BV6
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 562082

CAS#: 1001600-56-1

Description: BV6 is an inhibitor of apoptosis (IAP) proteins. It acts by promoting glioblastoma cancer stem-like cell differentiation by activating NF-κB.


Price and Availability

Size
Price

1mg
USD 215
Size
Price

5mg
USD 430
Size
Price

10mg
USD 715

BV6, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 562082
Name: BV6
CAS#: 1001600-56-1
Chemical Formula: C70H96N10O8
Exact Mass: 1204.7413
Molecular Weight: 1205.6
Elemental Analysis: C, 69.74; H, 8.03; N, 11.62; O, 10.62


Synonym: BV6; BV-6; BV 6; Smac mimetic BV6;

IUPAC/Chemical Name: (2S)-1-[(2S)-2-Cyclohexyl-2-[[(2S)-2-(methylamino)propanoyl]amino]acetyl]-N-[(2S)-1-[6-[[(2S)-2-[[(2S)-1-[(2S)-2-cyclohexyl-2-[[(2S)-2-(methylamino)propanoyl]amino]acetyl]pyrrolidine-2-carbonyl]amino]-3,3-diphenylpropanoyl]amino]hexylamino]-1-oxo-3,3-diphenylpropan-2-yl]pyrrolidine-2-carboxamide

InChi Key: DPXJXGNXKOVBJV-YLOPQIBLSA-N

InChi Code: InChI=1S/C70H96N10O8/c1-47(71-3)63(81)75-59(53-37-21-11-22-38-53)69(87)79-45-27-41-55(79)65(83)77-61(57(49-29-13-7-14-30-49)50-31-15-8-16-32-50)67(85)73-43-25-5-6-26-44-74-68(86)62(58(51-33-17-9-18-34-51)52-35-19-10-20-36-52)78-66(84)56-42-28-46-80(56)70(88)60(54-39-23-12-24-40-54)76-64(82)48(2)72-4/h7-10,13-20,29-36,47-48,53-62,71-72H,5-6,11-12,21-28,37-46H2,1-4H3,(H,73,85)(H,74,86)(H,75,81)(H,76,82)(H,77,83)(H,78,84)/t47-,48-,55-,56-,59-,60-,61-,62-/m0/s1

SMILES Code: O=C([C@H]1N(C([C@H](C2CCCCC2)NC([C@@H](NC)C)=O)=O)CCC1)N[C@@H](C(C3=CC=CC=C3)C4=CC=CC=C4)C(NCCCCCCNC([C@@H](NC([C@H]5N(C([C@H](C6CCCCC6)NC([C@@H](NC)C)=O)=O)CCC5)=O)C(C7=CC=CC=C7)C8=CC=CC=C8)=O)=O


Technical Data

Appearance:
A crystalline solid

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).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Schmidt N, Haydn T, Schneider I, Busch H, Boerries M, Fulda S. Smac mimetic induces an early wave of gene expression via NF-κB and AP-1 and a second wave via TNFR1 signaling. Cancer Lett. 2018 Feb 5. pii: S0304-3835(18)30123-X. doi: 10.1016/j.canlet.2018.01.082. [Epub ahead of print] PubMed PMID: 29421152.

2: Cekay MJ, Roesler S, Frank T, Knuth AK, Eckhardt I, Fulda S. Smac mimetics and type II interferon synergistically induce necroptosis in various cancer cell lines. Cancer Lett. 2017 Dec 1;410:228-237. doi: 10.1016/j.canlet.2017.09.002. Epub 2017 Sep 18. PubMed PMID: 28923396.

3: Bhatti IA, Abhari BA, Fulda S. Identification of a synergistic combination of Smac mimetic and Bortezomib to trigger cell death in B-cell non-Hodgkin lymphoma cells. Cancer Lett. 2017 Oct 1;405:63-72. doi: 10.1016/j.canlet.2017.07.008. Epub 2017 Jul 14. PubMed PMID: 28716527.

4: Sun D, Zhao L, Lin J, Zhao Y, Zheng Y. Cationic liposome co-encapsulation of SMAC mimetic and zVAD using a novel lipid bilayer fusion loaded with MLKL-pDNA for tumour inhibition in vivo. J Drug Target. 2018 Jan;26(1):45-54. doi: 10.1080/1061186X.2017.1339192. Epub 2017 Jul 11. PubMed PMID: 28649853.

5: Fischer K, Tognarelli S, Roesler S, Boedicker C, Schubert R, Steinle A, Klingebiel T, Bader P, Fulda S, Ullrich E. The Smac Mimetic BV6 Improves NK Cell-Mediated Killing of Rhabdomyosarcoma Cells by Simultaneously Targeting Tumor and Effector Cells. Front Immunol. 2017 Mar 7;8:202. doi: 10.3389/fimmu.2017.00202. eCollection 2017. PubMed PMID: 28326081; PubMed Central PMCID: PMC5339542.

6: Siegmund D, Kums J, Ehrenschwender M, Wajant H. Activation of TNFR2 sensitizes macrophages for TNFR1-mediated necroptosis. Cell Death Dis. 2016 Sep 22;7(9):e2375. doi: 10.1038/cddis.2016.285. PubMed PMID: 27899821; PubMed Central PMCID: PMC5059883.

7: Safferthal C, Rohde K, Fulda S. Therapeutic targeting of necroptosis by Smac mimetic bypasses apoptosis resistance in acute myeloid leukemia cells. Oncogene. 2017 Mar;36(11):1487-1502. doi: 10.1038/onc.2016.310. Epub 2016 Nov 21. PubMed PMID: 27869161.

