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58-22-0Relevant articles and documents
Covalent Immobilization of Human Placental 17β-Hydroxysteroid Dehydrogenase Type 1 onto Glutaraldehyde Activated Silica Coupled with LC-TOF/MS for Anti-Cancer Drug Screening Applications
Bai, Yin,Zhou, Wen-Di,Mu, Xian-Min,Zhang, Qian,Yu, Chen,Di, Bin,Su, Meng-Xiang
, p. 482 - 494 (2017)
Human 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1), a potential target in breast cancer prevention and therapy, was extracted from human placenta and immobilized on nonporous silica (～5?μm) with a covalent method for the first time. The optimum initial enzyme concentration and immobilization time during the immobilization process were 0.42?mg?mL?1 and 12?h, repectively. The binding was confirmed by scanning electron microscope (SEM) and infrared spectroscopy (FT-IR). It could improve the pH, thermal and storage stability compared to free enzyme. Moreover, the immobilized enzyme could be reused at least four times. A screening method based on it coupled with liquid chromatography–time-of-flight mass spectrometer (LC-TOF/MS) was established, and the half-maximal inhibitory concentration (IC 50) of apigenin for the immobilized enzyme was 291?nM. Subsequently, 10 natural products were evaluated leading to inhibition of the activity of 17β-HSD1 at the concentration of 25?μM, and six of them inhibit the activity over 50%.
STEREOSELECTIVE SYNTHESIS OF (+)-TESTOSTERONE VIA INTRAMOLECULAR 1,3-DIPOLAR CYCLOADDITION OF NITRILE OXIDE
Ihara, Masataka,Tokunaga, Yuji,Taniguchi, Nobuaki,Fukumoto, Keiichiro
, p. 6635 - 6648 (1991)
A new approach for construction of the A/B ring system of steroids was developed by way of an intramolecular 1,3-dipolar cycloaddition of a nitrile oxide 4, followed by an incorporation of a C3 unit.A highly stereocontrolled synthesis of (+)-testosterone 1 was accomplished by this strategy. Key Words: Steroids, testosterone, 1,3-dipolar cycloaddition, nitrile oxide, chiral synthesis
Influence of whole microalgal cell immobilization and organic solvent on the bioconversion of androst-4-en-3,17-dione to testosterone by Nostoc muscorum
Arabi,Yazdi, M. Tabatabaei,Faramarzi
, p. 213 - 217 (2010)
The use of free, immobilized and reused immobilized cells of the microalga Nostoc muscorum was studied for bioconversion of androst-4-en-3,17-dione (AD) to testosterone in hexadecane. Among polymers such as agar, agarose, κ-carrageenan, polyacrylamide, polyvinyl alcohol, and sodium alginate that were examined for cell entrapment, sodium alginate with a concentration of 2% (w/v) proved to be the proper matrix for N. muscorum cells immobilization. The bioconversion characteristics of immobilized whole algal cells at ranges of temperatures, substrate concentrations, and shaking speeds were studied followed by a comparison with those of free cells. The conditions were 30°C, 0.5. g/L, and 100. rpm, respectively. The immobilized N. muscorum showed higher yield (72 ± 2.3%) than the free form (24 ± 1.3%) at the mentioned conditions. The bioconversion yield did not decrease during reuse of immobilized cells and remained high even after 5 batches of bioreactions while Na-alginate 3% was used; however, reuse of alginate 2% beads did not give a satisfactory result.
