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PubMed1992

Fatty acid and drug binding to a low-affinity component of human serum albumin, purified by affinity chromatography.

Binding equilibria for decanoate to a defatted, commercially available human serum albumin preparation were investigated by dialysis exchange rate determinations. The binding isotherm could not be fitted by the general binding equation. It was necessary to assume that the preparation was a mixture of two albumin components about 40% of the albumin having high affinity and about 60% having low affinity. By affinity chromatography we succeeded in purifying the low-affinity component from the mixture. The high-affinity component, however, could not be isolated. We further analyzed the fatty acid and drug binding abilities of the low-affinity component. The fatty acids decanoate, laurate, myristate and palmitate were bound with higher affinity to the mixture than to the low-affinity component. Diazepam was bound with nearly the same affinity to the low-affinity component as to the albumin mixture, whereas warfarin was not bound at all to the low-affinity component.

Chromatography, Affinity↗

PubMed1996

The protein conformation of Cd-substituted horse liver alcohol dehydrogenase and its metal-site coordination geometry in binary and ternary inhibitor complexes.

The coordination geometry of the metal at the active site in Cd-substituted horse liver alcohol dehydrogenase (LADH) has been investigated for the binary complexes of LADH with imidazole, isobutyramide, decanoic acid and Cl-, and for the ternary complexes of LADH with NADH and imidazole, NADH and isobutyramide, NAD+ and decanoic acid and NAD+ and Cl-, by using the method of perturbed angular correlation of gamma-rays (PAC). The spectral results are consistent with a flexible structure around the metal for the binary complexes with inhibitors. For ternary complexes, however, a rigid structure is observed. An exception is the ternary complex between LADH, NADH and imidazole, in which the metal site is still flexible. Comparing with available structures determined by X-ray crystallography, we found a correlation between open structures and flexible metal sites, and between closed structures and rigid metal sites. This indicates that the PAC technique can be applied to distinguish the two conformations in solution. The spectral parameters, omega(o) and eta, of the experiments, except for the complexes with imidazole, fall into two groups: one with low omega(o) and one with high omega(o) (eta is relatively constant in all experiments). In this work it is clarified that the low omega(o) values are connected with the presence of a negatively charged solvent ligand. Using an angular-overlap approach to interpret the results, the low omega(o) values are found to be compatible with a coordination geometry where the S-Cd-S (Cys174 and Cys46 coordinate to the metal) angle is about 110 degrees as suggested in [Hemmingsen, L., Bauer, R., Danielsen, E., Bjerrum. M. J., Zeppezauer, M., Adolph, H. W., Formicka, G. & Cedergren-Zeppezauer, E. (1995) Biochemistry 34, 7145-7153], whereas high omega(o) values are compatible with an S-Cd-S angle of 130 degrees. The presence of a negatively charged metal ligand, therefore, might trigger the movement of the sulfur of Cys174. As it is believed that alcohols coordinate to the metal as alcoholate ions this could be important for catalysis.

Alcohol Dehydrogenase↗

PubMed1979

Weight changes with depot neuroleptic maintenance therapy.

A prospective study of schizophrenic patients prescribed injectable depot neuroleptic drugs as maintenance therapy showed a clinically significant weight gain in 55% of patients. No significant difference was shown between flupenthixol decanoate and fluphenazine decanoate, nor was a clinically meaningful relationship shown with dose, or the use of anti-parkinsonian drugs. The weight gain continued for at least 2 years following a mental state relapse. It is suggested that the monitoring of weight and giving of appropriate advice on diet are two essential in maintenance therapy of chronic schizophrenia.

Body Weight↗

PubMed1991

Biological activities of melanotropic peptide fatty acid conjugates.

Four fatty acids (FA, palmitic, myristic, decanoic, hexanoic) were individually conjugated to the N-terminus of the alpha-MSH fragment analog, H-Asp5-His6-D-Phe7-Arg8-Trp9-Lys10-NH2. This resulted in enhanced potency of the conjugates (compared to the unconjugated melanotropin analog) as determined in the lizard skin bioassay and in the mouse melanoma cell tyrosinase bioassay. The shorter conjugates of hexanoic and decanoic acid were at least equipotent to alpha-MSH in the lizard skin bioassay, whereas the longer myristoyl and palmitoyl analogs were 100 times less active. The myristoyl and palmitoyl conjugates exhibited a "creeping" potency in the lizard skin bioassay-that is, potency of the peptides increased with time in contact with the skins. These observations may be related to the more lipid nature of these FA-conjugates. In the tyrosinase assay, the conjugates were 10-100 times more active than alpha-MSH or the unconjugated analog. Each of the FA-melanotropic peptide conjugates exhibited prolonged (residual) melanotropic activity in both the lizard skin and melanoma cell bioassays. In other words, after removal of the melanotropin conjugates from contact with the skins or cells, responses were still manifested for hours or days thereafter. As little as 1 hr of contact with melanoma cells resulted in enhanced enzyme activity as measured 48 hr later. Since the conjugates, but not H-[Asp5, D-Phe7, Lys10]alpha-MSH5-10-NH2, exhibited prolonged activity, the conversion of reversible agonists to irreversible agonists was demonstrated.

