17-AAG (Tanespimycin)

Catalog No.S1141

17-AAG (Tanespimycin) 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. Phase 2.

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17-AAG (Tanespimycin) Chemical Structure

17-AAG (Tanespimycin) Chemical Structure
Molecular Weight: 585.69

Validation & Quality Control

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Related Compound Libraries

17-AAG (Tanespimycin) is available in the following compound libraries:

HSP (e.g. HSP90) Inhibitors with Unique Features

  • Selective HSP90 Inhibitor

    NVP-BEP800 HSP90β-selective, IC50=58 nM.

  • Most Potent HSP90 Inhibitor

    KW-2478 HSP90, IC50=3.8 nM.

  • HSP90 Inhibitor in Clinical Trial

    17-DMAG (Alvespimycin) HCl Phase II for Kidney Cancer.

  • Newest HSP90 Inhibitor

    XL888 ATP-competitive inhibitor of HSP90 with IC50 of 24 nM.

Product Information

  • Compare HSP (e.g. HSP90) Inhibitors
    Compare HSP (e.g. HSP90) Products
  • Research Area

Product Description

Biological Activity

Description 17-AAG (Tanespimycin) 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. Phase 2.
Targets HSP90 [1]
(Cell-free assay)
IC50 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. [1] 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. [3]
Cell Data
Cell LinesAssay TypeConcentrationIncubation TimeFormulationActivity DescriptionPMID
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... Click to View More Cell Line Experimental Data

In vivo 17-AAG displays significantly higher binding affinity for Hsp90 from 3T3-src, B16 or CT26 xenografts in nude mice with IC50 values of 8-35 nM as compared with that from the normal tissues with IC50 values of 200-600 nM. [1] Administration of 17-AAG (~50 mg/kg) causes significant decline in AR, HER2, HER3, and Akt expression in a dose-dependent manner with >50% decline at dose of 50 mg/kg, resulting in the dose-dependent inhibition of androgen-dependent (CWR22) and -independent (CWR22R and CWRSA6) prostate cancer xenografts growth by 67%, 80% and 68% at dose of 50 mg/kg, respectively. [2]
Features Displays very low toxicity toward normal cells.

Protocol(Only for Reference)

Kinase Assay: [1]

Hsp90 binding assays Purified native Hsp90 protein or cell lysates from HER-2-overexpressing cancer cells (BT474, N87, SKOV3 and SKBR3) or BT474 breast carcinoma cells in lysis buffer (20 mM HEPES, pH 7.3, 1 mM EDTA, 5 mM MgCl2, 100 mM KCl) are incubated with various concentrations of 17-AAG for 30 minutes at 4 °C, and then incubated with biotin-GM linked to BioMag streptavidin magnetic beads for 1 hour at 4 °C. Tubes are placed on a magnetic rack, and the unbound supernatant removed. The magnetic beads are washed three times in lysis buffer and heated for 5 minutes at 95 °C in SDS–PAGE sample buffer. Samples are analysed on SDS protein gels, and western blots done using indicated antibodies. Bands in the western blots are quantified using the Bio-rad Fluor-S MultiImager, and the percentage inhibition of binding of Hsp90 to the biotin-GM is calculated. The IC50 reported is the concentration of 17-AAG needed to cause half-maximal inhibition of binding.

Cell Assay: [1]

Cell lines BT474, SKBR3, N87, SKOV3, MCF7, MDA468, Hs578T, Hs578Bst, A549, HT29, U87, SKMG3, HT1080, RPTEC, NDF, HMVEC, HMEC, HUVEC, and PBMC cells
Concentrations Dissolved in DMSO, final concentrations ~10 μM
Incubation Time 5 days
Method Cells are seeded in 96-well plates at 2,000 cells per well in a final culture volume of 100 μL for 24 hours before the addition of increasing concentrations of 17-AAG that is incubated for 5 days. Viable cell number is determined using the Celltiter 96 AQueous Nonradioactive Cell Proliferation Assay. The value of the background absorbance at 490 nm (A490) of wells not containing cells is subtracted. Percentage of viable cells = (A490 of 17-AAG treated sample/A490 untreated cells) × 100. The IC50 is defined as the concentration that gave rise to 50% viable cell number.

Animal Study: [2]

Animal Models Male nu/nu athymic mice inoculated s.c. with androgen-dependent CWR22 xenograft, and female nu/nu athymic mice inoculated s.c. with androgen-independent xenografts CWR22R and CWRSA6
Formulation Dissolved in DMSO, and diluted in egg phospholipids (EPL) vehicle
Dosages ~50 mg/kg
Administration Injection i.p.

