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PubMed1986

Effect of acetylsalicylic acid on fatty acid omega-hydroxylation in rat liver.

The effect of acetylsalicylic acid on the cytochrome P-450-mediated fatty acid omega-hydroxylation system was assessed in male Sprague-Dawley rats after they were fed a diet containing 1% (w/w) acetylsalicylic acid. A 3-fold increase in the specific activity of laurate omega-hydroxylation was observed in the acetylsalicylic acid fed rats in comparison to control rats. This effect of acetylsalicylic acid was unique as the specific activities of other cytochrome P-450-mediated reactions were not increased. The induction of the laurate omega-hydroxylation system was also manifested in a rapid formation of its dicarboxylic acid derivative, dodecanedioic acid, as the omega-hydroxy derivative was further oxidized by alcohol and aldehyde dehydrogenases. These results suggest the acetylsalicylic acid is similar to other peroxisomal proliferating agents in that it also induces the microsomal fatty acid omega-hydroxylation system and may account for the appearance of unique dicarboxylic acids in Reye's syndrome patients.

Animals↗
PubMed2005

Effect of sucrose fatty acid esters on transdermal permeation of lidocaine and ketoprofen.

The effect of sucrose fatty acid esters on transdermal permeation of lidocaine (LC) and ketoprofen was examined. A drug solution was applied to excised hairless mouse skin pretreated with a sugar ester solution to examine the direct effects of the sugar esters on skin permeability. LC was applied with a pH 6 buffer solution (98.8% ionized), pH 10 buffer solution (99.2% unionized), or propylene glycol, while KP was applied with a pH 6 buffer solution (99.1% ionized), pH 2 buffer solution (98.9% unionized), or propylene glycol. Pretreatment with J-1216 (sucrose laurate, HLB = 16) or J-1205 (sucrose laurate, HLB = 5) significantly increased the permeation of LC from the pH 6 solution and KP from propylene glycol, respectively. The permeability coefficients of the ionized and unionized LC and KP were calculated from the permeability data. The ionized LC and KP permeated even through skin not pretreated with sugar esters, although the permeability coefficients were 24 times and 38 times less than those of the unionized LC and KP, respectively. J-1216 pretreatment increased the permeability of ionized LC from aqueous vehicle 2.7 fold. In the next series of experiments, we formulated 1.5% of J-1205 and J-1216 in various vehicles to examine their effect on the permeation of LC applied on the excised hairless mouse skin with no pretreatment. The results coincided with the results of the pretreatment experiment, and the effect of J-1205 in propylene glycol was more remarkable than that observed in the pretreatment study. When these sugar esters were dissolved in propylene glycol at 1.5%, J-1205 increased significantly the KP permeation rate as well as LC permeation rate, suggesting that the combination of J-1205 and propylene glycol would be a potent vehicle for transdermal formulations.

Administration, Cutaneous↗
PubMed2004

The role of carotenoids in the photoadaptation of the brown-colored sulfur bacterium Chlorobium phaeobacteroides.

The brown-colored sulfur bacterium Chlorobium (Cb.) phaeobacteroides 1549 (new name, Chlorobaculum limnaeum 1549) contains many kinds of carotenoids as well as bacteriochlorophyll (BChl) e. These carotenoids were identified with C18-high-performance liquid chromatography, absorption, mass and proton nuclear magnetic resonance spectroscopies and were divided into two groups: the first is carotenoid with one or two phi-end groups such as isorenieratene and beta-isorenieratene and the second is carotenoid with one or two beta-end groups such as p-zeacarotene, beta-carotene and 7,8-dihydro-beta-carotene. The latter 7,8-dihydro-beta-carotene was found to be a novel carotenoid in nature. OH-gamma-Carotene glucoside laurate and OH-chlorobactene glucoside laurate were also found as minor components. The distribution of BChl e homologs in Cb. phaeobacteroides cultivated under various light intensities did not change, but the carotenoid to BChl e ratio changed markedly: carotenoid with the phi-end group maintained the same ratio to BChl e, whereas that with the beta-end group increased with increasing light intensity. The cells cultured under low-light intensity contained more phi-end carotenoids than beta-end. In Cb. phaeobacteroides the wavelength of the Qy band of BChl e aggregates did not change. We suggested that Cb. phaeobacteroides photoadapts to light intensity by changing the carotenoid composition.

