Cell-permeable dibromocarbazolo-piperazinyl derivative that displays anti-apoptotic properties. Blocks Bid-induced cytochrome c release from HeLa cell mitochondria by inhibiting Bax channel forming activitiy.
Condiciones de almacenamiento de almacenamiento
Store at -20°C,Desiccated
Enviado en
Ice chest + Ice pads
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Nota
Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.
This compound belongs to the class of organic compounds known as polybrominated biphenyls. These are organic aromatic compounds containing a biphenyl moiety, which is substituted at two or more ring positions by a bromine atom.
External Descriptors
Not available
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
Certificados (CoA, COO, BSE/TSE y tabla de análisis)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propiedades químicas y físicas
Solubilidad
Soluble in DMSO
Índice de refracción
n20D~1.71 (Predicted)
Peso molecular
540.100 g/mol
XLogP3
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
4
Exact Mass
538.956 Da
Monoisotopic Mass
536.958 Da
Topological Polar Surface Area
40.400 Ų
Heavy Atom Count
27
Formal Charge
0
Complexity
422.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
1
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
3
Calculadoras de soluciones
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Reseñas
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Application Protocols
Item-specific tested applications/dilutions: Not specified for this item; refer to CoA/Spec Sheet.
Example workflows (literature/general; adjust per system)
DMSO stock preparation
Warm DMSO to room temperature in a dry environment. Dissolve compound to 10–50 mM. Vortex and, if needed, sonicate briefly. Aliquot under dry nitrogen/argon, store at −20 °C.
Liposome dye-release inhibition assay
Prepare large unilamellar vesicles (e.g., POPC:POPE:cardiolipin). Load with ANTS/DPX. Preincubate Bax Channel Blocker (e.g., 5–20 μM) with liposomes 15–30 min at 25–30 °C, then add activated Bax. Monitor fluorescence dequenching vs. vehicle.
Isolated mitochondria MOMP assay
Resuspend mitochondria in sucrose/HEPES buffer. Preincubate with Bax Channel Blocker (e.g., 1–10 μM, 10–20 min). Induce permeabilization with tBid-activated Bax. Quantify cytochrome c in supernatant by immunoblot/ELISA.
Cell-based apoptosis modulation
Pre-treat cells with Bax Channel Blocker (e.g., 0.5–10 μM, 30–60 min). Apply apoptotic stimulus. Measure caspase-3/7 activity, Annexin V/PI staining, or Cyt c release. Include vehicle and Bax-depleted controls.
Notes
Verify compound does not interfere with detection reagents. Titrate to determine minimally effective concentration and assess cytotoxicity independently.
Bax (Bcl-2–associated X protein) is a pro-apoptotic member of the Bcl-2 family. Upon activation, Bax undergoes conformational change, translocates/inserts into the mitochondrial outer membrane (MOM), oligomerizes, and forms proteolipid pores that mediate mitochondrial outer membrane permeabilization (MOMP).
Bax channel blockers are used to inhibit Bax pore formation and/or oligomerization on membranes, thereby modulating MOMP-driven release of proteins (e.g., cytochrome c) and downstream caspase activation in experimental systems.
These inhibitors enable temporal control of Bax activity, facilitating dissection of upstream activation events (e.g., BH3-only protein signaling) versus downstream execution phases in apoptosis research.
Selectivity considerations: Bcl-2 family proteins share structural motifs; rigorous studies include counterscreens with Bak and anti-apoptotic members (e.g., Bcl-xL, Mcl-1) to confirm Bax-centric effects.
Application scope: isolated mitochondria, permeabilized cells, liposome reconstitution systems, and intact cells—with attention to concentration-dependent off-target membrane effects.
Buffer Applications
Applicability
Not a buffering reagent. However, it is commonly used within defined biochemical buffers for mitochondrial and liposome-based assays (literature/general guidance).
Typical assay buffers (examples; literature)
Mitochondrial permeabilization buffer: 250 mM sucrose, 10 mM HEPES-KOH pH 7.4, 1 mM EGTA, 1 mM MgCl2, 0.1% BSA. Add Bax Channel Blocker from a DMSO stock to desired final μM concentration (keep DMSO ≤0.2% v/v).
Liposome dye-release buffer: 20–25 mM HEPES pH 7.4, 150 mM KCl, 1 mM DTT. Preincubate blocker with liposomes prior to adding Bax to assess inhibition of pore formation.
Practical notes
Ensure blocker addition does not change buffer pH/ionic strength appreciably; match vehicle across all conditions.
For fluorescence assays, check compound autofluorescence/absorbance in the chosen buffer and correct for inner-filter effects.
Filtration of working solutions (0.22 μm) can reduce particulate background in optical assays.
Green Alternatives
Context
As a bioactive small molecule used at micromolar concentrations, the main environmental impact arises from solvent choice and waste handling rather than the compound itself.
Greener handling strategies (general)
Prefer DMSO over DMF when feasible; DMSO has a more favorable safety profile and biodegradability. Use ethanol/water cosolvent systems for short exposures if compatible with the assay.
Minimize solvent volumes by preparing higher-concentration stocks and performing serial dilutions immediately before use.
Explore cyclodextrin-based aqueous delivery to reduce organic solvent content in assays.
Consolidate waste streams and segregate halogenated solvents; use adsorbent-filled waste caps to reduce vapor release.
Comparison (general; not item-specific)
DMSO: high solvating power, lower toxicity than DMF; widely accepted in bioassays.
Ethanol: renewable feedstock, lower toxicity, but limited solubility for strongly hydrophobic inhibitors.
PEG 400: useful as a co-solvent/vehicle in certain biochemical setups; verify assay compatibility.
Trade-offs
Reducing DMSO below solubility limits can cause precipitation and variability. Always validate greener solvent systems with appropriate controls and solubility checks.
Pharmaceutical Uses
Item-specific status
Research Use Only (from Product Data). Not for human or veterinary use. No pharmacopeial status is provided.
General context (non-clinical)
Bax channel blockers may be used as internal controls, tool compounds, or reference materials in discovery-stage apoptosis research and screening campaigns.
In pre-formulation research contexts, solubility profiling in DMSO/aqueous media, stability studies, and permeability assessments can be conducted to support assay design; these activities remain strictly non-clinical.
Compliance note
No medical, diagnostic, or therapeutic claims are made for this material. For any regulated application, obtain suitability data (identity, purity, impurities, stability) from the CoA/Spec Sheet for the specific lot.
Physical Properties
Item-specific (from Product Data)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general values (for Bax-channel–blocking small molecules; NOT item-specific)
Many Bax inhibitors are hydrophobic solids with good solubility in DMSO and limited solubility in water; exact BP/MP/density/logP/pKa are compound-dependent and not provided here.
Expected solubility behavior: readily soluble in polar aprotic solvents (DMSO, DMF) and moderately in ethanol or methanol; aqueous solubility often requires cosolvent or carrier (e.g., 0.1–1% DMSO final, or cyclodextrin).
Not available for this item (use CoA/Spec Sheet or SDS)
Melting point: Not specified for this item; refer to CoA/Spec Sheet.
Boiling point: Not specified for this item; refer to CoA/Spec Sheet.
Density: Not specified for this item; refer to CoA/Spec Sheet.
Refractive index: Not applicable/Not specified for this item; refer to CoA/Spec Sheet.
LogP, pKa: Not specified for this item; refer to CoA/Spec Sheet.
Quality and Grades
Item-specific (from Product Data)
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpretation (general)
Research-use small molecules are typically supplied at high chemical purity suitable for biochemical/cellular assays. If “≥95%” or similar is stated on the CoA, it generally reflects HPLC/UPLC area % purity (dry basis) with structure confirmed by NMR/MS.
Low water content and low residual solvent levels help reproducibility in activity assays. Any stabilizers, counter-ions, or salt forms will be specified on the CoA and may influence potency on a molar basis.
For quantitative studies, verify: purity basis (area vs. weight), residual solvents, water (Karl Fischer), and exact form (free base vs. salt). Adjust stock solution molarity accordingly.
