STUDIES ON THE METABOLISM OF C19 STEROIDS IN THE FOETO-PLACENTAL UNIT

1971 ◽  
Vol 66 (4) ◽  
pp. 653-665 ◽  
Author(s):  
G. Benagiano ◽  
M. Ermini ◽  
B. de la Torre ◽  
N. Wiqvist ◽  
E. Diczfalusy
Keyword(s):  
Sodium Salt ◽  
Human Placenta ◽  
Major Part ◽  
Isotopic Ratio ◽  
Water Soluble ◽  
Radioactive Material ◽  
Considerable Part ◽  
Maternal Urine ◽  
Unchanged Form ◽  
Urine Specimens

ABSTRACT Three midgestation placentas were perfused at laparotomy during fifteen minutes with tracer amounts of [1,2-3H] testosterone [35S] sulphate sodium salt, and metabolites present in the placentas, perfusates and maternal urine specimens were analyzed. Most of the radioactive material administered was present in the placentas and perfusates; approximately 2% of it was recovered from the urine. More than 99.5% of the radioactive material recovered from the placentas and the perfusates was in a water soluble (conjugated) form. No unconjugated testosterone was found in these sources. Radiochemically homogeneous [1,2-3H] testosterone [35S] sulphate was isolated from the placentas, perfusates and urine specimens collected during the first 24 hours of experiment. The isotopic ratio of the conjugate isolated from these sources was very similar to that of the perfused material. Seventy per cent of the double labelled radioactive material recovered from the Day 1 urine samples was radiochemically homogeneous testosterone sulphate. The relative amounts of testosterone sulphate present in the Day 2 and Day 3 urine specimens showed a gradual decrease. This decrease was associated with an increase in tritium to sulphur-35 ratio. From the pooled extracts of all urine specimens, small amounts of exclusively tritium labelled conjugated 5α-androsterone and 5β-androsterone were also isolated. No 17β-oestradiol 17-sulphate was detected in any of the sources studied. It is concluded that little, if any, testosterone sulphate is hydrolyzed by the midgestation human placenta, and that a considerable part of the testosterone sulphate secreted by the foetus is transferred across the placenta to the mother in an unchanged form. The major part of the transferred testosterone sulphate is excreted in the urine; a smaller part of it undergoes hydrolysis with a subsequent metabolism of the steroid moiety.

METABOLISM OF DEHYDROEPIANDROSTERONE SULPHATE AND OESTRONE SULPHATE FOLLOWING IN SITU PLACENTAL PERFUSION AT MIDPREGNANCY

1971 ◽  
Vol 66 (4) ◽  
pp. 637-647 ◽  
Author(s):  
J. Schwers ◽  
T. Vancrombreucq ◽  
M. Govaerts ◽  
G. Eriksson ◽  
E. Diczfalusy
Keyword(s):  
Radioactive Material ◽  
Dehydroepiandrosterone Sulphate ◽  
Placental Perfusion ◽  
Carbon 14 ◽  
Maternal Urine ◽  
Oestrone Sulphate ◽  
Unchanged Form ◽  
Urine Specimens

ABSTRACT Two midgestation placentas were perfused in situ with a combination of [7α-3H] dehydroepiandrosterone sulphate and [4-14C] oestrone sulphate and metabolites were isolated from the placentas, perfusates and maternal urine specimens. Approximately 70 per cent of the perfused radioactive material was recovered from these three sources. The bulk of the administered radioactive material was recovered in an unchanged form from the perfusates; some 2–4 per cent was excreted in the urine and less than 0.5% was found in the placentas. The tritium to carbon-14 ratio of the unconjugated material isolated from the perfusates and placentas was higher, and that of the conjugated material recovered from the same sources was lower than the ratio of the administered material. In addition, more tritium than carbon-14 labelled material was present in the urine. Approximately 2 per cent of the perfused dehydroepiandrosterone sulphate was recovered in the form of phenolic steroids, mostly from the urine. From this source double labelled oestrone, oestriol, 16α-hydroxy-oestrone and 16-epioestriol were isolated. The tritium to carbon-14 ratio of all oestrogens isolated from the urine was higher than that of the perfused material. From the urine specimens 10 to 15 times more double labelled oestriol than oestrone was isolated.

