11β-Chloromethylestradiol
![]() | |
Clinical data | |
---|---|
Other names | 11β-CME2; CME; ORG-4333; 11β-(Chloromethyl)estra-1,3,5(10)-trien-3,17β-diol |
Drug class | Estrogen |
Identifiers | |
| |
CAS Number | |
PubChem CID | |
ChemSpider | |
UNII | |
KEGG | |
ChEBI | |
CompTox Dashboard (EPA) | |
Chemical and physical data | |
Formula | C19H25ClO2 |
Molar mass | 320.86 g·mol−1 |
3D model (JSmol) | |
| |
|
11β-Chloromethylestradiol (11β-CME2; developmental code name ORG-4333) is a synthetic steroidal estrogen which was never marketed.[1][2][3][4][5][6] It has very high affinity for the estrogen receptor and dissociates from it relatively slowly.[1][2][4][5][7][8] It was originally thought that 11β-CME2 might be a covalent ligand of the estrogen receptors, but its binding was subsequently shown to be fully reversible.[3] The relative binding affinity of 11β-CME2 for the estrogen receptors ranges from 230 to 3,320% of that of estradiol depending on the study.[5][9][7][8][10][11] 11β-CME2 also has about 14% of the relative binding affinity of estradiol for sex hormone-binding globulin (SHBG).[11] The compound has been developed as a radiolabel for the ERs.[3][4]
See also
[edit]References
[edit]- ^ a b Sasson S (January 1991). "Equilibrium binding analysis of estrogen agonists and antagonists: relation to the activation of the estrogen receptor". Pathologie-Biologie. 39 (1): 59–69. PMID 2011412.
- ^ a b Bindal RD, Carlson KE, Reiner GC, Katzenellenbogen JA (October 1987). "11 beta-chloromethyl-[3H]estradiol-17 beta: a very high affinity, reversible ligand for the estrogen receptor". Journal of Steroid Biochemistry. 28 (4): 361–370. doi:10.1016/0022-4731(87)91052-1. PMID 3669657.
- ^ a b c Ratajczak T, Atrache V, Antes P, Comber M, Hähnel R (1988). "A comparison of 11 beta-chloromethylestradiol and tamoxifen aziridine as affinity labeling reagents for estrogen receptors". Steroids. 51 (5–6): 499–518. doi:10.1016/0039-128x(88)90047-5. PMID 3242173. S2CID 11598932.
- ^ a b c Ratajczak T, Sheppard PN, Capon RJ, Hähnel R (November 1981). "The synthesis and study of some potential affinity labeling reagents for estrogen receptors". Steroids. 38 (5): 537–555. doi:10.1016/0039-128x(81)90053-2. PMID 7324085. S2CID 37503105.
- ^ a b c Reiner GC, Katzenellenbogen BS, Bindal RD, Katzenellenbogen JA (June 1984). "Biological activity and receptor binding of a strongly interacting estrogen in human breast cancer cells". Cancer Research. 44 (6): 2302–2308. PMID 6547074.
- ^ Soto AM, Sonnenschein C, Chung KL, Fernandez MF, Olea N, Serrano FO (October 1995). "The E-SCREEN assay as a tool to identify estrogens: an update on estrogenic environmental pollutants". Environmental Health Perspectives. 103 (Suppl 7): 113–122. doi:10.1289/ehp.95103s7113. PMC 1518887. PMID 8593856.
- ^ a b Sasson S, Katzenellenbogen JA (November 1989). "Reversible, positive cooperative interaction of 11 beta-chloromethyl-[3H]estradiol-17 beta with the calf uterine estrogen receptor". Journal of Steroid Biochemistry. 33 (5): 859–865. doi:10.1016/0022-4731(89)90233-1. PMID 2601330.
- ^ a b Katzenellenbogen JA, Muthyala R (2003). "Interactions of exogenous endocrine active substances with nuclear receptors". Pure and Applied Chemistry. 75 (11–12): 1797–1817. doi:10.1351/pac200375111797. ISSN 1365-3075. S2CID 86680540.
- ^ Fink BE, Mortensen DS, Stauffer SR, Aron ZD, Katzenellenbogen JA (April 1999). "Novel structural templates for estrogen-receptor ligands and prospects for combinatorial synthesis of estrogens". Chemistry & Biology. 6 (4): 205–219. doi:10.1016/S1074-5521(99)80037-4. PMID 10099132.
- ^ Wolohan P, Reichert DE (March 2007). "CoMSIA and docking study of rhenium based estrogen receptor ligand analogs". Steroids. 72 (3): 247–260. doi:10.1016/j.steroids.2006.11.011. PMC 1964785. PMID 17280694.
- ^ a b Quivy J, Leclercq G, Deblaton M, Henrot P, Velings N, Norberg B, et al. (September 1996). "Synthesis, structure and biological properties of Z-17alpha-(2-iodovinyl)-11beta-chloromethyl estradiol-17beta (Z-CMIV), a high affinity ligand for the characterization of estrogen receptor-positive tumors". The Journal of Steroid Biochemistry and Molecular Biology. 59 (1): 103–117. doi:10.1016/s0960-0760(96)00007-6. PMID 9009243. S2CID 54359888.