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Research Article

Inhibitors of type 1 17β-hydroxysteroid dehydrogenase with reduced estrogenic activity: Modifications of the positions 3 and 6 of estradiol

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Pages 153-163 | Received 30 Aug 2004, Accepted 09 Dec 2004, Published online: 03 Oct 2008

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Matías I. Quindt, Stefano Protti, Daniele Merli & Sergio M. Bonesi. (2023) Photoinduced One‐Electron Oxidation of Estrone Derivatives: A Combined Steady‐State and Time‐Resolved Spectroscopy Investigation. ChemPhotoChem 7:10.
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Matías I. Quindt, Gabriel F. Gola, Cristian R. Rodriguez, Javier A. Ramirez & Sergio M. Bonesi. (2022) Product selectivity in the photoreaction of aryl sulfonates and mesylate of estrone derivatives in sustainable and micellar media: a steady-state investigation. New Journal of Chemistry 46:32, pages 15504-15520.
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Matías I. Quindt, Gabriel F. Gola, Javier A. Ramirez & Sergio M. Bonesi. (2020) Photochemical Behavior of Some Estrone Aryl and Methyl Sulfonates in Solution: Preparative and Mechanistic Studies. Photochemistry and Photobiology 97:1, pages 8-21.
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René Maltais, Martin Perreault, Jenny Roy & Donald Poirier. (2020) Minor chemical modifications of the aminosteroid derivative RM-581 lead to major impact on its anticancer activity, metabolic stability and aqueous solubility. European Journal of Medicinal Chemistry 188, pages 111990.
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René Maltais & Donald Poirier. (2019) Development of a Gram-Scale Synthesis of PBRM, an Irreversible Inhibitor of 17β-Hydroxysteroid Dehydrogenase Type 1. Organic Process Research & Development 23:11, pages 2323-2335.
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Matías I. Quindt, Gabriel F. Gola, Javier A. Ramirez & Sergio M. Bonesi. (2019) Photo-Fries Rearrangement of Some 3-Acylestrones in Homogeneous Media: Preparative and Mechanistic Studies. The Journal of Organic Chemistry 84:11, pages 7051-7065.
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Mohamed Salah, Ahmed S. Abdelsamie & Martin Frotscher. (2019) Inhibitors of 17β-hydroxysteroid dehydrogenase type 1, 2 and 14: Structures, biological activities and future challenges. Molecular and Cellular Endocrinology 489, pages 66-81.
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Jovana Trifunović, Vladan Borčić, Saša Vukmirović & Momir Mikov. (2017) Structural insights into anticancer activity of D-ring modified estrone derivatives using their lipophilicity in estimation of SAR and molecular docking studies. Drug Testing and Analysis 9:10, pages 1542-1548.
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Diana Ayan, René Maltais, Jenny Roy & Donald Poirier. (2012) A New Nonestrogenic Steroidal Inhibitor of 17β-Hydroxysteroid Dehydrogenase Type I Blocks the Estrogen-Dependent Breast Cancer Tumor Growth Induced by Estrone. Molecular Cancer Therapeutics 11:10, pages 2096-2104.
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Carina Neto, Maria Cristina Oliveira, Lurdes Gano, Fernanda Marques, Takumi Yasuda, Thies Thiemann, Torsten Kniess & Isabel Santos. (2012) Novel 7α-alkoxy-17α-(4′-halophenylethynyl)estradiols as potential SPECT/PET imaging agents for estrogen receptor expressing tumours: Synthesis and binding affinity evaluation. Steroids 77:11, pages 1123-1132.
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Donald Poirier. (2011) Contribution to the development of inhibitors of 17β-hydroxysteroid dehydrogenase types 1 and 7: Key tools for studying and treating estrogen-dependent diseases. The Journal of Steroid Biochemistry and Molecular Biology 125:1-2, pages 83-94.
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Gabriele Möller, Bettina Husen, Dorota Kowalik, Leena Hirvelä, Dariusz Plewczynski, Leszek Rychlewski, Josef Messinger, Hubert Thole & Jerzy Adamski. (2010) Species Used for Drug Testing Reveal Different Inhibition Susceptibility for 17beta-Hydroxysteroid Dehydrogenase Type 1. PLoS ONE 5:6, pages e10969.
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Juliette A. Aka, Mausumi Mazumdar, Chang-Qing Chen, Donald Poirier & Sheng-Xiang Lin. (2010) 17β-Hydroxysteroid Dehydrogenase Type 1 Stimulates Breast Cancer by Dihydrotestosterone Inactivation in Addition to Estradiol Production. Molecular Endocrinology 24:4, pages 832-845.
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Gabriele Möller, Dominga Deluca, Christian Gege, Andrea Rosinus, Dorota Kowalik, Olaf Peters, Peter Droescher, Walter Elger, Jerzy Adamski & Alexander Hillisch. (2009) Structure-based design, synthesis and in vitro characterization of potent 17β-hydroxysteroid dehydrogenase type 1 inhibitors based on 2-substitutions of estrone and D-homo-estrone. Bioorganic & Medicinal Chemistry Letters 19:23, pages 6740-6744.
