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Query: UMLS:C0338671 (Steroids)
 9,479 document(s) hit in 31,850,051 MEDLINE articles (0.00 seconds)

A novel synthesis of sodium 17-oxo-16 alpha-hydroxy-1,3,5(10)-estratrien-3-yl sulfate (4), sodium 16 alpha, 16 beta-dihydroxy-1,3,5(10)-estratrien-3-yl sulfate (5) and sodium 16-oxo-17 beta-hydroxy-1,3,5(10)-estratrien-3-yl sulfate (6) is described. 16 alpha-Bromo-3-hydroxy-1,3,5(10)-estratrien-17-one (1) was efficiently synthesized in one step with 70-97% yield by bromination of 3-hydroxy-1,3,5(10)-estratrien-17-one with cupric bromide. 3,16 alpha-Dihydroxy-1,3,5(10)-estratrien-17-one (3) was quantitatively obtained by controlled stereospecific hydrolysis of the bromoketone 1 with sodium hydroxide in aqueous pyridine. The bromoketone 1 was converted to the 16 alpha-hydroxy-17-ketone 3-sulfate 4 by sulfation with chlorosulfonic acid in pyridine and a subsequent controlled hydrolysis in a high yield without formation of the other ketols. Treatment of the sulfate 4 with sodium borohydride have the triol sulfate 5. The sulfate 4 was also rearranged to the 17 beta-hydroxy-16-ketone 6 with sodium hydroxide in water in a quantitative yield.
Steroids 1981 Nov
PMID:A short efficient synthesis of 16-oxygenated estratriene 3-sulfates. 627 76

Bromocriptine treatment in rats (3 mg/kg per day, 7 days) significantly reduced alpha-msh and aldosterone plasma levels 2 hrs after the final treatment in animals on low, normal and high sodium diets. Alpha-MSH dose response curves for corticosterone and 18-hydroxydeoxycorticosterone (18-OH-DOC) in subsequently incubated glomerulosa cells gave stimulation at lower concentrations of alpha-MSH (10(-10) moles per litre) than in cells from untreated animals (10(-9) moles per 1). Curves for aldosterone (ald) and 18-hydroxycorticosterone (18-OH-B) were also affected in cells from animals on a low sodium diet. Fasciculata-reticularis cell responses to ACTH were unaffected. Metoclopramide (4 mg/kg per day, 7 days) elevated plasma alpha-MSH, although ald was unaffected, but inhibited the glomerulosa cell response to alpha-MSH in vitro. Acute dopaminergic responses in plasma ald may be mediated through alpha-MSH in rats, but chronically alpha-MSH may down- regulate glomerulosa cell alpha-MSH receptors. It is unlikely that alpha-MSH mediates the adrenocortical response to sodium depletion.
Steroids 1982 Feb
PMID:Dopaminergic control of aldosterone: modulation of the response of rat adrenal zona glomerulosa cells to alpha-Msh by pretreatment with bromocriptine or metoclopramide. 628 Mar 45

Synthetic vitamin D3 sulfate was prepared by reacting cholecalciferol with sulfamic acid in pyridine. Vitamin D3 sulfate ammonium salt was purified by crystallisation and transformed in sulfate sodium salt. Homogeneity was controlled by reverse phase high pressure liquid chromatography (HPLC). Purified synthetic vitamin D3 sulfate sodium salt was used as a reference. Milk whey was obtained after protein precipitation by adding ethanol. Vitamin D3 sulfoconjugate was identified in supernatant (lyophylized) after purification by Sephadex LH 20 and HPLC. Milk whey purified fraction obtained exhibited the same ultra-violet absorption (UV) as synthetic vitamin D3 sulfate; after solvolysis, cholecalciferol was liberated from natural and synthetic sulfoconjugate. The results confirmed that vitamin D3 sulfate was present in human milk.
Steroids 1982 Apr
PMID:Cholecalciferol sulfate identification in human milk by HPLC. 629 30

