Chemical compound
Pharmaceutical compound
Diarylpropionitrile (DPN ), also known as2,3-bis(p-hydroxyphenyl)propionitrile (2,3-BHPPN ), is asynthetic ,nonsteroidal , and highlyselective agonist ofERβ (IC50 = 15 nM)[ 1] scientific research to study the function of thisreceptor .[ 2] [ 3] ERα ,[ 4] affinity forGPER (GPR30) relative toestradiol .[ 5] antidepressant - andanxiolytic -like effects in animals via activation of theendogenous oxytocin system.[ 6] prinaberel (ERB-041, WAY-202041),WAY-200070 , and8β-VE2 in 2004,ERB-196 (WAY-202196) in 2005, and certainphytoestrogens likeliquiritigenin andnyasol (cis -hinokiresinol) since 2007.[ 7]
DPN is aracemic mixture of twoenantiomers , (R)-DPN and (S)-DPN. Relative to (R)-DPN, (S)-DPN has between 3- and 7-fold higheraffinity for ERβ and appears to have higherintrinsic activity in activating ERβ.[ 8] [ 9] [ 8] scientific research .[ 8]
^ "2,3-Bis(4-hydroxyphenyl)propionitrile" .Sigmaaldrich.com . Retrieved26 April 2022 .^ Pfaus JG, Jone LS, Flanagan-Cato LM, Blaustein JD (15 November 2014)."Female Sexual Behavior" . In Plant TM, Zeleznik AJ (eds.).Knobil and Neill's Physiology of Reproduction: Two-Volume Set . Academic Press. pp. 2311–.ISBN 978-0-12-397769-4 ^ Fex Svenningsen A, Wicher G, Lundqvist J, Pettersson H, Corell M, Norlin M (May 2011). "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.doi :10.1016/j.neuint.2011.01.024 .PMID 21300119 .S2CID 6438705 . ^ Hwang KA, Choi KC (5 November 2015)."Endocrine-Disrupting Chemicals with Estrogenicity Posing the Risk of Cancer Progression in Estrogen-Responsive Gene" .Advances in Molecular Toxicology . Academic Press. pp. 16–.ISBN 978-0-12-802430-0 ^ Rossi DV, Dai Y, Thomas P, Carrasco GA, DonCarlos LL, Muma NA, Li Q (August 2010)."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.doi :10.1016/j.psyneuen.2010.01.003 .PMC 2891004 PMID 20138435 . ^ Kudwa AE, McGivern RF, Handa RJ (April 2014)."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.doi :10.1016/j.physbeh.2014.03.004 .PMC 5802969 PMID 24631553 . ^ Deroo BJ, Buensuceso AV (September 2010)."Minireview: Estrogen receptor-beta: mechanistic insights from recent studies" .Molecular Endocrinology .24 (9):1703– 1714.doi :10.1210/me.2009-0288 PMC 5417404 PMID 20363876 . ^a b c Carroll VM, Jeyakumar M, Carlson KE, Katzenellenbogen JA (January 2012)."Diarylpropionitrile (DPN) enantiomers: synthesis and evaluation of estrogen receptor β-selective ligands" .Journal of Medicinal Chemistry .55 (1):528– 537.doi :10.1021/jm201436k .PMC 3381613 PMID 22122563 . ^ Weiser MJ, Wu TJ, Handa RJ (April 2009)."Estrogen receptor-beta agonist diarylpropionitrile: biological activities of R- and S-enantiomers on behavior and hormonal response to stress" .Endocrinology .150 (4):1817– 1825.doi :10.1210/en.2008-1355 .PMC 2659273 PMID 19074580 .
