 52% overall yield and used to incorporate pyrene residue(s) into oligonucleotides. Oligonucleotides 6 and 7, bearing one or two pyrenes at the 5'-terminus, have been prepared by means of that ... More
Spectrofluorometric determination of lipase activity.
AuthorsLiodakis A, Drew J, Chan RY, Sawyer WH
JournalBiochem Int
PubMed ID1715704
A fluorescent triglyceride, 1(3)-pyrenylbutanoyl-2,3(1,2)-dipalmitoyl-sn-glycerol, was synthesised, characterised by NMR and mass spectrometry, incorporated into a lipid emulsion and used as a fluorescent substrate for pancreatic lipase. It is shown that the product of the reaction, pyrene butyric acid, diffuses into the aqueous phase resulting in a decrease in the excimer ... More
Measurement of tissue oxygen with a fluorescent probe.
AuthorsLongmuir IS, Knopp JA
JournalJ Appl Physiol
PubMed ID985408
Evidence is presented that pyrenebutyric acid is nontoxic at the concentrations required for the measurement of fluorescence quenching by physiological concentrations of oxygen. It appears that this molecule can be used to measure tissue oxygen since it does not interfere with oxygen consumption. Equally, tissue components do not interfere with ... More
Detection of lyso-platelet-activating factor by high-performance liquid chromatography after derivatisation with fluorescent fatty acids.
AuthorsSalari H, Eigendorf GK
JournalJ Chromatogr
PubMed ID2387879
Lyso-platelet-activating factor (lyso-PAF) was derivatised with 9-anthracenepropionic acid in the presence of dicyclohexylcarbodiimide, p-toluenesulfonic acid and 4-dimethylaminopyridine. The reaction yield exceeded 90% when the fatty acid was present in double molar amounts versus lyso-PAF. The procedure was equally effective in the derivatisation of other lysophospholipids. The derivatized phospholipids are detected ... More
Pyrenebutyric acid as an optical oxygen probe in the intact cerebral cortex.
AuthorsMitnick MH, Jöbsis FF
JournalJ Appl Physiol
PubMed ID985407
The application of the fluorochrome pyrenebutyric acid (PBA) as an in vivo quantitative probe for intracellular oxygen tension (iPO2) is reported. PBA is nontoxic, noninvasive, nonconsumptive, and allows optical monitoring of iPO2 on line. Cats were anesthetized with ether and lesioned midcollicularly to produce cerveau isolé preparations with optical monitoring ... More
[Biosynthetic incorporation of fluorescently labelled fatty acids in Escherichia coli]
AuthorsTsukerman AI, Dobretsov GE, Golovinova VB, Dombrovskii AM
JournalMikrobiologiia
PubMed ID6755195
Escherichia coli cells were cultivated in a medium containing 1-pyrene butanoic acid, a fluorescent probe. Total lipids were extracted from the cells, and the extract was separated by thin-layer chromatography. The fluorescent fractions were examined using spectrofluorimetry. The starting 1-pyrene butanoic acid was shown to be biosynthetically incorporated into the ... More
Kinetics of rac-1-oleyl-2-[4-(3-pyrenyl)butanoyl]glycerol transfer between high density lipoproteins.
AuthorsCharlton SC, Hong KY, Smith LC
JournalBiochemistry
PubMed ID210788
The mechanism of transfer of diglyceride between high density lipoproteins (HDL) was investigated with a pyrene-containing analogue whose fluorescent properties depend on the microscopic concentration in the lipoprotein. Transfer rates were first order, rapid (3.5s-1), and invariant over a 100-fold range of HDL concentration and over a 10-fold range of ... More
Characterization of the oxygen probe pyrenebutyric acid in rabbit heart mitochondria.
AuthorsSnow TR, Jöbsis FF
JournalBiochim Biophys Acta
PubMed ID947363
The fluorescence of pyrenebutyric acid is quenched by oxygen and the quenching is a linear function of the oxygen concentration. In addition, pyrenebutyric acid has been shown to be readily taken up by the cell with a partition coefficient of approx. 200. Results are presented on the effect of pyrenebutyric ... More
Nanosecond spectroscopy of a dimeric enzyme: plasma amine oxidase.
