Key Documents

17-(Allylamino)-17-demethoxygeldanamycin

Name: 17-(Allylamino)-17-demethoxygeldanamycin
Brand: SIGMA

≥98% (HPLC), Hsp90 inhibitor, 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:

75747-14-7

Molecular Weight:

585.69

UNSPSC Code:

12352200

PubChem Substance ID:

329770957

NACRES:

NA.77

MDL number:

MFCD04973892

Assay:

≥98% (HPLC)

Form:

solid

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Properties

Product Name

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

Quality Segment

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)

Description

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 p185^erB2.

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.

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This Item	100068	100069
Sigma-Aldrich A8476 17-(Allylamino)-17-demethoxygeldanamycin	Sigma-Aldrich 100068 17-AAG	Sigma-Aldrich 100069 17-DMAG
description ≥98% (HPLC), solid	description A less toxic, potent, synthetic derivative of the ansamycin benzoquinone antibiotic Geldanamycin, Streptomyces hygroscopicus.	description A potent antitumor analog of 17-AAG that binds to the ATPase site of human Hsp90α with high affinity and displays excellent bioavailability and aqueous solubility.
assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥95% (TLC)
form solid	form medium granules (dehydrated (DCM)), solid	form solid
Quality Level 200	Quality Level 100	Quality Level 100
storage temp. −20°C	storage temp. −20°C	storage temp. −20°C
solubility methanol: soluble, DMSO: soluble	solubility DMSO: 10 mg/mL, methanol: 10 mg/mL	solubility DMSO: 5 mg/mL, water: 10 mg/mL
shipped in wet ice	shipped in wet ice	shipped in wet ice

Storage Class

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

PPE (personal protective equipment)

Eyeshields, Gloves, type N95 (US)

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