19-Hydroxylation ofΔ 4-androstene-3,17-dione and dehydroepiandrosterone by bovine adrenals

Meyer, A. S.

doi:10.1007/bf02161690

Cited by 79 publications

(18 citation statements)

References 25 publications

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“…Since the discovery ofhuman placental aromatase in 1955 by Meyer (1,2), there has been a sustained interest in elucidating its mechanism of action. The role of estrogens in promoting some forms of neoplasm, particularly breast cancer, is well documented (3)(4)(5).…”

mentioning

confidence: 99%

Conversion of a 3-desoxysteroid to 3-desoxyestrogen by human placental aromatase.

Cole

Bean

Robinson

1990

Proc. Natl. Acad. Sci. U.S.A.

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Human placental aromatase is a cytochrome P.450 enzyme system which converts androgens to estrogens by three successive oxidative reactions. The first two steps have been shown to be hydroxylations at the androgen 19-carbon, but the third step remains unknown. A leading theory for the third step involves ferric peroxide attack on the 19-oxo group to produce a 19,19-hydroxyferric peroxide intermediate and subsequent collapse to estrogen. We had previously developed a nonenzymatic peroxide model reaction which was based on the above-mentioned theory, and we demonstrated the importance of 3-ketone enolization in facilitating aromatization. This study discusses the synthesis and nonenzymatic and enzymatic study of a 3-desoxy-2,4-diene-19-oxo androgen analogue. This compound was found to be a potent nonenzymatic model substrate and competitive inhibitor of aromatase (K1 = 73 nM).Furthermore, in an unprecedented event, this compound served as a substrate for aromatase, with conversion to the corresponding 3-desoxyestrogen.

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mentioning

confidence: 99%

Conversion of a 3-desoxysteroid to 3-desoxyestrogen by human placental aromatase.

Cole

Bean

Robinson

1990

Proc. Natl. Acad. Sci. U.S.A.

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“…Im Gegensatz zu den in Stellung 6,7 gesattigten 19-Hydroxy-d4-3-Ketonen, die bei der Behandlung mit Basen eine avinyloge Retroaldolspaltungo erleiden und in die entsprechenden 19-nor-Verbindungen iibergehen [9], sind 19-Hydro~y-A~?~-3-Ketone vom Typus IV in dieser Beziehung relativ stabilg).…”

unclassified

“…5,6 [13] 5,75,5,80 (Schulter),6,01,6,15,6,28,8,15,9,55. 9,65,10,40 und 2,74,5,75,5,81 (Schulter),6,00,6,15,6,29,7,27,7,35,8,16,8,95,9,42 und 11,38 p. UV. 2,75, 5,77, 6,01, 6,17, 6,30, 7,37,8,20,8,60,9,42 und 11,38p.…”

unclassified

“…2,75, 5,77, 6,01, 6,17, 6,30, 7,37,8,20,8,60,9,42 und 11,38p. UV.-Spektrum: A, , , 5,83 (Schulter),6,00,6,15,6,26,7,27,7,35,8,15,8,96,9,57,10,35 und 11,40 p. UV.-Spektrum: A , , , = 288 nm (E = 21700).…”

unclassified

“…2,84,5,75,5,78 (Schulter),5,85 (Schulter),6,00,6,15,6,27,7,35,8,60,8,97,9,56,10,35 und 11,40 Banden ma. bei 5,75, 5,79, 8,05, 8,25, 9,15, 9,25, 9,57 und 1,155).…”

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19‐nor‐Steroide V. Neue Synthese von 6‐Dehydro‐19‐nor‐Steroiden. Über Steroide, 208. Mitteilung

Kalvoda

Anner

1967

Helvetica Chimica Acta

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The biosynthesis of estrogens

Engel

1957

Cancer

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19-Hydroxylation ofΔ 4-androstene-3,17-dione and dehydroepiandrosterone by bovine adrenals

Cited by 79 publications

References 25 publications

Conversion of a 3-desoxysteroid to 3-desoxyestrogen by human placental aromatase.

Conversion of a 3-desoxysteroid to 3-desoxyestrogen by human placental aromatase.

19‐nor‐Steroide V. Neue Synthese von 6‐Dehydro‐19‐nor‐Steroiden. Über Steroide, 208. Mitteilung

The biosynthesis of estrogens

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