TY - JOUR
T1 - The ferrocenylethynyl unit
T2 - A stable hormone tag
AU - Osella, Domenico
AU - Nervi, Carlo
AU - Galeotti, Francesco
AU - Cavigiolio, Giorgio
AU - Vessières, Anne
AU - Jaouen, Gérard
PY - 2001
Y1 - 2001
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0035217158&partnerID=8YFLogxK
U2 - 10.1002/1522-2675(20011114)84:11<3289::AID-HLCA3289>3.0.CO;2-D
DO - 10.1002/1522-2675(20011114)84:11<3289::AID-HLCA3289>3.0.CO;2-D
M3 - Article
SN - 0018-019X
VL - 84
SP - 3289
EP - 3298
JO - Helvetica Chimica Acta
JF - Helvetica Chimica Acta
IS - 11
ER -