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 MkjpVJJwdGmoZYLheIlwdiCjc4PhfS=> NGfWcFBEd22yb4Xu[EB4[XNiZY\hcJVifGWmIH\vdkBidnSrcILvcIln\XKjdHn2[UBi[3Srdnn0fUBi\2GrboP0JIh2dWGwIH;2ZZJq[W5iY3HyZ4lvd22jIHPlcIwhdGmwZTDBNlc5OCxiSVO1NF0{NjRizszN NEf0PGgyOTVzNEG0OS=>
SW620 cell MkXnS5Jwf3SqIHnubIljcXSrb36gZZN{[Xl? NIX2NJpKdmirYnn0c5J6KGOxbnPlcpRz[XSrb36gZYdicW6|dDDoeY1idiClb3zvdoVkfGGuIHPhdoNqdm:vYTDTW|YzOCClZXzsJIxqdmW|LDDJR|UxRTZwMjDuUS=> NWjIbXdZOTV4NUi4O|k>
MCF-7 cell MmLKS5Jwf3SqIHnubIljcXSrb36gZZN{[Xl? NEj0NnZKdmirYnn0c5J6KGOxbnPlcpRz[XSrb36gZYdicW6|dDDoeY1idiCkcnXhd5Qh[2GwY3XyJG1ETi15IHPlcIwhdGmwZYOsJGlEPTB;Nj61JI5O NX3hWlRIOTV4NUi4O|k>
SKBR3 cells MUXQdo9tcW[ncnH0bY9vKGG|c3H5 MoDWO|IhcA>? NGLrSItCdnSrcILvcIln\XKjdHn2[UBi[3Srdnn0fUBi\2GrboP0JIV{fHKxZ3XuJJJm[2WydH;yJIRm\mmlaXXueEBpfW2jbjDTT2JTOyClZXzsd{Bi\nSncjC3NkBpenNuIFnDOVA:QC53IH7N M4G2[FI{PjR6MUiw
MCF7 cells NYLwOFRoWHKxbHnm[ZJifGmxbjDhd5NigQ>? M1TmNFczKGh? MnjDRY51cXC{b3zp[oVz[XSrdnWgZYN1cX[rdImgZYdicW6|dDDoeY1idiCPQ1[3JINmdGy|IHX4dJJme3Orbneg[ZN1em:pZX6gdoVk\XC2b4KgZYZ1\XJiN{KgbJJ{NCCLQ{WwQVkvQCCwTR?= Mny0NlM3PDhzOEC=
MDA-kb2 cells MlfLSpVv[3Srb36gZZN{[Xl? NYDGeJZjOThiaB?= NVXENZByUW6qaXLpeIlwdiCxZjDIV3A6OCCrbjDoeY1idiCPRFGtb4IzKGOnbHzzJIF{e2W|c3XkJIF{KHKnZIXjeIlwdiCrbjDncJVkd2OxcoTpZ49q\CC{ZXPldJRwei2mZYDlcoRmdnRibIXjbYZmemG|ZTDlfJBz\XO|aX;uJIFnfGW{IEG4JIhzeyCkeTDmbZJm\my7IHz1Z4ln\XKjc3WgdoVxd3K2ZYKg[4Vv\SCjc4PhfUwhUUN3ME2xNEBvVQ>? MUGyOFk5PDl|Nh?=
human SK-BR-3 cells M4e0[XBzd2yrZnXyZZRqd25iYYPzZZk> NITpRWVCdnSrcILvcIln\XKjdHn2[UBi[3Srdnn0fUBi\2GrboP0JIh2dWGwIGPLMWJTNTNiY3XscJMtKEmFNUC9NVUvQCCwTR?= Mkn3NVk5QTZ6NEi=
HUVEC cells MU\DfZRwfG:6aXRCpIF{e2G7 M1zVS|czKGh? MV3DfZRwfG:6aXPpeJkh[WejaX7zeEBJXV[HQzDj[YxteyCjZoTldkA4OiCqcoOgZpkhVVSWIHHzd4F6NCCLQ{WwQVE6KG6P NXvmWGtqOjV{N{ewOlc>
human HCT116 cells MX7Hdo94fGhiaX7obYJqfGmxbjDhd5NigQ>? MlPDS5Jwf3SqIHnubIljcXSrb36gc4YhcHWvYX6gTGNVOTF4IHPlcIx{NCCJSUWwQVIyKG6P NWXH[JlIOTh{NEO3NFM>
K562 cell NV3UcFFCT3Kxd4ToJIlvcGmkaYTpc44h[XO|YYm= Mn3XTY5pcWKrdH;yfUBkd26lZX70doF1cW:wIHHnZYlve3RiaIXtZY4hdGW3a3XtbYEhUzV4MjDj[YxtKGyrbnXzMEBKSzVyPUKyMlEhdk1? MX:xOVY2QDh5OR?=
HT-29 cell NFK5WmlIem:5dHigbY5pcWKrdHnvckBie3OjeR?= NU[2RVJ4UW6qaXLpeI9zgSClb37j[Y51emG2aX;uJIFo[Wmwc4SgbJVu[W5iY3;sc5Jm[3SjbDDjZZJkcW6xbXGgTHQuOjliY3XscEBtcW6nczygTWM2OD1{ND61JI5O MXGxOVY2QDh5OR?=
HCT116 cells M4X4OnBzd2yrZnXyZZRqd25iYYPzZZk> MYfBcpRqeHKxbHnm[ZJifGm4ZTDhZ5Rqfmm2eTDh[4FqdnO2IHj1cYFvKEiFVEGxOkBk\WyuczDifUBtfW2rbnXzZ4Vv[2ViYYPzZZktKEWFNUC9NE4xOyEQvF2= M4jjRlIyPjB3OUe1
NCI-H1975 cells NV\HOZVHWHKxbHnm[ZJifGmxbjDhd5NigQ>? MX3BcpRqeHKxbHnm[ZJifGm4ZTDhZ5Rqfmm2eTDh[4FqdnO2IHj1cYFvKE6FST3INVk4PSClZXzsd{whUUN3ME2zOkBvVQ>? NFW4TFAzOTdzNUG2OS=>
human DLD1 cells NWfYfItYT3Kxd4ToJIlvcGmkaYTpc44h[XO|YYm= NUT1NmNDT3Kxd4ToJIlvcGmkaYTpc44hd2ZiaIXtZY4hTEyGMTDj[YxteyxiR1m1NF0{PyCwTR?= MojZNVgzPDN5MEO=
human A431 cells MYHDfZRwfG:6aXRCpIF{e2G7 M3nvVFczKGh? NGfCRXlEgXSxdH;4bYNqfHliYXfhbY5{fCCqdX3hckBCPDNzIHPlcIx{KGGodHXyJFczKGi{czDifUBOXFRiYYPzZZktKEmFNUC9OFAhdk1? MX6yOVI4PzB4Nx?=
human HepG2 cells Mlm0R5l1d3SxeHnjxsBie3OjeR?= NIX6c404OiCq MYTDfZRwfG:6aXPpeJkh[WejaX7zeEBpfW2jbjDI[ZBIOiClZXzsd{Bi\nSncjC3NkBpenNiYomgUXRVKGG|c3H5MEBKSzVyPUSwJI5O M4LadVI2Ojd5ME[3
human BGC823 cells NXPvN|ltS3m2b4TvfIlkyqCjc4PhfS=> M{PnOFczKGh? NITZWnhEgXSxdH;4bYNqfHliYXfhbY5{fCCqdX3hckBDT0N6MkOgZ4VtdHNiYX\0[ZIhPzJiaILzJIJ6KE2WVDDhd5NigSxiSVO1NF01OCCwTR?= M3fZcVI2Ojd5ME[3
human SKBR3 cells M1TSWmN6fG:2b4jpZ:Kh[XO|YYm= M1fhN|czKGh? M3vIWWN6fG:2b4jpZ4l1gSCjZ3HpcpN1KGi3bXHuJHNMSlJ|IHPlcIx{KGGodHXyJFczKGi{czDifUBk\WyudHn0[ZIu\2yxIHHzd4F6NCCLQ{WwQVQyKG6P M4S2N|E6PDB3NUK4
human MDA-MB-231 cells M{TpdmN6fG:2b4jpZ:Kh[XO|YYm= MWq3NkBp MmjGR5l1d3SxeHnjbZR6KGGpYXnud5QhcHWvYX6gUWRCNU2ELUKzNUBk\WyuczDh[pRmeiB5MjDodpMh[nliTWTUJIF{e2G7LDDJR|UxRTVyIH7N M325R|I2Ojd5ME[3
human A549 cells M3TpRmdzd3e2aDDpcohq[mm2aX;uJIF{e2G7 MnviS5Jwf3SqIHnubIljcXSrb36gc4YhcHWvYX6gRVU1QSClZXzsd{whT0l3ME22OEBvVQ>? NVfV[Id2OTh{NEO3NFM>
Sf9 cells NV;HfFRPTnWwY4Tpc44h[XO|YYm= M1vjeWRqe3CuYXPlcYVvfCCxZjDHUU1DV0SLUGmg[pJwdSCqdX3hckBnfWyuIHzlcod1cCCKU2C5NEBidHCqYTDlfJBz\XO|ZXSgbY4h[mGldXzveolzfXNvaX7m[YN1\WRiU3[5JINmdGy|IHHmeIVzKDF4IHjyd{BjgSCobIXvdoV{[2WwY3WgdI9t[XKrenH0bY9vKGG|c3H5MEBKSzVyPUe0JI5O M1zaXFI1PzVzNESx
human U87MG cells MmqwVJJwdGmoZYLheIlwdiCjc4PhfS=> NXXt[JpESW62aYDyc4xq\mW{YYTpeoUh[WO2aY\peJkh[WejaX7zeEBpfW2jbjDVPFdOTyClZXzsd{whUUN3ME24PUBvVQ>? M2rYclIyPzF3MU[1
human A549 cells NVHiXpQ6S3m2b4TvfIlkyqCjc4PhfS=> NV3SV3Z1PzJiaB?= MX;DfZRwfG:6aXPpeJkh[WejaX7zeEBpfW2jbjDBOVQ6KGOnbHzzJIFnfGW{IEeyJIhzeyCkeTDNWHQh[XO|YYmsJGlEPTB;OUegcm0> MnzONlUzPzdyNke=
mouse P19 cells NIL3V3FEgXSxdH;4bYPDqGG|c3H5 NYfRWmxCOThiaB?= MoT2R5l1d3SxeHnjbZR6KGGpYXnud5QhdW:3c3WgVFE6KGOnbHzzJIFnfGW{IEG4JIhzeyxiSVO1NF0xNjFizszN NYjTV5ViOTd2NEK1OlU>
human HL7702 cells NWnaSW45S3m2b4TvfIlkyqCjc4PhfS=> M1TPU|czKGh? NFrRWJhEgXSxdH;4bYNqfHliYXfhbY5{fCCqdX3hckBJVDd5MEKgZ4VtdHNiYX\0[ZIhPzJiaILzJIJ6KE2WVDDhd5NigSxiSVO1NF0xNjF2MTFOwG0> M4H4XlI2Ojd5ME[3
human A549 cells MV7DfZRwfG:6aXRCpIF{e2G7 NWfBdo9mOiCmYYnz MoK0R5l1d3SxeHnjbZR6KGGpYXnud5QhcHWvYX6gRVU1QSClZXzsd{Bi\nSncjCyJIRigXNiYomgRYxidWG{Qnz1[UBie3OjeTygTWM2OD1yLkG1JO69VQ>? NGHEcZQzOzl2N{e5OC=>
human A431 cells M2fUO3Bzd2yrZnXyZZRqd25iYYPzZZk> MYi3NkBp MlHhRY51cXC{b3zp[oVz[XSrdnWgZYN1cX[rdImgZYdicW6|dDDoeY1idiCDNEOxJINmdGy|IHHmeIVzKDd{IHjyd{whUUN3ME2wMlIh|ryP NVLxemhWOjB4NUWyN|c>
human HepG2 cells NE\qeWREgXSxdH;4bYPDqGG|c3H5 NHn5OINEgXSxdH;4bYNqfHliYXfhbY5{fCCqdX3hckBJ\XCJMjDj[YxteyCkeTDNWHQh[XO|YYmsJGlEPTB;MD6zJO69VQ>? NYHETohWOjN4NU[1OVY>
human SW480 cells NUTyXW5DS3m2b4TvfIlkyqCjc4PhfS=> MUK3NkBp M2qwPGN6fG:2b4jpZ4l1gSCjZ3HpcpN1KGi3bXHuJHNYPDhyIHPlcIx{KGGodHXyJFczKGi{czDifUBOXFRiYYPzZZktKEmFNUC9NE4{OSEQvF2= NI\vbGozPTJ5N{C2Oy=>
human LNCAP cells NGq0R5REgXSxdH;4bYPDqGG|c3H5 MW[3NkBp M{nCXGN6fG:2b4jpZ4l1gSCjZ3HpcpN1KGi3bXHuJGxPS0GSIHPlcIx{KGGodHXyJFczKGi{czDifUBOXFRiYYPzZZktKEmFNUC9NE41OyEQvF2= NGnheZUzPTFyNUmyOC=>
human LS174T cells MVfDfZRwfG:6aXRCpIF{e2G7 MljqR5l1d3SxeHnjbZR6KGGpYXnud5QhcHWvYX6gUHMyPzSWIHPlcIx{KGK7IF3UV{Bie3OjeTygTWM2OD1yLkS1JO69VQ>? M37nUFE4ODN2MUO1
human HeLa cells MWfDfZRwfG:6aXRCpIF{e2G7 MVG3NkBp M2PGSGN6fG:2b4jpZ4l1gSCjZ3HpcpN1KGi3bXHuJGhmVGFiY3XscJMh[W[2ZYKgO|IhcHK|IHL5JG1VXCCjc4PhfUwhUUN3ME2wMlc6QCEQvF2= NInyO5kzPTJ5N{C2Oy=>
rat L6 cells M1PJOGN6fG:2b4jpZ:Kh[XO|YYm= NVzFPYRyPzJiaB?= NXXUfnRQS3m2b4TvfIlkcXS7IHHnZYlve3RicnH0JGw3KGOnbHzzJIFnfGW{IEeyJIhzeyCkeTDBcIFu[XJiQnz1[UBie3OjeTygTWM2OD13IN88US=> M3zGeVI1PThyNUOx
human MCF7 cells M3;rdWN6fG:2b4jpZ:Kh[XO|YYm= NHHrNHREgXSxdH;4bYNqfHliYXfhbY5{fCCqdX3hckBOS0Z5IHPlcIx{KGK7IGPSRkBie3OjeTygTWM2OD17Lk[g{txO MXOxPVU3ODN3Mx?=
human MCF7 cells MnLNS5Jwf3SqIHnubIljcXSrb36gZZN{[Xl? NGS2cVZIem:5dHigbY5pcWKrdHnvckBw\iCqdX3hckBOS0Z5IHPlcIx{KGGodHXyJIRigXNiYomgV3JDKGG|c3H5MEBIUTVyPUO1MlYh|ryP M3rOZVE4QDZ7MEm4
HEK293T cells NGDCOW9HfW6ldHnvckBie3OjeR?= NWS3VmhNUW6qaXLpeIlwdiCxZjDUUmYu[WyyaHGtbY5lfWOnZDDOSk1s[XCyYVKgZYN1cX[jdHnvckBmgHC{ZYPz[YQhcW5iSFXLNlk{XCClZXzsd{BjgSCudXPp[oVz[XOnIILldI9zfGW{IHflcoUh[XO|YYm= NXrvOWdPOTh2MEi3NVM>
human Jurkat cells MVnGeY5kfGmxbjDhd5NigQ>? NVvYVos1UW6qaXLpeIlwdiCxZjDUUmYu[WyyaHGtbY5lfWOnZDDOSk1s[XCyYVKgZYN1cX[jdHnvckBmgHC{ZYPz[YQhcW5iRlHESEBl\W[rY3nlcpQhcHWvYX6gTpVzc2G2IHPlcIx{KGK7IHz1Z4ln\XKjc3WgdoVxd3K2ZYKg[4Vv\SCjc4PhfS=> M3;pcFE5PDB6N{Gz
human SKBR3 cells MYDGeY5kfGmxbjDhd5NigQ>? NEixOFYzPCCq M37jN2lvcGmkaYTpc44hd2ZiSIPwPVAudWWmaXH0[YQhUEWUMjDk[Ydz[WSjdHnvckBqdiCqdX3hckBUU0KUMzDj[YxteyCjZoTldkAzPCCqcoOgZpkhX2W|dHXyckBjdG:2 NFPRNIwyQDhzNkGxNS=>

... 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