17-DMAG hydrochloride

• CAT Number: I003619
• CAS Number: 467214-21-7
• Molecular Formula: C₃₂H₄₈N₄O₈•HCl
• Molecular Weight: 653.21
• Purity: ≥95%
• Synonyms: [(3R,5S,6R,7S,8E,10S,11S,12Z,14E)-21-[2-(dimethylamino)ethylamino]-6-hydroxy-5,11-dimethoxy-3,7,9,15-tetramethyl-16,20,22-trioxo-17-azabicyclo[16.3.1]docosa-1(21),8,12,14,18-pentaen-10-yl] carbamate;hydrochloride
• Target: HSP
• Solubility: DMSO: ≥ 50 mg/mL
• Storage: 3 years -20℃ powder
• IC50: 62 nM
• IUPAC Name: [(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-19-[2-(dimethylamino)ethylamino]-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl] carbamate;hydrochloride
• InChI: InChI=1S/C32H48N4O8.ClH/c1-18-14-22-27(34-12-13-36(5)6)24(37)17-23(29(22)39)35-31(40)19(2)10-9-11-25(42-7)30(44-32(33)41)21(4)16-20(3)28(38)26(15-18)43-8;/h9-11,16-18,20,25-26,28,30,34,38H,12-15H2,1-8H3,(H2,33,41)(H,35,40);1H/b11-9-,19-10+,21-16+;/t18-,20
• InChIKey: DFSYBWLNYPEFJK-IHLRWNDRSA-N
• SMILES: CC1CC(C(C(C=C(C(C(C=CC=C(C(=O)NC2=CC(=O)C(=C(C1)C2=O)NCCN(C)C)C)OC)OC(=O)N)C)C)O)OC.Cl

17-DMAG hydrochloride (Cat.No: I003619) is a synthetic derivative of the naturally occurring antibiotic geldanamycin. It is a potent inhibitor of heat shock protein 90 (Hsp90), a chaperone protein that is involved in the folding and stabilization of other proteins, including many oncogenic proteins. 17-DMAG hydrochloride has shown potential as an anticancer agent in preclinical studies, particularly in the treatment of breast, lung, and prostate cancers.

Reference

[1]. Smith V et al.Comparison of 17-dimethylaminoethylamino-17-demethoxy-geldanamycin (17DMAG) and 17-allylamino-17-demethoxygeldanamycin (17AAG) in vitro: effects on Hsp90 and client proteins in melanoma models Cancer Chemother Pharmacol. 2005 Aug;56(2):126
[2]. Jhaveri K, Miller K, Rosen L, Schneider B, Chap L, Hannah A, Zhong Z, Ma W, Hudis C, Modi S.A Phase I Dose-Escalation Trial of Trastuzumab and Alvespimycin Hydrochloride (KOS-1022; 17 DMAG) in the Treatment of Advanced Solid Tumors.Clin Cancer Res. 2012 Aug 3.
[3]. Pacey S, Wilson RH, Walton M, Eatock MM, Hardcastle A, Zetterlund A, Arkenau HT, Moreno-Farre J, Banerji U, Roels B, Peachey H, Aherne W, de Bono JS, Raynaud F, Workman P, Judson I.A phase I study of the heat shock protein 90 inhibitor alvespimycin (17-DMAG) given intravenously to patients with advanced solid tumors.Clin Cancer Res. 2011 Mar 15;17(6):1561-70. Epub 2011 Jan 28.
[4]. Lancet JE, Gojo I, Burton M, Quinn M, Tighe SM, Kersey K, Zhong Z, Albitar MX, Bhalla K, Hannah AL, Baer MR.Phase I study of the heat shock protein 90 inhibitor alvespimycin (KOS-1022, 17-DMAG) administered intravenously twice weekly to patients with acute myeloid leukemia.Leukemia. 2010 Apr;24(4):699-705. Epub 2010 Jan 28.
[5]. Smith MA, Morton CL, Phelps DA, Kolb EA, Lock R, Carol H, Reynolds CP, Maris JM, Keir ST, Wu J, Houghton PJ.Stage 1 testing and pharmacodynamic evaluation of the HSP90 inhibitor alvespimycin (17-DMAG, KOS-1022) by the pediatric preclinical testing program.Pediatr Blood Cancer. 2008 Jul;51(1):34-41.