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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: 17-AAG - CAS 75747-14-7 - Calbiochem, NSC-330507, 17-AG, 17-(Allylamino)-17-demethoxygeldanamycin, 17-Allylaminogeldanamycin

  • CAS Number 75747-14-7

  • Empirical Formula (Hill Notation) C31H43N3O8

  • Molecular Weight 585.69

  •  MDL number MFCD04973892

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Properties

Quality Level   100
assay   ≥98% (HPLC)
form   medium granules (dehydrated (DCM))
  solid
mfr. no.   Calbiochem®
  Granucult®
storage condition   OK to freeze
  protect from light
storage conditions   -20C
application(s)   microbiological culture: suitable
  microbiology: suitable
color   purple
solubility   DMSO: 10 mg/mL
  methanol: 10 mg/mL
Featured Industry   Food and Beverages
shipped in   wet ice
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.

Packaging

500 μg in Plastic ampoule

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

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

Safety & Documentation

Safety Information

Safety Information for this product is unavailable at this time.
Protocols & Articles

Articles

Detection and Enumeration of Campylobacter spp. in Food & Environmental Samples According to International Standards

Campylobacter spp. is a leading human pathogen worldwide that causes the foodborne illness Campylobacteriosis. The testing workflow is regulated by international organizations to ensure consumer safe...
Keywords: Anaerobic, Microbiology, Safety industry

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