Chemistry:Diarylpropionitrile
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| Other names | SC-4473 |
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| Formula | C15H13NO2 |
| Molar mass | 239.274 g·mol−1 |
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Diarylpropionitrile (DPN), also known as 2,3-bis(p-hydroxyphenyl)propionitrile (2,3-BHPPN), is a synthetic, nonsteroidal, and highly selective agonist of ERβ (IC50 = 15 nM)[1] that is used widely in scientific research to study the function of this receptor.[2][3] It is 70-fold more selective for ERβ over ERα,[4] and has 100-fold lower affinity for GPER (GPR30) relative to estradiol.[5] DPN produces antidepressant- and anxiolytic-like effects in animals via activation of the endogenous oxytocin system.[6] First reported in 2001, DPN was the first selective ERβ agonist to be discovered, and was followed by prinaberel (ERB-041, WAY-202041), WAY-200070, and 8β-VE2 in 2004, ERB-196 (WAY-202196) in 2005, and certain phytoestrogens like liquiritigenin and nyasol (cis-hinokiresinol) since 2007.[7]
DPN is a racemic mixture of two enantiomers, (R)-DPN and (S)-DPN. Relative to (R)-DPN, (S)-DPN has between 3- and 7-fold higher affinity for ERβ and appears to have higher intrinsic activity in activating ERβ.[8][9] However, both enantiomers have very high affinity, potency, selectivity for ERβ and efficaciously activate ERβ.[8] In any case, it has been suggested that (S)-DPN might be the preferred enantiomer to use for scientific research.[8]
See also
References
- ↑ "2,3-Bis(4-hydroxyphenyl)propionitrile". http://www.sigmaaldrich.com/catalog/product/sigma/h5915?lang=en®ion=US.
- ↑ "Female Sexual Behavior". Knobil and Neill's Physiology of Reproduction: Two-Volume Set. Academic Press. 15 November 2014. pp. 2311–. ISBN 978-0-12-397769-4. https://books.google.com/books?id=I1ACBAAAQBAJ&pg=PA2311.
- ↑ "Effects on DHEA levels by estrogen in rat astrocytes and CNS co-cultures via the regulation of CYP7B1-mediated metabolism". Neurochemistry International 58 (6): 620–4. May 2011. doi:10.1016/j.neuint.2011.01.024. PMID 21300119.
- ↑ "Endocrine-Disrupting Chemicals with Estrogenicity Posing the Risk of Cancer Progression in Estrogen-Responsive Gene". Advances in Molecular Toxicology. Academic Press. 5 November 2015. pp. 16–. ISBN 978-0-12-802430-0. https://books.google.com/books?id=NSeiBQAAQBAJ&pg=PA16.
- ↑ "Estradiol-induced desensitization of 5-HT1A receptor signaling in the paraventricular nucleus of the hypothalamus is independent of estrogen receptor-beta". Psychoneuroendocrinology 35 (7): 1023–33. August 2010. doi:10.1016/j.psyneuen.2010.01.003. PMID 20138435.
- ↑ "Estrogen receptor β and oxytocin interact to modulate anxiety-like behavior and neuroendocrine stress reactivity in adult male and female rats". Physiology & Behavior 129: 287–296. April 2014. doi:10.1016/j.physbeh.2014.03.004. PMID 24631553.
- ↑ "Minireview: Estrogen receptor-beta: mechanistic insights from recent studies". Molecular Endocrinology 24 (9): 1703–1714. September 2010. doi:10.1210/me.2009-0288. PMID 20363876.
- ↑ 8.0 8.1 8.2 "Diarylpropionitrile (DPN) enantiomers: synthesis and evaluation of estrogen receptor β-selective ligands". Journal of Medicinal Chemistry 55 (1): 528–537. January 2012. doi:10.1021/jm201436k. PMID 22122563.
- ↑ "Estrogen receptor-beta agonist diarylpropionitrile: biological activities of R- and S-enantiomers on behavior and hormonal response to stress". Endocrinology 150 (4): 1817–1825. April 2009. doi:10.1210/en.2008-1355. PMID 19074580.
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