| Identification | Back Directory | [Name]
BV6 | [CAS]
1001600-56-1 | [Synonyms]
BV6
CS-2877
CS-1501
BV-6;BV6
BV-6 TFA
CHEBI:47924
BV6 USP/EP/BP
CHEBI:47924; BV-6 BV 6
4,4'-(1,6-Hexanediyl)bis[N-methyl-L-alanyl-(2S)-2-cyclohexylglycyl-L-prolyl-β-phenyl-L-Phenylalanin
L-Phenylalaninamide, 4,4'-(1,6-hexanediyl)bis[N-methyl-L-alanyl-(2S)-2-cyclohexylglycyl-L-prolyl-β-phenyl-
4,4'-(1,6-Hexanediyl)bis[N-methyl-L-alanyl-(2S)-2-cyclohexylglycyl-L-prolyl-beta-phenyl-L-phenylalaninamide
N,N'-(hexane-1,6-diyl)bis(1-{(2S)-2-cyclohexyl-2-[(N-methyl-L-alanyl)amino]acetyl}-L-prolyl-beta-phenyl-L-phenylalaninamide):trifluoroacetic acid(1:x) | [Molecular Formula]
C70H96N10O8.xCF3COOH | [MDL Number]
MFCD28168021 | [MOL File]
1001600-56-1.mol | [Molecular Weight]
1205.57 |
| Chemical Properties | Back Directory | [Boiling point ]
1376.7±65.0 °C(Predicted) | [density ]
1.177±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,Store in freezer, under -20°C | [solubility ]
≥60.28 mg/mL in DMSO; insoluble in H2O; ≥12.6 mg/mL in EtOH with ultrasonic | [form ]
solid | [pka]
12.89±0.20(Predicted) | [color ]
White to off-white | [InChIKey]
DPXJXGNXKOVBJV-YLOPQIBLSA-N |
| Hazard Information | Back Directory | [Description]
BV6 is a bivalent Smac mimetic and an antagonist of the inhibitor of apoptosis (IAP) proteins that binds to IAP1 and XIAP (Kds = 0.46 and 1.3 nM, respectively).1 It induces autoubiquitination and proteasomal degradation of IAP1 and XIAP in MDA-MB-231 cells when used at a concentration of 5 μM. BV6 (4 μM) induces NF-κB activation and TNF-dependent apoptosis in A2058 and MDA-MB-231 cells. It enhances radiosensitization and increases apoptosis in HCC193 and H460 non-small cell lung cancer (NSCLC) cell lines.2 BV6 (1 μM) induces cell death in a panel of 40 primary, patient-derived B cell precursor acute lymphoblastic leukemia (BCP-ALL) samples in a TNF-dependent manner.3 In vivo, BV6 (10 mg/kg) increases survival and the time to relapse in a high-risk BCP-ALL patient-derived xenograft (PDX) mouse model. | [Uses]
BV-6 is a SMAC mimetic and inhibitor of apoptosis (IAP) inhibitor. Apoptosis agent. | [Definition]
ChEBI: N,N'-(hexane-1,6-diyl)bis(1-{(2S)-2-cyclohexyl-2-[(N-methyl-L-alanyl)amino]acetyl}-L-prolyl-beta-phenyl-L-phenylalaninamide) is a polyamide consisting of hexane-1,6-diamine having a 1-{(2S)-2-cyclohexyl-2-[(N-methyl-L-alanyl)amino]acetyl}-L-prolyl-beta-phenyl-L-phenylalanyl moiety attached to both nitrogens. It is functionally related to a methyl 1-{(2S)-2-cyclohexyl-2-[(N-methyl-L-alanyl)amino]acetyl}-L-prolyl-beta-phenyl-L-phenylalaninate. | [in vivo]
Murine cIAP-1, cIAP-2 and XIAP expressions are clearly observed in the cytoplasm of both epithelial and stromal cells of implants, whereas Survivin is mainly expressed in the nuclei BV6 treatment for 4 weeks attenuated the intensity of IAPs expression. The size of lesions range from ~2 to 7 mm in diameter. The monolayer epithelial cell lining of the cyst is shown. After immunohistochemical staining, cytokeratin and vimentin are positively stained, whereas calretinin is negative. After BV6 treatment for 4 weeks, the total number of lesions (4.6 versus 2.8/mouse), the average weight (78.1 versus 32.0 mg/mouse) and the surface area (44.5 versus 24.6 mm2/mouse) of lesions are significantly less than in the controls. In the endometrial gland epithelia or stroma, the percentage of Ki67-positive cells decreases after BV6 treatment[2]. | [References]
[1] EUGENE VARFOLOMEEV. IAP antagonists induce autoubiquitination of c-IAPs, NF-kappaB activation, and TNFalpha-dependent apoptosis.[J]. Cell, 2007, 131 4: 669-681. DOI: 10.1016/j.cell.2007.10.030
[2] MD W L, PHD , PHD. BV6, an IAP Antagonist, Activates Apoptosis and Enhances Radiosensitization of Non-small Cell Lung Carcinoma In Vitro[J]. Journal of Thoracic Oncology, 2011, 6 11: Pages 1801-1809. DOI: 10.1097/jto.0b013e318226b4a6
[3] M SCHIRMER. Intrinsic and chemo-sensitizing activity of SMAC-mimetics on high-risk childhood acute lymphoblastic leukemia[J]. Cell Death & Disease, 2016, 7 1: e2052-e2052. DOI: 10.1038/cddis.2015.382 |
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