Bacteriochlorophylls↗
PubMed1992

Acyloxyacyl hydrolase, a leukocyte enzyme that deacylates bacterial lipopolysaccharides, has phospholipase, lysophospholipase, diacylglycerollipase, and acyltransferase activities in vitro.

Human acyloxyacyl hydrolase (AOAH) is a leukocyte enzyme that hydrolyzes acyloxyacyl bonds in the lipid A region of bacterial lipopolysaccharide (LPS), thereby detoxifying the LPS. We report here that the enzyme also acts in vitro on glycerophospholipids, lysophospholipids, and diacylglycerol. While AOAH preferentially removes palmitate or stearate from the sn-1 position of phospholipid and diacylglycerol substrates that have unsaturated acyl chains in the sn-2 position, it is able to cleave both palmitates from sn-1,2-dipalmitoylphosphatidylcholine and sn-1,2-dipalmitoylglycerol. This apparent preference for removing saturated (or shorter) acyl chains from glycerolipids is consistent with its ability to cleave laurate more rapidly than palmitoleate from lipopolysaccharide (Erwin, A. L., and Munford, R. S. (1990) J. Biol. Chem. 265, 16444-16449). AOAH also catalyzes acyl transfer from LPS and phosphatidylethanolamine to acceptor lipids; approximately equal amounts of laurate and myristate are transferred from LPS to monooleoylglyceryl ether, forming acyloleoylglyceryl ether. The demonstration that AOAH has phospholipase, lysophospholipase, diacylglycerol lipase, and acyltransferase activities in vitro suggests that the enzyme may have roles in addition to LPS deacylation (detoxification) in phagocytic cells.

Acyltransferases↗
PubMed1991

Phycochemical studies on Scinaia fascicularis (Bonnemaisoniales, Rhodophyta).

The sterol composition of marine red alga, Scinaia fascicularis (Bphirg.) Huisman has been studied and cholesta-5, 20, 24-trien-3beta-ol, 22-dehydrocholesterol, brassicasterol, 24-methylene cholesterol, 24-methyl cholesterol, nor 31-cycloartanol, ergost-5-en-3,25-diol and lanostan-3beta-ol were identified through mass and 1H-NMR spectroscopy. All of them were present in more or less equal amount. The fatty acid methyl esters, analysed through GC-MS, were found to be methyl laurate, tridecylate, myristate, pentadecylate, palmitate, margarate, stearate and nonadecylate. Methyl myristate was present in largest and laurate in smallest quantity, no unsaturated fatty acid could be detected.

Journal Article↗
PubMed1975

Long chain fatty acid binding to human plasma albumin.

The binding of six physiologically important long chain fatty acids to defatted human plasma albumin was measured at 37 degrees in a calcium-free Krebs-Ringer phosphate buffer, pH 7.4. The data were analyzed in terms of multiple stepwise equilibria. With the saturated acids, the magnitude of the equilibrium (association) constants, Ki, increased as the chain length increased: laurate smaller than myristate smaller than palmitate smaller than stearate. Oleate was bound more tightly than stearate; by contrast, linoleate was bound less tightly than stearate. The equilibrium constants, K1 through K12, ranged from 2.4 times 10-6 - 3.5 times 10-3 m-1 for laurate to 2.6 times 10-8 - 3.5 times 10-5 m-1 for oleate. Successive values of Ki decrease for each of the acids, indicating that major cooperative binding effects do not occur over the physiological range of fatty acid concentrations. In no case could the Ki be segregated into distinct classes, suggesting that any grouping of albumin binding sites is somewhat arbitrary. The results were inconclusive concerning whether premicellar association of unbound fatty acid occurs. Although corrections for premicellar association produced very little change in the Ki values for myristate, they raised the Ki for palmitate and stearate by 300 to 700 per cent. A sigmoidal relationship was obtained when the logarithm of Ki was plotted against chain length for the saturated fatty acids containing 6 to 18 carbon atoms, indicating that the binding energy is not simply a statistical process dependent only on the fatty acid chain length. This selectivity that albumin contributes to the binding process may be due to varying degrees of configurational adaptability of its binding sites as the fatty acid increases in length.