Homoursodeoxycholic acid and [11,12-3H]homoursodeoxycholic acid were synthesized from ursodeoxycholic acid and homocholic acid, respectively. Ursodeoxycholic acid (Ia) was converted to 3 alpha, 7 beta-diformoxy-5 beta-cholan-24-oic acid (Ib) using formic acid. Reaction of the diformoxy derivative (Ib) with thionyl chloride yielded the acid chloride (II) which was treated with diazomethane to produce 3 alpha, 7 beta-diformoxy-25-diazo-25-homo-5 beta-cholan-24-one (III). Homoursodeoxycholic acid (IV) was formed from the diazoketone (III) by means of the Wolff rearrangement of the Arndt-Eistert synthesis. N-Bromosuccinimide oxidation of homocholic acid (V), which was prepared from cholic acid by the same procedure described above, afforded 3 alpha, 12 alpha-dihydroxy-7-oxo-25-homo-5 beta-cholan-25-oic acid (VI). Reduction of the 7-ketohomodeoxycholic acid (VI) with sodium in 1-propanol gave 3 alpha, 7 beta, 12 alpha-trihydroxy-25-homo-5 beta-cholan-25-oic acid (VII). The methyl ester of 7-epihomocholic acid (VII) was partially acetylated to give methyl 3 alpha, 7 beta-diacetoxy-12 alpha-hydroxy-25-homo-5 beta-cholan-25-oate (VIII) using a mixture of acetic anhydride, pyridine and benzene. Dehydration of the diacetoxy derivative (VIII) with phosphorus oxychloride yielded methyl 3 alpha, 7 beta-diacetoxy-25-homo-5 beta-chol-11-en-25-oate (IX). Reduction of the unsaturated ester (IX) with tritium gas in the presence of platinum oxide catalyst followed by alkaline hydrolysis gave [11,12-3H]homoursodeoxycholic acid.
Steroids 1984 Dec
PMID:Synthesis of homoursodeoxycholic acid and [11,12-3H]homoursodeoxycholic acid. 640 Jan 51

Sodium (1-14C)acetate and (5-3H) mevalonate were incubated with Bufo arenarum toad parotid gland and liver tissues. Both labelled compounds were incorporated into cholesterol produced by liver while the incubations with parotid gland produced no labelled cholesterol. Low and high density lipoproteins isolated from toad plasma were iodinated and used for binding studies. Membrane preparations of parotid gland showed high affinity binding sites for 125I-LDL and 125I-HDL. In addition, while colchicine inhibits the in vitro uptake of (3H)cholesteryl linoleate-LDL into parotid gland tissue an opposite effect was seen with (3H)cholesteryl linoleate-HDL. The above mentioned results would support the hypothesis that the cholesterol used by the parotid gland for the biosynthesis of bufadienolides would be produced in the liver, transported by the circulating lipoproteins and incorporated by the glands by a receptor-mediated mechanism.
Steroids 1984 Jul
PMID:Biosynthesis of bufadienolides in toads. V. The origin of the cholesterol used by toad parotid glands for biosynthesis of bufadienolides. 644 65

The systemic activities of methyl prednisolonate and methyl 17-deoxyprednisolonate (1) were studied in rats. Methyl 17-deoxyprednisolonate produced significant changes in the amount of sodium ion (decreased) and potassium ion (increased) in urine; however, methyl prednisolonate had no effect on electrolyte balance. Both methyl prednisolonate and methyl 17-deoxyprednisolonate had no effect on liver glycogen content, plasma corticosterone level and relative adrenal weight. In contrast, the parent compound prednisolone caused a significant decrease in liver glycogen content, plasma corticosterone level and relative adrenal weight.
Steroids 1984 Jun
PMID:Systemic effects of chronically administered methyl prednisolonate and methyl 17-deoxyprednisolonate. 653 43