Amino Acid Sequence↗

PubMed1976

Chilling cells enhances the bactericidal action of fatty acids on Escherichia coli.

Preincubation at 0 C considerably increased the bactericidal action of 0.4% nonanoic and decanoic acids on Escherichia coli K-12 154. This lethal effect seemed to be dependent on the media used to grow the bacteria. Stationary-phase cells were more sensitive than those from exponential cultures. A mutant (FA31) resistant to the bactericidal action of "cold shock" and 0.4% deconoic acid was isolated from E. coli FA23 (AN E. coli 154 derivative able to grow on 0.1% decanoic acid) by a recycling selection procedure. Other E. coli strains tested showed behavior similar to that of strain K-12 154. The chilling of cells as a tool to improve the bactericidal action of fatty acids in foods is discussed.

Anti-Bacterial Agents↗

PubMed2005

Biosynthetic pathway of Pseudomonas aeruginosa 4-hydroxy-2-alkylquinolines.

The role of intercellular communication in the regulation of bacterial multicellular behavior has received widespread attention, and a variety of signal molecules involved in bacterial communication have been discovered. In addition to the N-acyl-homoserine lactones, 4-hydroxy-2-alkylquinolines (HAQs), including the Pseudomonas quinolone signal, have been shown to function as signal molecules in Pseudomonas aeruginosa. In this study we unraveled the biosynthetic pathway of HAQs using feeding experiments with isotope-labeled precursors and analysis of extracted HAQs by gas chromatography-mass spectrometry and nuclear magnetic resonance spectroscopy. Our results show that the biosynthesis of various HAQ metabolites is directed via a common metabolic pathway involving a "head-to-head" condensation of anthranilic acid and beta-keto fatty acids. Moreover, we provide evidence that the beta-keto-(do)decanoic acids, crucial for the biosynthesis of the heptyl and nonyl derivatives of the 4-hydroxyquinolines in P. aeruginosa, are at least in part derived from a common pool of beta-hydroxy(do)decanoic acids involved in rhamnolipid biosynthesis.

Chromatography, Gas↗

PubMed2007

Mechanisms underlying nutrient-induced segmentation in isolated guinea pig small intestine.

Mechanisms underlying nutrient-induced segmentation within the gut are not well understood. We have shown that decanoic acid and some amino acids induce neurally dependent segmentation in guinea pig small intestine in vitro. This study examined the neural mechanisms underlying segmentation in the circular muscle and whether the timing of segmentation contractions also depends on slow waves. Decanoic acid (1 mM) was infused into the lumen of guinea pig duodenum and jejunum. Video imaging was used to monitor intestinal diameter as a function of both longitudinal position and time. Circular muscle electrical activity was recorded by using suction electrodes. Recordings from sites of segmenting contractions showed they are always associated with excitatory junction potentials leading to action potentials. Recordings from sites oral and anal to segmenting contractions revealed inhibitory junction potentials that were time locked to those contractions. Slow waves were never observed underlying segmenting contractions. In paralyzed preparations, intracellular recording revealed that slow-wave frequency was highly consistent at 19.5 (SD 1.4) cycles per minute (c/min) in duodenum and 16.6 (SD 1.1) c/min in jejunum. By contrast, the frequencies of segmenting contractions varied widely (duodenum: 3.6-28.8 c/min, median 10.8 c/min; jejunum: 3.0-27.0 c/min, median 7.8 c/min) and sometimes exceeded slow-wave frequencies for that region. Thus nutrient-induced segmentation contractions in guinea pig small intestine do not depend on slow-wave activity. Rather they result from a neural circuit producing rhythmic localized activity in excitatory motor neurons, while simultaneously activating surrounding inhibitory motor neurons.

Action Potentials↗

PubMed1991

Effects of training and an anabolic steroid on murine red skeletal muscle. A stereological analysis.

