Synthesis and biological activity of new halo-steroidal antiestrogens.

Levesque, Charles; Merand, Yves; Dufour, Jean Marc; Labrie, Claude; Labrie, Fernand

doi:10.1021/jm00109a014

Cited by 81Estrogen and related hormone effectsSynthesis and biological activitySteroid Chemistry and Biochemistry

Synthesis and biological activity of new halo-steroidal antiestrogens.

Levesque, Charles, Merand, Yves, Dufour, Jean Marc, Labrie, Claude, Labrie, Fernand·1991·Journal of Medicinal Chemistry

DOI 10.1021/jm00109a014

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Abstract

Antiestrogen therapy is the most widely used endocrine manipulation for the treatment of breast cancer, especially in postmenopausal women. Unfortunately, the compounds presently available possess mixed agonistic/antagonistic activity, thus potentially limiting their therapeutic efficacy. Following the observations that an aliphatic chain at the 7 alpha-position of 17 beta-estradiol does not prevent binding to the estrogen receptor while halogenation of estradiol can increase the affinity of its binding (expressed as RBA) to the estrogen receptor, we have synthesized a series of new steroidal antiestrogens (6-10) which possess both an 7 alpha-undecanamide group and an halogen atom (Cl, Br, or I) at the 16 alpha-position. The stereochemistry of these compounds was unambiguously established by high-field (400-MHz) nuclear magnetic resonance. Some of the compounds obtained possess potent in vivo antiestrogenic activity. At the low twice daily 3-micrograms dose, 16 alpha-chloro 3,17 beta-diol amide, 16 alpha-iodo 3,17 beta-diol amide, 16 alpha-bromo 3,17 beta-diol amide, 16 alpha-chloro 3,17 alpha-diol amide, and 16 alpha-bromo 3,17 alpha-diol amide inhibit by 74, 63, 52, 35, and 60%, respectively, the estradiol-induced stimulation of uterine weight in ovariectomized Balb/c mice while 78-99% blockade of estradiol action is achieved at the 20-micrograms dose. These new antiestrogens show no estrogenic activity on uterine weight at the doses used while tamoxifen (2-[4-(1,2-diphenyl-1-butenyl)phenoxy]-N,N- dimethylethanamine) shows full estrogenic activity and is only a weak partial antiestrogen in the same assay.

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The pure steroidal antiestrogen EM-139 not only completely reversed the effect of E2 but further inhibited cell number by 30% below control values (P<0.01).
“the pure steroidal antiestrogen EM-139 (228), on the other hand, not only completely reversed the effect of E 2 but further inhibited cell number by 30% below control values (P Ͻ 0.01; Fig. 18B).”
From Endocrine and intracrine sources of androgens in women: inhibition of breast cancer and other roles of androgens and their precursor dehydroepiandrosterone (2003) · cites this paper as [228]

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Self-citation
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Self-citation
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Self-citation
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Self-citation
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Self-citation
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Self-citation
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BackgroundMethodSelf-citation
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Self-citation
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“…attention has thus focused on the development of blockers of estrogen biosynthesis and action (Wakeling & Bowler 1988, Dauvois et al. 1991, de Launoit et al. 1991, Lévesque et al. 1991, Gronemeyer et al. 1992, Labrie et al. 1992a, 1995a, Gauthier et al. 1997) for the treatment of breast cancer.”
Self-citation
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Self-citation
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Ngatcha, B. T., Laplante, Y., Labrie, F., Luu-The, V., & Poirier, D. (2005) · Molecular and Cellular Endocrinology · doi:10.1016/j.mce.2005.10.023 · Cited by 9 · see citing works
Self-citation
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Okamoto, M., Naka, K., Kitagawa, Y., et al. (2015) · Nuclear Medicine and Biology · doi:10.1016/j.nucmedbio.2015.03.005 · Cited by 7 · see citing works
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Third- and Fourth-Generation SERMs
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Self-citation
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Entwicklungsstrategien für Arzneistoffe zur Therapie hormonabhängiger Tumoren
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Crystal Structures of Human 17β-Hydroxysteroid Dehydrogenase Type 1 Complexed with the Dual-Site Inhibitor EM-139
Li, T., Zhu, D., Labrie, F., & Lin, S. (2018) · Health · doi:10.4236/health.2018.108081 · Cited by 1 · see citing works
“N-n-Butyl-N-methyl-ll-(16'α-chloro-3',17'βdihydroxyes-tra-1',3',5'(10')-trien-7'α-yl) undecanamide (EM-139) is a 7α-alkyl, 16α-halo estradiol derivative which was first synthesized as a pure antiestrogen (Figure 1) [19].”
BackgroundSelf-citation
Hormones, Estrogens and Antiestrogens
Guo, J. Z., Hahn, D. W., & Wachter, M. P. (2000) · Kirk-Othmer Encyclopedia of Chemical Technology · doi:10.1002/0471238961.05192018072115.a01 · Cited by 1 · see citing works
ESTROGENS, ANTIESTROGENS, AND OTHER ESTRANE COMPOUNDS
Leclercq, G. (1992) · Elsevier eBooks · doi:10.1016/b978-0-12-105952-1.50007-9 · Cited by 1 · see citing works
Endocrinology
Vogel, H. G. (2007) · Springer eBooks · doi:10.1007/978-3-540-70995-4_15 · Cited by 1 · see citing works
t-Butyl Hypochlorite
Simpkins, N. S., & Cha, J. K. (2006) · Encyclopedia of Reagents for Organic Synthesis · doi:10.1002/047084289x.rb388.pub2
Use of preclinical and early clinical data for dose selection of a selective estrogen receptor modulator toremifene in treatment of breast cancer
Ellmén, J. (2012) · UTUPub (University of Turku)
Endocrinology1
Vogel, H. G., Vogel, W. H., Schölkens, B. A., Sandow, J., Müller, G. A., & Vogel, W. F. (2002) · Springer eBooks · doi:10.1007/3-540-29837-1_15
Pure Antiestrogens
Wakeling, A. E. (2009) · Humana Press eBooks · doi:10.1007/978-1-59259-152-7_7
Ovarian Hormones
Sandow, J. (2015) · Springer eBooks · doi:10.1007/978-3-319-05392-9_77
Endocrinology
Vogel, H. G., & Vogel, W. H. (1997) · Springer eBooks · doi:10.1007/978-3-662-03333-3_13
Ovarian Hormones
Sandow, J. (2015) · Springer eBooks · doi:10.1007/978-3-642-27728-3_77-1
Antiestrogens and Partial Agonists
Angerer, E. V. (1999) · Handbook of experimental pharmacology · doi:10.1007/978-3-642-58616-3_4

Authors: Levesque, C., Merand, Y., Dufour, J. M., Labrie, C., & Labrie, F.
Venue: Journal of Medicinal Chemistry
Publisher: American Chemical Society (ACS)
Published: 1991-05
Volume: 34
Issue: 5
Pages: 1624-1630
ISSN: 0022-2623 (ISSN-L)
1520-4804
DOI: 10.1021/jm00109a014
OpenAlex: W2019517738
Cited by: 81
References: 0
Citations by year: 2018: 1 · 2017: 1 · 2015: 3 · 2012: 2
FWCI: 1.71
Type: journal article
Language: en
Open access: closed
Locations: Journal of Medicinal Chemistry (publishedVersion)
PubMed (publishedVersion)
Topics: Life Sciences › Biochemistry, Genetics and Molecular Biology › Genetics › Estrogen and related hormone effects
Physical Sciences › Chemistry › Organic Chemistry › Synthesis and biological activity
Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Steroid Chemistry and Biochemistry
Keywords: estrogen receptor binding affinity, breast cancer endocrine therapy, uterine weight, tamoxifen comparison, estrogenic activity, structure-activity relationship
MeSH terms: Animals, Chemistry, Estradiol, Estrogen Antagonists, Female, Mice, Inbred BALB C, Structure-Activity Relationship, Uterus, Mice, Chemical Phenomena

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Synthesis and biological activity of new halo-steroidal antiestrogens.

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