The ferrocenylethynyl unit: A stable hormone tag

Domenico Osella, Carlo Nervi, Francesco Galeotti, Giorgio Cavigiolio, Anne Vessières, Gérard Jaouen

Risultato della ricerca: Contributo su rivistaArticolo in rivistapeer review

Abstract

We prepared the organometallic complex 17α-(ferrocenylethynyl)estradiol (= [(3,17β- dihydroxyestra-1,3,5(10)-trien-17α-yl)ethynyl]ferrocene; FcEE; 1) by a novel synthetic method. This metallocene possesses sufficient stability in aqueous media to permit the study of its biological properties. Thus, we were able to show that, despite the addition of a bulky substituent at the 17α position of the steroid, the metallocene is still well-recognized by an antibody specific to estradiol (CR = 40%) and by both subtypes (ERα, ERβ) of the estrogen receptor (at 0°, RBA = 28 and 37%, resp.). A DCI-MS study of the stability of the carbocation [FcEE - OH]+ showed moderate stabilization of the carbocation, in agreement with the pKR- value of -0.72 found for the metallocene by means of Deno's method. The presence of the ferrocene allows the electrochemical detection of FcEE (1) by HPLC-ED, with a detection limit of ca. 1 nM, suitable for quantitative pharmacological analysis.

Lingua originaleInglese
pagine (da-a)3289-3298
Numero di pagine10
RivistaHelvetica Chimica Acta
Volume84
Numero di pubblicazione11
DOI
Stato di pubblicazionePubblicato - 2001
Pubblicato esternamente

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