STUDIES ON THE AROMATISATION OF NEUTRAL STEROIDS IN PREGNANT WOMEN

1964 ◽  
Vol 45 (4) ◽  
pp. 560-575 ◽  
Author(s):  
E. Bolté ◽  
S. Mancuso ◽  
G. Eriksson ◽  
N. Wiqvist ◽  
E. Diczfalusy
Keyword(s):  
Amniotic Fluid ◽  
Pregnant Women ◽  
Human Placenta ◽  
Uterine Artery ◽  
Urine Samples ◽  
Radioactive Material ◽  
Free Form ◽  
Maternal Circulation ◽  
Urine Specimens

ABSTRACT Tracer amounts of dehydroepiandrosterone-4-14C (DHA-4-14C) and dehydroepiandrosterone-7α-3H sulphate (DHAS-7α3H) were injected simultaneously into a uterine artery in two patients twelve to fifteen minutes prior to therapeutic interruption of pregnancy at laparotomy and the amniotic fluid, foetuses, placentas and urine samples were analysed for radioactive material. No radioactivity was found in the amniotic fluid. Regardless of the tracer administered, approximately 80 per cent of the radioactive material recovered from the placentas was in an unconjugated (free) form, whereas more than 80 per cent of the radioactivity present in the foetuses was in a conjugated form. More than 67 per cent of the total radioactive material in the two placentas and more than 87 per cent of that in the two foetuses was present as phenolic material. Approximately half of this phenolic material was identified as oestrone (OE1) and 17β-oestradiol (OE2). The 3H to 14C ratio of OE1 and OE2 isolated from the foetuses and urine specimens was lower than the ratio of the injected material. Corresponding 3H to 14C ratios in placental OE1 and OE2 were higher than those in foetal or urinary OE1 and OE2. Labelled oestriol (OE3) could be detected in the placentas, but not in the foetuses. However, a 16-hydroxylated phenolic intermediate (probably 16α-hydroxyoestrone) was found in one foetus studied. The results indicate that the DHA and DHAS of the maternal circulation can serve as direct precursors to placental OE2 and OE1 and as indirect precursors – via a foetal intermediate – to placental OE3. Both compounds reach the foetus mostly as phenolic material, the free form being a better precursor than the sulphate. It is suggested that – around midpregnancy at least – the human placenta functions as a barrier limiting the transfer to the foetus of androgens present in the maternal circulation.

PLACENTAL TRANSFER OF 3H-OESTRIOL-3-SULPHATE-16-GLUCOSIDURONATE AND 3H-OESTRIOL-16-GLUCOSIDURONATE-14C

1972 ◽  
Vol 70 (1) ◽  
pp. 132-142 ◽  
Author(s):  
U. Goebelsmann ◽  
J. M. Roberts ◽  
R. B. Jaffe
Keyword(s):  
Placental Transfer ◽  
Conclusive Evidence ◽  
Radioactive Material ◽  
Maternal Urine ◽  
Urine Specimens

ABSTRACT Four human placentas were perfused in situ at midpregnancy, two with biosynthetically prepared 3H-oestriol-16-glucosiduronate-14C (OE3-16Gl) and two with 3H-oestriol-3-sulphate-16-glucosiduronate (OE3-3S,16Gl). The radioactive material recovered from the placentas, perfusates and maternal urine was quantitated and identified. Only 0.8 to 3.7% of the labelled material administered was recovered from urine specimens; the bulk of the labelled material perfused was found in the extracts of placentas and perfusates. The double-labelled material isolated from the three sources following perfusion with 3H-OE3-16Gl-14C was identified as OE3-16Gl. The 3H/14C ratios measured in these fractions were virtually identical with those of the tracers perfused. Following perfusion with 3H-OE3-3S,16Gl, three-fourths of the 3H-labelled material recovered from the urine was identified as OE3-3S,16Gl and a small but significant portion of the tritiated material extracted from the placentas and perfusates was shown to be 3H-OE3-16Gl. No significant quantities of unconjugated labelled material could be detected in any of the four placental perfusions. The data presented provide conclusive evidence that both OE3-16Gl and OE3-3S,16Gl are transferred across the placenta in situ without previous hydrolysis. The placenta in vivo is capable of converting some OE3-3S,16Gl to OE3-16Gl. The latter conjugate remains unhydrolysed.

