Binds Hsp90 and GRP94, inhibits growth of cancer cells
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Geldanamycin

Item No. 13355

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
13R-hydroxy-8S,14S,19-trimethoxy-4,10,12S,16R-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4E,6E,10E,18-pentaen-9S-yl, carbamate
CAS Number
30562-34-6
Synonyms
  • NSC 122750
Molecular Formula
C29H40N2O9
Formula Weight
560.6
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/ml
λmax
257, 306 nm
SMILES
COC(C(C=C1N2)=O)=C(C1=O)C[C@@H](C)C[C@H](OC)[C@H](O)[C@@H](C)/C=C(C)/[C@H](OC(N)=O)[C@@H](OC)/C=C/C=C(C)/C2=O
InChi Code
InChI=1S/C29H40N2O9/c1-15-11-19-25(34)20(14-21(32)27(19)39-7)31-28(35)16(2)9-8-10-22(37-5)26(40-29(30)36)18(4)13-17(3)24(33)23(12-15)38-6/h8-10,13-15,17,22-24,26,33H,11-12H2,1-7H3,(H2,30,36)(H,31,35)/b10-8+,16-9+,18-13+/t15-,17+,22+,23+,24-,26+/m1/s1
InChi Key
QTQAWLPCGQOSGP-PHLMVCJGSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $63

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    5 mg

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    Product Description

    Geldanamycin is a benzoquinone ansamycin antibiotic which binds heat shock protein 90 (Hsp90) and its paralog GRP94, altering their actions.1,2,3 Through its interaction with these chaperones, geldanamycin indirectly affects numerous client proteins with roles in diverse cellular processes, including gene expression, cell proliferation, apoptosis, and angiogenesis. For example, geldanamycin inhibits c-jun expression in human colon adenocarcinoma HT29 cells (IC50 = 75 nM), inhibiting AP-1 binding.4 It also reduces signaling through mitogenic signaling proteins and interferes with steroid receptor function.1,5,6,7 Inhibitors of Hsp90, including geldanamycin, show promise in cancer therapy.8

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Whitesell, L., Mimnaugh, E.G., De Costa, B., et al. Inhibition of heat shock protein Hsp90-pp60v-src heteroprotein complex formation by benzoquinone ansamycins: Essential role for stress proteins in oncogenic transformation. Proc. Natl. Acad. Sci. USA 91(18), 8324-8328 (1994).

    2. Hadden, M.K., Lubbers, D.J., and Blagg, B.S.J. Geldanamycin, radicicol, and chimeric inhibitors of the Hsp90 N-terminal ATP binding site. Curr. Top. Med. Chem. 6(11), 1173-1182 (2006).

    3. Chavany, C., Mimnaugh, E., Miller, P., et al. p185erbB2 binds to GRP94 in vivo. Dissociation of the p185erbB2/GRP94 heterocomplex by benzoquinone ansamycins precedes depletion of p185erbB2. The Journal of Biological Chemisty 271(9), 4974-4977 (1996).

    4. Vasilevskaya, I.A., and O'Dwyer, P.J. Effects of geldanamycin on signaling through activator-protein 1 in hypoxic HT29 human colon adenocarcinoma cells. Cancer Res. 59(16), 3935-3940 (1999).

    5. Stancato, L.F., Silverstein, A.M., Owens-Grillo, J.K., et al. The hsp90-binding antibiotic geldanamycin decreases Raf levels and epidermal growth factor signaling without disrupting formation of signaling complexes or reducing the specific enzymatic activity of Raf kinase. The Journal of Biological Chemisty 272(7), 4013-4020 (1997).

    6. Fukuyo, Y., Hunt, C.R., and Horikoshi, N. Geldanamycin and its anti-cancer activities. Cancer Lett. 290(1), 24-35 (2010).

    7. Smith, D.F., Whitesell, L., Nair, S.C., et al. Progesterone receptor structure and function altered by geldanamycin, an hsp90-binding agent. Mol. Cell. Biol. 15(12), 6804-6812 (1995).

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