100068

17-AAG

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

• Synonym(s): 17-AAG, NSC-330507, 17-AG, 17-(Allylamino)-17-demethoxygeldanamycin, 17-Allylaminogeldanamycin
• Empirical Formula (Hill Notation): C₃₁H₄₃N₃O₈
• CAS Number: 75747-14-7
• Molecular Weight: 585.69
• MDL number: MFCD04973892

Properties

• Quality Level: 100
• 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

Description

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.

Biochem/physiol Actions

Cell permeable: no

EC50 = 7.2 µM for Hsp90

Primary Target
Hsp90

Product does not compete with ATP.

Reversible: no

Packaging

Packaged under inert gas

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