1: Elsawy MA, Tikhonova IG, Martin SL, Walker B. Smac-derived Aza-peptide As an Aminopeptidase-resistant XIAP BIR3 Antagonist. Protein Pept Lett. 2015 Jun 21. [Epub ahead of print] PubMed PMID: 26095377.
2: Ebert G, Allison C, Preston S, Cooney J, Toe JG, Stutz MD, Ojaimi S, Baschuk N, Nachbur U, Torresi J, Silke J, Begley CG, Pellegrini M. Eliminating hepatitis B by antagonizing cellular inhibitors of apoptosis. Proc Natl Acad Sci U S A. 2015 May 5;112(18):5803-8. doi: 10.1073/pnas.1502400112. Epub 2015 Apr 20. PubMed PMID: 25902530; PubMed Central PMCID: PMC4426438.
3: Papaevangelou E, Almeida GS, Jamin Y, Robinson SP, deSouza NM. Diffusion-weighted MRI for imaging cell death after cytotoxic or apoptosis-inducing therapy. Br J Cancer. 2015 Apr 28;112(9):1471-9. doi: 10.1038/bjc.2015.134. Epub 2015 Apr 16. PubMed PMID: 25880014; PubMed Central PMCID: PMC4453679.
4: Brady SW, Zhang J, Tsai MH, Yu D. PI3K-independent mTOR activation promotes lapatinib resistance and IAP expression that can be effectively reversed by mTOR and Hsp90 inhibition. Cancer Biol Ther. 2015;16(3):402-11. doi: 10.1080/15384047.2014.1002693. PubMed PMID: 25692408.
5: Lee EW, Seong D, Seo J, Jeong M, Lee HK, Song J. USP11-dependent selective cIAP2 deubiquitylation and stabilization determine sensitivity to Smac mimetics. Cell Death Differ. 2015 Jan 23. doi: 10.1038/cdd.2014.234. [Epub ahead of print] PubMed PMID: 25613375.
6: Eytan DF, Snow GE, Carlson SG, Schiltz S, Chen Z, Van Waes C. Combination effects of SMAC mimetic birinapant with TNFα, TRAIL, and docetaxel in preclinical models of HNSCC. Laryngoscope. 2015 Mar;125(3):E118-24. doi: 10.1002/lary.25056. Epub 2014 Nov 28. PubMed PMID: 25431358; PubMed Central PMCID: PMC4336212.
7: Mak PY, Mak DH, Ruvolo V, Jacamo R, Kornblau SM, Kantarjian H, Andreeff M, Carter BZ. Apoptosis repressor with caspase recruitment domain modulates second mitochondrial-derived activator of caspases mimetic-induced cell death through BIRC2/MAP3K14 signalling in acute myeloid leukaemia. Br J Haematol. 2014 Nov;167(3):376-84. doi: 10.1111/bjh.13054. Epub 2014 Jul 31. PubMed PMID: 25079338; PubMed Central PMCID: PMC4357400.
8: Condon SM, Mitsuuchi Y, Deng Y, LaPorte MG, Rippin SR, Haimowitz T, Alexander MD, Kumar PT, Hendi MS, Lee YH, Benetatos CA, Yu G, Kapoor GS, Neiman E, Seipel ME, Burns JM, Graham MA, McKinlay MA, Li X, Wang J, Shi Y, Feltham R, Bettjeman B, Cumming MH, Vince JE, Khan N, Silke J, Day CL, Chunduru SK. Birinapant, a smac-mimetic with improved tolerability for the treatment of solid tumors and hematological malignancies. J Med Chem. 2014 May 8;57(9):3666-77. doi: 10.1021/jm500176w. Epub 2014 Apr 15. PubMed PMID: 24684347.
9: Benetatos CA, Mitsuuchi Y, Burns JM, Neiman EM, Condon SM, Yu G, Seipel ME, Kapoor GS, Laporte MG, Rippin SR, Deng Y, Hendi MS, Tirunahari PK, Lee YH, Haimowitz T, Alexander MD, Graham MA, Weng D, Shi Y, McKinlay MA, Chunduru SK. 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. doi: 10.1158/1535-7163.MCT-13-0798. Epub 2014 Feb 21. Erratum in: Mol Cancer Ther. 2014 Sep;13(9):2246-7. Dosage error in article text. PubMed PMID: 24563541.
10: Carter BZ, Mak PY, Mak DH, Shi Y, Qiu Y, Bogenberger JM, Mu H, Tibes R, Yao H, Coombes KR, Jacamo RO, McQueen T, Kornblau SM, Andreeff M. Synergistic targeting of AML stem/progenitor cells with IAP antagonist birinapant and demethylating agents. J Natl Cancer Inst. 2014 Feb;106(2):djt440. doi: 10.1093/jnci/djt440. PubMed PMID: 24526787; PubMed Central PMCID: PMC3952202.

Chemical
CAS Num	1260251-31-7
Chemical Formula	C42H56F2N8O6
Molecular Weight	806.94
IUPAC Chemical Name	(2S)-N-[(2S)-1-[(2R,4S)-2-[[6-fluoro-2-[6-fluoro-3-[[(2R,4S)-4-hydroxy-1-[(2S)-2-[[(2S)-2-(methylamino)propanoyl]amino]butanoyl]pyrrolidin-2-yl]methyl]-1H-indol-2-yl]-1H-indol-3-yl]methyl]-4-hydroxypyrrolidin-1-yl]-1-oxobutan-2-yl]-2-(methylamino)propanam
Exact Mass	806.42909
Elemental Analysis	C, 62.51; H, 6.99; F, 4.71; N, 13.89; O, 11.90
Synonym	TL32711; TL-32711; TL 32711; SMAC mimetic; Birinapant
Solubility	Soluble in DMSO, not in water
SMILES Code	C[C@H](NC)C(N[C@@H](CC)C(N1[C@H](CC2=C(C(N3)=C(C[C@H]4N(C([C@@H](NC([C@@H](NC)C)=O)CC)=O)C[C@@H](O)C4)C5=C3C=C(F)C=C5)NC6=C2C=CC(F)=C6)C[C@H](O)C1)=O)=O
Biological
Targets and Effects	Apoptosis Protein inhibitor
Pathways	Apoptosis
Physical
Appearance	white solid powder
Purity	>98% (or refer to the Certificate of Analysis)
Shipping Condition	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 Condition	Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Shelf Life	>2 years if stored properly