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SML2900

Sigma-Aldrich

AZD5582

≥98% (HPLC)

Synonym(s):

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], AZD 5582, AZD-5582

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About This Item

Empirical Formula (Hill Notation):
C58H78N8O8
CAS Number:
1258392-53-8
Molecular Weight:
1015.29
MDL number:
MFCD28411397
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

storage temp.

−20°C

SMILES string

CN[C@@H](C)C(N[C@@H](C1CCCCC1)C(N2[C@H](C(N[C@H]3C4=C(C=CC=C4)C[C@H]3OCC#CC#CCO[C@@H]5CC6=C(C=CC=C6)[C@@H]5NC([C@@H]7CCCN7C([C@H](C8CCCCC8)NC([C@H](C)NC)=O)=O)=O)=O)CCC2)=O)=O

Biochem/physiol Actions

AZD5582 is a divalent AVPI motif-based Smac (DIABLO) mimetic (SMC) that acts a potent apoptosis protein repeat (BIR) domain-targeting antagonist against inhibitor of apoptosis proteins (IAPs) cIAP1/2 (BIR3 IC50 = 15/21 nM against 2.5 nM AbuRPFK-5FAM) and XIAP (BIR2/3 IC50 = 21/15 nM). AZD5582 abolishes cellular XIAP-caspase-9 interaction (1 μM, 4 hrs), induces cIAP1/2 degradation (EC50 = 0.1 nM, 1 hr) and apoptosis (GI50 <60 pM, 48 hrs) in MDA-MB-231 breast cancer cultures. AZD5582 causes substantial tumor regression by inducing cIAP1 degradation and apoptosis in tumor cells in MDA-MB-231 xenograft-bearing mice in vivo (3.0 mg/kg/wk i.v.).

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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Edward J Hennessy et al.
Journal of medicinal chemistry, 56(24), 9897-9919 (2013-12-11)
A series of dimeric compounds based on the AVPI motif of Smac were designed and prepared as antagonists of the inhibitor of apoptosis proteins (IAPs). Optimization of cellular potency, physical properties, and pharmacokinetic parameters led to the identification of compound
Jai-Hee Moon et al.
Oncotarget, 6(29), 26895-26908 (2015-09-01)
Inhibitor of apoptosis proteins (IAPs) plays an important role in controlling cancer cell survival. IAPs have therefore attracted considerable attention as potential targets in anticancer therapy. In this study, we investigated the anti-tumor effect of AZD5582, a novel small-molecule IAP
Inbar Shlomovitz et al.
The FEBS journal, 286(3), 507-522 (2018-12-24)
Interleukin-33 (IL-33) is a pro-inflammatory cytokine that plays a significant role in inflammatory diseases by activating immune cells to induce type 2 immune responses upon its release. Although IL-33 is known to be released during tissue damage, its exact release
Lorenz Kadletz et al.
Acta oto-laryngologica, 137(3), 320-325 (2016-10-16)
On the one hand, AZD5582, an inhibitor of inhibitor of apoptosis family proteins (IAP), leads to cellular growth arrest and induction of apoptosis in head and neck squamous cell carcinoma (HNSCC) cell lines. On the other hand, it is a
Shawn T Beug et al.
Nature communications, 8 (2017-02-16)
Small-molecule inhibitor of apoptosis (IAP) antagonists, called Smac mimetic compounds (SMCs), sensitize tumours to TNF-α-induced killing while simultaneously blocking TNF-α growth-promoting activities. SMCs also regulate several immunomodulatory properties within immune cells. We report that SMCs synergize with innate immune stimulants
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