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A8476

Sigma-Aldrich

17-(Allylamino)-17-demethoxygeldanamycin

≥98% (HPLC), solid

Synonym(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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About This Item

Empirical Formula (Hill Notation):
C31H43N3O8
CAS Number:
Molecular Weight:
585.69
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Apoptosis, or programmed cell death (PCD), is a selective process for the removal of unnecessary, infected or transformed cells in various biological systems. As it plays a role in the homeostasis of multicellular organisms, apoptosis is tightly regulated through two principal pathways by a number of regulatory and effector molecules.

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