1. Apoptosis
  2. IAP

Birinapant (Synonyms: TL32711)

Cat. No.: HY-16591 Purity: 99.84%
Handling Instructions

Birinapant, a bivalent Smac mimetic, is a potent antagonist for XIAP and cIAP1 with Kds of 45 nM and less than 1 nM, respectively.

For research use only. We do not sell to patients.

Birinapant Chemical Structure

Birinapant Chemical Structure

CAS No. : 1260251-31-7

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10 mM * 1 mL in DMSO USD 128 In-stock
Estimated Time of Arrival: December 31
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10 mg USD 144 In-stock
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50 mg USD 336 In-stock
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100 mg USD 600 In-stock
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Customer Review

    Birinapant purchased from MCE. Usage Cited in: Front Microbiol. 2018 Sep 19;9:2022.

    ACH-2 cells are exposed to Birinapant (50 nM) in the presence or absence of PEP005 (5 nM), with TNF-α (10 ng/ml) co-treatment for 24 h, and cell lysates are used for WB analysis.

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    • Biological Activity

    • Protocol

    • Technical Information

    • Purity & Documentation

    • References

    Description

    Birinapant, a bivalent Smac mimetic, is a potent antagonist for XIAP and cIAP1 with Kds of 45 nM and less than 1 nM, respectively.

    IC50 & Target

    Kd: 45 nM (XIAP), <1 nM (cIAP1)

    In Vitro

    Birinapant causes significant degradation of cIAP1 and 2. Birinapant + TRAIL-treated cells show increased levels of active caspase-8 and caspase-3, as well as PARP cleavage, over single agents within 4 h of treatment, indicative of apoptosis-mediated cell death. Birinapan significantly decreases the viability of SUM190 cells in a dose-dependent manner. Birinapant treatment in the XIAP knockdown cell line (SUM190 shXIAP) causes an overall reduction in viability at lower doses (30-300 nM)[1]. Birinapant causes apoptosis in the sensitive cells. Birinapant in conbination with TNF-α, causes PARP cleavage in 451Lu and WM1366 cell lines[2]. Birinapant induces time-course of caspase-3 activation in HCT116 human colon carcinoma and MDA-MB-231 human breast adenocarcinoma cells[3].

    In Vivo

    Birinapant can inhibit tumor growth in melanoma xenotransplantation models. Staining for activated caspase-3 in biopsies of the same tumors show a modest increase in apoptotic cells in the birinapant treated animals[2]. Birinapant (15 mg/kg, i.p.) induces apoptosis in HCT116 tumor-bearing mouse[3].

    Clinical Trial
    Solvent & Solubility
    In Vitro: 

    DMSO : ≥ 40 mg/mL (49.57 mM)

    H2O : < 0.1 mg/mL (insoluble)

    *"≥" means soluble, but saturation unknown.

    Preparing
    Stock Solutions
    Concentration Solvent Mass 1 mg 5 mg 10 mg
    1 mM 1.2392 mL 6.1962 mL 12.3925 mL
    5 mM 0.2478 mL 1.2392 mL 2.4785 mL
    10 mM 0.1239 mL 0.6196 mL 1.2392 mL
    *Please refer to the solubility information to select the appropriate solvent.
    In Vivo:
    • 1.

      Add each solvent one by one:  10% DMSO    90% corn oil

      Solubility: ≥ 2.08 mg/mL (2.58 mM); Clear solution

    • 2.

      Add each solvent one by one:  10% DMSO    90% (20% SBE-β-CD in saline)

      Solubility: 2.08 mg/mL (2.58 mM); Suspended solution; Need ultrasonic

    • 3.

      Add each solvent one by one:  10% DMSO    40% PEG300    5% Tween-80    45% saline

      Solubility: ≥ 2.08 mg/mL (2.58 mM); Clear solution

    References
    Cell Assay
    [1]

    Trypan blue exclusion assay is performed as described. Cells are seeded in 6 well plates at 7.5×104 (SUM149) or 1.5×105 (SUM190) cells per well and allowed to adhere overnight. Cells are treated with TRAIL (0-100 ng/mL), Birinapant (0-10,000 nM), GT13402 (0-10,000 nM), TNF-α (50 ng/mL), TNF-α neutralizing antibody (10 μg/mL), pan-caspase inhibitor Q-VD-OPh (20 μM), or a combination as indicated. All treatments are applied for 24 h, and then the cells are trypsinized and resuspended in PBS. Next, 10 μL of cell suspension is added to 10 μL 0.4 % trypan blue, and 10 μL of the mixture is loaded onto a hemocytometer; cells are counted, and live and dead cell numbers are recorded.

    MCE has not independently confirmed the accuracy of these methods. They are for reference only.

    Animal Administration
    [2]

    Ten animals each are inoculated s.c. with 1×106 451Lu or 1205Lu human melanoma cells in a suspension of matrigel/complete media at a ratio of 1:1. After formation of palpable tumors, mice from both tumor models are randomized into two groups. Both groups are treated intraperitoneal three times/week with either vehicle control or birinapant 30 mg/kg for 21 days. Birinapant is dissolved in 12.5% Captisol in distilled water. Tumor size is assessed twice weekly by caliper measurement. Subsequently, satellite groups of ten and fifteen mice are inoculated in the same fashion with 451Lu and 1205Lu tumor cells respectively. After tumors have reached a mean volume of 200 mm3 animals are dosed with either birinapant or vehicle control as described above. After 48 hours and two doses, animals are sacrificed and tumors are harvested at four time points after the last treatment. Tumor samples are snap frozen in liquid nitrogen for subsequent protein analysis and preserved as FFPE blocks for immune-histochemistry.

    MCE has not independently confirmed the accuracy of these methods. They are for reference only.

    References
    Molecular Weight

    806.94

    Formula

    C₄₂H₅₆F₂N₈O₆

    CAS No.

    1260251-31-7

    SMILES

    FC1=CC2=C(C=C1)C(C[[email protected]]3N(C([[email protected]@H](NC([[email protected]@H](NC)C)=O)CC)=O)C[[email protected]@H](O)C3)=C(C(N4)=C(C[[email protected]]5N(C([[email protected]@H](NC([[email protected]@H](NC)C)=O)CC)=O)C[[email protected]@H](O)C5)C6=C4C=C(F)C=C6)N2

    Storage
    Powder -20°C 3 years
      4°C 2 years
    In solvent -80°C 6 months
      -20°C 1 month
    Shipping

    Room temperature in continental US; may vary elsewhere

    Purity: 99.84%

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    Product Name:
    Birinapant
    Cat. No.:
    HY-16591
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    Birinapant

    Cat. No.: HY-16591