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Query: UMLS:C0027960 (mole)
 21,279 document(s) hit in 31,850,051 MEDLINE articles (0.00 seconds)

Mitochondrial imports of acylcarnitine and carnitine have been measured by new methods based on the monitoring of deacylation of acylcarnitines and the acetylation of carnitine in the matrix, subsequent to their entry. These methods have shown higher import rates than those calculated from the uptake of radioactive carnitines into mitochondria as employed until presently. This new approach has permitted the import of long chain acylcarnitine to be followed unambiguously; the results have confirmed that the carnitine acylcarnitine translocase is indeed involved in this import which also proceeds by a mole to mole exchange-diffusion against internal carnitine. Depletion of matrix carnitine greatly decreased the substrate import rates based on their uptake assay but much less so when the deacylation and acylation techniques were employed to monitor imports. These results have revealed that there is a small pool of carnitine in the matrix which readily equilibrates with the medium carnitine through the translocase but which equilibrates with the larger matrix carnitine pool slowly. This finding has necessitated reinterpretation of several previous observations on the translocase that were based on the assumption of a single matrix carnitine pool and in which the translocase was assumed to constitute the rate-limiting step in the activity measurements.
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PMID:Mechanism of carnitine acylcarnitine translocase-catalyzed import of acylcarnitines into mitochondria. 643 Aug 96

The fat solubilities of some long chain fatty acids, alcohols, alkanes, and triacyglycerols, and of some aromatic, chlorinated aromatic, and chlorinated aliphatic hydrocarbons were measured in trioleoylglycerol. Above their melting temperature, all test compounds are theoretically miscible with liquid fat. Below their melting temperature the solubility of all test compounds can be estimated by the equation: log (mole fraction solubility) = (Formula: see text) where delta Sf, the entropy of fusion, can be estimated from chemical structure according to Yalkowsky and Valvani (J. Pharm. Sci. 1980. 69:912-922), and the melting point (Tm) is either known or experimentally determined. For long chain compounds, solubility in trioleoylglycerol dropped precipitously with an increase in melting point. For the aromatic and chlorinated compounds, the drop was more gradual. Since the entropy of fusion of rigid aromatic compounds is approximately 13.5 e.u. at room temperature, their solubility in triacylglycerol is a linear function of melting point.
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PMID:Solubility of fatty acids and other hydrophobic molecules in liquid trioleoylglycerol. 670 27

Adrenoleukodystrophy (ALD) is an inherited disorder of fatty acid metabolism marked by accumulation of very long chain saturated fatty acids (VLCFA), especially the 26-carbon acid, hexacosanoic acid (HA), in membranes and tissues. We have studied interactions of 13C-enriched HA with model membranes (phospholipid bilayer vesicles) and bovine serum albumin (BSA) by 13C NMR spectroscopy to compare properties of HA with those of typical dietary fatty acids. In phospholipid bilayers the carboxyl group of HA is localized in the aqueous interface, with an apparent pKa (7.4) similar to other fatty acids; the acyl chain must then penetrate very deeply into the membrane. Desorption of HA from vesicles (t1+2 = 3 h) is orders of magnitude slower than shorter chain fatty acids. In mixtures of vesicles and BSA, HA partitions much more favorably to phospholipid bilayers than typical fatty acids. BSA binds a maximum of only 1 mole of HA at one binding site. Calorimetric experiments show strong perturbations of acyl chains of phospholipids by HA. We predict that disruptive effects of VLCFA on cell membrane structure and function may explain the neurological manifestations of ALD patients. These effects will be further amplified by slow desorption of VLCFA from membranes and by the ineffective binding to serum albumin.
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PMID:Interactions of a very long chain fatty acid with model membranes and serum albumin. Implications for the pathogenesis of adrenoleukodystrophy. 765 17

Reports of the antiviral activity of aliphatic alcohols led us to investigate the effects of aliphatic alcohols, from 10 to 20 carbons in length, on the phase transition behaviour of model phospholipids and on the fusion of influenza to liposomes. Contrary to the effects of many other antiviral agents, we find that alcohols are potent promoters of the inverted hexagonal phase. However, we also find that aliphatic alcohols have little effect on influenza fusion to liposomes. Eicosanol is the only aliphatic alcohol tested which substantially increases in fusion of influenza virus. We also find that long chain alcohols display multi-component bilayer to hexagonal phase transitions at higher mole fractions. This suggests that eicosanol may be facilitating fusion by creating defects between alcohol-rich and alcohol-poor regions of the lipid bilayer.
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PMID:Fusion of influenza to liposomes is not inhibited by aliphatic primary alcohols. 803 7

