Basic information Description Targets In vitro Safety Supplier Related
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17-AAG

Basic information Description Targets In vitro Safety Supplier Related

17-AAG Basic information

Product Name:
17-AAG
Synonyms:
  • GELDANAMYCIN,17-DEMETHOXY-17-(2-PROPENYLAMINO)-
  • CP 127374
  • ALLYLAMINOGELDANAMYCIN
  • NSC-330507
  • 17-(ALLYLAMINO)-17-DEMETHOXYGELDANAMYCIN
  • 17-(ALLYLAMINO)-17-DESMETHOXYGELDANAMYCIN
  • 17-(ALLYLAMINO)-17-DIMETHOXYGELDANAMYCIN
  • 17-ALLYLAMINOGELDANAMYCIN
CAS:
75747-14-7
MF:
C31H43N3O8
MW:
585.69
Product Categories:
  • antibiotic
  • Amines
  • Heterocycles
  • Inhibitors
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Heat Shock Protein 90
  • APIs
Mol File:
75747-14-7.mol
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17-AAG Chemical Properties

Melting point:
201-203°C
Boiling point:
797.8±60.0 °C(Predicted)
Density 
1.21
RTECS 
LX8932000
Flash point:
>110°(230°F)
storage temp. 
Keep in dark place,Sealed in dry,Store in freezer, under -20°C
solubility 
DMSO: soluble
form 
solid
pka
8.62±0.70(Predicted)
color 
Purple or dark red
Water Solubility 
Soluble in DMSO at 150 mg/mL; soluble in ethanol at 5 mg/mL. Very poorly soluble in water
Sensitive 
Light Sensitive
Stability:
Stable for 1 year from date of purchase as supplied. Protect from moisture. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
InChIKey
AYUNIORJHRXIBJ-HTLBVUBBSA-N
SMILES
C12C(=O)C(=CC(=O)C=1NCC=C)NC(=O)C(C)=CC=C[C@H](OC)[C@@H](OC(=O)N)C(C)=C[C@H](C)[C@@H](O)[C@@H](OC)C[C@H](C)C2 |t:17,19,30|
CAS DataBase Reference
75747-14-7
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
22-24/25-36-26
WGK Germany 
3
HS Code 
29419090

MSDS

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17-AAG Usage And Synthesis

Description

Tanespimycin (17-AAG, CP127374, NSC-330507, KOS 953) (75747-14-7) is a potent HSP90 inhibitor with IC50 of 5 nM in a cell-free assay, having a 100-fold higher binding affinity for HSP90 derived from tumour cells than HSP90 from normal cells. Tanespimycin (17-AAG) induces apoptosis, necrosis, autophagy and mitophagy. Phase 3.

Targets

HSP90 5 nM.

In vitro

17-AAG, an analog of geldanamycin, exhibits greater than 100 times higher binding affinity for Hsp90 derived from HER-2-overexpressing cancer cells (BT474, N87, SKOV3 and SKBR3) or BT474 breast carcinoma cells with IC50 values of 5-6 nM. 17-AAG causes the degradation of HER2, HER3, Akt, and both mutant and wild-type androgen receptor (AR), leading to the RB-dependent G1 growth arrest of prostate cancer cells such as LNCaP, LAPC-4, DU-145, and PC-3 with IC50 values of 25-45 nM. [2] In addition to inducing apoptosis of Ba/F3 cells transformed with wild-type BCR-ABL with an IC50 of 5.2 μM, 17-AAG has the ability to induce apoptosis of cells transformed with imatinib mesylate-resistant T315I and E255K BCR-ABL mutants with IC50 values of 2.3 μM and 1.0 μM, respectively, by inducing the degradation of both wild-type BCR-ABL protein and mutants.

Description

17-AAG (75747-14-7) is a semi-synthetic analog of geldanamycin (Cat.# 10-1084) which is less toxic and more stable. 17-AAG selectively binds to and inhibits HSP90 from tumor cells. Anti-angiogenic activity. Cell permeable.

Chemical Properties

Dark Purple Solid

Uses

Geldanamycin is a potent inhibitor of Hsp90 that exhibits severe hepatotoxicity when used in vivo. 17-AAG is an analog of geldanamycin which has potent in vivo activity and reduced toxicity. Like other Hsp90 inhibitors, 17-AAG has diverse anti-tumor actions and has potential in treating certain types of cancer. 17-AAG inhibits the growth of prostate cancer cell lines (IC50 = 25-45 nM). 17-AAG promotes the degradation of HER2 and induces growth arrest and apoptosis in breast cancer cells overexpressing HER2 (IC50 = 4-72 nM).

Uses

17-(Allylamino)-17-demethoxygeldanamycin (17-AAG) inhibits heat shock protein 90 (Hsp90), the expression of heat shock factor-1, and the activity of oncogenic proteins such as N-ras, Ki-ras, c-Akt, and p185erB2. In addition to its anti-tumor effects, 17-AAG also induces apoptosis.

Uses

Potent inhibitor of heat shock protein 90 (Hsp90). 17-AAG is a less toxic analog than Geldanamycin. It induces apoptosis and displays antitumor effects. 17-AAG inhibits the activity of oncogenic proteins such as N-ras, Ki-ras, c-Akt, and p185erB2.

Definition

ChEBI: A 19-membered macrocyle that is geldanamycin in which the methoxy substituent attached to the benzoquinone moiety has been replaced by an allylamino group. It is a potent inhibitor of heat shock protein 90 (Hsp90). A less toxic analogue than geldanamycin, t induces apoptosis and displays antitumour effects.

General Description

Chemical structure: benzenoid

Biological Activity

Inhibitor of heat shock protein 90 (Hsp90) chaperone activity, and an analog of geldanamycin (9,13-Dihydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-2-azabicyclo[16.3.1]docosa-4,6,10,18,21-pentaene-3,20,22-trione, 9-carbamate ). Subsequently inhibits the activity of oncogenic proteins such as p185 erbB-2 (IC 50 = 31 nM), N-ras, Ki-ras and c-Akt. Antitumor in vivo .

Biochem/physiol Actions

17-(Allylamino)-17-demethoxygeldanamycin (17-AAG) is a benzoquinone and is an analog of geldanamycin.

storage

-20°C

References

1) Schulte et al. (1998), The benzoquinone ansamycin 17-allylamino-17-demethoxygeldanamycin binds to HSP90 and shares important biologic activities with geldanamycin; Cancer Chemother. Pharmacol. 42 273 2) Kamal et al. (2003), A high-affinity conformation of Hsp90 confers tumour selectivity on Hsp90 inhibitors; Nature, (b>425 407 3) Kaur et al. (2004), Therapeutic and diagnostic implications of Hsp90 activation; Clinical Cancer Res. 10 4813

17-AAGSupplier

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