If UV-Vis background is relevant (e.g., high-content screening), consult the Spec Sheet for UV cutoff/absorbance profile when available.
Documentation
For assay-critical work, request the most recent CoA/Spec Sheet and SDS for this exact lot. Record lot numbers in data packages to ensure traceability.
Reaction and Applications
Applicability
This product is a bioactive research tool, not a synthetic reagent. It is not typically used to mediate or catalyze chemical reactions. See Biological Roles, Buffer Applications, and Application Protocols for relevant guidance.
Research applications (literature/general)
In vitro apoptosis studies: used to inhibit Bax-mediated mitochondrial outer membrane permeabilization (MOMP), thereby preventing cytochrome c release in isolated mitochondria assays.
Liposome dye-release assays: blocks Bax-induced pore formation in model membranes; useful to dissect Bax activation/oligomerization.
Cell-based experiments: employed to probe Bax dependence in apoptosis pathways; vehicle controls and Bax-knockout/siRNA lines recommended for specificity assessment.
Practical tips (general)
Pre-dissolve in dry DMSO; filter-sterilize stocks when sterility is required (PTFE or PVDF, 0.22 μm).
Include time-matched vehicle controls; titrate inhibitor to identify minimally effective concentration without off-target cytotoxicity.
For mitochondrial or liposome assays, preincubate blocker with membranes before adding activated Bax to maximize inhibitory effect.
Consider temperature dependence: some Bax activation steps are temperature sensitive; keep conditions consistent across controls and treated samples.
Reaction Conditions
Applicability
Not a reagent for chemical transformations. This section provides general conditions for biological/biochemical use (literature/general guidance), not item-specific specifications.
Typical usage ranges (optimize empirically)
Concentration: 0.5–20 μM in cell-based assays; 1–50 μM in liposome or isolated mitochondria assays, depending on Bax activation state and membrane composition.
Vehicle: DMSO final 0.05–0.2% v/v (match across controls). Higher vehicle levels may perturb membranes.
Temperature: 25–37 °C for cell-free assays; maintain physiological temperature for live-cell experiments.
Incubation: 15–60 minutes preincubation with membranes prior to Bax addition can enhance observed inhibition.
Controls and readouts
Include vehicle control, positive control for MOMP (e.g., tBid-activated Bax in mitochondria assays), and specificity counterscreens (e.g., Bak-driven permeabilization) where feasible.
Readouts: cytochrome c ELISA/immunoblot, fluorophore leakage from liposomes (ANTS/DPX), mitochondrial potential dyes (note: verify no direct dye interaction).
Safety and Handling
Item-specific (from Product Data)
Storage: Store at −20 °C, desiccated.
Shipping: Cold-packed (ice chest + ice pads).
GHS/Signal word/H-statements/Pictograms: Not specified for this item; refer to SDS.
General laboratory safety (literature/general; defer to SDS for authoritative guidance)
Handle in a chemical fume hood; avoid inhalation, ingestion, and skin/eye contact. Wear appropriate PPE: lab coat, nitrile gloves, safety glasses.
Avoid prolonged exposure of the solid or solutions to ambient humidity; hygroscopic uptake may impact mass accuracy and performance.
Solvent considerations: prepare and handle concentrated stocks in DMSO or other suitable organic solvent. Prevent contact with strong oxidizers and bases/acids until compatibility is known.
First aid (general): in case of skin/eye contact, rinse with water for at least 15 minutes; if inhaled, move to fresh air; if swallowed, seek medical attention. Always follow institutional SOPs.
Waste: dispose according to local regulations for organic, bioactive laboratory chemicals. Segregate halogenated from non-halogenated solvent waste.
Special risks (general for lipophilic bioactives)
Potential for membrane interactions; minimize aerosolization. Use secondary containment for transport within the lab.
Solvent Selection
Compound context
Bax Channel Blocker is a hydrophobic, membrane-active small molecule (literature/general). It is typically prepared as a concentrated DMSO stock for biochemical or cell-based assays.
Practical recommendations (general)
Primary solvent: DMSO (analytical or cell-culture grade). Typical stock concentrations: 10–50 mM, depending on solubility.