Conversion of different model animals based on BSA (Value based on data from FDA Draft Guidelines)

SpeciesMouseRatRabbitGuinea pigHamsterDog
Weight (kg)0.020.151.80.40.0810
Body Surface Area (m2)0.0070.0250.150.050.020.5
Km factor36128520
Animal A (mg/kg) = Animal B (mg/kg) multiplied by  Animal B Km
Animal A Km

For example, to modify the dose of resveratrol used for a mouse (22.4 mg/kg) to a dose based on the BSA for a rat, multiply 22.4 mg/kg by the Km factor for a mouse and then divide by the Km factor for a rat. This calculation results in a rat equivalent dose for resveratrol of 11.2 mg/kg.

Rat dose (mg/kg) = mouse dose (22.4 mg/kg) ×  mouse Km(3)  = 11.2 mg/kg
rat Km(6)
1

References

[1] Kamal A, et al. Nature, 2003, 425(6956), 407-410.

[2] Solit DB, et al. Clin Cancer Res, 2002, 8(5), 986-993.

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Clinical Trial Information( data from http://clinicaltrials.gov, updated on 2016-07-23)

NCT Number Recruitment Conditions Sponsor
/Collaborators
Start Date Phases
NCT00577889 Completed Adenocarcinoma of the Pancreas|Recurrent Pancreatic Cancer|Stage IV Pancreatic Cancer National Cancer Institute (NCI) March 2008 Phase 2
NCT00546780 Completed Multiple Myeloma Bristol-Myers Squibb February 2008 Phase 3
NCT00093496 Completed Primary Peritoneal Cavity Cancer|Recurrent Ovarian Epithelial Cancer|Stage III Ovarian Epithelial Cancer|Stage IV Ovarian Epithelial Cancer National Cancer Institute (NCI) October 2007 Phase 2
NCT00514371 Completed Multiple Myeloma Bristol-Myers Squibb August 2007 Phase 2|Phase 3
NCT00779428 Completed Advanced Malignancies Bristol-Myers Squibb July 2006 Phase 2

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Chemical Information

Download 17-AAG (Tanespimycin) SDF
Molecular Weight (MW) 585.69
Formula

C31H43N3O8

CAS No. 75747-14-7
Storage 3 years -20℃powder
6 months-80℃in solvent
Synonyms CP127374,NSC-330507, KOS 953
Solubility (25°C) * In vitro DMSO 100 mg/mL (170.73 mM)
Ethanol 5 mg/mL (8.53 mM)
Water <1 mg/mL (<1 mM)
In vivo
* <1 mg/ml means slightly soluble or insoluble.
* Please note that Selleck tests the solubility of all compounds in-house, and the actual solubility may differ slightly from published values. This is normal and is due to slight batch-to-batch variations.
Chemical Name 17-demethoxy-17-(2-propenylamino)- [(3R,5R,6S,7R,8E,10R,11R,12Z,14E)-6-Hydroxy-5,11,21-trimethoxy-3,7,9,15-tetramethyl-16,20,22-trioxo-17-azabicyclo[16.3.1]docosa-1(21),8,12,14,18-pentaen-10-yl] carbamate

Customer Product Validation(7)


Click to enlarge
Rating
Source PNAS, 2011, 108: 7535-40. 17-AAG (Tanespimycin) purchased from Selleck
Method Western Blot
Cell Lines H3122 & H3122 CR cells
Concentrations 10 nM
Incubation Time 72 h
Results As shown in Fig. A, 17-AAG potently suppressed cell growth in both parental H3122 and H3122 CR cells. However, in contrast to NVP-TAE684 and AP26113, 17-AAG also inhibited the viability of SKBR3 and BT474 cell lines. 17-AAG treatment decreased both p-ALK 眏Ỵ眐㠞眎膉癠 皐﷘ř᐀ŔřĀ 㺣癞帉癞Ѐ瑖兽ﱔᆊࣿřĀࣾ彿兾奋兾巫兾婶ࣿ橢ࣿ彿兾

Click to enlarge
Rating
Source Oncotarget 2014 5, 4269-82. 17-AAG (Tanespimycin) purchased from Selleck
Method Western blot
Cell Lines Ls-174T, HCT116, Caco2, Hke3 cells
Concentrations 0.5, 2 uM
Incubation Time 24 h
Results Colon cancer cells harboring WT or MT K-Ras were treated with 17-AAG and effects on the Ras expression were analyzed by WB. Results in Figure showed that incubation with 17-AAG only down-regulates K-Ras in K-Ras MT cells but decreases Raf-1 {an established Hsp90 client} in all cell lines. The result, for the first time, demonstrated that both transfected and endogenous MT K-Ras is an Hsp90 client protein.

Click to enlarge
Rating
Source Oncotarget, 2015, 51: S659-S660. 17-AAG (Tanespimycin) purchased from Selleck
Method Western Blot
Cell Lines MOLT-4 & RS4;11 cells
Concentrations
Incubation Time 22 h
Results In both MOLT-4 and RS4;11 cells, the combined treatment inhibited the interactions between Hsp90 and BIP/Grp78 more effectively than CX-4945 single treatment and to the same extent as tanespimycin (17-AAG).