Fatty Acids↗
PubMedDate not supplied

Azoreduction of N,N-dimethyl-4-aminoazobenzene (DAB) by rat hepatic microsomes. Selective induction by clofibrate.

Metabolism of the hepatocarcinogen, N,N-dimethyl-4-aminoazobenzene (DAB) by rat liver microsomes proceeds via N-demethylation, ring hydroxylation, and azoreduction. DAB azoreduction was induced in microsomes from rats treated with the hypolipidemic drug, clofibrate, whereas oxidative metabolism of the carcinogen was inhibited. In contrast, treatment with nafenopin, another hypolipidemic drug, inhibited microsomal azoreduction of DAB, whereas oxidative pathways were only slightly affected. No direct effect of either drug on azoreductase activity was observed. Both drugs markedly induced microsomal laurate hydroxylation. DAB azoreduction was increased slightly in microsomes from rats treated with beta-naphthoflavone while treatment with phenobarbital led to partial inhibition. Pretreatment with isosafrol or pregnenolone-16 alpha-carbonitrile did not significantly alter DAB reduction. Metyrapone, added in vitro, inhibited microsomal DAB azoreductase activity only in phenobarbital-treated microsomes, whereas alpha-napthoflavone and SKF 525-A inhibited activity in control and all induced microsomes. DAB azoreduction proceeds readily in air and is not sensitive to carbon monoxide. Neither clofibrate nor nafenopin affected NADPH-cytochrome c reductase activity. It is concluded that clofibrate-induced azoreductase activity is probably attributable to a specific isoform of cytochrome P-450 which can be distinguished from those which catalyze oxidative pathways of DAB or laurate hydroxylation.

Animals↗
PubMed1985

Ester synthesis at extraordinarily low temperature of -3 degrees C by modified lipase in benzene.

The lipoprotein lipase from Pseudomonas fluorescens was modified with 2,4-bis(O-methoxypolyethylene glycol)-6-chloro-s-triazine. The modified lipase in which 55% of the amino groups in the enzyme molecule were coupled with polyethylene glycol was found to be soluble in benzene and catalyzed the reactions of ester synthesis, ester exchange, aminolysis and ester hydrolysis in benzene. The modified lipase had an extraordinary temperature-dependency: enzymic activity for methyl laurate synthesis from methyl alcohol and lauric acid increased with decreasing temperature and attained the maximum at the extremely low temperature of -3 degrees C. The optimum temperature for hydrolysis of methyl laurate was as low as -4 degrees C.

Benzene↗
PubMed1979

Crystal structure of cholesteryl decanoate.

Cholesteryl decanoate (C37H64O2) is monoclinic, space group P2I, with cell dimensions a = 12.931 (6), b = 9.066 (2), c = 30.22 (1) A, beta = 91.14 (4) degrees, and Z = 4. The atomic coordinates from cholesteryl laurate were used in an initial trial structure which was refined by block diagonal least-squares methods with 1846 observed X-ray reflections (R = 0.129). Molecules A and B have almost fully extended conformations, except at the ester bonds and towards the end of the decanoate B chain. The molecules are arranged in antiparallel array forming monolayers of thickness d001 = 30.22 A, with the molecular long axis making an angle of about 67 degrees with the layer interface. The crystal structure is very similar to that of cholesteryl nonanoate and cholesteryl laurate.

Cholesterol Esters↗
PubMed1980

Uptake and metabolism of fatty acids by dispersed adult rat heart myocytes. I. Kinetics of homologous fatty acids.