Skin permeation of testosterone and its ester derivatives in rats
Kim, Mi-Kyeong,Lee, Chi-Ho,Kim, Dae-Duk
, p. 369 - 375 (2000)
To establish the optimum conditions for improving the transdermal delivery of testosterone, we studied the relationship between the lipophilicity of testosterone ester derivatives and the rat skin permeation rate of testosterone. We performed a rat skin permeation study of testosterone and its commercially available ester derivatives, testosterone hemisuccinate, testosterone propionate and testosterone-17β-cypionate, using an ethanol/water co-solvent system. The aqueous solubility and rat skin permeation rate of each drug, saturated in various compositions of an ethanol/water system, was determined at 37°C. The aqueous solubility of testosterone and its ester derivatives increased exponentially as the volume fraction of ethanol increased up to 100% (v/v). The stability of testosterone propionate in both the skin homogenate and the extract was investigated to observe the enzymatic degradation during the skin permeation process. Testosterone propionate was found to be stable in the isotonic buffer solution and in the epidermis-side extract for 10 h at 37°C. However, in the skin homogenate and the dermis-side extract testosterone propionate rapidly degraded producing testosterone, implying that testosterone propionate rapidly degraded to testosterone during the skin permeation process. The steady-state permeation rates of testosterone in the ethanol/water systems increased exponentially as the volume fraction of ethanol increased, reaching the maximum value (2.69 ± 0.69 μg cm-2h-1) at 70% (v/v) ethanol in water, and then decreasing with further increases in the ethanol volume fraction. However, in the skin permeation study with testosterone esters saturated in 70% (v/v) ethanol in water system, testosterone esters were hardly detected in the receptor solution, probably due to the rapid degradation to testosterone during the skin permeation process. Moreover, a parabolic relationship was observed between the permeation rate of testosterone and the log P values of ester derivatives. Maximum flux was achieved at a log P value of around 3 which corresponded to that of testosterone (log P = 3.4). The results showed that the skin permeation rate of testosterone and its ester derivatives was maximized when these compounds were saturated in a 70% ethanolic solution. It was also found that a log P value of around 3 is suitable for the skin permeation of testosterone related compounds.
DEVELOPMENTAL PATTERN OF Δ5 3β-HYDROXYSTEROID DEHYDROGENASE ACTIVITY IN ISOLATED RAT LEYDIG CELLS
Paz, Gedalia F.,Winter, Jeremy S. D.,Reyes, Francisco I.,Faiman, Charles
, p. 661 - 674 (1980)
A direct method for determination of Δ5 3β-hydroxysteroid dehydrogenase (3β-HSD) activity was employed in isolated Leydig cells (LC) derived from rats on fetal day 19 (F19) and postnatal (N) days 1, 12, 24, 34 and 45 and adults.The activity of 3β-HSD in the adult LC was 1.15 +/- 0.02 (μmole/μg DNA/hr, mean +/- SEM, n=73).Activities in the other groups, expressed as a percentage of the respective adult control, were: F19 - 38percent; N1 - 39percent; N12 - 8percent; N24 - 89percent; N34 - 166percent; and N45 - 118percent.A good correlation was found between histochemical staining for 3β-HSD and the quantitative method employed.Using (3H)-DHA as a substrate, LC isolated from F19, N1 and N12 produced testosterone in appreciable amounts (41percent, 55percent and 20percent of the total products respectively) whereas at advanced stages of development (N24 to adulthood) the major product was androstenedione (93 +/- 1percent).These findings may be explained by the observed decrease in 17β-hydroxysteroid dehydrogenase (17β-HSD) activity, due to an insufficient supply of NADPH, in the older vs. earlier stages of development.This study indicates the presence of steroidogenic enzymatic activity in LC throughout development in the rat.It also provides a relatively simple in vitro model for studies of testicular regulation during development.
ANDROSTENEDIONE AND TESTOSTERONE BIOSYNTHESIS BY THE ANDRENAL CORTEX OF THE HORSE
Silberzahn, Pierre,Rashed, Fakhri,Zwain, Ismail,Leymarie, Pierre
, p. 147 - 152 (1984)
An homogenate from cortical tissue of mare adrenals was incubated in the presence of tritiated pregnenolone.The (3H) androstenedione and the (3H) testosterone synthesized during the incubation were extracted, purified, and co-crystallized to constant specific activity in the presence of unlabeled carriers.The rate of conversion of pregnenolone to androstenedione and testosterone was of the order of 5 and 0.15 per cent respectively.The high ratio of (3H) androstenedione to (3H) testosterone observed in this study suggests that androstenedione is the main androgen produced by mare adrenals.It is concluded that adrenals could contribute to the production of blood androgens in normal as well as hyperandrogenic mares.
