G3381

Geldanamycin from Streptomyces hygroscopicus

Name: Geldanamycin from <I>Streptomyces hygroscopicus</I>
Brand: SIGMA
Price: 663 USD

from Streptomyces hygroscopicus, ≥98% (HPLC), Nuclear hormone receptor inhibitor, powder

Synonym(s):

NSC 122750

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1 MG

$663.00

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About This Item

Empirical Formula (Hill Notation):

C₂₉H₄₀N₂O₉

CAS Number:

30562-34-6

Molecular Weight:

560.64

UNSPSC Code:

12352200

PubChem Substance ID:

329799914

NACRES:

NA.77

MDL number:

MFCD00274570

Key Documents

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Product Name

Geldanamycin from Streptomyces hygroscopicus, ≥98% (HPLC), powder

SMILES string

CO[C@H]1C[C@H](C)CC2=C(OC)C(=O)C=C(NC(=O)\C(C)=C\C=C[C@H](OC)[C@@H](OC(N)=O)\C(C)=C\[C@H](C)[C@H]1O)C2=O

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

InChI key

QTQAWLPCGQOSGP-KSRBKZBZSA-N

sterility

non-sterile

assay

≥98% (HPLC)

form

powder

color

yellow to orange

solubility

DMSO: soluble

antibiotic activity spectrum

neoplastics

mode of action

enzyme | inhibits

storage temp.

−20°C

Quality Level

300

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Show Differences

1 of 4

This Item	SML1277	SML1278	R0395
Sigma-Aldrich G3381 Geldanamycin from Streptomyces hygroscopicus	Sigma-Aldrich SML1277 Geldanamycin-FITC	Sigma-Aldrich SML1278 Geldanamycin Ready Made Solution	Sigma-Aldrich R0395 Rapamycin from Streptomyces hygroscopicus
assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay -	assay ≥95% (HPLC)
form powder	form powder	form DMSO solution	form powder
Quality Level 300	Quality Level 200	Quality Level 200	Quality Level 300
storage temp. −20°C	storage temp. −20°C	storage temp. −20°C	storage temp. −20°C
solubility DMSO: soluble	solubility DMSO: soluble 5 mg/mL	solubility -	solubility ethanol: 2 mM, DMSO: soluble
color yellow to orange	color yellow to yellow-orange	color -	color off-white

Biochem/physiol Actions

Geldanamycin is a potent antitumor antibiotic active at nanomolar concentration against 60 cell lines.

Geldanamycin is a potent antitumor antibiotic active at nanomolar concentration against 60 cell lines.
Geldanamycin binds specifically to the heat shock protein Hsp90 and to its endoplasmic reticulum homologue GP96, and thus interferes with conformational maturation of proteins and the cellular stress response. In addition, Geldanamycin is a potent inhibitor of the nuclear hormone receptor family.

Features and Benefits

This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound is featured on the Met page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

General description

Chemical structure: benzenoid

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Destabilization of the epidermal growth factor receptor (EGFR) by a peptide that inhibits EGFR binding to heat shock protein 90 and receptor dimerization.

Aarif Ahsan et al.

The Journal of biological chemistry, 288(37), 26879-26886 (2013-07-31)

An eight-amino acid segment is known to be responsible for the marked difference in the rates of degradation of the EGF receptor (ErbB1) and ErbB2 upon treatment of cells with the Hsp90 inhibitor geldanamycin. We have scrambled the first six

Heat shock protein-90-beta facilitates enterovirus 71 viral particles assembly.

Robert Y L Wang et al.

Virology, 443(2), 236-247 (2013-05-29)

Molecular chaperones are reported to be crucial for virus propagation, but are not yet addressed in Human Enterovirus 71 (EV71). Here we describe the specific association of heat shock protein-90-beta (Hsp90β), but not alpha form (Hsp90α), with EV71 viral particles

Targeting heat-shock-protein 90 (Hsp90) by natural products: geldanamycin, a show case in cancer therapy.

Jana Franke et al.

Natural product reports, 30(10), 1299-1323 (2013-08-13)

Covering 2005 to 2013. In this review recent progress in the development of heat shock proteins (Hsp90) in oncogenesis is illuminated. Particular emphasis is put on inhibitors such as geldanamycin and analogues that serve as a natural product show case.

Activation of eNOS in endothelial cells exposed to ionizing radiation involves components of the DNA damage response pathway.

Masaki Nagane et al.

Biochemical and biophysical research communications, 456(1), 541-546 (2014-12-17)

In this study, the involvement of ataxia telangiectasia mutated (ATM) kinase and heat shock protein 90 (HSP90) in endothelial nitric oxide synthase (eNOS) activation was investigated in X-irradiated bovine aortic endothelial cells. The activity of nitric oxide synthase (NOS) and

Design of novel Geldanamycin analogue hsp90 alpha-inhibitor in silico for breast cancer therapy.

Sailendra Mahanta et al.

Medical hypotheses, 81(3), 463-469 (2013-07-19)

Geldanamycin, which is one of the most potent and effective hsp90 alpha inhibitor until date, is normally used to target breast cancer. Inhibition of hsp90 alpha leads to the degradation of client proteins involved in the initiation and progress of

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