.product-side h2 span {width: 50%;}.product-side h2 span.hover {}Related ProductsGDC-0152EmbelinUC 112SM-164Molarity CalculatorDilution Calculator Birinapant (TL32711)Potent XIAP/cIAP1 antagonistCatalog No.A4219SizePriceStockQty10mM (in 1mL DMSO)$125.00In stock 5mg$90.00In stock 10mg$140.00In stock 25mg$235.00In stock 50mg$335.00In stock Tel: +1-832-696-8203Email: sales@apexbt.comWorldwide Distributors Add to CartBulk InquiryFree samples Check OutSample solution is provided at 25 µL, 10mM.Product Citations1. De Vlaeminck Y, Lecocq Q, et al. "Single-domain antibody fusion proteins can target and shuttle functional proteins into macrophage mannose receptor expressing macrophages." J Control Release. 2019 Apr 10;299:107-120.PMID:307978662. Rosner A, Kravchenko O, et al. "IAP genes partake weighty roles in the astogeny and whole body regeneration in the colonial urochordate Botryllus schlosseri." Dev Biol. 2018 Oct 30. pii: S0012-1606(17)30904-1.PMID:303852753. Hao Q, Tang H. "Interferon-γ and Smac mimetics synergize to induce apoptosis of lung cancer cells in a TNFα-independent manner." Cancer Cell Int. 2018 Jun 14;18:84.PMID:299462234. Gradzka S, Thomas OS, et al. "Inhibitor of apoptosis proteins are required for effective fusion of autophagosomes with lysosomes." Cell Death Dis. 2018 May 9;9(5):529.PMID:297435505. van Wijk SJL, Fricke F,et al. "Linear ubiquitination of cytosolic Salmonella Typhimurium activates NF-κB and restricts bacterial proliferation." Nat Microbiol. 2017 May 8;2:17066.PMID:284813616. Wiman KG, Zhivotovsky B. "Understanding cell cycle and cell death regulation provides novel weapons against human diseases." J Intern Med. 2017 May;281(5):483-495.PMID:283745557. Hyun Jae Chung. "A Non-Canonical Function for NLRP3 and AIM2 in Kidney Diseases." university of calgary.2017.8. Shekhar TM, Miles MA, et al."IAP antagonists sensitize murine osteosarcoma cells to killing by TNFα."Oncotarget. 2016 Jun 7;7(23):33866-86.PMID:271291499. Chung H, Vilaysane A, et al. "NLRP3 regulates a non-canonical platform for caspase-8 activation during epithelial cell apoptosis." Cell Death Differ. 2016 Feb 19.PMID:26891693Hide ↑↑Related Compound Libraries DiscoveryProbe™ FDA-approved Drug LibraryDiscoveryProbe™ Bioactive Compound LibraryDiscoveryProbe™ Apoptosis Compound LibraryQuality Control Quality Control & MSDS View current batch: 321 Purity = 98.00% COA (Certificate Of Analysis) MSDS (Material Safety Data Sheet) Datasheet Purity = 98.80% COA (Certificate Of Analysis) HPLC NMR (Nuclear Magnetic Resonance) MSDS (Material Safety Data Sheet) Datasheet Purity = 98.30% COA (Certificate Of Analysis) HPLC(Retest) NMR (Nuclear Magnetic Resonance) MSDS (Material Safety Data Sheet) Datasheet Chemical structure Related Biological Data Related Biological Data Related Biological Data Related Biological Data Related Biological Data Related Biological Data Related Biological Data Biological ActivityDescriptionBirinapant is an antagonist of XIAP and cIAP1 with Kd value of 45 nM and TargetsXIAPcIAP1IC5045 nM (Kd)ProtocolCell experiment [1]:Cell linesSUM149 and SUM190 inflammatory breast cancer cellPreparation methodLimited solubility. General tips for obtaining a higher concentration: Please warm the tube at 37 ℃ for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below -20℃ for several months.Reaction Conditions24 h-96 hApplicationsBirinapant causes a significant degradation of cIAP1 and 2, which was not enhanced by the addition of TRAIL. Birinapant is also more effective in increasing TRAIL potency than GT13402 in SUM149. In addition, Birinapant markedly decreases the viability of SUM190 cells in a dose-dependent manner.Animal experiment [2]:Animal modelsMelanoma tumor xenotransplantation miceDosage formIntra-peritoneal; 30mg/kgPreparation methodDissolved in 12.5% Captisol in distilled water.ApplicationsCompared to vehicle control, cIAP1 protein is reduced to low levels at 3h post and this effect is sustained for 24 hours in the Birinapant treated mice. Staining for activated caspase-3 in biopsies of the same tumors shows a modest increase in apoptotic cells in the Birinapant treated mice compared to vehicle control, 24h post treatment.Other notesPlease test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal.References:1. Allensworth JL, Sauer SJ, Lyerly HK et al. Smac mimetic Birinapant induces apoptosis and enhances TRAIL potency in inflammatory breast cancer cells in an IAP-dependent and TNF-α-independent mechanism. Breast Cancer Res Treat. 2013 Jan;137(2):359-71.2. Krepler C, Chunduru SK, Halloran MB et al. The novel SMAC mimetic birinapant exhibits potent activity against human melanoma cells. Clin Cancer Res. 2013 Apr 1;19(7):1784-94.Birinapant (TL32711) Dilution CalculatorConcentration (start)xVolume (start)=Concentration (final)xVolume (final) femtomolar picomolar nanomolar micromolar millimolar molar nanoliter microliter milliliter liter femtomolar picomolar nanomolar micromolar millimolar molar microliter milliliter liter C1V1C2V2calculateBirinapant (TL32711) Molarity CalculatorMass=ConcentrationxVolumexMW* picograms nanograms micrograms milligrams grams kilograms femtomolar picomolar nanomolar micromolar millimolar molar nanoliter microliter milliliter liter g/molcalculate Chemical Properties Cas No. 1260251-31-7SDF Download SDF Synonyms N/A Chemical Name (2S,2"S)-N,N"-((2S,2"S)-((3S,3"S,5R,5"R)-5,5"-((6,6"-difluoro-1H,1"H-[2,2"-biindole]-3,3"-diyl)bis(methylene))bis(3-hydroxypyrrolidine-5,1-diyl))bis(1-oxobutane-2,1-diyl))bis(2-(methylamino)propanamide) Canonical SMILES CCC(C(=O)N1CC(CC1CC2=C(NC3=C2C=CC(=C3)F)C4=C(C5=C(N4)C=C(C=C5)F)CC6CC(CN6C(=O)C(CC)NC(=O)C(C)NC)O)O)NC(=O)C(C)NC Formula C42H56F2N8O6 M.Wt 806.94 Solubility ≥40.35 mg/mL in DMSO, ≥46.9 mg/mL in EtOH, Storage Store at -20°CPhysical AppearanceA solidShipping ConditionEvaluation sample solution : ship with blue ice.All other available size:ship with RT , or blue ice upon requestGeneral tipsFor obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. BackgroundBirinapant, also called TL32711, is a potent antagonist for XIAP with Kd value of 45 nM and cIAP1 with Kd value <1 nM [1].Birinapant not only binds to the isolated BIR3 domains of cIAP1, cIAP2, XIAP but the single BIR domain of ML-IAP with high affinity and degrades TRAF2-bound cIAP1 and cIAP2 rapidly accordingly inhibiting the activation of TNF-mediated NF- kB. Additionally, birinapantcan promote the formation of caspase-8: RIPK1 complex in response to TNF stimulation, which result in downstream caspasesactivation [4].In the inorganic SUM149- and SUM190-derived cells, which with differential XIAP expression (SUM149 wtXIAP, SUM190 shXIAP) and other high cIAP1/2 but low XIAP binding affinity bivalent Smac mimetic GT13402, XIAP inhibition are needed for increasing TRAIL potency. Opposite, single agent efficacy of Birinapant is owing to pan-IAP antagonism. Rapid cIAP1 degradation was caused by birinapant, as well as NF-κB activation, PARP cleavage andcaspase activation. While combined withTNF-α, showing strong combination activity, the combination was more effective than individual. The response in spheroid models was conserved, whereas in vivo birinapant inhibited tumor growth without adding TNF-α in vitro to resistant cell lines. In a parental cell line, TNF-αcombined withbirinapantinhibited the growth of a melanoma cell line with acquired resistance to the same extent of BRAF inhibition [1, 2].Drug treatment increased the mean [18F]ICMT-11 tumor uptake with a peak at 24 hours for CPA (40 mg/kg; AUC40-60: 8.04 ± 1.33 and 16.05 ± 3.35 %ID/mL × min at baseline and 24 hours, respectively) and 6 hours for birinapant (15 mg/kg; AUC40-60: 20.29 ± 0.82 and 31.07 ± 5.66 %ID/mL × min, at baseline and 6 hours, respectively). Voxel-based spatiotemporal analysis of tumor-intrinsic heterogeneity showed that [18F] ICMT-11 could detect the discrete pockets of caspase-3 activation. Caspase-3 activation that measured ex vivo associated with the increased tumor [18F] ICMT-11, and early radiotracer uptake predicted apoptosis, distinct from the glucose metabolism with [18F] fluorodeoxyglucose-PET, which depicted the continuous loss of cell viability [3].References: 1.Allensworth JL, Sauer S, Lyerly HK, et al. Smac mimetic Birinapant induces apoptosis and enhances TRAIL potency in inflammatory breast cancer cells in an IAP-dependent and TNF-a-independent mechanism. Breast Cancer Research, 2013, 137:359-371.2.Krepler C, Chunduru SK, Halloran MB, et al. The novel SMAC mimetic birinapant exhibits potent activity against human melanoma cells. Clinical Cancer Research, 2013, 19 (7): 1784-1794.3.Nguyen QD, Lavdas I, Gubbins J, et al. Temporal and Spatial Evolution of Therapy-Induced Tumor Apoptosis Detected by Caspase-3–Selective Molecular Imaging. Clinical Cancer Research, 2013, 19 (14): 3914-3924.4.Benetatos CA, Mitsuuchi Y, Burns JM, et al. Birinapant (TL32711), a Bivalent SMAC Mimetic, Targets TRAF2-Associated cIAPs, Abrogates TNF-Induced NF-kB Activation, and Is Active in Patient-Derived Xenograft Models. 2014, 13(4):867-879.