[CAS NO. 30562-34-6] Geldanamycin (NSC 122750)

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PRODUCTS SPECIFICATIONS [30562-34-6]

Catalog

SLK-S2713

Brand

Selleck

CAS

30562-34-6

DESCRIPTION [30562-34-6]

Overview

MDL	MFCD00274570
Molecular Weight	560.64
Molecular Formula	C29H40N2O9
SMILES	O(C)C1=C2C(=O)C(=CC1=O)NC(=O)\C(\C)=C\C=C/[C@H](OC)[C@@H](OC(N)=O)\C(\C)=C\[C@H](C)[C@@H](O)[C@@H](OC)C[C@H](C)C2

For research use only.

Storage

3 years,-20°C,powder
1 years,-80°C,in solvent

Shipping

Room temperature shipping(Stability testing shows this product can be shipped without any cooling measures.)

Description

Geldanamycin (NSC 122750) is a natural existing inhibitor with of 1.2 μM, specifically disrupts glucocorticoid receptor (GR)/HSP association. Geldanamycin attenuates virus infection-induced ALI (acute lung injury)/ARDS (acute respiratory distress syndrome) by reducing the host's inflammatory responses.

Targets

p185 ^[4] (SKBr3 cells)	HSP90 (N-terminal domain) ^[1] (Cell-free assay)	HSP90 ^[1] (Cell-free assay)
70 nM	0.78 μM(Kd)	1.2 μM(Kd)

In vitro

Geldanamycin binds in the ATP-binding site in the N-terminus domain of Hsp90s (residues 1-220). Geldanamycin inhibits the ATPase activity of Hsp90 in a dose-dependent manner. Geldanamycin causes a dose-dependent G2 arrest and reversible inhibiton o f entry into the S phase in A2780 human ovarian cell line. This inhibition is accompanied by p53 increase and finally demonstrated to be p53 dependent. Geldanamycin causes polyubiquitination and proteasomal degradation of the p185 receptor protein-tyrosin kinase and shows a IC50 with 70 nM. Geldanamycin is a typical anti-tumor reagent, shows a mean GI50 with 0.18 μM against the panel of 60 human tumor cell lines.

In vivo

Geldanamycin (50 mg//kg) shows 30% inhibition on pl85-associated phosphotyrosine levels in FRE/erbB-2 mice.

References

[1] Roe SM, et al, J Med Chem, 1999, 42(2), 260-266.
[2] Mcllwrath AJ, et al, Cancer Chemother Pharmacol, 1996, 37(5), 423-428.
[3] Mimnaugh EG, et al, J Biol Chem 1996, 271(37), 22796-22801.
[4] Miller P, et al, Cancer Res, 1994, 54(10), 2724-2730.
[5] Supko JG, et al, Cancer Chemother Pharmacol, 1995, 36(4), 305-315.
[6] Schnur RC, et al. J Med Chem, 1995, 38(19), 3806-3812.

Synonyms

Geldanamycin

2-Azabicyclo[16.3.1]docosa-4,6,10,18,21-pentaene-3,20,22-trione, 9,13-dihydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-, 9-carbamate

2-Azabicyclo[16.3.1]docosane, geldanamycin deriv.

2-Azabicyclo[16.3.1]docosa-4,6,10,18,21-pentaene-3,20,22-trione, 9-[(aminocarbonyl)oxy]-13-hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-, [8S-(4E,6Z,8R*,9R*,10E,12R*,13S*,14R*,16S*)]-

[8S-(4E,6Z,8R*,9R*,10E,12R*,13S*,14R*,16S*)]-9-[(Aminocarbonyl)oxy]-13-hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-2-azabicyclo[16.3.1]docosa-4,6,10,18,21-pentaene-3,20,22-trione

NSC 122750

NSC 212518

(+)-Geldanamycin

(8S,9S,12S,13R,14S,16R)-13-Hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl carbamate