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100068

Sigma-Aldrich

17-AAG - CAS 75747-14-7 - Calbiochem

A less toxic, potent, synthetic derivative of the ansamycin benzoquinone antibiotic Geldanamycin, Streptomyces hygroscopicus.

Synonym(s):
17-AAG - CAS 75747-14-7 - Calbiochem, NSC-330507, 17-AG, 17-(Allylamino)-17-demethoxygeldanamycin, 17-Allylaminogeldanamycin
Empirical Formula (Hill Notation):
C31H43N3O8
CAS Number:
Molecular Weight:
585.69
MDL number:

storage conditions

-20C

Quality Level

assay

≥98% (HPLC)

form

medium granules (dehydrated (DCM))
solid

manufacturer/tradename

Calbiochem®
Granucult®

storage condition

OK to freeze
protect from light

application(s)

microbiological culture: suitable
microbiology: suitable
pathogen testing: suitable

color

purple

solubility

DMSO: 10 mg/mL
methanol: 10 mg/mL

Featured Industry

Food and Beverages

shipped in

wet ice

storage temp.

−20°C

suitability

Listeria spp.

InChI

1S/C31H43N3O8/c1-8-12-33-26-21-13-17(2)14-25(41-7)27(36)19(4)15-20(5)29(42-31(32)39)24(40-6)11-9-10-18(3)30(38)34-22(28(21)37)16-23(26)35/h8-11,15-17,19,24-25,27,29,33,36H,1,12-14H2,2-7H3,(H2,32,39)(H,34,38)/b11-9+,18-10-,20-15+/t17-,19-,24-,25-,27+,29-/m1/s1

InChI key

AYUNIORJHRXIBJ-CQFHKJEWSA-N

General description

A less toxic, potent, synthetic derivative of the ansamycin benzoquinone antibiotic Geldanamycin Streptomyces hygroscopicus (Cat. No. 345805) that binds to Hsp90 (EC50 = 7.2 µM) and regulates its function. Reported to induce apoptosis and exhibit anti-tumor properties (IC50 = 4.1 nM in SKBR3 and 5.2 nM in MCF7 cells). Depletes cancer cells of erbB-1, erbB-2 (EC50 = 45 nM), mutant p53, (EC50 = 62 nM), Raf-1 (EC50 = 80 nM), and Akt. Hence, inhibits the Ras/Raf/MEK and PI3-Kinase signaling pathways. Shown to sensitize cancer cells to Paclitaxel (Cat. No. 580555) and Doxorubicin (Cat. No. 324380), and down-regulates vascular endothelial factor expression.

Packaging

500 μg in Plastic ampoule
Packaged under inert gas

Biochem/physiol Actions

EC50 = 7.2 µM for Hsp90
Product does not compete with ATP.
Reversible: no
Cell permeable: no
Primary Target
Hsp90

Warning

Toxicity: Standard Handling (A)

Reconstitution

Following reconstitution aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Basso, A.D., et al. 2002. Oncogene21, 1159.
Clarke, P.A., et al. 2002. Oncogene19, 4125.
Clarke, P.A., et al. 2000. Oncogene19, 4125.
Schulte, T.W., and Neckers, L.M. 1998. Cancer Chemother. Pharmacol.42, 273.
Schnur, R.C., et al. 1995. J. Med. Chem.38, 3806.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
GRANUCULT is a registered trademark of Merck KGaA, Darmstadt, Germany

Certificate of Analysis

Certificate of Origin

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