16α-Iodo-E2

Chemical compound (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 16-Iodoestradiol structure.svg skin-invert-image 220 7450-34-2 67087 60437 342892 18 23 1 2 C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H]([C@@H]2O)I)CCC4=C3C=CC(=C4)O 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 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. 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 Structure-based design of estrogen receptor-beta selective ligands J. Am. Chem. Soc. 126 46 15106–19 2004 15548008 10.1021/ja047633o Chen GG, Vlantis AC, Zeng Q, van Hasselt CA Regulation of cell growth by estrogen signaling and potential targets in thyroid cancer Curr Cancer Drug Targets 8 5 367–77 2008 18690843 10.2174/156800908785133150 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. 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. Hochberg RB, Zielinski JE, Duax WL, Strong P 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 1986 3795941 10.1016/0022-4731(86)90002-6 free Radiolabeled [16α-125I]iodo-E2 has been employed in imaging to study the estrogen receptor. Cummins CH Radiolabeled steroidal estrogens in cancer research Steroids 58 6 245–59 1993 8212070 10.1016/0039-128x(93)90069-y 29080385 See also 16α-LE2 Clomestrone Mytatrienediol GTx-758 References 30em Category:Estranes Category:Organoiodides Category:Synthetic estrogens