Birinapant free base · Synonyms: TL32711 | TL 32711

Birinapant is a SMAC mimetic antagonist.

For research use only. Not for human or veterinary use.

Target IAP Apoptosis HIV

Research area Cancer

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Data Sheet SDS COA

Birinapant structure

CAS No.: 1260251-31-7

Download structure (.mol)

Pack sizes & pricing

Size	Price	SKU	Stock
500 mg	USD 650.00	BP-02120-500mg	In stock	Get quote
1 g	USD 1,020.00	BP-02120-1g	In stock	Get quote
2 g	USD 1,950.00	BP-02120-2g	In stock	Get quote
3 g	USD 2,340.00	BP-02120-3g	In stock	Get quote
5 g	USD 3,300.00	BP-02120-5g	In stock	Get quote
10 g	Inquire	BP-02120-10g	In stock	Inquire

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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.

Biological activity

n Vitro Birinapant (TL32711) (30-10000 nM; 24 hours) significantly decreases the viability of SUM190 cells in a dose-dependent manner. Birinapant (TL32711) (30-1000 nM; 4 hours) shows a significant decrease in cIAP1 levels and enhanced PARP cleavage, and induces apoptosis. Birinapant (TL32711) binds with high affinity to the isolated BIR3 domains of cIAP1, cIAP2, and XIAP and the single BIR domain of ML-IAP and rapidly degrades TRAF2-bound cIAP1 and cIAP2 thereby inhibiting TNF-mediated NF-κB activation. In Vivo Birinapant (TL32711) (30 mg/kg; i.p.; every third day (*5)) shows antitumor efficacy and are devoid of overt toxicity in preclinical models.

Identifiers

SMILES: CC[C@H](NC(=O)[C@H](C)NC)C(=O)N1C[C@@H](O)C[C@H]1CC1=C(NC2=C1C=CC(F)=C2)C1=C(C[C@@H]2C[C@H](O)CN2C(=O)[C@H](CC)NC(=O)[C@H](C)NC)C2=C(N1)C=C(F)C=C2
InChIKey: PKWRMUKBEYJEIX-DXXQBUJASA-N

Specifications

MW (average): 806.9408
Formula: C₄₂H₅₆F₂N₈O₆
CAS No.: 1260251-31-7
Physical state: Solid
Color: Off-white to light yellow
Shipping: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage: Powder -20℃ 2 years; In solvent -20℃ 1 month;

Solubility

Soluble in DMSO

Documents

References

[1]. Allensworth JL, 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, et al. The novel SMAC mimetic birinapant exhibits potent activity against human melanoma cells. Clin Cancer Res. 2013 Apr 1;19(7):1784-94.

[3]. Nguyen QD, et al. Temporal and spatial evolution of therapy-induced tumor apoptosis detected by caspase-3-selective molecular imaging. Clin Cancer Res. 2013 Jul 15;19(14):3914-24.

[4]. Benetatos CA, et al. Birinapant (TL32711), a bivalent SMAC mimetic, targets TRAF2-associated cIAPs, abrogates TNF-induced NF-κB activation, and is active in patient-derived xenograft models. Mol Cancer Ther. 2014 Apr;13(4):867-79.

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