AZD 5582 dihydrochloride

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Cat.No. 5141 - AZD 5582 dihydrochloride | C58H78N8O8.2HCl
Description: Dimeric Smac mimetic; potent IAP inhibitor
Chemical Name: 3,3'-[2,4-Hexadiyne-1,6-diylbis[oxy[(1S,2R)-2,3-dihydro-1H-indene-2,1-diyl]]]bis[N-methyl-L-alanyl-(2S)-2-cyclohexylglycyl-L-prolinamide
Purity: ≥97% (HPLC)
Datasheet
Citations
Reviews
Literature
Pathways

Biological Activity

Dimeric Smac mimetic; potent inhibitor of X-linked (XIAP) and cellular (cIAP) inhibitor of apoptosis protein (IC50 values are 15, 15 and 21 nM for XIAP, cIAP1 and cIAP2 respectively). Binds to the BIR3 domain of XIAP to prevent interaction with caspase-9. Causes degradation of cIAP1 and cIAP2 and induces apoptosis in MDA-MB-231 breast cancer cells. Causes tumor regression in MDA-MB-231 xenograft-bearing mice.

Licensing Information

Sold with the permission of AstraZeneca UK Ltd

Technical Data

M. Wt 1088.21
Formula C58H78N8O8.2HCl
Storage Store at -20°C
Purity ≥97% (HPLC)
PubChem ID 90489014
InChI Key DAILKFFMJFAUCE-GXSVUDMFSA-N
Smiles CN[C@@H](C)C(N[C@@H]([C@H]1CCCCC1)C(N2[C@H]([C@](N[C@H]3C(C=CC=C5)=C5C[C@H]3OCC#CC#CCO[C@@H]4CC8=C(C=CC=C8)[C@@H]4N[C@@]([C@H](CCC7)N7C([C@H]([C@H]6CCCCC6)NC([C@H](C)NC)=O)=O)=O)=O)CCC2)=O)=O.Cl.Cl

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 108.82 100
water 108.82 100

Preparing Stock Solutions

The following data is based on the product molecular weight 1088.21. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 0.92 mL 4.59 mL 9.19 mL
5 mM 0.18 mL 0.92 mL 1.84 mL
10 mM 0.09 mL 0.46 mL 0.92 mL
50 mM 0.02 mL 0.09 mL 0.18 mL

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Product Datasheets

Safety Datasheet

References

References are publications that support the products' biological activity.

Hennessy et al (2013) Discovery of a novel class of dimeric Smac mimetics as potent IAP antagonists resulting in a clinical candidate for the treatment of cancer (AZD5582). J.Med.Chem. 56 9897 PMID: 24320998


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Citations for AZD 5582 dihydrochloride

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Literature in this Area

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Cancer

Cancer Research Product Guide

A collection of over 750 products for cancer research, the guide includes research tools for the study of:

  • Cancer Metabolism
  • Epigenetics in Cancer
  • Receptor Signaling
  • Cell Cycle and DNA Damage Repair
  • Angiogenesis
  • Invasion and Metastasis
Programmed Cell Death

Programmed Cell Death Poster

There are two currently recognized forms of programmed cell death: apoptosis and necroptosis. This poster summarizes the signaling pathways involved in apoptosis, necroptosis and cell survival following death receptor activation, and highlights the influence of the molecular switch, cFLIP, on cell fate.

Pathways for AZD 5582 dihydrochloride

Apoptosis

Apoptosis Signaling Pathway

Apoptosis is a physiological process for cell death that is critical during aging and development. It may also be referred to as cell 'suicide'. Apoptosis can be triggered by events both inside and outside of the cell.