A-6880 17-AAG, >99%
[17-(Allylamino)-17-demethoxygeldanamycin] [17-(Allylamino)geldanamycin] [Tanespimycin]
M.W. 585.69
C31H43N3O8
[75747-14-7]
Warning:  Toxic.
Storage:  Store at or below -20 ºC.  Solubility:  Soluble in DMSO at 150 mg/mL; soluble in ethanol at 5 mg/mL; very poorly soluble in water; maximum solubility in plain water is estimated to be about 20-50 µM; buffers, serum, or other additives may increase or decrease the aqueous solubility.  Disposal:  A
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Semi-synthetic derivative of geldanamycin, Cat. No. G-4500, demonstrating greater stability and lower in vivo toxicity than its parent compound.  17-AAG binds specifically to heat shock protein Hsp90 in a manner similar to geldanamycin, but the binding is weaker.  Schulte, T.W. and Neckers, L.M.  "The benzoquinone ansamycin 17-allylamino-17-demethoxygeldanamycin binds to HSP90 and shares important biologic activities with geldanamycin."  Cancer Chemother. Pharmacol. 42:  273-279 (1998).
Inhibits Akt activation and HER2 expression in tumor cells.  Basso, A.D., et al.  "Ansamycin antibiotics inhibit Akt activation and cyclin D expression in breast cancer cells that overexpress HER2."  Oncogene 21:  1159-1166 (2002).
Exhibits 100-fold higher binding affinity for tumor-cell-derived hsp90 over that derived from normal cells.  Kamal, A., et al.  "A high-affinity conformation of Hsp90 confers tumour selectivity on Hsp90 inhibitors."  Nature 425:  407-10 (2003).
Sensitizes tumor cells to growth arrest and apoptosis induced by paclitaxel, Cat. No. P-9600.  Nguyen, D.M., et al.  "Sequence-dependent enhancement of paclitaxel toxicity in non-small cell lung cancer by 17-allylamino 17-demethoxygeldanamycin."  J. Thorac. Cardiovasc. Surg. 118:  908-915 (1999) and Solit, D.B., et al.  "Inhibition of heat shock protein 90 function down-regulates Akt kinase and sensitizes tumors to Taxol."  Cancer Res. 63:  2139-2144 (2003).
Sensitizes colon cancer cells to cisplatin-induced cell death.  Vasilevskaya, I.A., et al.  "Quantitative effects on c-Jun N-terminal protein kinase signaling determine synergistic interaction of cisplatin and 17-allylamino-17-demethoxygeldanamycin in colon cancer cell lines."  Mol Pharmacol. 65:  235-243 (2004).
Inhibits angiogenesis.  Kaur, G, et al.  "Antiangiogenic properties of 17-(dimethylaminoethylamino)-17-demethoxygeldanamycin: an orally bioavailable heat shock protein 90 modulator."  Clin. Cancer Res. 10:  4813-4821 (2004).
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