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PubMed1980

Pharmacokinetic comparison of etilefrine to its prodrug, the stearic acid ester of etilefrine.

The relative bioavailability of a prodrug of etilefrine, its stearic acid ester, was determined by means of plasma levels and renal excretion. The comparison of the plasma levels and renal excretion was carried out in a cross-over design in six subjects. 3H-etilefrine (20 mg) and 3H-2-etylamino-1-(3-stearoylphenyl)ethanol hydrochloride (44.42 mg) were administered orally in equimolecular amounts. The stearic acid ester of etilefrine does not appear in the blood; the ester is split even during absorption. The relative bioavailability of the stearic acid ester of etilefrine, which was determined from the comparison of the areas under the plasma level and the renal excretion, amounts to 51% related to etilefrine. The investigation of the renal excretory products after administration of etilefrine and its prodrug showed the same metabolic pattern. The sulfuric acid ester of etilefrine is the main metabolite. In addition to etilefrine, two basic metabolites are excreted. According to mass- and NMR-spectrometric findings, these two metabolites are two isomeric tetrahydroisoquinolines which formally developed by condensation of etilefrine with formaldehyde. These tetrahydroisoquinolines are excreted free and conjugated with sulfuric acid.

Adult↗

PubMed1987

Increased erythrocyte stearic acid desaturation in rats with chemically induced colorectal carcinomas.

Our previous studies have demonstrated a desaturation of stearic acid related to oleic acid in the lipid layer of erythrocytes in patients with malignancies. This study investigated the stearic acid desaturation in red blood cell membranes of rats during the induction of colorectal tumours. Male Sprague-Dawley rats were injected weekly with dimethylhydrazine (DMH) and sacrificed at 4-week intervals. Blood was withdrawn via heart puncture, collected in EDTA bottle and erythrocytes separated by centrifugation. Total lipid extraction was carried out and analysed with gas liquid chromatography. In the control rats (injected with normal saline) the mean of the stearic to oleic acid ratio in erythrocyte membranes was 2.0 +/- 0.3 (n = 28, range 1.51-2.62) compared to a mean of 0.94 +/- 0.16 (n = 0.5-1.23) in tumour bearing rats (p less than 0.001). The increased desaturation occurred in parallel with appearance of tumours. These data suggest the regulation of stearic acid desaturation is an important adaptive mechanism of membrane fluidity and could be a useful chemical marker for malignancy.

Animals↗

PubMed1976

The metabolism of (1-14C) stearic acid in rat testicular tissue.

(1) The metabolism of stearic acid was studied in vivo following intratesticular injection of [1-14C] stearate. Soon after injection 14C activity was found mainly in the free fatty acid pool. This was followed at later time periods by transfer of label primarily to the phosphatide pool. During each time period significant amounts of label were recovered at 14CO2. (2) Analysis of 14C-labeled fatty acids from the injected testes demonstrated an initial rapid rate of oxidation and desaturation of [1-14C] stearate followed by a slower steady state rate. It was concluded that the initial rate was due to the rapid turnover of the highly labeled free fatty acid pool followed by a much slower rate as [14C] stearate was esterified to the more metabolically stable phospholipids. Elongation of the labeled stearic or its desaturated derivative was not observed. (3) The rate of desaturation in vitro of stearic acid was measured in microsomal preparations from rat testes and found to be 12.0 +/- 0.5 pmol/min/mg compared to the estimated in vivo value of 22 pmol/min/mg and the value of 390 pmol/min/mg for hepatic microsomal desaturase.

Animals↗

PubMed2007

Influence of gradual introduction of hydrophobic groups (stearic acid) in denatured atelocollagen on fibroblasts behavior in vitro.

To prepare new biocompatible hydrophobic collagen films for medical devices, innovative collagen derivatives were synthesized by reaction of the lysyl amino groups of the alpha-chains with activated stearic acid. Different collagens having different substitution degrees were obtained and used to prepare films crosslinked with oxidized glycogen. Their physicochemical surface properties were evaluated, and in vitro assays were performed to analyze the behavior of fibroblasts in contact with the materials. The assays were performed with cells in adhesion and growth phases. The hydrophobic properties increased with the number of stearic acid introduced in the collagen but only in the range of 1-12 stearic acids per molecule. For higher modifications a decrease of hydrophoby was observed. All the films induced a decrease of cells growth and adhesion but without cytotoxicity. These effects were more pronounced for the collagen containing about eight stearic acid residues. Cells behavior on modified collagens films seems to be related to the chemical groups exposed on the surface of the films. Indeed, the surface chemistry directly influences the adsorption of adhesion proteins and modulates their conformation therefore modifying the cell adhesion.

Biocompatible Materials↗

PubMed1986

A change in the lipid fluidity of the porcine intestinal brush-border membranes by lipid peroxidation. Studies using pyrene and fluorescent stearic acid derivatives.

The effect of lipid peroxidation on the lipid fluidity of porcine intestinal brush-border membranes was examined by measuring the rotational mobility and the accessibility to fluorescence quenchers (CH3COOT1, CuSO4 and KI) of pyrene or n-(9-anthroyloxy)stearic acid (n = 2 or 12) in the membranes. The harmonic mean of the rotational relaxation times of pyrene increased and the rate constants, kq, of the quenching reaction of pyrene and 2-(9-anthroyloxy)stearic acid incorporated in the membrane lipids decreased upon lipid peroxidation, indicating reduction of the lipid fluidity of the membranes by lipid peroxidation. In addition, the kq value of the reaction of 2-(9-anthroyloxy)stearic acid in the membranes with Cu2+ decreased in proportion to the amount of the products of lipid peroxidation. On the other hand, the kq value of the reaction of 12-(9-anthroyloxy)stearic acid with Cu2+ or I- was unaffected by lipid peroxidation. Based on these results, a localized change in the lipid fluidity of the membranes in association with lipid peroxidation has been discussed.

Animals↗

PubMed1990

Influence of stearic acid monolayers upon the procaine adsorption from underlying alkaline aqueous solutions.

Adsorption of procaine at the air/water interface and its penetration into stearic acid monolayers from aqueous subphase of pH 8 are studied by measuring surface tension of aqueous procaine solutions and by recording surface pressure vs. mean molecular area curves for stearic acid monolayers spread onto procaine solutions of different concentrations. The amount of procaine in the interface is derived by means of Gibbs' equation. Results are compared to those obtained earlier at pH 2 and on unbuffered subphases. With increasing pH an increasing procaine adsorption and procaine penetration is observed. This phenomenon is interpreted in terms of protolytic equilibria in which participate both surfactants procaine and stearic acid.

Adsorption↗

PubMed1997

In situ observation of bovine serum albumin-adsorbed stearic acid monolayer by Brewster angle microscopy.

The morphology of protein-adsorbed stearic acid monolayers containing a fluorescent probe (rhodamine B octadecylester perchloride: RBO) was observed by using fluorescence spectroscopy, fluorescence microscopy, and Brewster angle microscopy (BAM). The quenching of fluorescence of RBO was observed at the limiting area of the stearic acid monolayer. Thus, the fluorescence of RBO could be a good marker for packing of the matrix monolayer. On the other hand, the BAM image showed the morphology of not the matrix monolayer, but the adsorbed protein monolayer. Thus, the packing processes of the two could be distinguished. The present method is available for a protein that does not have visible absorption, such as bovine serum albumin (BSA). It is suggested that electrostatic interaction between matrix and protein molecules greatly affects the change in the morphology of the protein-adsorbed monolayer.

Adsorption↗

PubMed2000

An investigation into the release of cefuroxime axetil from taste-masked stearic acid microspheres. III. The use of DSC and HSDSC as means of characterising the interaction of the microspheres with buffered media.