ER Tooltip Estrogen receptor
Agonists Steroidal: 2-Hydroxyestradiol 2-Hydroxyestrone 3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol 3α-Androstanediol 3α,5α-Dihydrolevonorgestrel 3β,5α-Dihydrolevonorgestrel 3α-Hydroxytibolone 3β-Hydroxytibolone 3β-Androstanediol 4-Androstenediol 4-Androstenedione 4-Fluoroestradiol 4-Hydroxyestradiol 4-Hydroxyestrone 4-Methoxyestradiol 4-Methoxyestrone 5-Androstenediol 7-Oxo-DHEA 7α-Hydroxy-DHEA 7α-Methylestradiol 7β-Hydroxyepiandrosterone 8,9-Dehydroestradiol 8,9-Dehydroestrone 8β-VE2 10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED) 11β-Chloromethylestradiol 11β-Methoxyestradiol 15α-Hydroxyestradiol 16-Ketoestradiol 16-Ketoestrone 16α-Fluoroestradiol 16α-Hydroxy-DHEA 16α-Hydroxyestrone 16α-Iodoestradiol 16α-LE2 16β-Hydroxyestrone 16β,17α-Epiestriol (16β-hydroxy-17α-estradiol) 17α-Estradiol (alfatradiol )17α-Dihydroequilenin 17α-Dihydroequilin 17α-Epiestriol (16α-hydroxy-17α-estradiol) 17α-Ethynyl-3α-androstanediol 17α-Ethynyl-3β-androstanediol 17β-Dihydroequilenin 17β-Dihydroequilin 17β-Methyl-17α-dihydroequilenin Abiraterone Abiraterone acetate Alestramustine Almestrone Anabolic steroids (e.g.,testosterone andesters ,methyltestosterone ,metandienone (methandrostenolone) ,nandrolone andesters , many others; via estrogenic metabolites)Atrimustine Bolandiol Bolandiol dipropionate Butolame Clomestrone Cloxestradiol Conjugated estriol Conjugated estrogens Cyclodiol Cyclotriol DHEA DHEA-S ent -EstradiolEpiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol) Epimestrol Equilenin Equilin ERA-63 (ORG-37663) Esterified estrogens Estetrol Estradiol Estramustine Estramustine phosphate Estrapronicate Estrazinol Estriol Estrofurate Estrogenic substances Estromustine Estrone Etamestrol (eptamestrol) Ethinylandrostenediol Ethinylestradiol Ethinylestriol Ethylestradiol Etynodiol Etynodiol diacetate Hexolame Hippulin Hydroxyestrone diacetate Lynestrenol Lynestrenol phenylpropionate Mestranol Methylestradiol Moxestrol Mytatrienediol Nilestriol Norethisterone Noretynodrel Orestrate Pentolame Prodiame Prolame Promestriene RU-16117 Quinestradol Quinestrol Tibolone Xenoestrogens: Anise -related (e.g.,anethole ,anol ,dianethole ,dianol ,photoanethole )Chalconoids (e.g.,isoliquiritigenin ,phloretin ,phlorizin (phloridzin) ,wedelolactone )Coumestans (e.g.,coumestrol ,psoralidin )Flavonoids (incl.7,8-DHF ,8-prenylnaringenin ,apigenin ,baicalein ,baicalin ,biochanin A ,calycosin ,catechin ,daidzein ,daidzin ,ECG ,EGCG ,epicatechin ,equol ,formononetin ,glabrene ,glabridin ,genistein ,genistin ,glycitein ,kaempferol ,liquiritigenin ,mirificin ,myricetin ,naringenin ,penduletin ,pinocembrin ,prunetin ,puerarin ,quercetin ,tectoridin ,tectorigenin )Lavender oil Lignans (e.g.,enterodiol ,enterolactone ,nyasol (cis -hinokiresinol) )Metalloestrogens (e.g.,cadmium )Pesticides (e.g.,alternariol ,dieldrin ,endosulfan ,fenarimol ,HPTE ,methiocarb ,methoxychlor ,triclocarban ,triclosan )Phytosteroids (e.g.,digitoxin (digitalis ),diosgenin ,guggulsterone )Phytosterols (e.g.,β-sitosterol ,campesterol ,stigmasterol )Resorcylic acid lactones (e.g.,zearalanone ,α-zearalenol ,β-zearalenol ,zearalenone ,zeranol (α-zearalanol) ,taleranol (teranol, β-zearalanol) )Steroid -like (e.g.,deoxymiroestrol ,miroestrol )Stilbenoids (e.g.,resveratrol ,rhaponticin )Synthetic xenoestrogens (e.g.,alkylphenols ,bisphenols (e.g.,BPA ,BPF ,BPS ),DDT ,parabens ,PBBs ,PHBA ,phthalates ,PCBs )Others (e.g.,agnuside ,rotundifuran ) MixedSERMs Tooltip Selective estrogen receptor modulators ) Antagonists Coregulator-binding modulators: ERX-11
GPER Tooltip G protein-coupled estrogen receptor
Agonists Antagonists Unknown