The structure of lipid A from the lipopolysaccharide of Rhizobium leguminosarum bv. phaseoli (wild type strain CE3) was investigated by alkylation analysis, nuclear magnetic resonance spectroscopy, and electrospray and fast atom bombardment mass spectrometry of the de-O-acylated lipid A. The lipid A carbohydrate backbone was shown to be a trisaccharide containing galacturonic acid, glucosamine, and the unique sugar 2-amino-2-deoxygluconic acid, previously unreported in lipopolysaccharides. Nuclear magnetic resonance spectroscopy and ethylation analyses revealed that the galacturonic acid is alpha-1,4-linked to the glucosamine, while the amino aldonic acid residue, which may exist as the 1,5-lactone, is attached as an aglycone to the glucosamine and, thus, occupies the reducing end of the molecule. The resulting backbone is hydrophilic and analogous to the commonly observed bisphosphorylated glucosamine disaccharide from enteric bacterial lipopolysaccharides in that both the nonreducing and reducing ends carry negatively charged substituents. The fatty acids of the R. leguminosarum lipid A are attached both as O- and N-acyl substituents to glucosamine and 2-aminogluconate. All fatty acids are hydroxylated consisting of 3-hydroxymyristate (3-OH-C14.0), 3-hydroxypentadecanoate (3-OH-C15.0), 3-hydroxypalmitate (3-OH-C16.0), 3-hydroxystearate (3-OH-C18.0), and 27-hydroxyoctacosanoate (27-OH-C28.0) in the approximate mole ratio 3:0.2:1:0.6:1. Unlike lipid As from enteric bacteria, the R. leguminosarum lipid A lacks 3-acyloxyacyl substituents; however, the long chain 27-hydroxy fatty acid carries ester-linked beta-hydroxybutyrate at the 27-hydroxy position. Fast atom bombardment mass spectrometry of the de-O-acylated lipid A demonstrated the presence of 2 molecular species that differ by 28 mass units due to fatty acid heterogeneity at the two amide linkages. One species carries amide-linked 3-OH-C14.0 and 3-OH-C16.0; the second species carries 3-OH-C14.0 and 3-OH-C18.0. Each molecular species also exists as the aldonolactone, yielding molecular ions at ((M+H)+)-18. The heterogeneity in the amide-linked fatty acids further distinguishes the Rhizobium lipid A from enteric lipid As.
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PMID:Structure of lipid A component of Rhizobium leguminosarum bv. phaseoli lipopolysaccharide. Unique nonphosphorylated lipid A containing 2-amino-2-deoxygluconate, galacturonate, and glucosamine. 818 46

Extent of binding (gamma 2(1)) of cationic surfactants cetyltrimethyl ammonium bromide (CTAB), myristyltrimethyl ammonium bromide (MTAB) and dodecyl trimethyl ammonium bromide (DTAB) to calf-thymus DNA, bovine serum albumin (BSA) and to their binary mixture respectively have been measured as function of bulk concentration of the surfactant by using equilibrium dialysis technique. Binding of CTAB has been studied at different pH, ionic strength (mu), temperature and biopolymer composition and with native and denatured states of the biopolymers. The chain-length of different long chain amines plays a significant role in the extent of binding under identical solution condition. The binding ratios for CTAB to collagen, gelatin, DNA-collagen and DNA-gelatin mixtures respectively have also been determined. The conformational structures of different biopolymers are observed to play significant role in macromolecular interactions between protein and DNA in the presence of CTAB. From the experimental values of the maximum binding ratio (gamma 2m) at the saturation level for each individual biopolymer, ideal values (gamma 2m)id have been theoretically calculated for binary mixtures of biopolymers using additivity rule. The protein-DNA-CTAB interaction in mixture has been explained in terms of the deviation (delta) of (gamma 2m) from (gamma 2m)id in the presence of a surfactant in bulk. The binding of surfactants to biopolymers and to their binary mixtures are compared more precisely in terms of the Gibbs' free energy decrease (-delta G degree) for the saturation of the binding sites in the biopolymers or biopolymer mixtures with the change of the bulk surfactant activity from zero to unity in the rational mole fraction scale.
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PMID:Binding of cationic surfactants to DNA, protein and DNA-protein mixtures. 1065 Jul 15

Folylpoly-gamma-glutamate synthetase (FPGS) is the enzyme responsible for metabolic trapping of reduced folate cofactors in cells for use in nucleotide and amino acid biosynthesis. There are two isoforms of FPGS expressed in mouse tissues, one is expressed in differentiated tissue, principally liver and kidney, and the other in all rapidly proliferating cell types. The present study sought the functional difference that would explain the evolution of two mouse FPGS species. Recombinant cytosolic mouse isozymes were compared with respect to steady state kinetics, chain length of polyglutamate derivatives formed, and end-product inhibition by the major reduced folylpentaglutamate cofactors. Both isoforms were equally effective in catalyzing the addition of a mole of glutamic acid to reduced folate monoglutamate substrates. Each isoform was also capable of forming long chain polyglutamate derivatives of the model folate, 5,10-dideazatetrahydrofolate. In contrast, the FPGS isoform derived from rapidly proliferating tissue was much more sensitive to inhibition by (6R)-5,10-CH(2)-H(4)PteGlu(5) and (6S)-H(4)PteGlu(5) than the isoform expressed in differentiated tissues, as demonstrated by 13- and 6-fold lower inhibition constants (K(i)), respectively. Interestingly, each isozyme was equally sensitive to inhibition by (6R)-10-CHO-H(4)PteGlu(5). We drew the conclusion that the decreased sensitivity of the FPGS expressed in mouse liver and kidney to feedback inhibition by 5,10-CH(2)-H(4)PteGlu(5-6) and H(4)PteGlu(5-6) may have evolved to permit accumulation of a larger folate cofactor pool than that found within rapidly proliferating tissue.
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PMID:Mouse folylpoly-gamma-glutamate synthetase isoforms respond differently to feedback inhibition by folylpolyglutamate cofactors. 1177 20