The aging Leydig cell: 2. Two distinct populations of Leydig cells and the possible site of defective steroidogenesis
Chen,Lin,Murono,Osterman,Cole,Nankin
, p. 63 - 72 (1981)
Using metrizamide gradient centrifugation two populations of Leydig cells were found in both 60-90 day old and 24 month old rats. Cells from both Band 2 (B2) and Band 3 (B3) responded to LH stimulation with increased cyclic AMP formation; however, only B3 cells produced significant amounts of testosterone. Cells from both B2 and B3 of the old rats synthesized less cyclic AMP and testosterone than cells from their younger counterparts. In response to LH stimulation, 0.01 - 1.0 mIU/ml, no appreciable difference of cyclic AMP formation could be detected between young and old Leydig cells. Maximal testosterone production occurred when 1 mIU/ml LH was used. Only when LH concentration was increased to 10 and 100 mIU/ml, did young Leydig cells produce significantly more cyclic AMP than old Leydig cells. After addition of 5 x 10-7M of pregnenolone or progesterone to the incubation medium both young and old Leydig cells produced comparable amounts of testosterone. These results demonstrate no impairment of old rat Leydig cells to synthesize testosterone from pregnenolone and progesterone.
One-Step Chemo-, Regio- and Stereoselective Reduction of Ketosteroids to Hydroxysteroids over Zr-Containing MOF-808 Metal-Organic Frameworks
Llabrés i Xamena, F. X.,Mautschke, H.-H.
, p. 10766 - 10775 (2021/06/15)
Zr-containing MOF-808 is a very promising heterogeneous catalyst for the selective reduction of ketosteroids to the corresponding hydroxysteroids through a Meerwein-Ponndorf-Verley (MPV) reaction. Interestingly, the process leads to the diastereoselective synthesis of elusive 17α-hydroxy derivatives in one step, whereas most chemical and biological transformations produce the 17β-OH compounds, or they require several additional steps to convert 17β-OH into 17α-OH by inverting the configuration of the 17 center. Moreover, MOF-808 is found to be stable and reusable; it is also chemoselective (only keto groups are reduced, even in the presence of other reducible groups such as C=C bonds) and regioselective (in 3,17-diketosteroids only the keto group in position 17 is reduced, while the 3-keto group remains almost intact). The kinetic rate constant and thermodynamic parameters of estrone reduction to estradiol have been obtained by a detailed temperature-dependent kinetic analysis. The results evidence a major contribution of the entropic term, thus suggesting that the diastereoselectivity of the process is controlled by the confinement of the reaction inside the MOF cavities, where the Zr4+ active sites are located.
Synthesis method of alkyl acid testosterone
-
, (2020/12/10)
The invention discloses a synthesis method of alkyl acid testosterone, and belongs to the technical field of synthesis and processing of medicines. The method comprises the following steps of: taking4-androstenedione (4AD) as an initial raw material, firstly, carrying out enol ether protection on the keto group at the site 3, and reducing carbonyl at the site 17 into hydroxyl; or taking 4-androstenedione (4AD) as an initial raw material, firstly carrying out enol ether protection on the keto group at the site 3, then reducing carbonyl at the site 17 into hydroxyl, then carrying out hydrolysison the site 3 to obtain testosterone, and carrying out esterification and third-site hydrolysis to obtain the testosterone ester after testosterone third-site ketal protection. According to the method disclosed by the invention, the third site is protected during esterification reaction, the generation of impurities can be reduced, and an esterification reaction solvent is a water-insoluble organic solvent, so that after the reaction is completed, products can be directly extracted in a layered manner, a large amount of water does not need to be added to separate out the products, the amountof wastewater is reduced, the solvent can be recycled, and the process is more suitable for industrial production.
Microbial transformation of androstenedione by Cladosporium sphaerospermum and Ulocladium chartarum
Yildirim, Kudret,Kuru, Ali,Kü?ükba?ol, Eda
, p. 7 - 14 (2019/05/15)
In this work, incubations of androstenedione 1 with Cladosporium sphaerospermum MRC 70266 and Ulocladium chartarum MRC 72584 have been reported. C. sphaerospermum MRC 70266 mainly hydroxylated 1 at C-6β, accompanied by a hydroxylation at C-15α, a reduction at C-17, a 5α-reduction and oxidations at C-6 and C-16 following hydroxylations. U. chartarum MRC 72584 hydroxylated 1 at C-6β, C-7α, C-7β and C-14α, accompanied by an oxidation at C-6 following its hydroxylation, a reduction at C-17 and a 5α-reduction. 6β,17β-Dihydroxyandrost-4-en-3,16-dione 8, one of the metabolites from the incubation of 1 with C. sphaerospermum MRC 70266, was determined as a new compound.