5.33965

IAP Antagonist, BV6

• Synonym(s): IAP Antagonist, BV6, (S,S,2S,2ʹS)-N,Nʹ-((2S,2ʹS)-(hexane-1,6-diylbis(azanediyl))bis(3-oxo-1,1-diphenylpropane-3,2-diyl))bis(1-((S)-2-cyclohexyl-2-((S)-2-(methylamino)propanamido)acetyl)pyrrolidine-2-carboxamide)
• Empirical Formula (Hill Notation): C₇₀H₉₆N₁₀O₈
• CAS Number: 1001600-56-1
• Molecular Weight: 1205.57
• MDL number: MFCD28168021
• UNSPSC Code: 51111800
• NACRES: NA.77
• Assay: ≥98% (HPLC)
• Form: powder
• Storage condition: OK to freeze, desiccated (hygroscopic), protect from light

Properties

• assay: ≥98% (HPLC)
• Quality Segment: 100
• form: powder
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze, desiccated (hygroscopic), protect from light
• color: white
• solubility: DMSO: 50 mg/mL
• storage temp.: −20°C
• SMILES string: N2([C@@H](CCC2)C(=O)N[C@@H](C(c8ccccc8)c7ccccc7)C(=O)NCCCCCCNC(=O)[C@@H](NC(=O)[C@H]5N(CCC5)C(=O)[C@@H](NC(=O)[C@@H](NC)C)C6CCCCC6)C(c4ccccc4)c3ccccc3)C(=O)[C@@H](NC(=O)[C@@H](NC)C)C1CCCCC1
• InChI key: DPXJXGNXKOVBJV-YLOPQIBLSA-N

Description

General description

A bivalent SMAC mimetic that antagonizes cIAP1 and XIAP interaction with initiator caspases and triggers their proteasomal degradation. Shown to rapidly deplete levels of cIAP1 and XIAP in HCC193 (at 1 µM) and H460 (at 5 µM) lung cancer cell lines. Levels of cIAP1 are reduced within an hour following treatment while XIAP depletion takes up to 24 h. Effectively reduces the viability of HCC193 (IC₅₀ = 7.2 µM) and H460 (IC₅₀ = 30 µM) cells and synergistically enhances their sensitivity to radiation treatment. Reported to increase apoptosis via caspase-8 activation in HCC193 cells (~ 1 µM) and via caspase-9 in H460 cells (~ 5 µM). Also shown to increase the secretion of TNFa in HCC193 cells in a dose-dependent manner. Also enhances cytokine-induced killer (CIK) cell-mediated cytotoxicity against multiple hematological (H9, THP-1, Tanoue) and solid malignant cells (RH1, RH30, and TE671).

Please note that the molecular weight for this compound is batch-specific due to variable water content. Please refer to the vial label or the certificate of analysis for the batch-specific molecular weight. The molecular weight provided represents the baseline molecular weight without water.

Biochem/physiol Actions

Cell permeable: yes

Primary Target
IAP

Reversible: yes

Packaging

Packaged under inert gas

Physical form

Supplied as a trifluoroacetate salt.

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Rettinger, E., et al. 2014. Front in Pediatr.2, 75.
Li, W., et al. 2011. J. Thorac. Oncol.6, 1801.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable