Geldanamycin

For research use only.

Catalog No.S2713 Synonyms: NSC 122750

22 publications

Geldanamycin Chemical Structure

CAS No. 30562-34-6

Geldanamycin (NSC 122750) is a natural existing HSP90 inhibitor with Kd 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.

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Selleck's Geldanamycin has been cited by 22 publications

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Biological Activity

Description Geldanamycin (NSC 122750) is a natural existing HSP90 inhibitor with Kd 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. [1] 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. [2] Geldanamycin causes polyubiquitination and proteasomal degradation of the p185 receptor protein-tyrosin kinase and shows a IC50 with 70 nM. [3, 4] Geldanamycin is a typical anti-tumor reagent, shows a mean GI50 with 0.18 μM against the panel of 60 human tumor cell lines. [5]

Cell Data
Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID
A2780 cells M2DZTnBzd2yrZnXyZZRqd25iYYPzZZk> MVzDc41xd3WwZDD3ZZMh\X[jbIXheIVlKG[xcjDhcpRqeHKxbHnm[ZJifGm4ZTDhZ5Rqfmm2eTDh[4FqdnO2IHj1cYFvKG:4YYLpZY4h[2G{Y3nuc41iKGOnbHygcIlv\SCDMke4NEwhUUN3ME2zMlQh|ryP MV2xNVUyPDF2NR?=
SW620 cell MnywS5Jwf3SqIHnubIljcXSrb36gZZN{[Xl? MXvJcohq[mm2b4L5JINwdmOnboTyZZRqd25iYXfhbY5{fCCqdX3hckBkd2yxcnXjeIFtKGOjcnPpco9u[SCVV{[yNEBk\WyuIHzpcoV{NCCLQ{WwQVYvOiCwTR?= MmXlNVU3PTh6N{m=
MCF-7 cell M17Oemdzd3e2aDDpcohq[mm2aX;uJIF{e2G7 NGnxfIlKdmirYnn0c5J6KGOxbnPlcpRz[XSrb36gZYdicW6|dDDoeY1idiCkcnXhd5Qh[2GwY3XyJG1ETi15IHPlcIwhdGmwZYOsJGlEPTB;Nj61JI5O NEewW|UyPTZ3OEi3PS=>
SKBR3 cells M4f5V3Bzd2yrZnXyZZRqd25iYYPzZZk> Mny2O|IhcA>? M3;E[GFvfGmycn;sbYZmemG2aY\lJIFkfGm4aYT5JIFo[Wmwc4Sg[ZN1em:pZX6gdoVk\XC2b4Kg[IVncWOrZX70JIh2dWGwIGPLRnI{KGOnbHzzJIFnfGW{IEeyJIhzeyxiSVO1NF05NjVibl2= MlTKNlM3PDhzOEC=
MCF7 cells M2DES3Bzd2yrZnXyZZRqd25iYYPzZZk> MXK3NkBp M1jUOGFvfGmycn;sbYZmemG2aY\lJIFkfGm4aYT5JIFo[Wmwc4SgbJVu[W5iTVPGO{Bk\WyuczDlfJBz\XO|aX7nJIV{fHKxZ3XuJJJm[2WydH;yJIFnfGW{IEeyJIhzeyxiSVO1NF06Njhibl2= NUTWcmJnOjN4NEixPFA>
MDA-kb2 cells NULvW3VnTnWwY4Tpc44h[XO|YYm= NXTJT2x2OThiaB?= MWXJcohq[mm2aX;uJI9nKEiVUEmwJIlvKGi3bXHuJG1FSS2tYkKgZ4VtdHNiYYPz[ZN{\WRiYYOgdoVlfWO2aX;uJIlvKGeudXPvZ49zfGmlb3nkJJJm[2WydH;yMYRmeGWwZHXueEBtfWOrZnXyZZNmKGW6cILld5Nqd25iYX\0[ZIhOThiaILzJIJ6KG[rcnXmcJkhdHWlaX\ldoF{\SC{ZYDvdpRmeiCpZX7lJIF{e2G7LDDJR|UxRTFyIH7N M{Ple|I1QTh2OUO2
human SK-BR-3 cells MXHQdo9tcW[ncnH0bY9vKGG|c3H5 NXHjfmNtSW62aYDyc4xq\mW{YYTpeoUh[WO2aY\peJkh[WejaX7zeEBpfW2jbjDTT{1DWi1|IHPlcIx{NCCLQ{WwQVE2Njhibl2= NI\sRlEyQTh7Nki0PC=>
HUVEC cells MUfDfZRwfG:6aXRCpIF{e2G7 M1PpblczKGh? Mn\GR5l1d3SxeHnjbZR6KGGpYXnud5QhUFWYRVOgZ4VtdHNiYX\0[ZIhPzJiaILzJIJ6KE2WVDDhd5NigSxiSVO1NF0yQSCwTR?= MWqyOVI4PzB4Nx?=
human HCT116 cells MnvSS5Jwf3SqIHnubIljcXSrb36gZZN{[Xl? NIPwVFNIem:5dHigbY5pcWKrdHnvckBw\iCqdX3hckBJS1RzMU[gZ4VtdHNuIFfJOVA:OjFibl2= MVuxPFI1OzdyMx?=
K562 cell NEfTOZdIem:5dHigbY5pcWKrdHnvckBie3OjeR?= NWjVXIlOUW6qaXLpeI9zgSClb37j[Y51emG2aX;uJIFo[Wmwc4SgbJVu[W5ibHX1b4VucWFiS{W2NkBk\WyuIHzpcoV{NCCLQ{WwQVIzNjFibl2= NFrFfmcyPTZ3OEi3PS=>
HT-29 cell MmX0S5Jwf3SqIHnubIljcXSrb36gZZN{[Xl? MWnJcohq[mm2b4L5JINwdmOnboTyZZRqd25iYXfhbY5{fCCqdX3hckBkd2yxcnXjeIFtKGOjcnPpco9u[SCKVD2yPUBk\WyuIHzpcoV{NCCLQ{WwQVI1NjVibl2= Mke2NVU3PTh6N{m=
HCT116 cells NU[2TmMyWHKxbHnm[ZJifGmxbjDhd5NigQ>? NHHVS5lCdnSrcILvcIln\XKjdHn2[UBi[3Srdnn0fUBi\2GrboP0JIh2dWGwIFjDWFEyPiClZXzsd{BjgSCudX3pcoV{[2WwY3WgZZN{[XluIFXDOVA:OC5yMzFOwG0> M3PxRlIyPjB3OUe1
NCI-H1975 cells M13sdHBzd2yrZnXyZZRqd25iYYPzZZk> M{PF[mFvfGmycn;sbYZmemG2aY\lJIFkfGm4aYT5JIFo[Wmwc4SgbJVu[W5iTlPJMWgyQTd3IHPlcIx{NCCLQ{WwQVM3KG6P M1fXTlIyPzF3MU[1
human DLD1 cells NGPFfo5Iem:5dHigbY5pcWKrdHnvckBie3OjeR?= NFnYSG1Iem:5dHigbY5pcWKrdHnvckBw\iCqdX3hckBFVERzIHPlcIx{NCCJSUWwQVM4KG6P Mn;0NVgzPDN5MEO=
human A431 cells M1XqN2N6fG:2b4jpZ:Kh[XO|YYm= M{jvTlczKGh? NHvGTlBEgXSxdH;4bYNqfHliYXfhbY5{fCCqdX3hckBCPDNzIHPlcIx{KGGodHXyJFczKGi{czDifUBOXFRiYYPzZZktKEmFNUC9OFAhdk1? M2DDd|I2Ojd5ME[3
human HepG2 cells M1jPOmN6fG:2b4jpZ:Kh[XO|YYm= MY[3NkBp NXq3TlU{S3m2b4TvfIlkcXS7IHHnZYlve3RiaIXtZY4hUGWyR{KgZ4VtdHNiYX\0[ZIhPzJiaILzJIJ6KE2WVDDhd5NigSxiSVO1NF01OCCwTR?= MYeyOVI4PzB4Nx?=
human BGC823 cells NWHYN3F6S3m2b4TvfIlkyqCjc4PhfS=> MXq3NkBp MUXDfZRwfG:6aXPpeJkh[WejaX7zeEBpfW2jbjDCS2M5OjNiY3XscJMh[W[2ZYKgO|IhcHK|IHL5JG1VXCCjc4PhfUwhUUN3ME20NEBvVQ>? NIPoc4czPTJ5N{C2Oy=>
human SKBR3 cells NFn4bpREgXSxdH;4bYPDqGG|c3H5 NXTBfZM1PzJiaB?= MXfDfZRwfG:6aXPpeJkh[WejaX7zeEBpfW2jbjDTT2JTOyClZXzsd{Bi\nSncjC3NkBpenNiYomgZ4VtdHSrdHXyMYdtdyCjc4PhfUwhUUN3ME20NUBvVQ>? MVWxPVQxPTV{OB?=
human MDA-MB-231 cells MnPUR5l1d3SxeHnjxsBie3OjeR?= NHvWT204OiCq MmLWR5l1d3SxeHnjbZR6KGGpYXnud5QhcHWvYX6gUWRCNU2ELUKzNUBk\WyuczDh[pRmeiB5MjDodpMh[nliTWTUJIF{e2G7LDDJR|UxRTVyIH7N NUWxWHJEOjV{N{ewOlc>
human A549 cells MknHS5Jwf3SqIHnubIljcXSrb36gZZN{[Xl? MWfHdo94fGhiaX7obYJqfGmxbjDv[kBpfW2jbjDBOVQ6KGOnbHzzMEBIUTVyPU[0JI5O MVexPFI1OzdyMx?=
Sf9 cells NXfHS5RLTnWwY4Tpc44h[XO|YYm= NGT0O5NFcXOybHHj[Y1mdnRib3[gS20uSk:GSWDZJIZzd21iaIXtZY4h\nWubDDs[Y5ofGhiSGPQPVAh[WyyaHGg[ZhxemW|c3XkJIlvKGKjY4Xsc5ZqenW|LXnu[oVkfGWmIGPmPUBk\WyuczDh[pRmeiBzNjDodpMh[nliZnz1c5Jme2OnbnPlJJBwdGG{aYrheIlwdiCjc4PhfUwhUUN3ME23OEBvVQ>? NX3Ve41OOjR5NUG0OFE>
human U87MG cells M{GyN3Bzd2yrZnXyZZRqd25iYYPzZZk> MkfWRY51cXC{b3zp[oVz[XSrdnWgZYN1cX[rdImgZYdicW6|dDDoeY1idiCXOEfNS{Bk\WyuczygTWM2OD16OTDuUS=> NGn4cWEzOTdzNUG2OS=>
human A549 cells MXPDfZRwfG:6aXRCpIF{e2G7 MkXFO|IhcA>? MX\DfZRwfG:6aXPpeJkh[WejaX7zeEBpfW2jbjDBOVQ6KGOnbHzzJIFnfGW{IEeyJIhzeyCkeTDNWHQh[XO|YYmsJGlEPTB;OUegcm0> NWnjfFlHOjV{N{ewOlc>
mouse P19 cells MnnJR5l1d3SxeHnjxsBie3OjeR?= Ml[wNVghcA>? MkLWR5l1d3SxeHnjbZR6KGGpYXnud5QhdW:3c3WgVFE6KGOnbHzzJIFnfGW{IEG4JIhzeyxiSVO1NF0xNjFizszN NEOyV2kyPzR2MkW2OS=>
human HL7702 cells NWrWb20{S3m2b4TvfIlkyqCjc4PhfS=> M2LxNlczKGh? NIXmcndEgXSxdH;4bYNqfHliYXfhbY5{fCCqdX3hckBJVDd5MEKgZ4VtdHNiYX\0[ZIhPzJiaILzJIJ6KE2WVDDhd5NigSxiSVO1NF0xNjF2MTFOwG0> NFvTVWwzPTJ5N{C2Oy=>
human A549 cells NYXaOWI{S3m2b4TvfIlkyqCjc4PhfS=> MUGyJIRigXN? M4LYZ2N6fG:2b4jpZ4l1gSCjZ3HpcpN1KGi3bXHuJGE2PDliY3XscJMh[W[2ZYKgNkBl[Xm|IHL5JGFt[W2jclLseYUh[XO|YYmsJGlEPTB;MD6xOUDPxE1? MkXLNlM6PDd5OUS=
human A431 cells NUXyeXlkWHKxbHnm[ZJifGmxbjDhd5NigQ>? MXi3NkBp M{HZVWFvfGmycn;sbYZmemG2aY\lJIFkfGm4aYT5JIFo[Wmwc4SgbJVu[W5iQUSzNUBk\WyuczDh[pRmeiB5MjDodpMtKEmFNUC9NE4zKM7:TR?= MVKyNFY2PTJ|Nx?=
human HepG2 cells MXTDfZRwfG:6aXRCpIF{e2G7 MYDDfZRwfG:6aXPpeJkh[WejaX7zeEBpfW2jbjDI[ZBIOiClZXzsd{BjgSCPVGSgZZN{[XluIFnDOVA:OC5|IN88US=> Mnv0NlM3PTZ3NU[=
human SW480 cells NYDBc4ZKS3m2b4TvfIlkyqCjc4PhfS=> M{[zXlczKGh? M3nSXmN6fG:2b4jpZ4l1gSCjZ3HpcpN1KGi3bXHuJHNYPDhyIHPlcIx{KGGodHXyJFczKGi{czDifUBOXFRiYYPzZZktKEmFNUC9NE4{OSEQvF2= M3mx[|I2Ojd5ME[3
human LNCAP cells MoTNR5l1d3SxeHnjxsBie3OjeR?= Mn7qO|IhcA>? M{T3O2N6fG:2b4jpZ4l1gSCjZ3HpcpN1KGi3bXHuJGxPS0GSIHPlcIx{KGGodHXyJFczKGi{czDifUBOXFRiYYPzZZktKEmFNUC9NE41OyEQvF2= NUeyPWFQOjVzMEW5NlQ>
human LS174T cells NEf1fnREgXSxdH;4bYPDqGG|c3H5 MmTaR5l1d3SxeHnjbZR6KGGpYXnud5QhcHWvYX6gUHMyPzSWIHPlcIx{KGK7IF3UV{Bie3OjeTygTWM2OD1yLkS1JO69VQ>? NXm0W2tMOTdyM{SxN|U>
human HeLa cells M2[3TmN6fG:2b4jpZ:Kh[XO|YYm= MkTOO|IhcA>? MV;DfZRwfG:6aXPpeJkh[WejaX7zeEBpfW2jbjDI[WxiKGOnbHzzJIFnfGW{IEeyJIhzeyCkeTDNWHQh[XO|YYmsJGlEPTB;MD63PVgh|ryP M2nCNFI2Ojd5ME[3
rat L6 cells MnfER5l1d3SxeHnjxsBie3OjeR?= MYq3NkBp MmG5R5l1d3SxeHnjbZR6KGGpYXnud5QhemG2IFy2JINmdGy|IHHmeIVzKDd{IHjyd{BjgSCDbHHtZZIhSmy3ZTDhd5NigSxiSVO1NF02KM7:TR?= NYTaTWhKOjR3OEC1N|E>
human MCF7 cells MV3DfZRwfG:6aXRCpIF{e2G7 NU[weHJiS3m2b4TvfIlkcXS7IHHnZYlve3RiaIXtZY4hVUOINzDj[YxteyCkeTDTVmIh[XO|YYmsJGlEPTB;OT62JO69VQ>? MVixPVU3ODN3Mx?=
human MCF7 cells NFq4bpNIem:5dHigbY5pcWKrdHnvckBie3OjeR?= MVvHdo94fGhiaX7obYJqfGmxbjDv[kBpfW2jbjDNR2Y4KGOnbHzzJIFnfGW{IHThfZMh[nliU2LCJIF{e2G7LDDHTVUxRTN3Lk[g{txO NHPSWXMyPzh4OUC5PC=>
HEK293T cells MULGeY5kfGmxbjDhd5NigQ>? NFXwVlhKdmirYnn0bY9vKG:oIGTOSk1idHCqYT3pcoR2[2WmIF7GMYtieHCjQjDhZ5RqfmG2aX;uJIV5eHKnc4Pl[EBqdiCKRVuyPVNVKGOnbHzzJIJ6KGy3Y3nm[ZJie2VicnXwc5J1\XJiZ3Xu[UBie3OjeR?= M3rCVlE5PDB6N{Gz
human Jurkat cells NXXXNYVtTnWwY4Tpc44h[XO|YYm= NXrnW|RiUW6qaXLpeIlwdiCxZjDUUmYu[WyyaHGtbY5lfWOnZDDOSk1s[XCyYVKgZYN1cX[jdHnvckBmgHC{ZYPz[YQhcW5iRlHESEBl\W[rY3nlcpQhcHWvYX6gTpVzc2G2IHPlcIx{KGK7IHz1Z4ln\XKjc3WgdoVxd3K2ZYKg[4Vv\SCjc4PhfS=> MmXRNVg1ODh5MUO=
human SKBR3 cells MV;GeY5kfGmxbjDhd5NigQ>? NG\iU3UzPCCq NX7Se2pWUW6qaXLpeIlwdiCxZjDId5A6OC2vZXTpZZRm\CCKRWKyJIRm\3KjZHH0bY9vKGmwIHj1cYFvKFONQmKzJINmdGy|IHHmeIVzKDJ2IHjyd{BjgSCZZYP0[ZJvKGKub4S= Mor2NVg5OTZzMUG=

... Click to View More Cell Line Experimental Data

In vivo Geldanamycin (50 mg//kg) shows 30% inhibition on pl85-associated phosphotyrosine levels in FRE/erbB-2 mice. [6]

Protocol

Kinase Assay:

[1]

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Isothermal Titration Calorimetry (ITC) of Nucelotide Binding:

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 Research:

[2]

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  • Cell lines: A2780 human ovarian cell line
  • Concentrations: 0.001-10 μM
  • Incubation Time: 3 hours
  • Method:

    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.


    (Only for Reference)
Animal Research:

[6]

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  • Animal Models: FRE/erbB-2 tumors in nu/nu mice
  • Dosages: 50 mg/kg
  • Administration: Administered via i.p.
    (Only for Reference)

Solubility (25°C)

In vitro DMSO 36 mg/mL warmed (64.21 mM)
Water Insoluble
Ethanol Insoluble

* Please note that Selleck tests the solubility of all compounds in-house, and the actual solubility may differ slightly from published values. This is normal and is due to slight batch-to-batch variations.

Chemical Information

Molecular Weight 560.64
Formula

C29H40N2O9

CAS No. 30562-34-6
Storage powder
in solvent
Synonyms NSC 122750
Smiles CC1CC(C(C(C=C(C(C(C=CC=C(C(=O)NC2=CC(=O)C(=C(C1)C2=O)OC)C)OC)OC(=O)N)C)C)O)OC

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Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID