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Submit ReviewAZD 5582 dihydrochloride
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)
Biological Activity for AZD 5582 dihydrochloride
AZD 5582 dihydrochloride is a 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 for AZD 5582 dihydrochloride
| M. Wt | 1088.21 |
| Formula | C58H78N8O8.2HCl |
| Storage | Store at -20°C |
| Purity | ≥97% (HPLC) |
| CAS Number | 1883545-51-4 |
| 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.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for AZD 5582 dihydrochloride
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| water | 108.82 | 100 | |
| DMSO | 108.82 | 100 |
Preparing Stock Solutions for AZD 5582 dihydrochloride
The following data is based on the product molecular weight 1088.21. Batch specific molecular weights may vary from batch to batch due to the degree 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 for AZD 5582 dihydrochloride
References for AZD 5582 dihydrochloride
References are publications that support the biological activity of the product.
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
If you know of a relevant reference for AZD 5582 dihydrochloride, please let us know.
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3 Citations for AZD 5582 dihydrochloride
Citations are publications that use Tocris products. Selected citations for AZD 5582 dihydrochloride include:
Ying et al (2022) CAMK2/CaMKII activates MLKL in short-term starvation to facilitate autophagic flux. Autophagy 18 726-744 PMID: 34282994
Zinecker et al (2017) ICG-001 affects DRP1 activity and ER stress correlative with its anti-proliferative effect. Oncotarget 8 106764 PMID: 29290987
Patrick J et al (2023) A modular CRISPR screen identifies individual and combination pathways contributing to HIV-1 latency. PLoS Pathog 19 e1011101 PMID: 36706161
Do you know of a great paper that uses AZD 5582 dihydrochloride from Tocris? Please let us know.
Reviews for AZD 5582 dihydrochloride
Average Rating: 5 (Based on 1 Review.)
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It worked good.
By
Anonymous on 07/12/2020
Assay Type: In Vitro
Species: Human
Cell Line/Tissue: colorectal cancer cells
10 µM
Literature in this Area
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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
