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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GCTMV\Hdo94fGhiSX7obYJqfGmxbjDBd5NigQ>?MnvGTWM2OD12OT62PVc3KM7:TR?=NGXtWXZUSU6JRWK=

... 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 2016-07-30)

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

Frequently Asked Questions

  • Question 1
    What kind of subtypes does this compound inhibit? HSP90α or HSP90β ?

    Answer: 17-AAG can inhibit both HSP90α and HSP90β, but it is unclear how much are they affected respectively. You should note that Hsp90 derived from tumor cells has a 100-fold higher binding affinity for 17-AAG than that from normal cells according to this paper. http://www.nature.com.ezp-prod1.hul.harvard.edu/nature/journal/v425/n6956/full/nature01913.html

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.

Tel: +1-832-582-8158 Ext:3

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Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID
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