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    Geldanamycin
    Geldanamycin

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    This product is for research use only, not for human use. We do not sell to patients.
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    InvivoChem Cat #: V0891
    CAS #: 30562-34-6Purity ≥98%

    Description: Geldanamycin (U-29135; NSC-122750; NSC122750; U 29135) is a natural occurring, benzoquinone-based ,19-membered macrocyle ansamycin class of anticancer antibiotic. It is a crystalline antimicrobial and benzoquinone ansamycin compound extracted from the culture filtrates of Streptomyces hygroscopicus var. geldanus var. nova. Geldanamycin is a specific inhibitor of heat shock protein 90 (HSP90) with potential antineoplastic activity. It inhibits HSP90 with a Kd of 1.2 μM.

    References: J Med Chem. 1999;42(2):260-6; Cancer Res. 1994;54(10):2724-30; J Med Chem. 1995;38(19):3806-12.


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    Molecular Weight (MW)560.64
    FormulaC29H40N2O9
    CAS No.30562-34-6
    Storage-20℃ for 3 years in powder form
    -80℃ for 2 years in solvent
    Solubility (In vitro)DMSO: 50 mg/mL (89.18 mM)          
    Water: <1 mg/mL
    Ethanol: <1 mg/mL
    Other infoChemical Name: (4E,6Z,8S,9S,10E,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
    InChi Key: QTQAWLPCGQOSGP-KSRBKZBZSA-N
    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
    SMILES Code: NC(O[[email protected]@H](/C(C)=C/[[email protected]](C)[[email protected]@H](O)[[email protected]@H](OC)C[[email protected]](C)CC1=C2OC)[[email protected]@H](OC)/C=C\C=C(C)\C(NC(C1=O)=CC2=O)=O)=O
    SynonymsNSC 122750; U-29135; NSC-122750; NSC122750; U 29135; U29135


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    In Vitro

    In vitro activity: 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.


    Kinase Assay: The titration experiments are performed using the MSC system. In each experiment, 16 aliquots of 15 μL of geldanamycin (300 μM in 1% DMSO) are injected into 1.3 mL of protein (31 μM in 20 mMTris-HCl, pH 7.5, 1 mMEDTA) at 25 °C, and the resulting data are fit after subtracting the heats of dilution. Heats of dilution are determined in separate experiments from addition of geldanamycin into buffer and buffer into protein. No evidence for binding of DMSO in the nucleotide binding site is observed. Titration data are fit using a nonlinear least-squares curve-fitting algorithm with three floating variables: stoichiometry, binding constant (Kb) 1/Kd), and change of enthalpy of interaction (ΔH°). Dissociation constants estimated for geldanamycin binding to intact yeast Hsp90 is 1.22 μM, and for binding to Hsp90 N-terminal domain is 0.78 μM. No meaningful heat is observed with binding to the C-terminal fragment.


    Cell Assay: Exponentially growing cells are treated with Geldanamycin and at various times DNA synthesis is assessed by incorporation of bromodeoxyuridine (BrdUrd) and flow cytometric analysis. No marked difference in total cell number is noted during this time course for treated and untreated cultures. BrdUrd (10 μM) is incorporated over a 4-h incubation period at 37 °C and cells are harvested and fixed in 70% ethanol. After denaturation of the DNA with 2 N HC1, cells are incubated with an anti-BrdUrd mouse monoclonal antibody followed by a fluorescein isothiocyanate (FITC)-linked goat anti-mouse IgG. Cells are stained for 30 minutes at room temperature with propidium iodide and analysed by flow cytometry using a Coulter EPICS Profile Analyzer.

    In VivoIn mice bearing FRE/erbB-2 tumors, Geldanamycin (50 mg/kg) shows 30% inhibition on p185-associated phosphotyrosine levels.
    Animal modelFRE/erbB-2 tumors in nu/nu mice
    Formulation & DosageDissolved in DMSO; 50 mg/kg; i.p. injection
    References

    J Med Chem. 1999 Jan 28;42(2):260-6; Cancer Res. 1994 May 15;54(10):2724-30; J Med Chem. 1995 Sep 15;38(19):3806-12.


    These protocols are for reference only. InvivoChem does not independently validate these methods.

    Geldanamycin

    Overlaid crystal structures reveal the effect of 19-substitution on geldanamycin conformation and binding. Nat Chem. 2013 Apr; 5(4): 10.1038/nchem.1596.
     

    Geldanamycin

    Structures of 19-substituted geldanamycins bound in the ATP site of yeast Hsp90 as determined by protein X-ray crystallography. Nat Chem. 2013 Apr; 5(4): 10.1038/nchem.1596.  
     

    Geldanamycin

    Structures of 19-substituted geldanamycins bound in the ATP site of yeast Hsp90 as determined by protein X-ray crystallography. Nat Chem. 2013 Apr; 5(4): 10.1038/nchem.1596.


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