Birinapant

For research use only.

Catalog No.S7015 Synonyms: TL32711

39 publications

Birinapant Chemical Structure

CAS No. 1260251-31-7

Birinapant (TL32711) is a SMAC mimetic antagonist, mostly to cIAP1 with Kd of <1 nM in a cell-free assay, less potent to XIAP. Birinapant helps to induce apoptosis in latent HIV-1-infected cells. Phase 2.

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Selleck's Birinapant has been cited by 39 publications

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Biological Activity

Description Birinapant (TL32711) is a SMAC mimetic antagonist, mostly to cIAP1 with Kd of <1 nM in a cell-free assay, less potent to XIAP. Birinapant helps to induce apoptosis in latent HIV-1-infected cells. Phase 2.
Targets
cIAP1 [1]
(Cell-free assay)
XIAP [1]
(Cell-free assay)
<1 nM(Kd) 45 nM(Kd)
In vitro

Birinapant binds with XIAP and cIAP1 with Kd of 45 and <1 nM, respectively. Birinapant induces cell death as a single agent in TRAIL-insensitive SUM190 (ErbB2-overexpressing) cells (IC50, ~300 nM), and significantly increases potency of TRAIL-induced apoptosis in TRAIL-sensitive SUM149 (triple-negative, EGFR-activated) cells. Birinapant causes rapid cIAP1 degradation, caspase activation, PARP cleavage, and NF-κB activation. [1] Birinapant in combination with TNF-α exhibits a strong antimelanoma effect in vitro. Birinapant in combination with TNF-α(1 ng/mL) inhibits the growth of human melanoma cell lines WTH202, WM793B, WM1366 and WM164 with IC50s of 1.8, 2.5, 7.9 and 9 nM, respectively, while neither compound is effective individually. Birinapant singly treatment induces inhibition on proliferation of WM9 cells with IC50 of 2.4 nM. Birinapant significantly inhibits the target protein cIAP1 and cIAP2 in these cell lines.[2]

Cell Data
Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID
PANC-1 MlPtS5Jwf3SqIFnubIljcXSrb36gRZN{[Xl? NGL3fpc2OC9{MECvOVAxKG6P NEmzNYYxNTl4IHi= NX\QcXhMcW6qaXLpeJMh[2WubDDndo94fGhiaX6gZo91cCC2aX3lJIFv\CCmb4PlJIRmeGWwZHXueEBu[W6wZYK= NH;aemszPjJ3Mkm2PS=>
Molm13  NGXvOppHfW6ldHnvckBCe3OjeR?= MXyyM|IxNzJyMDDuUS=> M3;FPFI1KGh? MkTy[IVkemWjc3XzJINKSVBzIHHu[EwhfG9iYTDteYNpKGync4PldkBmgHSnboSsJINKSVB{LDDhcoQhYEmDUDD1coRmeiC4YYLpc5V{KGOxbnTpeIlwdnN? NFXFT2czPDV{Nke4Oy=>
WTH202 MUnHdo94fGhiSX7obYJqfGmxbjDBd5NigQ>? NFfIWmw4OiCq MXTJR|UxRTFwODDuUUwh[2:vYnnu[YQhf2m2aDCxcocwdWxiVF7GMe6y NGSwVIYzOzRyM{[zOC=>
WM793B MkDZS5Jwf3SqIFnubIljcXSrb36gRZN{[Xl? NF7hWnM4OiCq NXjacJhjUUN3ME2yMlUhdk1uIHPvcYJqdmWmIIfpeIghOW6pL33sJHRPTi4QsR?= NEH4eogzOzRyM{[zOC=>
WM9 NELselhIem:5dHigTY5pcWKrdHnvckBCe3OjeR?= MX:3NkBp MoLsTWM2OD1{LkSgcm0> NHLq[IMzOzRyM{[zOC=>
WM9 NHzXVoNIem:5dHigTY5pcWKrdHnvckBCe3OjeR?= MlL6O|IhcA>? M1HSXGlEPTB;Mj63JI5ONCClb33ibY5m\CC5aYToJFFv\y:vbDDUUmYu|rF? NUPWcoZXOjN2MEO2N|Q>
WM1366 NEGwPYpIem:5dHigTY5pcWKrdHnvckBCe3OjeR?= MkfaO|IhcA>? NV;lZ|JKUUN3ME23Mlkhdk1uIHPvcYJqdmWmIIfpeIghOW6pL33sJHRPTi4QsR?= MUCyN|QxOzZ|NB?=
WM164 MnviS5Jwf3SqIFnubIljcXSrb36gRZN{[Xl? M1PkdlczKGh? M2js[2lEPTB;OTDuUUwh[2:vYnnu[YQhf2m2aDCxcocwdWxiVF7GMe6y MmewNlM1ODN4M{S=
451Lu NXrTVYZ6T3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= MVK3NkBp MVXJR|UxRTF2LkKgcm0tKGOxbXLpcoVlKHerdHigNY5oN22uIGTOSk3PuQ>? MlfCNlM1ODN4M{S=
WM1341D NYXQOGZ7T3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= NGTabGg4OiCq MUTJR|UxRTV5Lk[gcm0tKGOxbXLpcoVlKHerdHigNY5oN22uIGTOSk3PuQ>? NHLjSFUzOzRyM{[zOC=>
WM3130 MWPHdo94fGhiSX7obYJqfGmxbjDBd5NigQ>? MlrBO|IhcA>? M4TrXGlEPTB;NkSuN{BvVSxiY3;tZolv\WRid3n0bEAydmdxbXygWG5HNc7z MnK4NlM1ODN4M{S=
WM1985 MlzVS5Jwf3SqIFnubIljcXSrb36gRZN{[Xl? MmrKO|IhcA>? NFq4R|hKSzVyPUm3JI5ONCClb33ibY5m\CC5aYToJFFv\y:vbDDUUmYu|rF? NHviblczOzRyM{[zOC=>
WM3854 MUDHdo94fGhiSX7obYJqfGmxbjDBd5NigQ>? NHO3d4s4OiCq M{DLbGlEPTB;MkK2JI5ONCClb33ibY5m\CC5aYToJFFv\y:vbDDUUmYu|rF? MkXtNlM1ODN4M{S=

... Click to View More Cell Line Experimental Data

Assay
Methods Test Index PMID
Western blot
cIAP1 / cIAP2 / XIAP; 

PubMed: 24526787     


Molm13 cells were cultured under standard conditions, standard conditions with mesenchymal stromal cell (MSC) coculture, or hypoxic conditions without or with MSC coculture and treated with birinapant. cIAP1, cellular inhibitor of apoptosis protein-2 (cIAP2), and X-linked inhibitor of apoptosis protein (XIAP) levels were determined by Western blot at 24 hours.

NF-κB(p65) / IκBa / Bcl-xl / NF-κB(p100) / p52; 

PubMed: 24526787     


OCI-AML3 cells were treated with birinapant (bir) for 24 hours. Protein levels in total cell lysates were determined by western blot.

BIRC2 / ARC; 

PubMed: 25079338     


Birinapant treatment decreases BIRC2 and increases ARC protein levels in AML cells and MSCs. OCI-AML3 and Molm13 cells were co-cultured with mesenchymal stem cells (MSCs) and treated with birinapant (bir). Cell lysates from OCI-AML3 and Molm13 cells were collected at 48 and 72 h by combining unattached cells and cells washed off from MSCs; lysates of MSCs were obtained from MSCs co-cultured with Molm13 cells after washing off Molm13 cells. The protein levels were determined by Western blot.

24526787 25079338
Immunofluorescence
Caspase 3/7; 

PubMed: 28665401     


MC38-Ova cells were seeded in chamber slides then overlaid with Pfn−/− OT-I T cells. After 8 h, cells were fixed, stained as indicated, then visualized by confocal microscopy. A minimum of 50 cells was counted in each condition. Error bars represent the mean±S.E.M. of triplicate determinations from a representative experiment, *P<0.05 by unpaired Student's t test.

28665401
Growth inhibition assay
Cell viability; 

PubMed: 28460471     


Cell viability was determined by CCK-8 assay. The data are representative results of three independent experiments.

28460471
In vivo Birinapant (30 mg/kg) treatment significantly induces abrogation of tumor growth in melanoma xenotransplantation models 451Lu with. [2]

Protocol

Kinase Assay:[1]
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Fluorescence polarization assay:

The binding affinities of compounds to XIAP and cIAP1 are determined using a fluorogenic substrate and are reported as Kd values. Initially, the dissociation constant (Kd) for the fluorescently labeled modified Smac peptide (AbuRPF-K(5-Fam)-NH2; FP pep-tide) is determined using a fixed concentration of peptide (5 nM) and titrating varying concentrations of protein (0.075–5 μM in half log dilutions). The dose–response curves are produced by a nonlinear least squares fit to a single-site binding model using GraphPad Prism, with 5 nM of FP peptide and 50 nM of XIAP used in the assay. Various concentrations of Smac mimetics (100–0.001 μM in half log dilutions) are added to FP peptide:protein binary complex for 15 min at room temperature in 100μL of 0.1 M potassium phosphate buffer, pH 7.5, containing 100 mg/mL bovine c -globulin. Following incubation, the polarization values are measured on a multi-label plate reader using a 485 nm excitation filter and a 520 nm emission filter.
Cell Research:[2]
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  • Cell lines: Human melanoma cell lines WM9
  • Concentrations: 1 nM-1 μM
  • Incubation Time: 3 days
  • Method: Cells are allowed to attach for 24 hours and subsequently incubated with Birinapant and/or TNF-α for 24 or 72 hours. Then MTS assay is conducted
    (Only for Reference)
Animal Research:[2]
- Collapse
  • Animal Models: Human melanoma xenografts 451Lu
  • Dosages: 30 mg/kg
  • Administration: 3 times per week intraperitoneally
    (Only for Reference)

Solubility (25°C)

In vitro DMSO 100 mg/mL (123.92 mM)
Ethanol 55 mg/mL (68.15 mM)
Water Insoluble

* Please note that Selleck tests the solubility of all compounds in-house, and the actual solubility may differ slightly from published values. This is normal and is due to slight batch-to-batch variations.

Chemical Information

Molecular Weight 806.94
Formula

C42H56F2N8O6

CAS No. 1260251-31-7
Storage powder
in solvent
Synonyms TL32711
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

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Clinical Trial Information

NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT01681368 Terminated Drug: Birinapant (TL32711) Epithelial Ovarian Cancer|Peritoneal Neoplasms|Fallopian Tube Neoplasms National Cancer Institute (NCI)|National Institutes of Health Clinical Center (CC) August 15 2012 Phase 2

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IAP Signaling Pathway Map

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Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID