A8476

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
• Empirical Formula (Hill Notation): C₃₁H₄₃N₃O₈
• CAS Number: 75747-14-7
• Molecular Weight: 585.69
• MDL number: MFCD04973892
• UNSPSC Code: 12352200
• PubChem Substance ID: 329770957
• NACRES: NA.77

Properties

• 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)

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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)