Water-soluble inhibitor of Hsp90
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17-DMAG

Item No. 11036

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
17-demethoxy-17-[[2-(dimethylamino)ethyl]amino]-geldanamycin
CAS Number
467214-20-6
Synonyms
  • Alvespimycin
  • KOS-1022
  • NSC 707545
Molecular Formula
C32H48N4O8
Formula Weight
616.8
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMF:PBS(pH 7.2)(1:1): 0.5 mg/mlDMSO: 13 mg/mlEthanol: 2 mg/ml
λmax
220, 332, 529 nm
SMILES
O=C(C(NCCN(C)C)=C1C[C@@H](C)C[C@H](OC)[C@H](O)[C@@H](C)/C=C(C)/[C@@H]2OC(N)=O)C=C(NC(/C(C)=C/C=C\[C@@H]2OC)=O)C1=O
InChi Code
InChI=1S/C32H48N4O8/c1-18-14-22-27(34-12-13-36(5)6)24(37)17-23(29(22)39)35-31(40)19(2)10-9-11-25(42-7)30(44-32(33)41)21(4)16-20(3)28(38)26(15-18)43-8/h9-11,16-18,20,25-26,28,30,34,38H,12-15H2,1-8H3,(H2,33,41)(H,35,40)/b11-9-,19-10+,21-16+/t18-,20+,25
InChi Key
KUFRQPKVAWMTJO-LMZWQJSESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $41

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    Cayman Chemical
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    17-DMAG is a water-soluble derivative of geldanamycin which potently inhibits Hsp90 (IC50 = 24 nM) and has excellent bioavailability and tissue distribution in animals.1 Like other Hsp90 inhibitors, 17-DMAG has diverse anti-tumor actions and has potential in treating certain types of cancer.2,3,4,5,6 This compound also suppresses inflammation by interfering with signaling through the NF-κB pathway.7,8 17-DMAG also ameliorates high fat diet-induced renal failure in a mouse model of diabetes.9

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Egorin, M.J., Lagattuta, T.F., Hamburger, D.R., et al. Pharmacokinetics, tissue distribution, and metabolism of 17-(dimethylaminoethylamino)-17-demethoxygeldanamycin (NSC 707545) in CD2F1 mice and Fischer 344 rats. Cancer Chemother. Pharmacol. 49, 7-19 (2002).

    2. Bull, E.E.A., Dote, H., Brady, K.J., et al. Enhanced tumor cell radiosensitivity and abrogation of G2 and S phase arrest by the Hsp90 inhibitor 17-(dimethylaminoethylamino)-17-demethoxygeldanamycin. Clin. Cancer Res. 10, 8077-8084 (2004).

    3. Taldone, T., Sun, W., and Chiosis, G. Discovery and development of heat shock protein 90 inhibitors. Bioorg. Med. Chem. 17(6), 2225-2235 (2009).

    4. Hackl, C., Lang, S.A., Moser, C., et al. Activating transcription factor-3 (ATF3) functions as a tumor suppressor in colon cancer and is up-regulated upon heat-shock protein 90 (Hsp90) inhibition. BMC Cancer 10(668), 1-9 (2010).

    5. Ramanathan, R.K., Egorin, M.J., Erlichman, C., et al. Phase I pharmacokinetic and pharmacodynamic study of 17-dimethylaminoethylamino-17-demethoxygeldanamycin, an inhibitor of heat-shock protein 90, in patients with advanced solid tumors. J. Clin. Oncol. 28(9), 1520-1526 (2010).

    6. Kobayashi, N., Toyooka, S., Soh, J., et al. The anti-proliferative effect of heat shock protein 90 inhibitor, 17-DMAG, on non-small-cell lung cancers being resistant to EGFR tyrosine kinase inhibitor. Lung Cancer 75, 161-166 (2012).

    7. Madrigal-Matute, J., López-Franco, O., Blanco-Colio, L.M., et al. Heat shock protein 90 inhibitors attenuate inflammatory responses in atherosclerosis. Cardiovasc. Res. 86, 330-337 (2010).

    8. Shimp, S.K., III, Parson, C.D., Regna, N.L., et al. HSP90 inhibition by 17-DMAG reduces inflammation in J774 macrophages through suppression of Akt and nuclear factor-κB pathways. Inflamm. Res. 1-13 (2012).

    9. Zhang, H.M., Dang, H., Kamat, A., et al. Geldanamycin derivative ameliorates high fat diet-induced renal failure in diabetes. PLoS One 7(3), 1-9 (2012).