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Merck

A8476

17-(Allylamino)-17-demethoxygeldanamycin

≥98% (HPLC), Hsp90 inhibitor, solid

Synonyme(s) :

17-(Allylamino)geldanamycin, 17-AAG, 17-Demethoxy-17-allylamino geldanamycin, CP 127374, Geldanamycin,17-demethoxy-17-(2-propenylamino)-, NSC 330507, Tanespimycin

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A propos de cet article

Formule empirique (notation de Hill) :
C31H43N3O8
Numéro CAS:
75747-14-7
Poids moléculaire :
585.69
UNSPSC Code:
12352200
PubChem Substance ID:
329770957
NACRES:
NA.77
MDL number:
MFCD04973892
Assay:
≥98% (HPLC)
Form:
solid
Quality level:
200

Principaux documents

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Nom du produit

17-(Allylamino)-17-demethoxygeldanamycin, ≥98% (HPLC), solid

Quality Level

200

assay

≥98% (HPLC)

form

solid

solubility

DMSO: soluble, methanol: soluble

antibiotic activity spectrum

neoplastics

mode of action

enzyme | inhibits

shipped in

wet ice

storage temp.

−20°C

SMILES string

CO[C@H]1C[C@H](C)CC2=C(NCC=C)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/C31H43N3O8/c1-8-12-33-26-21-13-17(2)14-25(41-7)27(36)19(4)15-20(5)29(42-31(32)39)24(40-6)11-9-10-18(3)30(38)34-22(28(21)37)16-23(26)35/h8-11,15-17,19,24-25,27,29,33,36H,1,12-14H2,2-7H3,(H2,32,39)(H,34,38)/b11-9-,18-10+,20-15+/t17-,19+,24+,25+,27-,29+/m1/s1

InChI key

AYUNIORJHRXIBJ-TXHRRWQRSA-N

Gene Information

human ... HSP90AA1(3320), HSP90AB1(3326)

Catégories apparentées

General description

Chemical structure: benzenoid

Application

17-(Allylamino)-17-demethoxygeldanamycin (17-AAG) has been used as a heat shock protein 90 (HSP90) inhibitor:
  • to study its effects on hippocampal neurons
  • to analyze its effects on yes-associated protein (YAP) phosphorylation in adenocarcinoma human alveolar basal epithelial cells and human breast epithelial cells
  • to study its effects on lifespan extension and health in Caenorhabditis elegans

Biochem/physiol Actions

17-(Allylamino)-17-demethoxygeldanamycin (17-AAG) is a benzoquinone and is an analog of geldanamycin.
Potent inhibitor of heat shock protein 90 (Hsp90). 17-AAG is a less toxic analog than geldanamycin. It induces apoptosis and displays antitumor effects. 17-AAG inhibits the activity of oncogenic proteins such as N-ras, Ki-ras, c-Akt, and p185erB2.

Features and Benefits

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

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificats d'analyse (COA)

Lot/Batch Number
0000143657
0000143657
049M4011V
14180914
0000125286

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Consulter la Bibliothèque de documents

Cinzia Giordano et al.
Journal of clinical medicine, 8(7) (2019-07-25)
Exosomes-small membrane vesicles secreted by both normal and malignant cells upon fusion of endosomal multivesicular bodies (MVBs) with the plasma membrane-play an important role in cell-to-cell communication. During the last decade, several reports have highlighted the involvement of these nanovesicles
Olivier Boucherat et al.
Scientific reports, 7(1), 4546-4546 (2017-07-05)
Pulmonary arterial hypertension (PAH) is a vascular remodeling disease with limited therapeutic options. Although exposed to stressful conditions, pulmonary artery (PA) smooth muscle cells (PASMCs) exhibit a "cancer-like" pro-proliferative and anti-apoptotic phenotype. HDAC6 is a cytoplasmic histone deacetylase regulating multiple
Ryohei Katayama et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 20(22), 5686-5696 (2014-09-18)
The first-generation ALK tyrosine kinase inhibitor (TKI) crizotinib is a standard therapy for patients with ALK-rearranged non-small cell lung cancer (NSCLC). Several next-generation ALK-TKIs have entered the clinic and have shown promising activity in crizotinib-resistant patients. As patients still relapse
Heather K Armstrong et al.
The Prostate, 76(16), 1546-1559 (2016-10-19)
While there is compelling rationale to use heat shock protein 90 (Hsp90) inhibitors for treatment of advanced prostate cancer, agents that target the N-terminal ATP-binding site of Hsp90 have shown little clinical benefit. These N-terminal binding agents induce a heat
Mohammad A Uddin et al.
Immunobiology, 224(4), 532-538 (2019-04-27)
The tumor suppressor protein P53 is strongly involved in orchestrating cellular defenses in the diverse variety of human tissues. Anomalies to lung endothelium permeability are streaming severe consequences towards human health, often associated with fatal outcomes. Ongoing investigations suggest that
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