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Chemical compound
16α-Iodo-E2
(8R,9S,13S,14S,16R,17R)-16-iodo-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
CAS Number
PubChem
CID
ChemSpider
ChEMBL
CompTox Dashboard (
EPA )
Formula C 18 H 23 I O 2
Molar mass 398.284 g·mol−1 3D model (
JSmol )
C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H]([C@@H]2O)I)CCC4=C3C=CC(=C4)O
InChI=1S/C18H23IO2/c1-18-7-6-13-12-5-3-11(20)8-10(12)2-4-14(13)15(18)9-16(19)17(18)21/h3,5,8,13-17,20-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,17+,18+/m1/s1
Key:SSYGGPAGDDGXAF-ZXXIGWHRSA-N
16α-Iodo-E2 , or 16α-iodoestradiol , is a
synthetic ,
steroidal , potent
estrogen with slight preference for the
ERα over the
ERβ that is used in
scientific research .
[1]
[2] The KD of 16α-iodo-E2 for the ERα is 0.6 nM and for the ERβ is 0.24 nM, a 4-fold difference in
affinity , whereas
estradiol is considered to have similar affinity for the two receptor subtypes.
[2] Unlike the case of the much weaker
estriol (16α-hydroxyestradiol), 16α-iodo-E2 is considered to be equipotent with estradiol in terms of estrogenic activity.
[3]
Radiolabeled [16α-125 I]iodo-E2 has been employed in
imaging to study the
estrogen receptor .
[4]
See also
References
^ Manas ES, Unwalla RJ, Xu ZB, Malamas MS, Miller CP, Harris HA, Hsiao C, Akopian T, Hum WT, Malakian K, Wolfrom S, Bapat A, Bhat RA, Stahl ML, Somers WS, Alvarez JC (2004). "Structure-based design of estrogen receptor-beta selective ligands". J. Am. Chem. Soc . 126 (46): 15106–19.
doi :
10.1021/ja047633o .
PMID
15548008 .
^
a
b Chen GG, Vlantis AC, Zeng Q, van Hasselt CA (2008). "Regulation of cell growth by estrogen signaling and potential targets in thyroid cancer". Curr Cancer Drug Targets . 8 (5): 367–77.
doi :
10.2174/156800908785133150 .
PMID
18690843 .
^ Hochberg RB, Zielinski JE, Duax WL, Strong P (1986). "The molecular structure of 16 alpha-iodo-17 beta-estradiol, a high affinity ligand for the estrogen receptor". J. Steroid Biochem . 25 (5A): 615–8.
doi :
10.1016/0022-4731(86)90002-6 .
PMID
3795941 .
^ Cummins CH (1993). "Radiolabeled steroidal estrogens in cancer research". Steroids . 58 (6): 245–59.
doi :
10.1016/0039-128x(93)90069-y .
PMID
8212070 .
S2CID
29080385 .
ER Tooltip Estrogen receptor
Agonists
Steroidal:
2-Hydroxyestradiol
2-Hydroxyestrone
3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol
3α-Androstanediol
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SERMs Tooltip Selective estrogen receptor modulators ) Antagonists
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ERX-11
GPER Tooltip G protein-coupled estrogen receptor
Agonists Antagonists Unknown