Stearic acid coated cefuroxime axetil (SACA) microspheres have been studied using differential scanning calorimetry (DSC) and high sensitivity DSC (HSDSC) in order to examine the interaction between the spheres and a range of buffer systems, with a view to further enhance the understanding of the mechanism of drug release developed in earlier studies [Robson et al., 1999, 2000]. DSC studies indicated that after immersion in Sorensens modified phosphate buffer (SMPB) pH 5.9 followed by washing and drying, no change in the thermal properties of the spheres was detected up to 60 min of immersion, with a single endotherm noted at circa 56 degrees C, that corresponded to the melting of the stearic acid used in this study; similar results were obtained for systems immersed in distilled water. After immersion in SMPB pH 7.0 and 8.0, however, a second peak was noted at approximately 67 degrees C that increased in magnitude relative to the lower temperature endotherm with increasing exposure time to the medium. Spheres that had not been previously washed prior to drying showed complete conversion to the higher temperature endotherm for these two buffers. Systems which had been exposed to a range of pH 7.0 buffers (citrate-phosphate buffer (CPB), phosphate buffer mixed (PBM), boric acid buffer (BAB)) were then examined. Only the CPB systems showed evidence for conversion to the higher melting form. PBM systems to which further sodium had been added were then examined. A maximum conversion was found at 0.05 M sodium, which was in agreement with the maximum in release rate found in a previous study [Robson et al., 2000]. HSDSC was then used to examine systems that were immersed in the buffer. For SMPB, pH 5.9 and distilled water, only the endotherm corresponding to the stearic acid melting was seen. However, for SMPB pH 7.0 and 8.0, three peaks were seen, two corresponding to those seen for the DSC studies and a further lower temperature peak at circa 44 degrees C. Studies on PBM systems to which additional sodium had been added showed small levels of conversion to the higher temperature form at higher sodium contents. The data was discussed in terms of the correlation with earlier dissolution studies on the same systems [Robson et al., 1999; 2000].

Buffers↗

PubMed1991

Incorporation into liver microsomal lipids of linoleic and stearic acids and of their respective products of delta 6 and delta 9 desaturation, gamma-linolenic and oleic acids: effect of age and of blackcurrant seed oil.

The incorporation of [1-14C]linoleic and [1-14C]stearic acid and of their delta 6 and delta 9 desaturation products (gamma-linolenic and oleic acids, respectively) into different classes of lipids was studied in liver microsomes of rats in function of the diet (blackcurrant seed oil diet, containing gamma-linolenic acid, versus control diet) and in function of age (3, 6 and 9 months). After delta 6 desaturation, total radioactivity was distributed between phospholipids, especially phosphatidylcholine, and neutral lipids. The desaturation product, gamma-linolenic acid, was totally recovered in the phospholipid fraction. Blackcurrant seed oil, which decreased the rate of delta 6 desaturation in 6- and 9-month-old rats, also decreased the incorporation of radioactivity in total phospholipids, especially in phosphatidylcholine. At 6 months of age, after delta 9 desaturation, the majority of radioactivity was recovered in neutral lipids principally as oleic acid, the desaturation product. The precursor, stearic acid, was highly incorporated into phospholipids, especially in rats on a diet of blackcurrant seed oil.

Aging↗

PubMed1998

Similar effects of diets rich in stearic acid or trans-fatty acids on platelet function and endothelial prostacyclin production in humans.

The effects of stearic acid (C18:0) and trans-fatty acids (trans-FAs) on measures of platelet function and prostacyclin (PGI2) production are poorly understood in humans. In this controlled dietary study, platelet function and endothelial PGI2 production were studied in healthy humans after they consumed diets rich in C18:0 or trans-FAs. For 5 weeks, 80 subjects consumed a baseline diet high in saturated FAs and were then switched to a diet containing 9.3% of energy as stearic acid or a diet containing 8.7 energy% as trans-FAs from hydrogenated vegetable oils for another 5 weeks. All diets contained 32.2 to 33.9 energy% fat, 14.6 to 15.8 energy% saturated plus trans-FAs, 12.2 to 12.5 energy% cis-monounsaturated, and 2.9 to 3.5 energy% polyunsaturated FAs. No significant differences between the C18:0 and trans-FA diets were found in the urinary excretion of 2,3-dinor-thromboxane B2 or 2,3-dinor-6-keto-prostaglandin F1alpha. In vitro production of thromboxane B2 by platelets as well as urinary excretion of beta-thromboglobulin were also similar after both diets. Collagen-induced in vitro aggregation was significantly enhanced after the C18:0 diet compared with the trans-FA diet (P=.02), whereas no differences between the diets were found with ADP. The results indicate similar effects of C18:0 and trans-FA diets on platelet activation and endothelial PGI2 production.