A series of radioiodinated pregnenolone esters was prepared in an effort to find an agent that would be rapidly and selectively taken up by adrenal cortical tissue. Achievement of such a goal would provide the basis for the development of an adrenal imaging agent having several advantages over those agents currently available for clinical use. The radioiodinated esters for this study were readily prepared by treating pregnenolone with the appropriate iodobenzoic acid in the presence of dicyclohexylcarbodiimide (DCC) and 4-dimethylamino-pyridine (DMAP). The resulting esters were readily labeled with radioiodine by isotope exchange with sodium iodide-125 in pivalic acid. Subsequent tissue distribution studies in rats revealed that those esters displaying the most stability towards hydrolysis achieved the highest concentration in adrenal cortical tissue. For example, the 2,3,5-triiodobenzoate (6) showed an adrenal uptake of 23% of administered dose per gram of tissue at 0.5 hours. The achievement of high levels of radioactivity in the adrenal with this agent at early time periods warrants further evaluation of this agent in other animals.
Steroids 1984 Jul
PMID:Potential tumor or organ-imaging agents, 24. Radioiodinated pregnenolone esters. 653 47

An efficient synthesis of 2-aminoestrone (14), 2 aminoestradiol (15), 2-amino-16 alpha-hydroxyestrone (16) and 2-aminoestriol (17) is described. 2,4-Dibromo estrogens 1 - 4 were regiospecifically converted to the corresponding 2-nitro-4-bromo derivatives 5 - 8 in quantitative yields, with Zincke nitration using sodium nitrite. Catalytic hydrogenation of the 2-nitro-4-bromides 5 - 8 over palladium-on-charcoal gave directly the desired 2-amino estrogens 14 - 17 in high yields. The 2-amino compounds 15 and 17 were also obtained by the reduction of the corresponding 2-nitro-4-bromides 6 and 8 with sodium borohydride in the presence of palladium chloride.
Steroids 1983 May
PMID:Novel and regiospecific synthesis of 2-amino estrogens via Zincke nitration. 665 98

Dihydrotestosterone receptor was prepared from both the cytoplasm and nucleus of human thymic tissue. Human cytoplasmic and nuclear dihydrotestosterone receptor possessed a KA greater than 1.0 and by competition assay was highly specific for dihydrotestosterone. Human thymic cytoplasmic dihydrotestosterone receptor prepared in standard buffer sedimented on 5-20% sucrose gradients in the 4s region but human thymic cytoplasmic dihydrotestosterone receptor prepared in buffer containing sodium molybdate (10 mM) sedimented in the 7s region on 5-20% sucrose gradients. It is concluded that the human thymic dihydrotestosterone receptor is similar to classic androgen receptor.
Steroids 1983 Jul
PMID:Characteristics of the cytoplasmic and nuclear dihydrotestosterone receptors of human thymic tissue. 667 76

The characteristics of cholic acid uptake by primary cultured hepatocytes was studied. The cholic acid uptake below 10 degrees C was unsaturable, while that determined at 20 degrees and 37 degrees C showed a biphasic type, which suggested the presence of a saturable process. This saturable process was a temperature-dependent and carrier-mediated transport process with an activation energy of 36.1 Kcal/mol. The apparent Km and Vmax values at 37 degrees C were 57.1 microM and 0.566 nmoles/mg protein/min, respectively. The saturable process was inhibited by 2,4-dinitrophenol and ouabain, and reduced significantly in the absence of sodium, suggesting that this process is energy- and sodium-dependent. The cholic acid uptake mediated by the saturable process in the absence of sodium was, however, significantly larger than that mediated by the unsaturable process. These results suggest that the transport of cholic acid in primary cultured hepatocytes may consist of three different types: unsaturable, sodium and energy-dependent carrier-mediated, and sodium-independent and energy-dependent processes, respectively. The presence of a common transport carrier for cholic acid and its conjugates with taurine and glycine in primary cultured hepatocytes was also suggested.
Steroids 1983 Aug
PMID:Characteristics of cholic acid uptake in primary cultured hepatocytes. 667 88


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