Diarylpropionitrile

Diarylpropionitrile
Systematic (IUPAC) name
2,3-bis(4-hydroxyphenyl)propanenitrile
Identifiers
CAS Number 1428-67-7
PubChem CID 102614
ChemSpider 92686
Synonyms SC-4473
Chemical data
Formula C15H13NO2
Molar mass 239.26922 g/mol

Diarylpropionitrile (DPN), also known as 2,3-bis(p-hydroxyphenyl)propionitrile (2,3-BHPPN), is a synthetic, non-steroidal, and highly selective agonist of ERβ (IC50 = 15 nM) that is used widely in scientific research to study the function of this receptor.[1][2] It is 70-fold more selective for ERβ over ERα,[3] and has 100-fold lower affinity for GPER (GPR30) relative to estradiol.[4] DPN produces antidepressant- and anxiolytic-like effects in animals via activation of the endogenous oxytocin system.[5]

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.[6][7] However, both enantiomers have very high affinity, potency, selectivity for ERβ and efficaciously activate ERβ.[6] In any case, it has been suggested that (S)-DPN might be the preferred enantiomer to use for scientific research.[6]

See also

References

  1. ↑ Tony M. Plant; Anthony J. Zeleznik (15 November 2014). Knobil and Neill's Physiology of Reproduction: Two-Volume Set. Academic Press. pp. 2311–. ISBN 978-0-12-397769-4.
  2. ↑ Advances in Neuroglia Research and Application: 2012 Edition. ScholarlyEditions. 26 December 2012. pp. 333–. ISBN 978-1-4649-9280-3.
  3. ↑ Advances in Molecular Toxicology. Academic Press. 5 November 2015. pp. 16–. ISBN 978-0-12-802430-0.
  4. ↑ Uterotonic Agents—Advances in Research and Application: 2012 Edition: ScholarlyBrief. ScholarlyEditions. 26 December 2012. pp. 51–. ISBN 978-1-4816-0836-7.
  5. ↑ Kudwa AE, McGivern RF, Handa RJ (2014). "Estrogen receptor β and oxytocin interact to modulate anxiety-like behavior and neuroendocrine stress reactivity in adult male and female rats". Physiol. Behav. 129: 287–96. doi:10.1016/j.physbeh.2014.03.004. PMID 24631553.
  6. 1 2 3 Carroll VM, Jeyakumar M, Carlson KE, Katzenellenbogen JA (2012). "Diarylpropionitrile (DPN) enantiomers: synthesis and evaluation of estrogen receptor β-selective ligands". J. Med. Chem. 55 (1): 528–37. doi:10.1021/jm201436k. PMC: 3381613. PMID 22122563.
  7. ↑ Weiser MJ, Wu TJ, Handa RJ (2009). "Estrogen receptor-beta agonist diarylpropionitrile: biological activities of R- and S-enantiomers on behavior and hormonal response to stress". Endocrinology 150 (4): 1817–25. doi:10.1210/en.2008-1355. PMC: 2659273. PMID 19074580.



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