An adult rat heart myocyte preparation was used to study the uptake and metabolism of the 1-(14)C-labeled free fatty acids decanoate, laurate, myristate, palmitate, and oleate at 37 degrees C in the absence of serum albumin. The rate of total uptake consisted of both a nonsaturable and a saturable component. The nonsaturable component corresponded to the fatty acid accumulating in the free fatty acid fraction, and the rate of this accumulation increased logarithmically as a function of chain length. The saturable component corresponded to that portion of fatty acid converted to the only detectable metabolic products: CO2, triglyceride, and polar lipid. The Km for this process was about 1 microM and was independent of chain length. The Vmax for the saturable component varied only slightly with chain length, from 20 +/- 1 nmol/h-mg of cell protein for decanoate to 47 +/- 18 nmol/h-mg of cell protein for palmitate. The relative product distribution did vary with chain length, however, ranging from primarily carbon dioxide for decanoate to approximately equal quantities of carbon dioxide, triglyceride, and polar lipid for palmitate. Two internal pools of free fatty acid are postulated: a minor pool that equilibrates rapidly with external fatty acid and serves as the precursor for fatty acid activation, and a major pool containing most of the accumulated free acid. These two pools are interconvertible. The data support a simple diffusion or membrane-partitioning process for the accumulation of fatty acid in the second pool. The data presented in this paper are not sufficient to distinguish between a simple diffusion or a carrier-mediated process for uptake into the first pool. The saturation kinetics observed appear to represent a metabolic step such as fatty acid activation, rather than a transport carrier. Evidence of toxicity at a higher concentration of the longer chain fatty acids limits the concentration range that can be studied in the absence of albumin. Decanoate did not appear to be toxic at concentrations up to 300 microM, but laurate at 10 microM and myristate at 5 microM appeared to uncouple respiratory control.

Animals↗
PubMed1995

Effect of isocarbacyclin methyl ester incorporated in lipid microspheres on experimental models of peripheral obstructive disease.

The effect of TTC-909 (isocarbacyclin methyl ester (CAS 88931-51-5, TEI-9090) incorporated into lipid microspheres) on obstruction of the peripheral artery was studied in two different animal models. The first was a peripheral occlusion model induced by intra-arterial injection of sodium laurate in rats. The second was a tail gangrene model induced by subcutaneous injection of both ergotamine and epinephrine in rats. Intravenous bolus-administered TTC-909 at 1.0 microgram/kg resulted in the inhibition of both progression of lesions induced by sodium laurate and the extension of tail gangrene by ergotamine and epinephrine. Moreover, the inhibitory effect of TTC-909 was more potent than that of PGE1 (LM) (prostaglandin E1 incorporated into lipid microspheres). These findings suggested that TTC-909 may be clinically useful for the therapy of peripheral vascular disorders such as thromboangiitis obliterans (TAO) and atherosclerosis obliterans (ASO).

Alprostadil↗
PubMed1996

Immunomodulatory effect of some amphiphilic detergents on the human promyelocytic HL-60 cells.

The effect of two anionic (sodium dodecyl sulfate (SDS) and sodium laurate), two cationic (didodecyldimethylammonium bromide (DDAB) and [(1-methyldodecyl)-trimethylammonium bromide (2-ATDBr)] and a nonionic [(1-methyldodecyl)-dimethyl-amine N-oxide (2-ATDNO)] amphiphilic detergents on the metabolic activation of phagocytes derived from human promyelocytic leukemia cell line HL-60 was investigated. SDS in the concentrations of 10(-4) M significantly stimulated the INT-reduction and superoxide production by HL-60 cells which were preincubated with phorbol 12-myristate 13-acetate (PMA) for a macrophage-like differentiation. This effect was not significant in the case of cells differentiated along monocyte-like and granulocyte-like pathways. A similar influence was observed by sodium laurate, but this effect was significant (P < 0.01) by INT-reduction only. Concentrations higher than 5 x 10(-5) M DDAB, 2-ATDBr and 2-ATDNO inhibited INT-reduction and superoxide generation in HL-60 cells differentiated along all three ways. Our results indicated that differentiated HL-60 cells may be used for in vitro testing of immunotoxic effects on respiratory burst in phagocytes.

Detergents↗
PubMed1998

P-450-dependent metabolism of lauric acid in alcoholic liver disease: comparison between rat liver and kidney microsomes.