8: Rohde K, Kleinesudeik L, Roesler S, Löwe O, Heidler J, Schröder K, Wittig I, Dröse S, Fulda S. A Bak-dependent mitochondrial amplification step contributes to Smac mimetic/glucocorticoid-induced necroptosis. Cell Death Differ. 2017 Jan;24(1):83-97. doi: 10.1038/cdd.2016.102. Epub 2016 Nov 11. PubMed PMID: 27834956; PubMed Central PMCID: PMC5260489.

9: Seyfrid M, Marschall V, Fulda S. Reactive oxygen species contribute toward Smac mimetic/temozolomide-induced cell death in glioblastoma cells. Anticancer Drugs. 2016 Nov;27(10):953-959. PubMed PMID: 27669171.

10: Dächert J, Schoeneberger H, Rohde K, Fulda S. RSL3 and Erastin differentially regulate redox signaling to promote Smac mimetic-induced cell death. Oncotarget. 2016 Sep 27;7(39):63779-63792. doi: 10.18632/oncotarget.11687. PubMed PMID: 27588473; PubMed Central PMCID: PMC5325403.

11: El-Mesery M, Shaker ME, Elgaml A. The SMAC mimetic BV6 induces cell death and sensitizes different cell lines to TNF-α and TRAIL-induced apoptosis. Exp Biol Med (Maywood). 2016 Dec;241(18):2015-2022. doi: 10.1177/1535370216661779. Epub 2016 Jul 28. PubMed PMID: 27465142; PubMed Central PMCID: PMC5102137.

12: Lueck SC, Russ AC, Botzenhardt U, Schlenk RF, Zobel K, Deshayes K, Vucic D, Döhner H, Döhner K, Fulda S, Bullinger L. Smac mimetic induces cell death in a large proportion of primary acute myeloid leukemia samples, which correlates with defined molecular markers. Oncotarget. 2016 Aug 2;7(31):49539-49551. doi: 10.18632/oncotarget.10390. PubMed PMID: 27385100; PubMed Central PMCID: PMC5226527.

13: Hannes S, Abhari BA, Fulda S. Smac mimetic triggers necroptosis in pancreatic carcinoma cells when caspase activation is blocked. Cancer Lett. 2016 Sep 28;380(1):31-8. doi: 10.1016/j.canlet.2016.05.036. Epub 2016 Jun 3. PubMed PMID: 27267809.

14: Simon PS, Bardhan K, Chen MR, Paschall AV, Lu C, Bollag RJ, Kong FC, Jin J, Kong FM, Waller JL, Pollock RE, Liu K. NF-κB functions as a molecular link between tumor cells and Th1/Tc1 T cells in the tumor microenvironment to exert radiation-mediated tumor suppression. Oncotarget. 2016 Apr 26;7(17):23395-415. doi: 10.18632/oncotarget.8246. PubMed PMID: 27014915; PubMed Central PMCID: PMC5029635.

15: Reiter M, Eckhardt I, Haferkamp A, Fulda S. Smac mimetic sensitizes renal cell carcinoma cells to interferon-α-induced apoptosis. Cancer Lett. 2016 May 28;375(1):1-8. doi: 10.1016/j.canlet.2016.02.019. Epub 2016 Feb 18. PubMed PMID: 26912071.

16: Roesler S, Eckhardt I, Wolf S, Fulda S. Cooperative TRAIL production mediates IFNα/Smac mimetic-induced cell death in TNFα-resistant solid cancer cells. Oncotarget. 2016 Jan 26;7(4):3709-25. doi: 10.18632/oncotarget.6915. PubMed PMID: 26788912; PubMed Central PMCID: PMC4826164.

17: Schirmer M, Trentin L, Queudeville M, Seyfried F, Demir S, Tausch E, Stilgenbauer S, Eckhoff SM, Meyer LH, Debatin KM. Intrinsic and chemo-sensitizing activity of SMAC-mimetics on high-risk childhood acute lymphoblastic leukemia. Cell Death Dis. 2016 Jan 14;7:e2052. doi: 10.1038/cddis.2015.382. PubMed PMID: 26775704; PubMed Central PMCID: PMC4816168.

18: Czaplinski S, Abhari BA, Torkov A, Seggewiß D, Hugle M, Fulda S. Differential role of RIP1 in Smac mimetic-mediated chemosensitization of neuroblastoma cells. Oncotarget. 2015 Dec 8;6(39):41522-34. doi: 10.18632/oncotarget.6308. PubMed PMID: 26575016; PubMed Central PMCID: PMC4747171.

19: Hehlgans S, Oppermann J, Reichert S, Fulda S, Rödel C, Rödel F. The SMAC mimetic BV6 sensitizes colorectal cancer cells to ionizing radiation by interfering with DNA repair processes and enhancing apoptosis. Radiat Oncol. 2015 Sep 17;10:198. doi: 10.1186/s13014-015-0507-4. PubMed PMID: 26383618; PubMed Central PMCID: PMC4573682.

20: Marschall V, Fulda S. Smac mimetic-induced upregulation of interferon-β sensitizes glioblastoma to temozolomide-induced cell death. Cell Death Dis. 2015 Sep 17;6:e1888. doi: 10.1038/cddis.2015.235. PubMed PMID: 26379193; PubMed Central PMCID: PMC4650438.