Adult↗

PubMed2001

Microstructure and Ion Exchange in Stearic Acid Langmuir-Blodgett Films Studied by Fourier Transform Infrared-Attenuated Total Reflection Spectroscopy.

Fourier transform infrared-attenuated total reflection (FTIR-ATR) spectra have been recorded of 11-layer Langmuir-Blodgett (LB) films of stearic acid deposited at various surface pressures (0.1, 15, and 35 mN/m), and the molecular orientation angles were evaluated quantitatively, which supplied insight into the molecular order with the alkyl chains tightly packed like crystal in the LB films deposited at the zero and higher surface pressures. These experimental results indicate that, in the Langmuir film as the precursor of LB films, stearic acid molecules self-aggregate to form two-dimensional crystalline domains already even at the zero surface pressure, which results in the inhomogeneity of monolayer. The analysis of dependence of nu(C=O) intensity on the surface pressure, surface density, and subphase temperature leads to the conclusion that the defects in LB films originate from the Langmuir film and be conserved upon deposition. Annealing below 50 degrees C and cooling could improve the monolayer homogeneity, and thus a defect-free or low-defect LB films can be deposited. Furthermore, ion exchange conducted in the LB films, on the other hand, confirms the existence of structure defects in LB films of stearic acid. The polar plane microstructure, lateral transport along the polar planes and the coordination types of stearic acid/cation system may be the rate-limiting process. The results have implication on the possible uses of stearic acid LB films as ion-exchange materials or sensors. Copyright 2001 Academic Press.

Journal Article↗

PubMed1993

Different mechanisms of uptake of stearic acid and cholesterol into rabbit jejunal brush border membrane vesicles.

The rate of uptake of stearic acid and cholesterol solubilized in taurocholic acid (TC) was examined in rabbit jejunal brush border membrane vesicles (BBMV). For stearic acid (18:0) or cholesterol there was an initial rapid rate of uptake, which reached a plateau within approximately 1 min and remained stable thereafter. At low concentrations of 18:0 and 20 mM, but not 2 mM, TC, there was a curvilinear relationship between the concentration of 18:0 and uptake, whereas the relationship between cholesterol uptake and concentration was linear over a wide range of values. When the concentration of TC was held constant at increasing concentrations of 18:0 or cholesterol, there was a linear increase in the rate of uptake. When the concentration of 18:0 or cholesterol was held constant and the concentration of TC was increased from 2 to 20 mM, the uptake of 18:0 declined, but the rate of uptake of cholesterol increased. When the concentrations of 18:0 plus TC, or cholesterol plus TC, were both increased in unison and their ratio was held constant, their rate of uptake increased. Thus, (i) BBMV may be used to assess the rate of uptake of lipids; (ii) the partitioning of cholesterol from bile acid micelles into the BBMV appears to be by way of "collision" of the cholesterol with the membrane. In contrast, the uptake of 18:0 from the micelle into the membrane vesicles may be by both the collision and the aqueous/dissociation models; and (iii) 18:0 uptake may be mediated by both a concentration-dependent and a concentration-independent component.(ABSTRACT TRUNCATED AT 250 WORDS)

Animals↗

PubMed1983

[Absorption routes of stearic acid and leucine in the small intestine of the rat after gamma irradiation].