AuthorsMassey JB, Churchich JE
JournalBiophys Chem
PubMed ID427247
The fluorescence dye 1-anilino-naphthalene-8-sulphonic acid (ANS) was used as a probe of non-polar binding sites in the enzyme plasma amine oxidase. Steady fluorescence measurements indicate that ANS binds to a single binding site of the dimeric enzyme with a dissociation constant of 5 microns. This binding site is different from ... More
Characterization of bacteria by mixed-dye fluorometry.
AuthorsShelly DC, Warner IM, Quarles JM
JournalClin Chem
PubMed ID6401604
We describe an indirect detection method for bacterial identification and differentiation, based on selective adsorption of several fluorescent dyes. The lipid, protein, and nucleic acid components of fixed whole cells are stained with two mixtures, each containing two fluorochromes. The unadsorbed dyes were measured simultaneously with a video fluorometer [Clin ... More
Albumin-induced changes of fluorescence spectra of 1-pyrenebutyric acid.
AuthorsMatsushita Y, Tsukiori M, Suzuki T, Moriguchi I
JournalJ Pharm Sci
PubMed ID3958932
Changes in the fluorescence spectra and quantum yield of 1-pyrenebutyric acid (1) induced by human, bovine, rabbit, and dog serum albumins and healthy adult serum, liver-disease patient serum, and renal-disease patient serum were compared at pH 7.4. Human serum albumin, healthy adult serum, and liver-disease patient serum caused marked quenching ... More
Use of an encapsulated fluorescent probe to measure intracellular PO2.
AuthorsPodgorski GT, Longmuir IS, Knopp JA, Benson DM
JournalJ Cell Physiol
PubMed ID7251688
The objectives of this investigation were to produce a reliable, sensitive probe to measure intracellular PO2 with a high degree of resolution and to apply this technique to biological systems. A fluorescent molecule, pyrene dissolved in paraffin oil, was encapsulated in polyacrylamide to form a probe of nanometer dimensions. The ... More
The study of rous sarcoma virus-transformed baby hamster kidney cells using fluorescent probes.
AuthorsEdwards HE, Thomas JK, Burleson GR, Kulpa CF
JournalBiochim Biophys Acta
PubMed ID184839
The fluorescent probes pyrene, pyrene butyric acid and N-phenyl 1-naphthylamine have been used to investigate the changes that accompany in vitro transformation of a baby hamster kidney cell line using Rous sarcoma virus. The fluorescent probes which reside in the membrane were used to compare the changes in microviscosity ... More
Direct and rapid cytosolic delivery using cell-penetrating peptides mediated by pyrenebutyrate.
AuthorsTakeuchi T, Kosuge M, Tadokoro A, Sugiura Y, Nishi M, Kawata M, Sakai N, Matile S, Futaki S
JournalACS Chem Biol
PubMed ID17163758
Intracellular delivery of bioactive molecules using arginine-rich peptides, including oligoarginine and HIV-1 Tat peptides, is a recently developed technology. Here, we report a dramatic change in the methods of internalization for these peptides brought about by the presence of pyrenebutyrate, a counteranion bearing an aromatic hydrophobic moiety. In the absence ... More
Membrane fluidity and oxygen diffusion in cholesterol-enriched erythrocyte membrane.
This work studied the effect of cholesteryl hemisuccinate incorporation on membrane fluidity and on the kinetics of oxygen diffusion at different depths in the erythrocyte membrane. Cholesterol concentration in the membrane was expressed as the cholesterol-protein ratio (C/Pt). The membrane fluidity, as assessed by a fluorescence polarization method with diphenyl-hexatriene ... More
Nanosecond fluorescence spectroscopy of pyrenebutyrate anti-pyrene antibody complexes.
AuthorsLovejoy C, Holowka DA, Cathou RE
JournalBiochemistry
PubMed ID889814
The utility of the long-lived fluorophore, pyrene, as a probe in nanosecond fluorescence depolarization measurements was investigated using pyrenebutyrate bound in the combining sites of rabbit antipyrenebutyrate immunoglobulin G. The time dependent anisotropy decay data points showed very little scatter in the time interval 0-350 ns, which is more than ... More
Interactions of pyrene derivatives with lipid bilayers and with (Ca2+-Mg2+)-ATPase.