The purpose of this study was the evaluation of changes induced by training (swimming 1 h/day, 5 days/week, 6 weeks) and an anabolic hormone (nandrolone decanoate, intramuscular injections of 15 mg.kg-1 per week) on fiber size, capillarization and mitochondrial fraction of murine soleus muscle. The animals (n = 32) were divided into 4 groups: a control group (C), that received the arachis oil carrier; a steroid group (S), that received the hormone; a training group (T), and a group that was submitted to training and to the administration of hormone (S + T). The soleus muscle was selected for quantitative light- and electron-microscopic evaluation. The muscle fiber size was increased in group T and decreased in groups S and S + T. The axial length of capillaries per unit volume of muscle decreased significantly in groups S and T. The number of capillaries per number of fibers showed a significant decrease in groups S and S + T and an increase in group T. The mitochondrial content decreased in group S, which suggested that anabolic steroids can be harmful for these organelles. This hypothesis was confirmed by histological evaluation at the electron-microscopic level. Many swollen and disrupted mitochondria were found in groups S and S + T. The results suggest that administration of nandrolone decanoate may have some deleterious effects on the muscle respiratory system (capillaries and mitochondria).

Animals↗

PubMed1988

Prospective controlled study of androgen therapy in the anemia of chronic renal disease: effects on iron kinetics.

Ferrokinetic and RBC mass determinations were made at 3-month intervals in iron-replete hemodialysis patients randomized to a control group or to nandrolone decanoate therapy. After 3 months, RBC mass increased in two of 4 androgen-treated patients. Erythron iron turnover, an index of RBC production, increased in the one responder studied but not in the two nonresponders. Similarly, in a fifth subject, who was not restudied until 6 months of androgen therapy were completed, an increase in RBC mass was associated with an increase in erythron iron turnover. However, between 3 and 6 months, RBC mass increased in all 4 androgen-treated patients studied even though erythron iron turnovers remained unchanged and dialysis-associated blood losses did not decrease. Thus, at least two androgen-treated patients had increases in RBC mass without ever increasing their erythron iron turnover. Two of three control subjects also had increased erythron iron turnovers, which in one case was related to increased dialysis-associated blood losses. Changes in RBC mass were not consistently paralleled by changes in Hb. These findings suggest that increases in RBC mass during nandrolone decanoate therapy result from two mechanisms: increased erythropoiesis (shown by simultaneous increases in RBC mass and erythron iron turnover) and increased RBC survival (indirectly shown by increases in RBC mass without increases in erythron iron turnover). The importance of control groups, RBC mass determinations and the monitoring of dialysis-associated blood losses in studying the effects of androgens on erythropoiesis in chronic hemodialysis patients is also demonstrated.

Anemia↗

PubMed1995

Physiologic effects of nutritional support and anabolic steroids in patients with chronic obstructive pulmonary disease. A placebo-controlled randomized trial.

Nutritional depletion commonly occurs in patients with COPD, causing muscle wasting and impaired physiologic function. Two hundred seventeen patients with COPD participated in a placebo-controlled, randomized trial investigating the physiologic effects of nutritional intervention alone (N) for 8 wk or combined with the anabolic steroid nandrolone decanoate (N + A). Nandrolone decanoate or placebo (P) was injected intramuscularly (women, 25 mg; men, 50 mg) in a double-blind fashion on Days 1, 15, 29, and 43. Nutritional intervention consisted of a daily high caloric supplement (420 kcal; 200 ml). Also, all patients participated in an exercise program. In the depleted patients, both treatment regimens induced a similar significant body weight gain (2.6 kg) but different body compositional changes. Particularly in the last 4 wk of treatment, weight gain in the N group was predominantly due to an expansion of fat mass (p < 0.03 versus P and N + A), whereas the relative changes in fat-free mass (FFM) and other measures of muscle mass were more favorable in the N + A group (p < 0.03 versus P). Maximal inspiratory mouth pressure improved within both treatment groups in the first 4 wk of treatment, but after 8 wk only N + A was significantly different from P (p < 0.03). Nutritional supplementation in combination with a short course of anabolic steroids may enhance the gain in FFM and respiratory muscle function in depleted patients with COPD without causing adverse side effects.

Anabolic Agents↗

PubMed2004

Endocrinological and pathological effects of anabolic-androgenic steroid in male rats.