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Rating
Source Mol Cell Biol 2013 33(12), 2375-87. 17-AAG (Tanespimycin) purchased from Selleck
Method Western blot
Cell Lines NIH 3T3 cells
Concentrations 25, 50 uM
Incubation Time 4 h
Results 17-AAG and SNX-2112, both of which induce the UPR by targeting the chaperone HSP90, decreased mSmoM2 protein levels (lanes 2 to 5 compared to lane 1), further supporting the sensitivity of active Smo mutants to UPR induction.

Click to enlarge
Rating
Source J Biol Chem 2012 287, 44109-20. 17-AAG (Tanespimycin) purchased from Selleck
Method Western Blot
Cell Lines Dopaminergic Neuronal Cell lines
Concentrations 10-20uM
Incubation Time
Results As expected, both complex IV activity and Hsp60 levels exhibited a dose-dependent decrease in response to treatment with 17-AAG (Fig. 4A). However, 17-AAG treatment did not alter levels of Hsp90 and LRPPRC levels

Click to enlarge
Rating
Source Mol Cancer 2014 13, 150. 17-AAG (Tanespimycin) purchased from Selleck
Method Western blot
Cell Lines SKBR3 cells
Concentrations 1, 2 uM
Incubation Time 24 h
Results Hsp90 and Cdc37 protein levels showed no distinct change according to a drug concentration gradient, whereas Hsp70, a marker of Hsp90 inhibition, the protein level was greatly induced by treatment with 17AAG or FW-04-806.

Click to enlarge
Rating
Source Age 2013 35, 549-62. 17-AAG (Tanespimycin) purchased from Selleck
Method Western Blot
Cell Lines HFSN1 cells
Concentrations 0.1/0.5uM
Incubation Time 24 h
Results Figure 2c shows that the decrease in the level of Hsp90 after treatment with 0.5 μM of 17-AAG was accompanied by a decrease in the level of both the survivin and phospho-survivin proteins.

Tech Support

Answers to questions you may have can be found in the inhibitor handling instructions. Topics include how to prepare stock solutions, how to store inhibitors, and issues that need special attention for cell-based assays and animal experiments.

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    PU-H71 is a potent and selective inhibitor of HSP90 with IC50 of 51 nM. Phase 1.

  • KNK437

    KNK437 is a pan-HSP inhibitor, which inhibits the synthesis of inducible HSPs, including HSP105, HSP72, and HSP40.

  • VER155008

    VER-155008 is a potent Hsp70 family inhibitor with IC50 of 0.5 μM, 2.6 μM, and 2.6 μM in cell-free assays for HSP70, HSC70, and GRP78, respectively, >100-fold selectivity over HSP90.

  • Luminespib (AUY-922, NVP-AUY922)

    Luminespib (AUY-922, NVP-AUY922) is a highly potent HSP90 inhibitor for HSP90α/β with IC50 of 13 nM /21 nM in cell-free assays, weaker potency against the HSP90 family members GRP94 and TRAP-1, exhibits the tightest binding of any small-molecule HSP90 ligand. Phase 2.

  • Ganetespib (STA-9090)

    Ganetespib (STA-9090) is an HSP90 inhibitor with IC50 of 4 nM in OSA 8 cells, induces apoptosis of OSA cells while normal osteoblasts are not affected; active metabolite of STA-1474. Phase 3.

  • 17-DMAG (Alvespimycin) HCl

    17-DMAG (Alvespimycin) HCl is a potent HSP90 inhibitor with IC50 of 62 nM in a cell-free assay. Phase 2.

    Features:A synthetic derivative Geldanamycin, with lower hepatotoxicity than parent antibiotic & higher potency and bioavailability than the similar derivative 17-AAG.

  • Geldanamycin

    Geldanamycin is a natural existing HSP90 inhibitor with Kd of 1.2 μM, specifically disrupts glucocorticoid receptor (GR)/HSP association.

  • HSP990 (NVP-HSP990)

    NVP-HSP990 (HSP990) is a novel, potent and selective HSP90 inhibitor for HSP90α/β with IC50 of 0.6 nM/0.8 nM.

    Features:NVP-HSP990 is an orally available HSP90 inhibitor and is structurally distinct from other clinical HSP90 inhibitors.

  • Elesclomol (STA-4783)

    Elesclomol (STA-4783) is a novel potent oxidative stress inducer that elicits pro-apoptosis events among tumor cells. Phase 3.

  • Onalespib (AT13387)

    Onalespib (AT13387) is a selective potent Hsp90 inhibitor with IC50 of 18 nM in A375 cells, displays a long duration of anti-tumor activity. Phase 2.

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