AuthorsJones OT, Lee AG
JournalBiochemistry
PubMed ID3158348
The intensities of fluorescence emission for pyrene and a number of its derivatives increase on binding to lipid bilayers and to the (Ca2+-Mg2+)-ATPase purified from rabbit muscle sarcoplasmic reticulum. The effect is particularly marked for the less water-soluble derivatives. Changes in intensity for monomer and excimer emission as a function ... More
Monitoring the myosin ATPase reaction using a sensitive fluorescent probe: pyrene-labeled ATP.
AuthorsHiratsuka T
JournalBiophys J
PubMed ID9017209
A pyrene-labeled ATP (Pyr-ATP) in which a pyrene fluorophore is linked to the ribose moiety of ATP with a butyryl chain has been synthesized, together with the corresponding analog of ADP. The spectroscopic properties of two fluorescent analogs were found to be similar to those of 1-pyrenebutyric acid, making them ... More
Binding of pyrene-1-butyric acid to serum albumin: species differences.
AuthorsMatsushita Y, Moriguchi I
JournalJ Pharmacobiodyn
PubMed ID2635734
Changes of the fluorescence spectra and quantum yield of pyrene-1-butyric acid (PYB) induced by rat (RSA), horse (HoSA), and pig serum albumins (PSA) and rat serum were compared at pH 7.4. RSA and rat serum caused marked quenching of the PYB fluorescence. On the contrary, HoSA and PSA increased the ... More
Molecular imprinting of bulk, microporous silica
AuthorsKatz A, Davis ME
JournalNature
PubMed ID10659842
Molecular imprinting aims to create solid materials containing chemical functionalities that are spatially organized by covalent or non-covalent interactions with imprint (or template) molecules during the synthesis process. Subsequent removal of the imprint molecules leaves behind designed sites for the recognition of small molecules, making the material ideally suited for ... 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
Biotin-pyrene conjugates with poly(ethylene glycol) spacers are convenient fluorescent probes for avidin and streptavidin.
AuthorsMarek M, Kaiser K, Gruber HJ
JournalBioconjug Chem
PubMed ID9258456
Conventional biotin-fluorophore conjugates with approximately 14 atom spacers are strongly quenched when bound to avidin or streptavidin, whereas fluorescence becomes insensitive to receptor binding if typical fluorophores are linked to biotin via poly(ethylene glycol) (PEG) chains (Gruber et al., see the second of three papers in this issue). In the ... More
1-Pyrene-butyrylcholine: a fluorescent probe for the cholinergic system.
The action of 1-pyrene-butyrylcholine, a new cholinergic fluorescent probe, has been studied at the cellular level using electrophysiological and fluorescence techniques. The spectroscopic properties of the probe were found to be similar to those pf pyrene-butyric acid, the excited-state lifetime in air-saturated aqueous solutions being 92 nsec. At micromolar concentrations ... More
Metabolism and distribution of intramolecular excimer-forming dipyrenebutanoyl glycerophospholipids in human fibroblasts. Marked resistance to metabolic degradation.
AuthorsKasurinen J, Somerharju P
JournalBiochemistry
PubMed ID7849063
Metabolism and intracellular distribution of fluorescent 1, 2-dipyrenebutanoyl derivatives of phosphatidylcholine, -ethanolamine, and -serine and phosphatidic acid (diPyr4PC, -PE, -PS, and -PA, respectively) in human skin fibroblasts (HF) has been studied. When HF cells were co-incubated with phospholipid vesicles containing diPyr4PC at 8 degrees C, considerable amounts of fluorescent lipid ... More
Distribution of shape-changing compounds across the red cell membrane.
AuthorsMatayoshi ED
JournalBiochemistry
PubMed ID7407050
The effects of two oppositely charged pyrene derivatives, 1-pyrenebutyrylcholine (PBC) and 1-pyrenebutyric acid (PBA), on red blood cell shape have been examined. Both compounds convert normal biconcave erythrocytes into echinocytes. However, with extended incubation time at elevated temperature, the morphology of PBC-induced echinocytes is reversed. Examination of probe uptake confirmed ... More
Metabolism of pyrenyl fatty acids in baby hamster kidney fibroblasts. Effect of the acyl chain length.