PLACENTAL TRANSFER OF OESTRIOL GLUCOSIDURONATES

1968 ◽  
Vol 59 (3) ◽  
pp. 426-432 ◽  
Author(s):  
U. Goebelsmann ◽  
N. Wiqvist ◽  
E. Diczfalusy
Keyword(s):  
Placental Transfer ◽  
Conclusive Evidence ◽  
Radioactive Material ◽  
Experimental Conditions ◽  
Unchanged Form ◽  
Urine Specimens

ABSTRACT Two human placentas were perfused in situ at midpregnancy with a combination of oestriol-15-3H-3-glucosiduronate (OE3-3Gl) and oestriol-16-14C-16-glucosiduronate (OE3-16Gl) and the radioactive material recovered from the placentas, perfusates and urine specimens was analysed. Only 1 to 2 per cent of the tracers administered was recovered from the urine; the bulk of the administered material was found in the perfusates and placentas. Under the experimental conditions used, no evidence for the metabolism of the two conjugates was found. The OE33Gl isolated from the three sources contained only 3H-label, and the OE3-16Gl only 14C-label. Whereas the evidence indicating the placental transfer of OE3-16Gl in an unchanged form is circumstantial, conclusive evidence is presented that OE3-3Gl is transferred across the placenta without hydrolysis.

METABOLISM OF OESTRONE GLUCOSIDURONATE AT MIDPREGNANCY

1967 ◽  
Vol 56 (1) ◽  
pp. 71-84 ◽  
Author(s):  
G. Zucconi ◽  
U. Goebelsmann ◽  
N. Wiqvist ◽  
E. Diczfalusy
Keyword(s):  
Intravenous Infusion ◽  
Isotopic Ratio ◽  
Umbilical Vein ◽  
Radioactive Material ◽  
Therapeutic Abortion ◽  
Maternal Circulation ◽  
Glucuronidase Activity ◽  
Oestrone Sulphate ◽  
Foetal Liver ◽  
Unchanged Form

ABSTRACT Oestrone-6,7-3H-glucosiduronate-14C (OE1-3H-Gl-14C) has been prepared biosynthetically and its metabolism studied in two cases of therapeutic abortion following the administration of the tracer at laparotomy into the umbilical vein. The bulk of the radioactive material recovered was in the foetus and placenta; only small amounts were present in the urine of the mother. Minute quantities of the radioactive material recovered from any of these sources were in an unconjugated form. Following reduction with KBH4 of the extract of the foetal liver oestriol-3-glucosiduronate (OE3-3Gl) was isolated from this source with the same isotopic ratio as that of the injected material. Following hydrolysis with β-glucuronidase, 3H-labelled oestrone, 17β-oestradiol and oestriol were isolated in a radiochemically homogeneous form from the foetal liver and from the urine of the mother, and oestrone and 17β-oestradiol from the placenta. From the urine of the mothers OE1-3H-Gl-14C was also isolated. It exhibited the same isotopic ratio as the injected material. Following the intravenous infusion to two women at midpregnancy of a combination of 3H-labelled OE1-Gl and 14C-labelled oestrone sulphate (OE1-S), the tracer administered as OE1-Gl was eliminated in the urine far more rapidly than that infused in the form of OE1-S. It is concluded that at midpregnancy a) the foetus is capable of metabolizing OE1-Gl without any preceding hydrolysis, b) the placenta exhibits no β-glucuronidase activity, c) only a limited amount of OE1-Gl is transferred from the foeto-placental circulation to the mother and exclusively in an unchanged form, and d) OE1-Gl is eliminated from the maternal circulation much more rapidly than OE1-S.

