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AZD5582, 含 2 的杆状病毒 IAP 重复序列拮抗剂；含 3 的杆状病毒 IAP 重复序列拮抗剂；X-连锁细胞凋亡抑制因子拮抗剂

XIAP 选择性抑制剂 | 拮抗剂
COA COA
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货号 (SKU) 包装规格 是否现货 价格 数量
A413749-5mg
 5mg 现货 Stock Image
A413749-10mg
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A413749-25mg
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Apoptosis (7108) baculoviral IAP repeat containing 2 Antagonist (5) baculoviral IAP repeat containing 3 Antagonist (4) IAP (40) Intrinsic Pathway (1438) X-linked inhibitor of apoptosis Antagonist (5)
main product photo

基本描述

英文别名 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
规格或纯度 Moligand™, ≥98%
英文名称 AZD5582
生化机理 新型小分子 IAP 抑制剂 AZD5582 能与 cIAP1、cIAP2 和 XIAP 的 BIR3 结构域有效结合，IC50 值分别为 15、21 和 15
储存温度 -20°C储存,充氩
运输条件 超低温冰袋运输
作用类型 拮抗剂
作用机制 含 2 的杆状病毒 IAP 重复序列拮抗剂；含 3 的杆状病毒 IAP 重复序列拮抗剂；X-连锁细胞凋亡抑制因子拮抗剂
产品介绍

AZD5582 是 IAP 拮抗剂，可以有效与 cIAP1，cIAP2 和 XIAP 的 BIR3 结构域结合, IC50 值分别为 15，21，15 nM。AZD5582 诱导凋亡 (apoptosis)。

Information

AZD5582, a novel small-molecule IAP inhibitor, binds potently to the BIR3 domains ofcIAP1,cIAP2, andXIAPwithIC50values of 15, 21, and 15


Targets

cIAP1 (Cell-free assay); XIAP (Cell-free assay); cIAP2 (Cell-free assay) 15 nM; 15 nM; 21 nM


In vitro

Human pancreatic cancer cells display different sensitivities to the synthetic IAP antagonist, AZD5582. Treating human pancreatic cancer cells with AZD5582 differentially induces apoptosis, dependent on the expression of p-Akt and p-XIAP. It targets cIAP1 to induce TNF-α-induced apoptosis. AZD5582 induces a decrease of Mcl-1 protein, a member of the Bcl-2 family, but not that of Bcl-2 and Bcl-xL. HNSCC (head and neck squamous cell carcinoma) cell lines SCC25, Cal27, and FaDu show a dose-dependent cytotoxic effect after treatment with AZD5582.


In vivo

After AZD5582 treatment, tumor growth and weight decrease, whereas cleaved caspase 3 expression increases in Panc-1-derived xenograft model. When administered intravenously to MDA-MB-231 xenograft-bearing mice, AZD5582 results in cIAP1 degradation and caspase-3 cleavage within tumor cells and causes substantial tumor regressions following two weekly doses of 3.0 mg/kg. Following a modest 0.5 mg/kg intravenous bolus dose of AZD5582 in mice, unbound plasma levels remain above the concentrations at which apoptosis induction and cell death are observed in MDA-MB-231 cells over the course of several hours. Although cIAP1 degradation happens very quickly upon exposure to AZD5582 apoptosis induction (as measured by the amount of cleaved caspase-3) takes longer to reach a maximal effect. A single agent AZD5582 does not exhibit broad-based cytotoxicity but instead should be employed in selected tumor settings expected to be sensitive to IAP inhibitors or in rational combinations with other targeted therapies. The dihydrochloride salt of AZD5582 has sufficient aqueous solubility (>7 mg/mL at pH 4−6) to enable formulation for intravenous administration at the projected efficacious doses. With respect to chemical stability, AZD5582 is found to be photostable and hydrolytically stable between pH 4−6, although some amide hydrolysis is observed under strongly acidic (pH < 1) and basic (pH > 8) conditions. In addition, the compound is stable in the plasma of multiple species, with no compound degradation observed after several hours under physiological conditions.


Cell Research(from reference)

Cell lines：The human pancreatic cancer cell lines including BxPC-3, Miapaca-2, Panc-1, Panc0813, PL45, Capan-1, Capan-2 and AsPC-1 

Concentrations：0, 0.01, 0.1, 0.5 μM 

Incubation Time：72 h 


Product Describtion:

AZD5582 is an antagonist of the inhibitor of apoptosis proteins (IAPs), which binds to the BIR3 domains cIAP1, cIAP2, and XIAP with IC50s of 15, 21, and 15 nM, respectively. AZD5582 induces apoptosis
纯度 ≥98%

产品属性

IC50 XIAP, IC50: 15 nM
ALogP 5.317
hba_count 8
HBD Count 6
Rotatable Bond 21

关联靶点（人）

BIRC2 Tchem 杆状病毒 IAP 重复蛋白 2(Baculoviral IAP repeat-containing protein 2) (3 活性数据)
活性类型 活性值-log(M) 作用机制 期刊 参考文献(PubMed IDs)
BIRC3 Tchem 杆状病毒 IAP 重复蛋白 3(Baculoviral IAP repeat-containing protein 3) (2 活性数据)
活性类型 活性值-log(M) 作用机制 期刊 参考文献(PubMed IDs)
XIAP Tchem E3 泛素蛋白连接酶 XIAP(E3 ubiquitin-protein ligase XIAP) (3 活性数据)
活性类型 活性值-log(M) 作用机制 期刊 参考文献(PubMed IDs)
ABL1 Tclin Tyrosine-protein kinase ABL (18331 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
GSK3B Tclin Glycogen synthase kinase-3 beta (11785 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
CSNK1D Tchem Casein kinase I delta (4546 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
CDK2 Tchem Cyclin-dependent kinase 2 (9050 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
AURKA Tchem Serine/threonine-protein kinase Aurora-A (10240 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
XIAP Tchem Inhibitor of apoptosis protein 3 (3673 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
Caco-2 (12174 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
U2OS (164939 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
HepG2 (196354 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
MDA-MB-231 (73002 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
BT-549 (31254 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
BIRC3 Tchem Baculoviral IAP repeat-containing protein 3 (320 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
BIRC2 Tchem Baculoviral IAP repeat-containing protein 2 (984 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
BRD4 Tchem Bromodomain-containing protein 4 (13122 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
TRIM24 Tchem Transcription intermediary factor 1-alpha (2087 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
BRPF1 Tchem Peregrin (2217 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
HEK-293T (167025 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID

关联靶点（其它种属）

Mapk1 MAP kinase ERK2 (650 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
Hdac6 Histone deacetylase 6 (222 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
Fgfr3 Fibroblast growth factor receptor 3 (21 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
Mus musculus (284745 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
Rattus norvegicus (775804 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
rep Replicase polyprotein 1ab (378 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
SARS-CoV-2 (38078 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID

作用机制

作用机制 Action Type target ID Target Name Target Type Target Organism Binding Site Name 参考文献

名称和识别符

PubChem SID 488201441
分子类型 未知
IIUPAC Name (2S)-1-[(2S)-2-cyclohexyl-2-[[(2S)-2-(methylamino)propanoyl]amino]acetyl]-N-[(1S,2R)-2-[6-[[(1S,2R)-1-[[(2S)-1-[(2S)-2-cyclohexyl-2-[[(2S)-2-(methylamino)propanoyl]amino]acetyl]pyrrolidine-2-carbonyl]amino]-2,3-dihydro-1H-inden-2-yl]oxy]hexa-2,4-diynoxy]-2,3-dihydro-1H-inden-1-yl]pyrrolidine-2-carboxamide
INCHI 1S/C58H78N8O8/c1-37(59-3)53(67)61-49(39-21-9-7-10-22-39)57(71)65-31-19-29-45(65)55(69)63-51-43-27-15-13-25-41(43)35-47(51)73-33-17-5-6-18-34-74-48-36-42-26-14-16-28-44(42)52(48)64-56(70)46-30-20-32-66(46)58(72)50(40-23-11-8-12-24-40)62-54(68)38(2)60-4/h13-16,25-28,37-40,45-52,59-60H,7-12,19-24,29-36H2,1-4H3,(H,61,67)(H,62,68)(H,63,69)(H,64,70)/t37-,38-,45-,46-,47+,48+,49-,50-,51-,52-/m0/s1
InChi Key WLMCRYCCYXHPQF-ZVMUOSSASA-N
Smiles CC(C(=O)NC(C1CCCCC1)C(=O)N2CCCC2C(=O)NC3C(CC4=CC=CC=C34)OCC#CC#CCOC5CC6=CC=CC=C6C5NC(=O)C7CCCN7C(=O)C(C8CCCCC8)NC(=O)C(C)NC)NC
Isomeric SMILES C[C@@H](C(=O)N[C@@H](C1CCCCC1)C(=O)N2CCC[C@H]2C(=O)N[C@@H]3[C@@H](CC4=CC=CC=C34)OCC#CC#CCO[C@@H]5CC6=CC=CC=C6[C@@H]5NC(=O)[C@@H]7CCCN7C(=O)[C@H](C8CCCCC8)NC(=O)[C@H](C)NC)NC
MeSH Entry Terms AZD5582;N,N'-(2,2'-(hexa-2,4-diyne-1,6-diylbis(oxy))bis(2,3-dihydro-1H-indene-2,1-diyl))bis(1-(2-cyclohexyl-2-(2-(methylamino)propanamido)acetyl)pyrrolidine-2-carboxamide)
分子量 1015.29
Reaxy-Rn 51753401
Reaxys-RN link address https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=51753401&ln=

化学和物理性质

溶解性 Solubility (25°C) In vitro Water: 100 mg/mL (98.49 mM);    
敏感性 对光线敏感
Water(mg / mL) Max Solubility 100
Water(mM) Max Solubility 98.49402634
分子量 1015.300 g/mol
XLogP3 5.900
氢键供体数Hydrogen Bond Donor Count 6
氢键受体数Hydrogen Bond Acceptor Count 10
可旋转键计数Rotatable Bond Count 19
精确质量Exact Mass 1014.59 Da
单同位素质量Monoisotopic Mass 1014.59 Da
拓扑极表面积Topological Polar Surface Area 200.000 Ų
重原子数Heavy Atom Count 74
形式电荷Formal Charge 0
复杂度Complexity 1950.000
同位素原子数Isotope Atom Count 0
定义的原子立体中心计数Defined Atom Stereocenter Count 10
未定义的原子立体中心计数Undefined Atom Stereocenter Count 0
定义的键立体中心计数Defined Bond Stereocenter Count 0
未定义的键立体中心计数Undefined Bond Stereocenter Count 0
所有立体化学键的总数The total count of all stereochemical bonds 0
共价键合单元计数Covalently-Bonded Unit Count 1

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批号(Lot Number) 证书类型 货号
D2321592 分析证书 A413749
D2321593 分析证书 A413749
D2321594 分析证书 A413749
D2321595 分析证书 A413749
D2321596 分析证书 A413749
D2321588 分析证书 A413749

引用文献

1. Hennessy EJ, Adam A, Aquila BM, Castriotta LM, Cook D, Hattersley M, Hird AW, Huntington C, Kamhi VM, Laing NM 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  (24): (9897-919).  [PMID:24320998]

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