From Wikipedia, the free encyclopedia
Chemical compound
MIBE
|
|
Ethyl 3-[5-(2-ethoxycarbonyl-1-methylvinyloxy)-1-methyl-1H-indol-3-yl]but-2-enoate
|
|
Formula | C21H25NO5 |
---|
Molar mass | 371.433 g·mol−1 |
---|
3D model (
JSmol) | |
---|
C(OC(/C=C(/OC1=CC=C2C(C(/C(/C)=C/C(OCC)=O)=CN2C)=C1)\C)=O)C
|
InChI=1S/C21H25NO5/c1-6-25-20(23)10-14(3)18-13-22(5)19-9-8-16(12-17(18)19)27-15(4)11-21(24)26-7-2/h8-13H,6-7H2,1-5H3/b14-10+,15-11+ Key:VFEAHZYKQWLUSD-WFYKWJGLSA-N
|
MIBE is a
synthetic,
nonsteroidal
antiestrogen that acts as a dual
antagonist of the
ERα and the
GPER.
[1]
[2] It was found to prevent
estradiol-induced
proliferation of
MCF-7
breast cancer
cells, an action that was mediated via inhibition of both receptors.
[1]
[2] The drug was
synthesized in 2012.
[1] It has been suggested that drugs like MIBE might be superior agents in the treatment of breast cancer compared to current antiestrogens like
tamoxifen and
fulvestrant, which are antagonistic at the ERα but were found in 2005 to be GPER agonists.
[1]
[2]
References
- ^
a
b
c
d Lappano R, Santolla MF, Pupo M, Sinicropi MS, Caruso A, Rosano C, Maggiolini M (2012).
"MIBE acts as antagonist ligand of both estrogen receptor α and GPER in breast cancer cells". Breast Cancer Res. 14 (1): R12.
doi:
10.1186/bcr3096.
PMC
3496129.
PMID
22251451.
- ^
a
b
c Rosano C, Lappano R, Santolla MF, Ponassi M, Donadini A, Maggiolini M (2012). "Recent advances in the rationale design of GPER ligands". Curr. Med. Chem. 19 (36): 6199–206.
doi:
10.2174/092986712804485755.
PMID
23116143.
|
---|
ERTooltip 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 and
esters,
methyltestosterone,
metandienone (methandrostenolone),
nandrolone and
esters, many others; via estrogenic metabolites)
-
Atrimustine
-
Bolandiol
-
Bolandiol dipropionate
-
Butolame
-
Clomestrone
-
Cloxestradiol
-
Conjugated estriol
-
Conjugated estrogens
-
Cyclodiol
-
Cyclotriol
-
DHEA
-
DHEA-S
-
ent-Estradiol
-
Epiestriol (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)
|
---|
Mixed (
SERMsTooltip Selective estrogen receptor modulators) | |
---|
Antagonists |
- Coregulator-binding modulators:
ERX-11
|
---|
|
---|
GPERTooltip G protein-coupled estrogen receptor | Agonists | |
---|
Antagonists | |
---|
Unknown | |
---|
|
---|
|