The aim of the investigation was to study transport of 3H-stearic acid in ultrastructural compartments of epitheliocytes during absorbtion, resynthesis and translocation of lipids having the form of chylomicrons after a local large fractionated gamma-irradiation of the rat small intestine with a total dose of 35 Gr. In the anesthesized animals the ligated fragments of the jejunum, which kept their blood supply and innervation, were separated, fatty emulsion with 3H-stearic acid (a label) was administered into their lumen. Intensity of the label incorporation was quantitatively estimated in the electron microscopic autographs every 2, 5, 10 and 20 min after the isotope administration. Time distribution of the label concentration after irradiation characterized the sequence of the transport stages of 3H-stearic acid across microvilli and the terminal reticulum (MV + TR) triglycerides resynthesis in the agranular and granular endoplasmic reticulum (AER, GER), chylomicrons formation in Golgi complex (GC), as well as their exudation into the lacunar intercellular space (LIS), basal membrane and capillaries. Transport deceleration of the label at the level MV + TR and decreasing synthesis of triglycerides in GER was accompanied with a delay in the chylomicrons formation in the GC and their excretion into the LIS. Conglomerates of the aggregated chylomicrons were formed in the LIS. The radioautographic data on 3H-leucine incorporation characterized a decreased activity of the protein-synthesizing system of epitheliocytes.

Animals↗

PubMed1989

Uncoupling of cardiac cells by doxyl stearic acids specificity and mechanism of action.

The influence of doxyl stearic acids (DSAs) on gap junctional conductance (gj) between pairs of neonatal rat heart cells was studied. DSAs are spin probes that perturb the membrane at different depths depending on position of the doxyl group on the fatty acyl chain. 16-DSA and 12-DSA rapidly and reversibly reduced gj to unmeasureable levels in a dose- and time-dependent manner. Single channel events observed when gj was low were of the same unitary size as those observed under control conditions. The methyl esters of 16- and 12-DSA, stearic acid itself, and TEMPO, an analogue of the doxyl group that has no fatty acyl chain, had no effect on gj. Protonation of the carboxyl head group (by acidifying the solution) reduced the potency of 16- or 12-DSA. Spontaneous beating activity and action potentials were observed at concentrations of the DSAs 15-20 times that necessary for uncoupling. These results indicate that uncoupling by the DSAs requires the presence of the charged carboxyl group and localized perturbation of the channel at the lipid-channel interface by the doxyl group. Furthermore, they predict that unsaturated free fatty acids, which accumulate during ischemia, may exert their arrhythmogenic effect by reducing gj, and thereby slowing conduction.

Action Potentials↗

PubMed1993

Membrane lipid fluidity affects the nitroxide radical decay of 5-doxyl stearic acids in isolated rat hepatocytes.

We investigated the effect of membrane fluidity on the nitroxide radical decay rate of 5-doxyl stearic acid in spin-labeled rat hepatocytes. The half-time (t1/2) for the EPR signal decay of 5-doxyl stearic acids incorporated into the membranes of isolated rat hepatocytes was 12 min (mean value). When spin-labeled hepatocytes were separated into membrane and cytosol fractions, the t1/2 of the membrane fraction was prolonged by more than 2 hrs. However, when the cytosolic fraction was added to the membrane fraction, the radical decay reaction recovered (t1/2 was 27 min). Incubation of hepatocytes with a stream of 95% O2 at 37 degrees C for 2 hrs prolonged t1/2 by 106% and was associated with a 18% decrease in water-soluble antioxidant content. When the measurement temperature was changed from 24 degrees C to 37 degrees C, t1/2 was shortened with a decrease in the order parameter (S). The t1/2 and S in hepatocytes treated with phosphatidylcholine (PC) were reduced by 14% and 0.008, respectively. Conversely, after treatment with phosphatidylethanolamine (PE), PC+cholesterol and PE+cholesterol, t1/2 and S increased by 14% and 0.014, 20% and 0.018 and 29% and 0.040, respectively. These findings suggest that the nitroxide radical decay of 5-doxyl stearic acids incorporated into hepatocyte membranes is mediated by the antioxidants in the cytosol fraction, and that the nitroxide radical decay rate is affected not only by water-soluble antioxidant content but also by the membrane lipid fluidity of the hepatocytes.