Many athletes use drugs, especially anabolic androgenic steroids (AAS), but there are few reports on the endocrinological and pathological changes in AAS abusers. In this study we reported the results of endocrinological examinations in rats administered AAS and also physical changes. We separated 37 male Wistar rats (7 weeks old) into 3 groups: Group A was medicated with nandrolone decanoate, metenolone acetate, and dromostanolone; Group B with nandrolone decanoate and saline; and Group C was given only saline. They were given subcutaneous injections of the medications or the control vehicle once a week for 6 weeks. Medications were stopped for 4 weeks, and then resumed for another 6 weeks. After that, rats were sacrificed. Serum testosterone level in Group A was significantly higher than that in Group C. Serum dihydrotestosterone in Group A was significantly higher than that in both Groups B and C. Serum estradiol-17beta levels in Groups A and B were significantly higher than that in Group C. In pathological evaluation, heart, testis, and adrenal gland were severely damaged. These findings indicate that there is a high degree of risk related to the use of AAS.

Adrenal Glands↗

PubMed1985

Experimental work with anabolics in autoimmunity models.

19-nortestosterone (nandrolone) or its decanoate was tested in six animal models for autoimmune disease. The compound was found capable of inhibiting the development of disease symptoms or the deterioration of certain immune parameters in three out of five models of spontaneous autoimmune disease: NZB/NZW F1 (NZB/W) mice (lupus glomerulonephritis, Sjögren's disease-like syndrome), NZB (lupus glomerulonephritis, autoimmune haemolytic anaemia) and OS chickens (thyroiditis). No effect of the compound was seen in MRL lpr/lpr mice (lupus glomerulonephritis, lymphoproliferative disease) and in BB rats (insulin-dependent diabetes mellitus; IDDM). Nandrolone decanoate also seems to be active in myasthenia gravis evoked in rats immunised with acetylcholine receptor but further experiments are necessary to confirm this. In a first experiment also ethylestrenol was found to give favourable effects in the model.

Animals↗

PubMed1999

Effects of anabolic steroid (19-nortestosterone) on the secretion of testicular hormones in the stallion.

The aim of this study was to clarify the effect of anabolic steroids on the testicular endocrine function of mature stallions. Mature thoroughbred stallions were treated with 800 mg nandrolone decanoate every 3 weeks for 3 months. After the first treatment, plasma concentrations of LH, immunoreactive inhibin and testosterone decreased rapidly to the nadir. These hormones were maintained at significantly lower concentrations compared with concentrations in intact stallions. Histology of the testicular tissue indicated the arrest of advanced spermatogenesis in the seminiferous tubules and a severe depletion of the number of Leydig cells in the interstitial compartment as a result of treatment. Most of the immunopositive cells for the inhibin alpha-subunit and steroidogenesis enzymes in the interstitial compartment decreased below detectable amounts, whereas immunopositive reactions of inhibin alpha-subunit in the seminiferous tubules were clearly observed. In conclusion, the treatment of mature stallions with nandrolone decanoate caused a decrease in the secretion of ir-inhibin and testosterone from the testis, the depletion of the number of Leydig cells and a decrease below detectable amounts of inhibin alpha-subunit and steroidogenesis enzymes. The concentration of ir-inhibin in the peripheral blood may be a useful marker for the examination of testicular activity in stallions being treated with anabolic steroids.

3-Hydroxysteroid Dehydrogenases↗

PubMed1996

Effects of androgen therapy on prostatic markers in hemodialyzed patients.

We have prospectively studied the evolution of serum levels of the prostatic-specific antigen and prostatic acid phosphatase in 14 male hemodialyzed patients, receiving a cycle of nandrolone decanoate (200 mg intramuscularly, once a week, for six months) as treatment for anemia. Androgen administration did not produce significant increases in serum concentrations of both tumor markers (basal: 0.9 +/- 0.5 and 0.7 +/- 0.3 ng/ml; at six months: 1.3 +/- 1.1 and 0.8 +/- 0.7 ng/ml respectively). Only one patient had a value of prostatic-specific antigen over the normal range: 4.2 ng/mol at the sixth month period, with a rapid decrease after the withdrawal of androgens. All the remaining values of both markers were within the normal range. In another six patients undergoing a prolonged treatment with androgens (between 9 to 24 months), the serum levels of prostatic-specific antigen and prostatic acid phosphatase were within the normal range in all of them. Nandrolone decanoate administration does not induce increases in prostate tumor markers when it is used as treatment for anemia in hemodialyzed patients.

Acid Phosphatase↗

PubMed1981

Biochemical modulation of the submandibular salivary gland of castrated male mice treated with anabolic steroids.

