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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:

Quality Level

assay

≥98% (HPLC)

form

medium granules (dehydrated (DCM))
solid

manufacturer/tradename

Calbiochem®
GranuCult®

storage condition

OK to freeze
protect from light

technique(s)

microbiological culture: suitable

color

purple

solubility

DMSO: 10 mg/mL
methanol: 10 mg/mL

application(s)

food and beverages
microbiology
pathogen testing

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

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

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

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