LACK OF AROMATISATION OF CIRCULATING DEHYDROEPIANDROSTERONE AND DEHYDROEPIANDROSTERONE SULPHATE IN AMENORRHOEIC WOMEN STIMULATED WITH HUMAN GONADOTROPHINS

1965 ◽  
Vol 49 (2) ◽  
pp. 248-261 ◽  
Author(s):  
S. Mancuso ◽  
Francesca P. Mancuso ◽  
K.-G. Tillinger ◽  
E. Diczfalusy
Keyword(s):  
Pregnant Women ◽  
Ovarian Stimulation ◽  
Interstitial Cell ◽  
Follicular Phase ◽  
Radioactive Material ◽  
Dehydroepiandrosterone Sulphate ◽  
Experimental Conditions ◽  
Human Menopausal Gonadotrophin ◽  
Urine Specimens ◽  
Stimulating Hormone

ABSTRACT Two amenorrhoeic women were given a course of 10 injections of human menopausal gonadotrophin (HMG) in daily doses corresponding to 260 IU of follicle stimulating hormone (FSH) activity and 165 IU of interstitial cell stimulating hormone (ICSH) activity. In both patients an extensive ovarian stimulation was observed as indicated by the greatly increased urinary excretion of oestrone, 17β-oestradiol and oestriol. When HMG-treatment was followed subsequently by the administration of human chorionic gonadotrophin (HCG) for 5 days in a total dose of 18 000 and 30 000 IU, respectively, functional corpus luteum tissue was formed in both patients as evidenced by a huge rise in urinary pregnane-3α,20α-diol excretion and by the secretory transformation of a previously atrophic endometrium. At the approximate height of the follicular phase tracer doses of 3H-labelled dehydroepiandrosterone sulphate (DHAS) and 14C-labelled dehydroepiandrosterone (DHA) were administered to both patients in the form of a continuous intravenous infusion of 10 hours' duration. Infusion of the same dose was repeated under identical experimental conditions at the approximate height of the luteal phase. In both patients, very little radioactive material was associated with oestrone and 17β-oestradiol and none with oestriol isolated from 96-hours' urine specimens obtained at both phases of ovarian stimulation. It is concluded that — in contradistinction to the situation in pregnant women — circulating DHAS is not a significant precursor of urinary oestrogens in non-pregnant women.

scholarly journals Synthesis of Water-Soluble 7-O-Carboxymethyl-Genistein

2017 ◽  
Vol 41 (3) ◽  
pp. 183-185
Author(s):  
Zhiling Cao ◽  
Qiao Wu ◽  
Jing Cheng ◽  
Dandan Zhu ◽  
Wengqi Teng ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Sodium Salt ◽  
Water Solubility ◽  
Clinical Chemistry ◽  
Water Soluble ◽  
Aqueous Acetic Acid ◽  
Carboxylate Group ◽  
Target Compound ◽  
Catalysed Reaction

A three-step synthesis from genistein of the water-soluble sodium salt of 7-O-carboxymethyl-genistein is described. Base-catalysed reaction of genistein with t-butyl bromoacetate gave 7-O-(carbo-t-butoxy)methyl-genistein, which was hydrolysed by aqueous acetic acid to 7-O-carboxymethyl-genistein and neutralised (NaHCO3) to give the target compound. The carboxylate group enhanced the water-solubility of genistein more than a thousand-fold and the new derivate will be useful as a candidate compound in pharmacological and clinical chemistry studies of isoflavones.

Effect of Glutathione Depletion on Haemoglobin and Membrane Integrity of Red Blood Cells of Rats

1996 ◽  
Vol 24 (1) ◽  
pp. 40-46 ◽  
Author(s):  
K S Park ◽  
M J Kim ◽  
J S Ho ◽  
C K Ryu ◽  
J H Chung
Keyword(s):  
Red Blood Cells ◽  
Sodium Salt ◽  
Blood Cells ◽  
Membrane Integrity ◽  
Water Soluble ◽  
Glutathione Depletion ◽  
Haemoglobin Content

The effects of streptozocin (streptozotocin) and water-soluble menadione (menadione bisulphite, sodium salt) on the haemoglobin content and membrane integrity of red blood cells were investigated. Both menadione bisulphite and streptozocin significantly depleted glutathione but menadione bisulphite was much more effective in reducing glutathione than was streptozocin. Menadione bisulphite, at concentrations above 0.1 mM, caused substantial conversion of oxygenated haemoglobin into methaemoglobin while streptozocin did not alter the haemoglobin content of the red blood cells at concentrations of up to 100 mM. Both agents demonstrated only a modest ability to haemolyse the red blood cells, even at concentrations up to 300 mM. These results suggest that depletion of glutathione by menadione causes the conversion of oxyhaemoglobin to methaemoglobin. In contrast, streptozocin-induced glutathione depletion does not seem to be well correlated with alterations in haemoglobin content.

Syntheses and properties of acetylene-linked bis- and trisporphyrins toward two-photon photodynamic therapy

2007 ◽  
Vol 11 (06) ◽  
pp. 406-417 ◽  
Author(s):  
Yusuke Inaba ◽  
Kazuya Ogawa ◽  
Yoshiaki Kobuke
Keyword(s):  
Photodynamic Therapy ◽  
Cross Section ◽  
Sodium Salt ◽  
Absorption Cross Section ◽  
Water Soluble ◽  
Photon Absorption ◽  
Absorption Cross ◽  
Two Photon Absorption ◽  
Photon Irradiation ◽  
Two Photon

Acetylene-bridged bisporphyrins and trisporphyrins having branched bulky bis(carboxylethyl)methyl meso-substituents were synthesized. These compounds showed large effective two-photon absorption cross-section values at 890 nm measured by using a nanosecond Z-scan method. Sodium salt of hydrolyzed trisporphyrins showed broad and red-shifted Q-bands over 900 nm. Two-photon absorption cross-section values of water-soluble dimers in water were similar to, or slightly larger than, those of ester forms evaluated in toluene. Furthermore, the generation of singlet oxygen upon one-photon irradiation for dimers in water was confirmed.

Spectral properties of ionic derivatives of pyrene and their aggregates with anionic surfactant and polyelectrolyte

1995 ◽  
Vol 73 (11) ◽  
pp. 1948-1954 ◽  
Author(s):  
Pavol Hrdlovič ◽  
Lubica Horinová ◽  
Štefan Chmela
Keyword(s):  
Butyric Acid ◽  
Sodium Salt ◽  
Polyacrylic Acid ◽  
Sodium Dodecylsulfate ◽  
Green Emission ◽  
Water Soluble ◽  
Diffusion Controlled ◽  
Packed Structure ◽  
Bimolecular Quenching ◽  
Derivatives Of

A multifunctional probe based on pyrene, the chloride of the 2,2,6,6-tetramethyl-4-hydroxy-piperidinium ester of 4-(1-pyrene)butyric acid, at a concentration of 5 × 10−5 mol dm−3 exhibits excimer-like green emission with the maximum at 480 nm in the presence of sodium dodecylsulfate below its critical micelle concentration. A similar effect has been observed for this probe in the presence of the sodium salt of polyacrylic acid in the same concentration range. 1-Pyrenemethylammonium chloride exhibits a broad green excimer-like emission for sodium dodecylsulfate but not for the sodium salt of polyacrylic acid. The quenching constants of the monomeric and excimer-like emissions were determined for acrylamide, 1-oxo-2,2,6,6-tetramethyl-4-hydroxypiperidine, potassium iodide, and copper(II) sulfate, representing neutral, ionic, and free-radical types of quenchers. The rate constants of quenching for N-oxyl radicals indicate that the monomeric emission from both water-soluble probes is diffusion controlled. For other types of quenchers the rate constant of bimolecular quenching is lower. The quenching of the excimer-like emission of an aggregate of the chloride of the 2,2,6,6-tetramethyl-4-hydroxypiperidinium ester of 4-(1-pyrene)butyric acid is less efficient than in the case of 1-pyrenemethylammonium chloride, which indicates a more packed structure of the former aggregate. Keywords: pyrene, ionic derivative, emission, micelle, aggregation, quenching.

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