Secondary solvents: DMF, ethanol, or methanol can be used for intermediate dilutions. When diluting into aqueous buffers, keep final organic content ≤0.1–0.5% v/v DMSO to minimize vehicle effects (optimize per assay).
Aqueous delivery aids: include 0.01–0.1% non-ionic surfactant (e.g., Pluronic F-127) or employ cyclodextrin inclusion (e.g., 2–10 mM HP-β-CD) to enhance apparent solubility; verify no interference with readouts.
Avoid: high ionic-strength buffers during initial dissolution; instead, dissolve in organic solvent first, then add buffer slowly with mixing.
Selection notes (comparison; literature/general)
DMSO vs ethanol: DMSO provides higher solubility and stability for many hydrophobes; ethanol may be preferable for sensitive cells but offers lower solubility.
DMF can match DMSO for solubility but is less preferred in biological systems. For purely biochemical liposome/mitochondria assays, both DMSO and DMF are often acceptable with proper controls.
Storage and Reconstitution
Item-specific (from Product Data)
Storage conditions: Store at −20 °C, desiccated.
Shipping: Ice chest with ice pads.
General guidance (literature/practice; not item-specific specifications)
Solid handling: Allow container to equilibrate to room temperature in a desiccator before opening to prevent moisture condensation. Reseal promptly under dry atmosphere.
Reconstitution: Prepare concentrated stock solutions in anhydrous DMSO (typical 10–50 mM). Mix thoroughly; gentle warming or brief sonication may aid dissolution. Optionally sterile-filter (0.22 μm PTFE/PVDF) for cell-based work.
Aliquoting: Dispense single-use aliquots to avoid repeated freeze–thaw. Store sealed aliquots at −20 °C or below, protected from light and moisture.
Working solutions: Prepare immediately before use. Avoid prolonged storage of dilute aqueous solutions; many hydrophobic inhibitors adsorb to plastic and degrade in water-rich media.
Stability checks: Periodically verify integrity by LC-MS or HPLC when used in critical studies. Discard solutions showing precipitation, discoloration, or unexpected activity loss.
Compatibility: Confirm that the final DMSO percentage and any solubilizers (e.g., cyclodextrin, surfactant) are compatible with the specific assay system.
Structure and Identity
Item-specific (from Product Data)
SKU: B276142
Product Name: Bax Channel Blocker
CAS: 335165-68-9
PubChem CID: 2729026
InChIKey: 132683 (provided)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general context
Compound type: small-molecule inhibitor used to block Bax-mediated channel/pore activity on the mitochondrial outer membrane (MOM) in apoptosis research.
Structural features (general): Bax channel blockers reported in the literature are typically hydrophobic, aromatic small molecules designed to interfere with Bax conformational activation and oligomerization on membranes; specific ring systems/functional groups vary by chemotype and are not confirmed for this item.
2D structural description: Not available for this catalog entry. Based on the name, the compound is expected to be a non-peptidic, membrane-active small molecule; precise atom connectivity and stereochemistry are not specified here.
Synthetic Utility
Applicability
This product is a bioactive small molecule used as a tool compound; it is not typically employed as a building block or reagent in synthetic organic chemistry.
General notes (when relevant)
If analog development or SAR studies are intended, this compound can serve as a reference standard for comparative biochemical evaluation (IC50/EC50 benchmarking) rather than as a synthetic precursor.
For analytical chemistry workflows, it may be used to validate LC-MS methods (retention time, ionization behavior) in complex biological matrices or buffer systems.
Target Specificity
Item-specific
Target/antigen specificity, cross-reactivity, and binding parameters are not specified for this item; refer to primary literature or contact technical support with the CAS/CID for guidance.
General considerations (literature)
Functional target: Bax-mediated pore/channel activity on the mitochondrial outer membrane.
Selectivity validation often includes: lack of effect on anti-apoptotic Bcl-2 proteins, limited activity against Bak-dependent permeabilization, and minimal impact on unrelated ion channels at working concentrations. Empirical verification is required in each system.
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