ArticleJournal of medicinal chemistry2012
Diarylpropionitrile (DPN) enantiomers: synthesis and evaluation of estrogen receptor β-selective ligands.
Article in Journal of medicinal chemistry, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed, 51 citations in OpenAlex.
- Uroprotective effect of diarylpropionitrile versus finasteride on rat model of testosterone-induced prostatic hyperplasia.Naunyn-Schmiedeberg's archives of pharmacology · 2026Article
- Interrogating Estrogen Signaling Pathways in Human ER-Positive Breast Cancer Cells Forming Bone Metastases in Mice.Endocrinology · 2024Article
- Review
- The effects of early life stress on motivated behaviors: A role for gonadal hormones.Neuroscience and biobehavioral reviews · 2020Review
- Synthesis and evaluation of 17α-triazolyl and 9α-cyano derivatives of estradiol.Bioorganic & medicinal chemistry · 2020Article
- Promyelocytic Leukemia (PML) gene regulation: implication towards curbing oncogenesis.Cell death & disease · 2019Article
- ERβ agonist alters RNA splicing factor expression and has a longer window of antidepressant effectiveness than estradiol after long-term ovariectomyJournal of psychiatry & neuroscience : JPN · 2019Article
- Estrogen Receptor (ER) Subtype Selectivity Identifies 8-Prenylapigenin as an ERβ Agonist from Glycyrrhiza inflata and Highlights the Importance of Chemical and Biological Authentication.Journal of natural products · 2018Article
- 17β-estradiol regulates the RNA-binding protein Nova1, which then regulates the alternative splicing of estrogen receptor β in the aging female rat brain.Neurobiology of aging · 2018Article
- Nudging oligodendrocyte intrinsic signaling to remyelinate and repair: Estrogen receptor ligand effects.The Journal of steroid biochemistry and molecular biology · 2016Review
- International Union of Basic and Clinical Pharmacology. XCVII. G Protein-Coupled Estrogen Receptor and Its Pharmacologic Modulators.Pharmacological reviews · 2015Review
- Estrogen receptors alpha (ERα) and beta (ERβ): subtype-selective ligands and clinical potential.Steroids · 2014Review
- Agonist activation of estrogen receptor beta (ERβ) sensitizes malignant pleural mesothelioma cells to cisplatin cytotoxicity.Molecular cancer · 2014Article
- ESR1 and ESR2 differentially regulate daily and circadian activity rhythms in female mice.Endocrinology · 2014Article
- Estrogen receptor β and oxytocin interact to modulate anxiety-like behavior and neuroendocrine stress reactivity in adult male and female rats.Physiology & behavior · 2014Article
- Neuroprotection by diarylpropionitrile in mice with spinal cord injury.EXCLI journal · 2014Article
- Estrogen receptor-β regulates human tryptophan hydroxylase-2 through an estrogen response element in the 5' untranslated region.Journal of neurochemistry · 2013Article
- Estrogen receptor β activation impairs mitochondrial oxidative metabolism and affects malignant mesothelioma cell growth in vitro and in vivo.Oncogenesis · 2013Article
- Aggressive prostate cancer is prevented in ERαKO mice and stimulated in ERβKO TRAMP mice.Endocrinology · 2012Article
- Anxiolytic effects and neuroanatomical targets of estrogen receptor-β (ERβ) activation by a selective ERβ agonist in female mice.Endocrinology · 2012Article
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
Two estrogen receptor (ER) subtypes, ERα and ERβ, mediate the actions of estrogens in diverse reproductive and nonreproductive target tissues. ER subtype-selective ligands, which bind to and activate these subtypes differentially, have proved to be useful in elucidating which actions of estrogens proceed through ERα vs ERβ. Some of these ligands show potential as novel therapeutic agents. Diarylpropionitrile (DPN), an ERβ selective ligand that we developed, is a chiral molecule, but it has been studied almost exclusively as the racemic mixture (rac-DPN, 1). Herein we report the development of an efficient enantioselective synthesis of the two isomers, R-DPN (3) and S-DPN (2), and we have compared the in vitro ligand binding affinities, coactivator binding affinities, recruitment potencies, and cellular transcriptional potencies of these isomers. Both enantiomers show a very high affinity and potency preference for ERβ over ERα, typically in the range of 80-300-fold. Although the enantioselectivity is only modest (3-4-fold), the R-enantiomer is the higher affinity and more potent isomer. While ERβ can be effectively and selectively stimulated by rac-DPN or by either R-DPN or S-DPN, R-DPN might be the preferred member of this isomeric series for biological studies of ERβ function.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.