Steroid conjugates I. The use of sulfamic acid for the preparation of steroid sulfates

Joseph, Joseph P.; Dusza, John P.; Bernstein, Seymour

doi:10.1016/0039-128x(66)90145-0

Cited by 34 publications

(4 citation statements)

References 14 publications

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“…Yields ranging from 30 to 66% have been achieved with the following steroids: nylestradiol,221 and ethynylestradiol 3-methyl ether. 221 The syntheses of vitamin D2 sulfate,223 using sulfamic acid, of adenosine 5'-sulfate (65%) and D-galactose 6-sulfate (55%), using cyclohexylsulfamic acid in anhydrous pyridine, and of riboflavin sulfate (23%), using morpholine-/V-sulfonic acid in Me2SO-pyridine, have been achieved. 224 Sulfates of 48225 and 49226 were prepared with sulfamic acid.…”

Section: Sulfationmentioning

confidence: 99%

Sulfamic acid and its N-substituted derivatives

Benson¹,

Spillane²

1980

Chem. Rev.

117

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Section: Sulfationmentioning

confidence: 99%

Sulfamic acid and its N-substituted derivatives

Benson¹,

Spillane²

1980

Chem. Rev.

117

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“…Preparation of steroid sulphates Sulphation of androstanediols was carried out according to Joseph, Dusza & Bernstein (1966) with modifications by M. Herning of Ikapharm, Ramat Gan, Israel (unpublished). To 1 g of steroid, 14 ml pyridine and 1-6 g sulphonic acid were added.…”

Section: Animalsmentioning

confidence: 99%

Androstanediol Sulphates in Peripheral Blood of Immature Rats and Some of Their Biological Effects

Ravid¹,

Eckstein²

1976

Journal of Endocrinology

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The conjugation of 5alpha-androstane-3alpha,17beta-diol (3alpha-A) and its 3beta epimer (3beta-A) was determined in the peripheral blood of immature female rats. About two thirds of these steroids were present in blood as sulphates and one third as glucuronides; no free steroids were detected. Administration of 3beta-A sulphate (25mug/100 g body weight/day) and of 3alpha-A sulphate (50 mug/100 g/day) from day 21 of life until the day of vaginal opening, advanced the day of the first ovulation. Administration of the 3beta-A sulphate did not induce precocious vaginal opening whereas the free alcohol was active in this respect. Implantation of 3beta-A sulphate, but not of the 3alpha epimer, into the basal medial hypothalamus resulted in the dealth of all animals within 24 h.

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“…Carrier oestrogen sulphates were prepared by the sulphamic acid method (Joseph, Dusza & Bernstein, 1966). The solvent system for thin-layer chromatography comprised méthylène chloride : methanol : ammonia (70:22:8, by vol.)…”

Section: Chromatographymentioning

confidence: 99%

Uptake and Metabolism of Tritiated Oestradiol and Oestrone by Human Endometrial and Myometrial Tissue in Vitro

Gabb¹,

Stone²

1974

Journal of Endocrinology

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Human endometrial and myometrial tissues were incubated in vitro with [3H]oestradiol-17\g=b\ and [3H]oestrone to study the uptake and interconversion of these two steroids by the tissues. Endometrial tissue displayed a higher capacity for oestrogen interconversion than myometrial tissue and the oxidation of oestradiol-17\g=b\ to oestrone was favoured, rather than the reverse reaction. A greater degree of oxidation was found in tissue taken from uteri in the secretory phase than in the proliferative phase. A study of the distribution of radiometabolites between 'soluble' and 'particulate' fractions of tissue homogenates showed that a greater proportion of the tissue radioactivity was associated with the 'particulate' fraction in the proliferative phase than in the secretory phase. After incubation of endometrial tissue from the secretory phase with tritiated oestrogens there was evidence of the formation of chloroform-insoluble radiometabolites and some of these were tentatively identified as oestrogen sulphates. In a second experiment, the uptake and metabolism of the same two oestrogens by tissue from leiomyomata uteri (fibroids) and normal myometrial tissue were compared. No significant difference between these tissues was found.The results suggest that the levels of 17\g=b\-hydroxysteroiddehydrogenase in the human uterus may be dependent upon the levels of oestrogens in the blood. The lack of a difference in the treatment of oestrogens by fibroid and normal myometrial tissue suggests that these tissues may have a similar mechanism for the uptake and retention of oestrogens.

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Steroid conjugates I. The use of sulfamic acid for the preparation of steroid sulfates

Cited by 34 publications

References 14 publications

Sulfamic acid and its N-substituted derivatives

Sulfamic acid and its N-substituted derivatives

Androstanediol Sulphates in Peripheral Blood of Immature Rats and Some of Their Biological Effects

Uptake and Metabolism of Tritiated Oestradiol and Oestrone by Human Endometrial and Myometrial Tissue in Vitro

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