The possibility that 19-nortestosterone decanoate, an anabolic steroid which has no androgenic effect in mice, may promote the recovery of certain biochemical parameters of the submandibular gland of castrated mice had been studied. It was demonstrated that protein, RNA and sialic acid concentrations, as well as, protease, acid phosphatase and succinate dehydrogenase activities were found to be similar to control values in the castrated mice treated with 19-nortestosterone decanoate (anabolic steroid) or testosterone propionale. The effects on seminal vesicle and levator ani muscle were also considered. The interaction between 19-nortestosterone decanoale and androgen-binding receptors in the submandibular gland is discussed.

Animals↗

PubMed1994

Anabolic steroids in the treatment of malnourished CAPD patients: a retrospective study.

OBJECTIVE: To assess the effect of anabolic steroids on malnutrition of continuous ambulatory peritoneal dialysis (CAPD) patients. DESIGN: Retrospective analysis of medical records, charts, and computer-generated laboratory and medication data. SETTING: Peritoneal Dialysis Unit of The Toronto Hospital. PATIENTS: Thirteen patients with moderate to severe malnutrition who had received nandrolone decanoate (ND) intramuscularly (IM) for at least three months. Nine of these patients (group A), with a mean age of 59.4 years, received only ND (100-200 mg IM monthly). Group B consisted of 4 patients (mean age 74.0 years) who, in addition to ND, received intraperitoneal (IP) amino acids. RESULTS: In group A, serum albumin, while declining before ND treatment (34.4 +/- 3.2 to 31.5 +/- 3.35, x +/- SEM, g/L at -2 and 0 months), showed a progressive and significant (p < 0.001) increase during treatment, sustained up to the third month (36.57 +/- 1.51). In group B, serum albumin did not increase significantly (30.25 +/- 2.62, 30.75 +/- 1.9, and 31.5 +/- 4.8, mean +/- SEM, g/L at -2, 0, and +3 months, respectively. In group A, serum creatinine was increased significantly (p < 0.01) from 0 to +3 months (731 +/- 185 to 938 +/- 92.5 mmol/L). Blood urea, bicarbonate, and total protein levels did not change significantly. In group B, serum creatinine fluctuated considerably with an insignificant trend to rise. Blood urea showed a steady trend to increase without reaching statistical significance. In relation to time 0, bicarbonate levels (28.7 +/- 3.3) were decreased significantly (p < 0.05) (27 +/- 0.8, 24.6 +/- 1.5, and 25 +/- 1 mEq/L, at +1, +2, and +3 months, respectively). CONCLUSIONS: Nandrolone decanoate alone, in relatively low doses, exerted a definite anabolic effect in 9 malnourished CAPD patients. The lack of a similar effect in 4 patients, who in addition to ND received amino acids IP, could be explained by the low dose of ND, the concurrent acidosis, the severity of malnutrition, and the older age of this group.

Adult↗

PubMed1978

Long-acting oral vs injectable antipsychotic drugs in schizophrenics: a one-year double-blind comparison in multiple episode schizophrenics.

Sixty patients meeting the criteria established for schizophrenia who attained a clinical plateau following hospital discharge were randomized to receive for one year either penfluridol, 20 to 160 mg orally once each week, or fluphenazine decanoate, 0.5 to 4 ml every two weeks. The relapse rate for both treatments was low and equal. The rate of recurrence of psychosis for patients receiving penfluridol was 7% and for those receiving fluphenazine decanoate 10%. A retrospective comparison of the penfluridol group was made to a similar group of patients assigned to placebo in an earlier study. Placebo-treated patients had a relapse rate of 68%. Penfluridol patients had statistically fewer psychotic relapses. Questions about the possible carcinogenicity of penfluridol in animals will have to be resolved before it can be widely used. This study demonstrates the feasibility of using an oral, long-acting antipsychotic agent. It would be a useful psychopharmacologic addition in the treatment of outpatient schizophrenics.

Administration, Oral↗

PubMed1988

Differential effect of low and conventional doses of fluphenazine on schizophrenic outpatients with good or poor information-processing abilities.

Thirty-six stabilized schizophrenic outpatients were randomly assigned to receive either 5 or 25 mg of fluphenazine decanoate biweekly and were followed up for two years. The best and worst outcomes were found in groups with good or poor information-processing abilities (as measured by a partial-report span-of-apprehension task) given the same 25-mg dose of fluphenazine decanoate. The 86% two-year survival rate of the patients with poor span performance was considerably better, while the 44% one-year and the 21% two-year survival rates of patients with good span performance were considerably lower than previously reported survival rates for schizophrenic patients receiving a conventional dose of fluphenazine. The significant correlations in a patient's span performance for periods up to one year were consistent with the hypothesis that this task taps processes associated with vulnerability to schizophrenic disorder.

Adult↗