Next Article in Journal
Analysis of Artifacts Caused by Pulse Imperfections in CPMG Pulse Trains in NMR Relaxation Dispersion Experiments
Previous Article in Journal
Supervised Learning to Predict Sperm Sorting by Magnetophoresis
Article Menu
Issue 3 (September) cover image

Export Article

Open AccessArticle
Magnetochemistry 2018, 4(3), 32; https://doi.org/10.3390/magnetochemistry4030032

Structure Confirmation and Evaluation of a Nonsteroidal Inhibitor of 17β-Hydroxysteroid Dehydrogenase Type 10

1
Endocrinology and Nephrology Unit, Laboratory of Medicinal Chemistry, CHU de Québec—Research Center, Québec, QC G1V 4G2, Canada
2
Department of Molecular Medicine, Faculty of Medicine, Université Laval, Québec, QC G1V 4G2, Canada
*
Author to whom correspondence should be addressed.
Received: 30 April 2018 / Revised: 13 July 2018 / Accepted: 16 July 2018 / Published: 23 July 2018
Full-Text   |   PDF [1580 KB, uploaded 23 July 2018]   |  

Abstract

17β-Hydroxysteroid dehydrogenase type 10 (17β-HSD10) is a steroidogenesis enzyme known for its potential role in Alzheimer’s disease. For comparison purposes between steroidal and nonsteroidal 17β-HSD10 inhibitors 1 and 2, respectively, we attempted the chemical synthesis of benzothiazole phosphonate derivative 2. Instead of a one-pot synthesis, we report a two-step synthesis with characterization of both imine intermediate 5 and final compound 2. Furthermore, complete assignation of 1H and 13C nuclear magnetic resonance (NMR) signals of 2 is provided, as we observed a divergence of NMR data with those published previously. Finally, biological assays showed that 1 and 2 inhibited the oxidation of estradiol (E2) into estrone (E1) by the 17β-HSD10 recombinant protein. However, in human embryonic kidney (HEK)-293 intact cells transfected with 17β-HSD10, only the steroidal inhibitor 1 induced a dose-dependent inhibition of E2 to E1 transformation. View Full-Text
Keywords: NMR; chemical synthesis; enzyme inhibitor; 17β-HSD10; Alzheimer’s NMR; chemical synthesis; enzyme inhibitor; 17β-HSD10; Alzheimer’s
Figures

Graphical abstract

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

Supplementary material

SciFeed

Share & Cite This Article

MDPI and ACS Style

Boutin, S.; Poirier, D. Structure Confirmation and Evaluation of a Nonsteroidal Inhibitor of 17β-Hydroxysteroid Dehydrogenase Type 10. Magnetochemistry 2018, 4, 32.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Magnetochemistry EISSN 2312-7481 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top