100068

17-AAG

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

• Synonym(e): 17-AAG, NSC-330507, 17-AG, 17-(Allylamino)-17-demethoxygeldanamycin, 17-Allylaminogeldanamycin
• Empirische Formel (Hill-System): C₃₁H₄₃N₃O₈
• CAS-Nummer: 75747-14-7
• Molekulargewicht: 585.69
• MDL-Nummer: MFCD04973892
• UNSPSC-Code: 12352200
• NACRES: NA.77

Eigenschaften

• Agentur: according to ISO 10272
• Qualitätsniveau: 100
• Produktlinie: GranuCult^® prime
• Assay: ≥98% (HPLC)
• Form: medium granules (dehydrated (DCM)); solid
• Hersteller/Markenname: Calbiochem^®; GranuCult^®
• Lagerbedingungen: OK to freeze; protect from light
• Methode(n): microbiological culture: suitable
• Farbe: purple
• Löslichkeit: DMSO: 10 mg/mL; methanol: 10 mg/mL
• Anwendung(en): food and beverages; microbiology; pathogen testing
• Versandbedingung: wet ice
• Lagertemp.: −20°C
• Eignung: 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
• InChIKey: AYUNIORJHRXIBJ-CQFHKJEWSA-N

Beschreibung

Allgemeine Beschreibung

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. Wirkung

Cell permeable: no

EC50 = 7.2 µM for Hsp90

Primary Target
Hsp90

Product does not compete with ATP.

Reversible: no

Verpackung

Packaged under inert gas

Warnhinweis

Toxicity: Standard Handling (A)

Rekonstituierung

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

Sonstige Hinweise

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.

Rechtliche Hinweise

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

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