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Geldanamycin

Cayman Chemical Item Number 13355

NSC 122750 (CAS 30562-34-6)

Geldanamycin (CAS 30562-34-6)

See more	Inhibitors (546) Apoptosis (191) Cancer (666) Cell Biology (303) Cell Cycle (72) Gene Regulation (203) Signal Transduction (328)

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

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 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 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. J Biol Chem 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 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. J Biol Chem 272(7) 4013-4020 (1997).

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

Synonyms	NSC 122750
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
Molecular Formula	C₂₉H₄₀N₂O₉
Formula Weight	560.6
Formulation	A crystalline solid
Purity	≥98%
Stability	2 years
Storage	-20°C
Shipping	Room temperature in continental US; may vary elsewhere
SMILES	Copy SMILES to clipboard 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

Background Reading

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 8324-8328 (1994).

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 3935-3940 (1999).

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. J Biol Chem 272(7) 4013-4020 (1997).

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 1173-1182 (2006).

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. J Biol Chem 271(9) 4974-4977 (1996).

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

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).

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

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Size	Price	Quantity	Subtotal
1 mg	$45.00		$0.00
5 mg	$98.00		$0.00
10 mg	$168.00		$0.00
Bulk	Contact
		Cart Total	$0.00

Pricing updated 2012-05-26. Prices are subject to change without notice.

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