11β-Chloromethylestradiol

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
	IUPAC name (8S,9R,11S,13S,14S,17S)-11-(chloromethyl)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol;
CAS Number	71794-60-0 ;
PubChem CID	67088;
ChemSpider	60438;
UNII	BRP4DW4SEE;
KEGG	C14307;
ChEBI	CHEBI:34142;
CompTox Dashboard (EPA)	DTXSID40992450 ;
Chemical and physical data
Formula	C19H25ClO2
Molar mass	320.86 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@]12C[C@@H]([C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4)O)CCl;
	InChI InChI=1S/C19H25ClO2/c1-19-9-12(10-20)18-14-5-3-13(21)8-11(14)2-4-15(18)16(19)6-7-17(19)22/h3,5,8,12,15-18,21-22H,2,4,6-7,9-10H2,1H3/t12-,15+,16+,17+,18-,19+/m1/s1; Key:CADGCTOWBAPSFQ-OQFXVXKWSA-N;

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]

References

^ ^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.

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[pmid2011412-1] 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.

[pmid3669657-2] 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.

[pmid3242173-3] 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.

[pmid7324085-4] 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.

[pmid6547074-5] 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.

[pmid8593856-6] 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.

[pmid2601330-7] 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.

[KatzenellenbogenMuthyala2003-8] 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.

[pmid10099132-9] 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.

[pmid17280694-10] 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.

[pmid9009243-11] 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.

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See also

References