AuthorsKasurinen J, Somerharju P
JournalJ Biol Chem
PubMed ID1551867
Biosynthetic labeling of cellular lipids with a fluorescent pyrenyl fatty acid (PyrxFA) moiety was studied in order to assess the usefulness of this approach in the introduction of fluorescent lipid molecules to living cells for transport and metabolic studies. PyrxFAs containing 4-14 aliphatic carbons were added to the culture medium ... More
Hydrolysis of fluorescent pyrenetriacylglycerols by lipases from human stomach and gastric juice.
AuthorsNègre A, Salvayre R, Dousset N, Rogalle P, Dang QQ, Douste-Blazy L
JournalBiochim Biophys Acta
PubMed ID3196738
Fluorescent triacylglycerols containing pyrenedecanoic (P10) and pyrenebutanoic (P4) acids were synthesized and their hydrolysis by lipases from human gastric juice and stomach homogenate was investigated. The existence in stomach homogenate of four different lipolytic enzymes hydrolyzing fluorescent triacylglycerols is suggested by the comparison of various enzymatic properties: acyl chain length ... More
Organization and dynamics of pyrene and pyrene lipids in intact lipid bilayers. Photo-induced charge transfer processes.
AuthorsBarenholz Y, Cohen T, Korenstein R, Ottolenghi M
JournalBiophys J
PubMed ID1883931
The dynamics of fluorescence quenching and the organization of a series of pyrene derivatives anchored in various depths in bilayers of phosphatidylcholine small unilamellar vesicles was studied and compared with their behavior in homogeneous solvent systems. The studies include characterization of the environmental polarity of the pyrene fluorophore based on ... More
Bis-pyrene-labeled oligonucleotides: sequence specificity of excimer and monomer fluorescence changes upon hybridization with DNA.
AuthorsYamana K, Iwai T, Ohtani Y, Sato S, Nakamura M, Nakano H
JournalBioconjug Chem
PubMed ID12440862
The design, synthesis, and properties of a new pyrene excimer-forming probe of DNA have been described. 2,2-(Aminomethyl)propanediol was converted by the reaction with 1-pyrenebutylic acid to bis-pyrene-modified propanediol as a fluorescent non-nucleosidic linker. The bis-pyrene-modified linker can be incorporated via phosphoramidite chemistry into the 5'-terminal or internal positions of oligonucleotides ... More
Topology of the binding site of blood-clotting factors in model membranes. A fluorescence study.
Factors II, X and IX are blood-clotting proteins which bind to phospholipid interfaces in the presence of Ca2+ to activate coagulation. The topology of their binding site on the membrane was investigated in two ways. First, the transition temperature changes of equimolar mixtures of dipalmitoylglycerophosphocholine/phosphatidylserine and dimyristoylglycerophosphocholine/dipalmitoylglycerophosphoserin e were examined ... More
Kinetic processes in Escherichia coli membranes and cells. A laser photolysis study using derivatives of pyrene.
AuthorsWong M, Kulpa CF, Thomas JK
JournalBiochim Biophys Acta
PubMed ID769828
Pyrene and several derivatives of pyrene are used to investigate photo-induced kinetic processes in whole cells and membranes extracted from Escherichia coli. A mutant of E. coli was used which, under appropriate growth conditions, produced a complete or incomplete lipopolysaccharide in the outer membrane. The pyrene derivatives used were: pyrene ... More
Identification of two classes of lipid molecule binding sites on the microsomal triglyceride transfer protein.
AuthorsAtzel A, Wetterau JR
JournalBiochemistry
PubMed ID7803401
The gene for the microsomal triglyceride transfer protein (MTP) is defective in subjects with the genetic disease abetalipoproteinemia, indicating that MTP is essential for the assembly of apolipoprotein B containing lipoproteins. In vitro, MTP is a lipid molecule binding protein that catalyzes lipid transport between membranes by a shuttle mechanism. ... More