100068

17-AAG

according to ISO 10272, A less toxic, potent, synthetic derivative of the ansamycin benzoquinone antibiotic Geldanamycin, Streptomyces hygroscopicus., GranuCult^® prime

• Synonyme(s) : 17-AAG, NSC-330507, 17-AG, 17-(Allylamino)-17-demethoxygeldanamycin, 17-Allylaminogeldanamycin
• Formule empirique (notation de Hill): C₃₁H₄₃N₃O₈
• Numéro CAS: 75747-14-7
• Poids moléculaire : 585.69
• Numéro MDL: MFCD04973892
• Code UNSPSC : 12352200
• Nomenclature NACRES : NA.77

Propriétés

• Agence: according to ISO 10272
• Niveau de qualité: 100
• Gamme de produits: GranuCult^® prime
• Pureté: ≥98% (HPLC)
• Forme: medium granules (dehydrated (DCM)); solid
• Fabricant/nom de marque: Calbiochem^®; GranuCult^®
• Conditions de stockage: OK to freeze; protect from light
• Technique(s): microbiological culture: suitable
• Couleur: purple
• Solubilité: DMSO: 10 mg/mL; methanol: 10 mg/mL
• Application(s): food and beverages; microbiology; pathogen testing
• Conditions d'expédition: wet ice
• Température de stockage: −20°C
• Adéquation: 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
• Clé InChI: AYUNIORJHRXIBJ-CQFHKJEWSA-N

Description

Description générale

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.

Actions biochimiques/physiologiques

Cell permeable: no

EC50 = 7.2 µM for Hsp90

Primary Target
Hsp90

Product does not compete with ATP.

Reversible: no

Conditionnement

Packaged under inert gas

Avertissement

Toxicity: Standard Handling (A)

Reconstitution

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

Autres remarques

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.

Informations légales

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

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