Transposon mutants of Acinetobacter calcoaceticus strain RAG-1 were studied in an effort to control fatty acid (FA) substitution patterns of emulsan, a bioemulsifier secreted by the organism. The disrupted genes, involved in the biosynthetic pathways of biotin, histidine, cysteine or purines, influenced the level and types of FAs incorporated into emulsan. The structural variants of emulsan generated by the transposon mutants were characterized for yield, FA content, molecular weight, and emulsification behavior when grown on a series of FAs of different chain lengths from C11 to C18. Yields of emulsan from the transposon mutants were found to be lower than the parent strain and depended on the type of FA used to supplement the growth medium. Mutants 13D (His-) and 52D (Cys-) grown on LB plus C16 or C14, respectively, exhibited enhanced emulsifying activity compared to A. calcoaceticus RAG-1. The presence and composition of long chain FAs on the polysaccharide backbone influenced emulsification behavior: particularly a high mole percentage of C16 (48%) and C18 (42%). The results provide important insight into the bioengineering of bioemulsifier-producing microorganisms and provide a path towards highly tailored novel amphipathic structures to utilize as biodegradable in environmental, biomedical, and personal care applications.
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PMID:Bioengineered emulsans from Acinetobacter calcoaceticusRAG-1 transposon mutants. 1211 Nov 49

The mixed self-assembled monolayers (SAM) prepared from long chain alkanethiols, HS(CH(2))(11)NH(2) and HS(CH(2))(10)COOH, on gold are employed as the model surface for investigating the interactions between the biological environment and synthetic surface. A distinctive SAM preparation scheme was utilized in this investigation. The triethylamine was added to the alkanethiol solution during SAM formation and then followed by additional rinsing of SAM with 10% CH(3)COOH or 1% HCl ethanolic solution. The contact angle values of NH(2) + COOH mixed SAMs were between those of the pure SAMs, except that it was prepared with solution mole fraction of amine-terminated alkanethiol at 0.2. X-ray photoelectron spectroscopy (XPS) analysis has indicated that these two distinctive SAM preparation procedures had both resulted in a reduction in oxidized sulfur species on pure --NH(2) terminated SAM. However, the procedure utilizing 1% HCl ethanolic washing solution was more effective in reducing the unbound thiol fraction and to form a pure --NH(2) SAM with better quality. XPS analysis has also revealed that the surface of NH(2) + COOH mixed SAMs was "amine-rich". In vitro platelet adhesion assay has shown that the amount of adherent platelets on pure positive charged --NH(2) terminated SAM is less than that on anionic --COOH terminated counterpart in both acidic ethanolic washing schemes. Moreover, the lowest platelet adhesion density was noted on the mixed SAM surfaces with surface amine mole fraction at 0.51 and 0.57. This finding suggests that the surface charge with near neutrality might be of importance in reducing platelet adhesion and activation on artificial biomaterial.
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PMID:Surface characterization and platelet adhesion studies for the mixed self-assembled monolayers with amine and carboxylic acid terminated functionalities. 1732 42

Lipid rafts are membrane microdomains intimately associated with cell signaling. These biochemical microstructures are characterized by their high contents of sphingolipids, cholesterol and saturated fatty acids and a reduced content of polyunsaturated fatty acids (PUFA). Here, we have purified lipid rafts of human frontal brain cortex from normal and Alzheimer's disease (AD) and characterized their biochemical lipid composition. The results revealed that lipid rafts from AD brains exhibit aberrant lipid profiles compared to healthy brains. In particular, lipid rafts from AD brains displayed abnormally low levels of n-3 long chain polyunsaturated fatty acids (LCPUFA, mainly 22:6n-3, docosahexaenoic acid) and monoenes (mainly 18:1n-9, oleic acid), as well as reduced unsaturation and peroxidability indexes. Also, multiple relationships between phospholipids and fatty acids were altered in AD lipid rafts. Importantly, no changes were observed in the mole percentage of lipid classes and fatty acids in rafts from normal brains throughout the lifespan (24-85 years). These indications point to the existence of homeostatic mechanisms preserving lipid raft status in normal frontal cortex. The disruption of such mechanisms in AD brains leads to a considerable increase in lipid raft order and viscosity, which may explain the alterations in lipid raft signaling observed in AD.
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PMID:Lipid alterations in lipid rafts from Alzheimer's disease human brain cortex. 2011 May 96


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