Monooxygenase enzymatic activities were measured in liver and kidney microsomes of control and ethanol-treated rats. Animals were administered alcohol by using a model for alcoholic liver injury. Several in vitro approaches were used to compare the laurate metabolism in liver and kidney microsomes: correlation studies between specific P-450 catalytic activities, immunoblot analysis, and chemical and immunoinhibitions. Ethanol treatment increased the liver and renal hydroxylations of chlorzoxazone and 4-nitrophenol. Moreover, lauric acid (omega-1)-hydroxylation was found to be significantly increased (-6-fold) after ethanol treatment in liver, but not in kidney microsomes. The laurate omega-1/omega ratio increased from 1.52 +/- 0.49 to 4.11 +/- 1.01 in liver microsomes of control and ethanol-treated rats, and from 0.29 +/- 0.06 to 0.44 +/- 0.07 in kidney microsomes. Immunoblot analysis using polyclonal anti-cytochrome P-450 (CYP) 2E1 or CYP4A antibodies showed an increase of CYP2E1 and CYP4A contents in both organs, but the increase was higher in liver than in kidney microsomes. Chemical inhibitions using CYP2E1 competitive inhibitors (such as chlorzoxazone and ethanol) led to a nonsignificant inhibition of the renal (omega-1)-hydroxylation of lauric acid. In contrast, 17-octadecynoic acid (a mechanism-based inhibitor of omega-hydroxylase) was able to inhibit both omega- and (omega-1)-hydroxylations of lauric acid in kidney microsomes. Immunoinhibitions specific to CYP2E1 significantly decreased the (omega-1)-hydroxylation of lauric acid in liver, but not in kidney microsomes, whereas the polyclonal anti-CYP4A1 antibody inhibited omega- and (omega-1)-hydroxylations of lauric acid in kidney microsomes. All of these results show that lauric acid hydroxylations in liver and kidney respond in different manners to ethanol treatment. Lauric acid (omega-1)-hydroxylation, a highly specific probe for CYP2E1 in rat and human liver microsomes, is mediated by a CYP4A isoform in rat kidney microsomes.

Animals↗
PubMed1998

Application of long chain amine activator in conventional acrylic bone cement.

A long chain acid derivative bearing an aromatic tertiary amine group, 4-N,N-dimethylaminobenzyl laurate (DML), which acts as an activator for the curing of acrylic cements at low temperature, has been synthesized and characterized to reduce the biological adverse effects usually associated with the classical activator N,N-dimethyl-4-toluidine (DMT). The effectiveness of the activator was tested on commercial formulations (e.g., Palacos R) and on experimental bone cements based on poly (methyl methacrylate) by using different benzoyl peroxide/amine molar ratios. The exotherms of polymerization were followed at three different temperatures: 25, 30, and 37 degrees C. The DML activator was found to be more sensitive to temperature than the corresponding DMT. DML provided exotherms of polymerization with decreasing peak temperatures and increasing setting times without impairing the mechanical properties. Residual monomer content was analyzed in a range of activator concentrations by keeping the benzoyl peroxide concentration constant. In all cases the residual monomer content was lower than 5%, indicating its good efficiency in the benzoyl peroxide initiated polymerization.

Bone Cements↗
PubMed1999

Water absorption characteristics and cytotoxic and biological evaluation of bone cements formulated with a novel activator.

A novel activator, N,N,Dimethylamino 4-benzyl laurate (DML) was used in the curing of acrylic bone cements, based on poly(methylmethacrylate). The water absorption characteristics were studied, and the behavior was found to be similar to commercial bone cements. The net amount of solubles were also in the same range as obtained for commercial cements cured with conventional activators. Biocompatibility tests were conducted on the neat activator (DML) and cured cements. The present study indicated that there were no toxic effects; furthermore, osteoblast-like cells were seen to proliferate and differentiate more readily on DML containing cements. The analysis of the effect of leachables from cements into the media showed continued cell proliferation and cell viability.

Bone Cements↗
PubMed2006

A novel reactive perstraction system based on liquid-core microcapsules applied to lipase-catalyzed biotransformations.

A novel reactive perstraction system has been developed based on liquid-core capsules, involving an enzyme-catalyzed reaction coupled with simultaneous in situ product recovery. Lipase-catalyzed reactions, hydrolysis of triprionin and nitrophenyl laurate, were selected to test the system and demonstrate the feasibility of immobilization of enzymes to the membranes of liquid-core capsules and the ability to extract hydrophobic products of the reaction within the capsule core. The lipase from Candida rugosa was immobilized to the microcapsules by adsorption and by covalent binding through activation with glutaraldehyde. In both cases improved temperature and operational stability were achieved. Both types of immobilization resulted in a basic shift of the pH optimum for activity, from 7.5 to 9.0. The presence of an organic phase within the capsule core allowed direct product separation and lead to a decrease in product inhibition of the lipase-catalyzed reaction.

Biotransformation↗
PubMed1998

Expression of recombinant psoriasis-associated fatty acid binding protein in Escherichia coli: gel electrophoretic characterization, analysis of binding properties and comparison with human serum albumin.

The psoriasis-associated fatty acid binding protein (PA-FABP, also known as FABP5) is a novel keratinocyte protein that is highly up-regulated in psoriatic plaques (P. Madsen, H. H. Rasmussen, H. Leffers, B. Honoré and J. E. Celis, J. Invest. Dermatol. 1992, 99, 299-305). Here we have expressed PA-FABP in Escherichia coli as a fusion protein containing an NH2-terminal hexa-His tag followed by a factor Xa cleavage site. The recombinant protein was expressed at a level of about 30% of the soluble proteins and was purified to homogeneity using a simple two-step protocol consisting of affinity chromatography on Ni2+-nitrilotriacetic acid agarose followed by gel filtration. The recombinant protein was then digested with factor Xa and characterized by two-dimensional gel electrophoresis. The ability of PA-FABP to bind saturated fatty acids ranging from 6 to 16 carbons was determined directly by dialysis and compared to human serum albumin (HSA). The results showed that PA-FABP binds multiple molecules of the fatty acids hexanoate (C6:0), octanoate (C8:0), decanoate (C10:0) and laurate (C12:0), all with a K1 of about 10(4) M(-l), and myristate (C14:0) with a K1 of 4.4 X 10(5) M(-l). Palmitate (C16:0) also bound strongly with multiple molecules. Due to the very low solubility of palmitate its affinity to PA-FABP was measured relatively to HSA and found to be 8.1 times lower. At ligand/protein ratios below 1, all fatty acids bound to PA-FABP with about one to three orders of magnitude lower affinity than to HSA. The difference in the fatty acid binding properties of the two proteins may reflect differences in their three-dimensional structures, which in the case of PA-FABP consists mainly of beta-sheets while HSA contains predominantly alpha-helices.

Albumins↗
PubMed2003

Fatigue and fracture toughness of acrylic bone cements modified with long-chain amine activators.

The composition of acrylic bone cement has been identified as one of the important parameters affecting its mechanical properties and may, in turn, ultimately influence the longevity of a cemented arthroplasty. Our aim in this study was to determine the influence of change of one compositional variable, the activator, on the fatigue performance and fracture toughness of specimens of the fully cured cement. To that end, three sets of cements were prepared, containing either the conventional activator, 4-N,N dimethyl p-toluidine (DMPT), or novel ones that are tertiary amines based on long-chain fatty acids, that is, 4-N,N dimethylaminobenzyl oleate (DMAO) and 4-N,N dimethylaminobenzyl laurate (DMAL). In the fatigue tests, the specimens were subjected to tension-tension loading, and the results (number of cycles to failure, Nf) were analyzed using the linearized form of the three-parameter Weibull equation. The fracture toughness (KIc) tests were conducted with rectangular compact tension specimens. All fracture surfaces were subsequently examined with scanning electron microscopy. We found that the Weibull mean fatigue lives for specimens fabricated using the DMPT, DMAL, and DMAO containing cements were 272,823, 453,551, and 583,396 cycles, respectively. The corresponding values for KIc were 1.94 +/- 0.05, 2.06 +/- 0.09, and 2.00 +/- 0.07 MPa radical m, respectively. Statistical analyses showed that for both the DMAL- and DMAO-containing cements, the mean values of Nf were significantly higher compared to the corresponding value for the DMPT-containing cement (Mann-Whitney test; alpha < 0.10). This result is attributed to the higher molecular weights of the former cements compared to the latter. The same trend was found for the mean KIc values (Mann-Whitney test; alpha < 0.05), with the trend being explained in terms of the differences seen in the crack morphologies. These results thus demonstrate that these novel amines are viable alternatives to DMPT for incorporation into acrylic bone cement formulations in the future.

Amines↗