Animals↗

PubMed1976

[Study of the passage of stearic acid through blood-brain barrier and its incorporation in cerebral membranes (especially in myelin)].

Subcutaneously injected stearic acid is uptaken by brain and is further incorporated into membrane lipids (especially myelin). The uptake increases regularly up to 20 hrs. in total membranes as in myelin. In total membranes, there is a decrease between 20 and 24 hrs. followed by a recovery of the previous maximal activity. Moreover, the myelin activity increases up to 3 days, so far. Cerebrosides, isolated from both types of preparations, present an activity regularly increasing; but free fatty acids have a stable specific activity and a decreasing relative activity. The injected labelled stearic acid is directly incorporated into membrane lipids or is metabolized inside brain in longer chains (thus providing arachidic behenic and lignoceric acids) or in acetate units (utilized for synthesis of medium chain fatty acids such as palmitic acid).

Animals↗

PubMed1998

A high-stearic acid diet does not impair glucose tolerance and insulin sensitivity in healthy women.

Results in epidemiological and experimental studies suggest that a diet rich in saturated fat may affect insulin sensitivity. However, no published data are available on the effect of stearic acid in this respect. Therefore, we examined the effects of a high-stearic acid diet and a high-oleic acid diet on glucose metabolism, serum lipids and lipoproteins, and blood coagulation factors in 15 healthy female subjects. Subjects followed the two experimental diets for 4 weeks according to a randomized crossover design. Both experimental diet periods were preceded by consumption of a baseline diet for 2 weeks. The diets provided 36% of energy (E%) as fat. In the experimental diets, 5 E% stearic or oleic acid was substituted for 5 E% of saturated fatty acids in the baseline diet. After the experimental diets, no differences were found in the insulin sensitivity index (mean+/-SEM, 5.4+/-1.9 v 5.2+/-1.6 x 10(-4) min(-1) x microU(-1) x mL(-1), nonsignificant [NS]), glucose effectiveness (0.026+/-0.006 v 0.026+/-0.003 min(-1), NS), or first-phase insulin reaction ([FPIR] 368+/-57 v 374+/-66 mU/L x min, NS). The concentration of serum lipids and lipoproteins and blood coagulation factors did not differ after the diet periods. In conclusion, a diet rich in stearic acid did not deteriorate glucose tolerance or insulin action in young healthy female subjects as compared with a diet rich in oleic acid.

Adult↗

PubMed2005

Lipid characterization of seed oils from high-palmitic, low-palmitoleic, and very high-stearic acid sunflower lines.

Information obtained in recent years regarding the enzymes involved in FA synthesis can now be applied to develop novel sunflower lines by incorporating enzymes with specific characteristics into lines with a defined background. We have generated three highly saturated mutant lines in this way and characterized their FA content. The new high-palmitic, low-palmitoleic lines CAS-18 and CAS-25, the latter on a high-oleic background, have been selected from the high-stearic mutant CAS-3 by introducing a deficient stearic acid desaturase in a high-palmitic background from the previously developed mutant lines CAS-5 and CAS-12, respectively. As such, the desaturation of palmitic acid and the synthesis of palmitoleic acid and its derivatives (asclepic and palmitolinoleic acids) were reduced in these high-palmitic lines, increasing the stearic acid content. Likewise, introducing a FA thioesterase from a high-palmitic line (e.g., CAS-5) into the high-stearic CAS-3 increased the stearic acid content from 27 to 32% in the new high-stearic line CAS-31. As previously described in high-palmitic lines, high growth temperatures did not reduce the linoleic acid content of the oil. Furthermore, the FA composition of TAG, DAG, and phospholipids was modified in these lines. Besides a high degree of saturation, the TAG from these new vegetable oils have a low content of saturated FA in the sn-2 position. The alpha asymmetric coefficient obtained also indicates that the saturated FA are asymmetrically distributed within the TAG molecules. Indeed, the disaturated TAG content rose from 31.8 to 48.2%. These values of disaturated TAG are the highest to date in a temperate oilseed.

Fatty Acids, Monounsaturated↗