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安全信息

A8476

Sigma-Aldrich

17-(Allylamino)-17-demethoxygeldanamycin

≥98% (HPLC), solid

别名:

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

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About This Item

经验公式（希尔记法）:
C31H43N3O8
CAS号:
75747-14-7
分子量:
585.69
MDL编号:
MFCD04973892
UNSPSC代码:
12352200
PubChem化学物质编号:
329770957
NACRES:
NA.77

质量水平

200

方案

≥98% (HPLC)

表单

solid

溶解性

DMSO: soluble
methanol: soluble

抗生素抗菌谱

neoplastics

作用机制

enzyme | inhibits

运输

wet ice

储存温度

−20°C

SMILES字符串

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

基因信息

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

一般描述

Chemical structure: benzenoid

应用

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

生化/生理作用

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.
17-(Allylamino)-17-demethoxygeldanamycin (17-AAG) is a benzoquinone and is an analog of geldanamycin.

特点和优势

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.

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)

法规信息

新产品

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
0000143657
0000143657
049M4011V
14180914
0000125286

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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
Encarnación Medina-Carmona et al.
Human molecular genetics, 26(18), 3531-3544 (2017-09-16)
Human proteins are vulnerable towards disease-associated single amino acid replacements affecting protein stability and function. Interestingly, a few studies have shown that consensus amino acids from mammals or vertebrates can enhance protein stability when incorporated into human proteins. Here, we
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
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
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