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17-AAG

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Products Intro: Product Name:17-AAG
CAS:75747-14-7
Purity:98% Package:10MG;50MG;100MG,1G,5G,10G.100G
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CAS:75747-14-7
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Products Intro: Product Name:17-Allylamino-17-Demethoxygeldanamycin-d5
CAS:75747-14-7
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CAS:75747-14-7
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Products Intro: Product Name:Tanespimycin
CAS:75747-14-7
Purity:99.83% Package:10mg;59USD|5mg;38USD|25mg;97USD Remarks:REAGENT;FOR LABORATORY USE ONLY

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  • 2020-01-03
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Related articles

  • What is 17-AAG?
  • 17-AAG is an Hsp90 inhibitor. This compound is a synthetic analog of geldanamycin, an antibiotic first purified in 1970 from S....
  • Oct 20,2023
17-AAG Basic information
Description Targets In vitro
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
EINECS:
Product Categories:antibiotic;Amines;Heterocycles;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Heat Shock Protein 90;APIs
Mol File:75747-14-7.mol
17-AAG Structure
17-AAG Chemical Properties
Melting point 201-203°C
Boiling point 797.8±60.0 °C(Predicted)
density 1.21
RTECS LX8932000
Fp >110°(230°F)
storage temp. Keep in dark place,Sealed in dry,Store in freezer, under -20°C
solubility DMSO: soluble
form solid
pka8.62±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.
InChIKeyAYUNIORJHRXIBJ-HTLBVUBBSA-N
SMILESC12C(=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 Reference75747-14-7
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 22-24/25-36-26
WGK Germany 3
HS Code 29419090
MSDS Information
ProviderLanguage
SigmaAldrich English
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.
TargetsHSP90 5 nM.
In vitro17-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.
Description17-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 PropertiesDark Purple Solid
UsesPotent 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.
UsesGeldanamycin 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).
Uses17-(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.
DefinitionChEBI: 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 DescriptionChemical structure: benzenoid
Biological ActivityInhibitor 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 Actions17-(Allylamino)-17-demethoxygeldanamycin (17-AAG) is a benzoquinone and is an analog of geldanamycin.
storage-20°C
References1) 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-AAG Preparation Products And Raw materials
Tag:17-AAG(75747-14-7) Related Product Information
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