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Michelle-Audrey Fournier & Donald Poirier. (2009) Estrogen formation in endometrial and cervix cancer cell lines: Involvement of aromatase, steroid sulfatase and 17β-hydroxysteroid dehydrogenases (types 1, 5, 7 and 12). Molecular and Cellular Endocrinology 301:1-2, pages 142-145.
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Yannick Laplante, Claudine Rancourt & Donald Poirier. (2009) Relative involvement of three 17β-hydroxysteroid dehydrogenases (types 1, 7 and 12) in the formation of estradiol in various breast cancer cell lines using selective inhibitors. Molecular and Cellular Endocrinology 301:1-2, pages 146-153.
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Marc Meier, Gabriele Möller & Jerzy Adamski. (2009) Perspectives in Understanding the Role of Human 17β-Hydroxysteroid Dehydrogenases in Health and Disease. Annals of the New York Academy of Sciences 1155:1, pages 15-24.
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Patrick Bydal, Van Luu-The, Fernand Labrie & Donald Poirier. (2009) Steroidal lactones as inhibitors of 17β-hydroxysteroid dehydrogenase type 5: Chemical synthesis, enzyme inhibitory activity, and assessment of estrogenic and androgenic activities. European Journal of Medicinal Chemistry 44:2, pages 632-644.
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D. Fournier, D. Poirier, M. Mazumdar & S.-X. Lin. (2008) Design and synthesis of bisubstrate inhibitors of type 1 17β-hydroxysteroid dehydrogenase: Overview and perspectives. European Journal of Medicinal Chemistry 43:11, pages 2298-2306.
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Sandrine Marchais-Oberwinkler, Patricia Kruchten, Martin Frotscher, Erika Ziegler, Alexander Neugebauer, Umadevi Bhoga, Emmanuel Bey, Ursula Müller-Vieira, Josef Messinger, Hubert Thole & Rolf W. Hartmann. (2008) Substituted 6-Phenyl-2-naphthols. Potent and Selective Nonsteroidal Inhibitors of 17β-Hydroxysteroid Dehydrogenase Type 1 (17β-HSD1): Design, Synthesis, Biological Evaluation, and Pharmacokinetics. Journal of Medicinal Chemistry 51:15, pages 4685-4698.
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Emmanuel Bey, Sandrine Marchais-Oberwinkler, Patricia Kruchten, Martin Frotscher, Ruth Werth, Alexander Oster, Oztekin Algül, Alexander Neugebauer & Rolf W. Hartmann. (2008) Design, synthesis and biological evaluation of bis(hydroxyphenyl) azoles as potent and selective non-steroidal inhibitors of 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1) for the treatment of estrogen-dependent diseases. Bioorganic & Medicinal Chemistry 16:12, pages 6423-6435.
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GÉRARD CHETRITE. 2008. Breast Cancer. Breast Cancer 11 48 .
Takumi Yasuda, Yuji Shima, Keiko Ideta, Cristina das Neves Oliveira & Thies Thiemann. (2008) 7α-Alkoxyestra-1,3,5(10)-Trienes. Journal of Chemical Research 2008:1, pages 32-37.
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Christine Cadot, Yannick Laplante, Fatima Kamal, Van Luu-The & Donald Poirier. (2007) C6-(N,N-butyl-methyl-heptanamide) derivatives of estrone and estradiol as inhibitors of type 1 17β-hydroxysteroid dehydrogenase: Chemical synthesis and biological evaluation. Bioorganic & Medicinal Chemistry 15:2, pages 714-726.
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Hironobu Sasano, Takashi Suzuki, Taisuke Nakata & Takuya Moriya. (2006) New development in intracrinology of breast carcinoma. Breast Cancer 13:2, pages 129-136.
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B. Husen, K. Huhtinen, M. Poutanen, L. Kangas, J. Messinger & H. Thole. (2006) Evaluation of inhibitors for 17β-hydroxysteroid dehydrogenase type 1 in vivo in immunodeficient mice inoculated with MCF-7 cells stably expressing the recombinant human enzyme. Molecular and Cellular Endocrinology 248:1-2, pages 109-113.
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Béatrice Tchédam Ngatcha, Yannick Laplante, Fernand Labrie, Van Luu-The & Donald Poirier. (2006) 3β-Alkyl-androsterones as inhibitors of type 3 17β-hydroxysteroid dehydrogenase: Inhibitory potency in intact cells, selectivity towards isoforms 1, 2, 5 and 7, binding affinity for steroid receptors, and proliferative/antiproliferative activities on AR+ and ER+ cell lines. Molecular and Cellular Endocrinology 248:1-2, pages 225-232.
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Donald Poirier, Roch P. Boivin, Martin R. Tremblay, Marie Bérubé,, Wei Qiu & Sheng-Xiang Lin. (2005) Estradiol−Adenosine Hybrid Compounds Designed to Inhibit Type 1 17β-Hydroxysteroid Dehydrogenase. Journal of Medicinal Chemistry 48:26, pages 8134-8147.
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