Aminoestradiol (AE2), also known as 17β-aminoestradiol (17βAE2) or as 17β-aminoestra-1,3,5(10)-trien-3-ol, is a
synthetic,
steroidalestrogen and a
17β-aminoestrogen with
anticoagulant effects that was never marketed.[1][2][3][4][5] It is an
analogue of
estradiol in which the C17β
hydroxyl group has been replaced with an
amine group.[1][2] AE2 has profoundly reduced estrogenic
potency compared to
estradiol; its
EC50 for activation of the
ERα was found to be 1.82 μM, whereas that of estradiol was 2.14 nM (relative potency 0.12 for AE2 versus 100 for estradiol, or roughly a 1,000-fold difference).[2] It binds with low relative
affinity to both the ERα and
ERβ and has estrogenic activity that is greatly mediated through the ERβ and to a lesser extent through the ERα.[2]
References
^
abLemini C, Rubio-Póo C, Franco Y, Jaimez R, Avila ME, Medina M, Lemus AE (2013). "In vivo profile of the anticoagulant effect of 17β-amino-1,3,5(10)estratrien-3-ol". Eur. J. Pharmacol. 700 (1–3): 210–6.
doi:
10.1016/j.ejphar.2012.12.030.
PMID23305838.
^
abcdLemini C, Jaimez R, Pozas R, Franco Y, Avila ME, Figueroa A, Medina M, Lemus AE, García-Becerra R, Ordaz-Rosado D, Larrea F (2015). "In vivo and in vitro estrogenic profile of 17β-amino-1,3,5(10)estratrien-3-ol". J. Steroid Biochem. Mol. Biol. 147: 40–7.
doi:
10.1016/j.jsbmb.2014.11.019.
PMID25448750.
S2CID195676484.
^Ye YH, Huang YS, Wang ZQ, Chen SM, Tian Y (1993). "Synthesis of new amino acid and peptide derivatives of estradiol and their binding affinities for the estrogen receptor". Steroids. 58 (1): 35–9.
doi:
10.1016/0039-128x(93)90015-f.
PMID8430443.
S2CID54308145.
^Li Z, Yan M, Li Z, Vuki M, Wu D, Liu F, Zhong W, Zhang L, Xu D (2012). "A multiplexed screening method for agonists and antagonists of the estrogen receptor protein". Anal Bioanal Chem. 403 (5): 1373–84.
doi:
10.1007/s00216-012-5933-7.
PMID22453607.
S2CID22670785.
^Lemini C, Cruz-Ramos E, Toscano RA, Cruz-Almanza R (1998). "A comparative structural study of the steroid epimers: 17 beta-amino-1,3,5(10)-estratrien-3-ol, 17 alpha-amino-1,3,5(10)-estratrien-3-ol, and some derivatives by 1H NMR, and x-ray diffraction analysis". Steroids. 63 (11): 556–64.
doi:
10.1016/s0039-128x(98)00063-4.
PMID9830681.
S2CID40400348.
Aminoestradiol (AE2), also known as 17β-aminoestradiol (17βAE2) or as 17β-aminoestra-1,3,5(10)-trien-3-ol, is a
synthetic,
steroidalestrogen and a
17β-aminoestrogen with
anticoagulant effects that was never marketed.[1][2][3][4][5] It is an
analogue of
estradiol in which the C17β
hydroxyl group has been replaced with an
amine group.[1][2] AE2 has profoundly reduced estrogenic
potency compared to
estradiol; its
EC50 for activation of the
ERα was found to be 1.82 μM, whereas that of estradiol was 2.14 nM (relative potency 0.12 for AE2 versus 100 for estradiol, or roughly a 1,000-fold difference).[2] It binds with low relative
affinity to both the ERα and
ERβ and has estrogenic activity that is greatly mediated through the ERβ and to a lesser extent through the ERα.[2]
References
^
abLemini C, Rubio-Póo C, Franco Y, Jaimez R, Avila ME, Medina M, Lemus AE (2013). "In vivo profile of the anticoagulant effect of 17β-amino-1,3,5(10)estratrien-3-ol". Eur. J. Pharmacol. 700 (1–3): 210–6.
doi:
10.1016/j.ejphar.2012.12.030.
PMID23305838.
^
abcdLemini C, Jaimez R, Pozas R, Franco Y, Avila ME, Figueroa A, Medina M, Lemus AE, García-Becerra R, Ordaz-Rosado D, Larrea F (2015). "In vivo and in vitro estrogenic profile of 17β-amino-1,3,5(10)estratrien-3-ol". J. Steroid Biochem. Mol. Biol. 147: 40–7.
doi:
10.1016/j.jsbmb.2014.11.019.
PMID25448750.
S2CID195676484.
^Ye YH, Huang YS, Wang ZQ, Chen SM, Tian Y (1993). "Synthesis of new amino acid and peptide derivatives of estradiol and their binding affinities for the estrogen receptor". Steroids. 58 (1): 35–9.
doi:
10.1016/0039-128x(93)90015-f.
PMID8430443.
S2CID54308145.
^Li Z, Yan M, Li Z, Vuki M, Wu D, Liu F, Zhong W, Zhang L, Xu D (2012). "A multiplexed screening method for agonists and antagonists of the estrogen receptor protein". Anal Bioanal Chem. 403 (5): 1373–84.
doi:
10.1007/s00216-012-5933-7.
PMID22453607.
S2CID22670785.
^Lemini C, Cruz-Ramos E, Toscano RA, Cruz-Almanza R (1998). "A comparative structural study of the steroid epimers: 17 beta-amino-1,3,5(10)-estratrien-3-ol, 17 alpha-amino-1,3,5(10)-estratrien-3-ol, and some derivatives by 1H NMR, and x-ray diffraction analysis". Steroids. 63 (11): 556–64.
doi:
10.1016/s0039-128x(98)00063-4.
PMID9830681.
S2CID40400348.