From Wikipedia, the free encyclopedia
Chemical compound
Triphenylethylene (TPE ) is a simple
aromatic hydrocarbon that possesses weak
estrogenic activity.
[1]
[2] Its estrogenic effects were discovered in 1937.
[3] TPE was derived from structural modification of the more potent estrogen
diethylstilbestrol , which is a member of the
stilbestrol group of
nonsteroidal estrogens.
[4]
TPE is the
parent compound of a group of nonsteroidal
estrogen receptor
ligands .
[1]
[2]
[5] It includes the
estrogens
chlorotrianisene ,
desmethylchlorotrianisene ,
estrobin (DBE),
M2613 ,
triphenylbromoethylene ,
triphenylchloroethylene ,
triphenyliodoethylene ,
triphenylmethylethylene ; the
selective estrogen receptor modulators (SERMs)
afimoxifene ,
brilanestrant ,
broparestrol ,
clomifene ,
clomifenoxide ,
droloxifene ,
endoxifen ,
etacstil ,
fispemifene ,
idoxifene ,
miproxifene ,
miproxifene phosphate ,
nafoxidine ,
ospemifene ,
panomifene , and
toremifene . The
antiestrogen
ethamoxytriphetol (MER-25) is also closely related, but is technically not a derivative of TPE and is instead a
triphenylethanol derivative. The tamoxifen
metabolite and
aromatase inhibitor
norendoxifen is also a TPE derivative. In addition to their estrogenic activity, various TPE derivatives like tamoxifen and clomifene have been found to act as
protein kinase C inhibitors .
[6]
The
affinity of triphenylethylene for the rat
estrogen receptor is about 0.002% relative to
estradiol .
[7]
[8] For comparison, the relative binding affinities of derivatives of triphenylethylene were 1.6% for
tamoxifen , 175% for
afimoxifene (4-hydroxytamoxifen), 15% for
droloxifene , 1.4% for
toremifene (4-chlorotamoxifen), 0.72% for
clomifene , and 0.72% for
nafoxidine .
[9]
[7]
[8]
See also
References
^
a
b Dragan YP, Pitot HC (5 February 2010).
"The Effect of Triphenylethylene Antiestrogens on Parameters of Multisage Hepatocarcinogenesis in the Rat" . In Jordan VD, Furr BJ (eds.). Hormone Therapy in Breast and Prostate Cancer . Springer Science & Business Media. pp. 95–.
ISBN
978-1-59259-152-7 .
^
a
b Maximov PY, McDaniel RE, Jordan VC (23 July 2013).
"Discovery and Pharmacology of Nonsteroidal Estrogens and Antiestrogens" . Tamoxifen: Pioneering Medicine in Breast Cancer . Springer Science & Business Media. pp. 4–.
ISBN
978-3-0348-0664-0 .
^ Li JJ (3 April 2009).
"Genesis of Statins" . Triumph of the Heart: The Story of Statins . Oxford University Press, USA. pp. 33–.
ISBN
978-0-19-532357-3 .
^ Avendano C, Menendez JC (11 June 2015).
"Anticancer Drugs that Modulate Hormone Action" . Medicinal Chemistry of Anticancer Drugs . Elsevier Science. pp. 81-131 (87).
doi :
10.1016/B978-0-444-62649-3.00003-X .
ISBN
978-0-444-62667-7 .
^ Marin F, Barbancho MC (22 September 2006).
"Clinical Pharmacology of Selective Estrogen Receptor Modulators (SERMs)" . In Cano A, Calaf i Alsina J, Duenas-Diez JL (eds.). Selective Estrogen Receptor Modulators: A New Brand of Multitarget Drugs . Springer Science & Business Media. pp. 52–.
ISBN
978-3-540-34742-2 .
^ O'Brian CA, Liskamp RM, Solomon DH, Weinstein IB (June 1986). "Triphenylethylenes: a new class of protein kinase C inhibitors". Journal of the National Cancer Institute . 76 (6): 1243–1246.
doi :
10.1093/jnci/76.6.1243 .
PMID
3458960 .
^
a
b Blair RM, Fang H, Branham WS, Hass BS, Dial SL, Moland CL, et al. (March 2000).
"The estrogen receptor relative binding affinities of 188 natural and xenochemicals: structural diversity of ligands" . Toxicological Sciences . 54 (1): 138–153.
doi :
10.1093/toxsci/54.1.138 .
PMID
10746941 .
^
a
b Fang H, Tong W, Shi LM, Blair R, Perkins R, Branham W, et al. (March 2001). "Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens". Chemical Research in Toxicology . 14 (3): 280–294.
doi :
10.1021/tx000208y .
PMID
11258977 .
^ Wittliff JL, Kerr II DA, Andres SA (2005).
"Estrogens IV: Estrogen-Like Pharmaceuticals" . In Wexler P (ed.). Encyclopedia of Toxicology . Vol. Dib–L (2nd ed.). Elsevier. pp. 254–258.
doi :
10.1016/B0-12-369400-0/01087-5 .
ISBN
978-0-08-054800-5 .
ER Tooltip Estrogen receptor
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17α-Dihydroequilenin
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17α-Ethynyl-3α-androstanediol
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anethole ,
anol ,
dianethole ,
dianol ,
photoanethole )
Chalconoids (e.g.,
isoliquiritigenin ,
phloretin ,
phlorizin (phloridzin) ,
wedelolactone )
Coumestans (e.g.,
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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 )
Mixed (
SERMs Tooltip Selective estrogen receptor modulators ) Antagonists
Coregulator-binding modulators:
ERX-11
GPER Tooltip G protein-coupled estrogen receptor
Agonists Antagonists Unknown