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Merck
CN

A8476

Sigma-Aldrich

17-(Allylamino)-17-demethoxygeldanamycin

≥98% (HPLC), Hsp90 inhibitor, 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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关于此项目

经验公式(希尔记法):
C31H43N3O8
化学文摘社编号:
分子量:
585.69
MDL编号:
UNSPSC代码:
12352200
PubChem化学物质编号:
NACRES:
NA.77
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产品名称

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

质量水平

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

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
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历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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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
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
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
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

商品

Apoptosis regulation involves multiple pathways and molecules for cellular homeostasis.

Cell cycle phases (G1, S, G2, M) regulate cell growth, DNA replication, and division in proliferating cells.

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