Synthesis of the allylic gonadal steroids, 3α-hydroxy-4-pregnen-20-one and 3α-hydroxy-4-androsten-17-one, and of 3α-hydroxy-5α-pregnan-20-one

Membrane 5α-pregnane-3,20-dione (5αP) receptors in MCF-7 and MCF-10A breast cancer cells are up-regulated by estradiol and 5αP and down-regulated by the progesterone metabolites, 3α-dihydroprogesterone and 20α-dihydroprogesterone, with associated changes in cell proliferation and detachment

“…Radiolabelled thymidine (methyl-3 H-thymidine; 48.0 Ci/mmol) was obtained from Amersham Biosciences (Piscataway, NJ). [9,11, …”

“…Radiolabelled [ 3 H]5␣P was synthesized by performing an oxidation of [9,11, H]5␣-pregan-3␣-ol-20-one as previously described [6]. Unlabelled 3␣HP was synthesized and purified according to our published procedures [10,11].…”

“…Unlabelled 3␣HP was synthesized and purified according to our published procedures [10,11]. Radiolabelled thymidine (methyl-3 H-thymidine; 48.0 Ci/mmol) was obtained from Amersham Biosciences (Piscataway, NJ).…”

Regulation of estrogen receptor (ER) levels in MCF-7 cells by progesterone metabolites

“…3␣HP was synthesized and purified according to published procedures [27]. [2,4,6, H]-Estradiol-17␤ (71 Ci/mmol) was purchased from Perkin Elmer Life Sciences (New England Nuclear; Woodbridge, Ontario).…”

Plasma Membrane Receptors for the Cancer-Regulating Progesterone Metabolites, 5α-Pregnane-3,20-dione and 3α-Hydroxy-4-pregnen-20-one in MCF-7 Breast Cancer Cells

“…The results suggest that the membrane receptors may play a role in facilitating the observed actions of 5␣P and 3␣HP on cell proliferation and adhesion. [ 3 H]-3␣HP, 3␣HP and 3␤HP were synthesized, isolated and purified as previously described (11,12). [9,11,12-3 H]-5␣-pregnan-3␣-ol-20-one (45 Ci/mmol) and [2,4,6,7-3 H]-estradiol-17␤ (92 Ci/mmol) were purchased from Mandel Scientific (New England Nuclear) (Guelph, Ontario).…”