Ibrutinib-MPEA - 10mM in DMSO , CAS No.1710768-30-1

CAS: 1710768-30-1 Cat. No.: I656407 Fórmula: C₃₂H₃₉N₉O₂ Peso molecular: 581.71 PubChem CID: 59799011

CALIDAD & PUREZA 10mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Descripción general

Ibrutinib-MPEA (Compound 20) is ibrutinib derivative. Ibrutinib is a covalent and irreversible inhibitor of Bruton's tyrosine kinase (BTK) that has been used to treat haematological malignancies.

Especificaciones

Especificaciones y pureza

10mM in DMSO

Mecanismos bioquímicos y fisiológicos

Ibrutinib-MPEA (Compound 20) is ibrutinib derivative. Ibrutinib is a covalent and irreversible inhibitor of Bruton's tyrosine kinase (BTK) that has been used to treat haematological malignancies.

Condiciones de almacenamiento de almacenamiento

Store at -80°C

Enviado en

Dry ice packs + Cold packs

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Nombres e identificadores

Isómeros SMILES

C1C[C@H](CN(C1)C(=O)/C=C/CN2CCN(CC2)CCN)N3C4=NC=NC(=C4C(=N3)C5=CC=C(C=C5)OC6=CC=CC=C6)N

PubChem CID

59799011

Peso molecular

581.71

Application Protocols

No tested-application data are supplied for this SKU. The following protocols are general starting points for covalent BTK-ligand chemotypes (not item-specific). Adjust to your system and verify with controls.

1. DMSO Stock and Working Solutions

• Warm compound briefly to RT in a desiccated environment. Dissolve to 10–20 mM in anhydrous DMSO. Vortex and, if needed, sonicate gently. Aliquot (10–50 µL) and store at −80°C. Avoid >1–2 freeze–thaw cycles.
• For assays, dilute stock into buffer to desired concentration, keeping final DMSO ≤0.5%.

2. Biochemical BTK Inhibition (time-dependent)

• Buffer: 50 mM HEPES pH 7.5, 0.01% Tween-20, 1 mM DTT (evaluate thiol effect), 5 mM MgCl2.
• Preincubate enzyme (1–10 nM) with compound (0–3 µM) for 30 min at 25°C. Initiate with ATP/substrate. Fit progress curves to obtain kobs; secondary plots yield kinact/KI.

3. Cellular Target Engagement (CETSA-style)

• Treat cells with serial dilutions (e.g., 0.01–1 µM) for 1 h (DMSO ≤0.1%). Subject to temperature gradient; analyze BTK by immunoblot.

4. LC–MS Confirmation of Covalent Adduct (protein digest)

• Incubate recombinant BTK with compound (1–5 µM) for 60 min at 25–37°C. Quench, digest with trypsin, analyze peptides for mass shifts consistent with covalent addition.

Note: These are generic procedures; refine based on the exact structure and purity of this SKU from its CoA.

Biological Roles

No item-specific biological characterization data are provided. The following context concerns ibrutinib chemotype behavior and BTK biology (general literature, not item-specific):

• BTK (Bruton’s tyrosine kinase) is a non-receptor tyrosine kinase central to B-cell receptor (BCR) signaling, modulating PLCγ2 activation, Ca2+ flux, and downstream NF-κB/MAPK pathways.
• Ibrutinib-class inhibitors bind the ATP site and covalently modify Cys481 near the hinge, leading to sustained kinase inhibition in systems where the target cysteine is accessible.
• Off-target considerations: Several Tec-family kinases and select unrelated kinases bearing a suitably placed cysteine can be covalently engaged depending on scaffold and warhead electronics.
• Cellular pharmacology: Time-dependent inhibition, residence time, and kinact/KI determine functional potency; DMSO concentration, serum protein binding, and intracellular glutathione can influence effective covalent labeling.
• Resistance mechanisms observed in literature for the class include point mutations at Cys481 (e.g., C481S) that decrease covalent adduct formation and increase reliance on reversible affinity.

Caveat: The precise target scope and potency of Ibrutinib‑MPEA are not specified for this SKU. Treat the following as hypotheses to be tested experimentally: BTK engagement, selectivity within Tec family, and potential off-target covalent labeling.

Buffer Applications

This product is a hydrophobic small-molecule library member rather than a buffering reagent. It is not used to set or maintain pH.

Practical tips (general, not item-specific):

• Choose buffers compatible with kinase assays (e.g., HEPES or Tris, pH 7.2–7.8) and keep DMSO ≤0.5–1% v/v on dilution from concentrated stocks.
• Include appropriate salts (NaCl, MgCl2 for ATP-binding kinases) and detergent (0.01–0.05% Tween-20) if nonspecific adsorption is a concern.
• Avoid high concentrations of free thiols (e.g., DTT, TCEP) when studying covalent kinetics unless intentionally testing competition effects.

Green Alternatives

Because this SKU is a specialized small-molecule tool, "green" considerations mainly relate to solvent selection and assay workflow rather than replacement of the active compound.

Greener solvent choices (general, not item-specific):

• Prefer water-based buffers with minimal DMSO (≤0.5–1% v/v) in biological assays.
• When analytical solubilization permits, consider acetonitrile over DMF for LC–MS workflows due to lower toxicity and better waste handling.
• Use ethanol or isopropanol as co-solvents where compatible, recognizing reduced solubilizing power for hydrophobic kinase inhibitors.

Comparison (general guidance):

| Use case | Conventional | Greener alternative | Trade-offs | |---|---|---|---| | Stock prep | DMSO | Water-rich buffer with minimal DMSO | Possible precipitation; limited solubility | | LC mobile phase | ACN/Water + FA | EtOH/Water + FA | Higher viscosity; pressure/retention changes | | Cleanup | Chlorinated solvents | EtOAc/IPA/MeOH | Solubility may be lower |

Operational improvements:

• Scale down assays (microplates, low dead-volume tips) to reduce solvent consumption.
• Consolidate waste streams and implement in-house solvent recycling for ACN/IPA when feasible.

Note: Any change in solvent system can affect inhibitor potency, permeability, and protein stability. Validate greener conditions with control experiments.

Pharmaceutical Uses

No therapeutic or clinical claims are made for this product. It is supplied strictly for research use only.

Formulation and development context (general, not item-specific):

• Ibrutinib-derived molecules may be used as reference materials or tool compounds in discovery workflows to benchmark assay performance, validate BTK-related biology, or compare to next-generation scaffolds.
• In preformulation research, stock solutions in DMSO can be used to assess solubility limits, precipitation tendencies in biorelevant media, and adsorption to plastics.
• For analytical development, such compounds can serve as system suitability standards for LC–MS methods targeting kinase inhibitors (retention windows, ionization efficiency), provided purity/identity are verified by CoA.

Regulatory note:

• Pharmacopeial monographs are generally unavailable for proprietary derivatives; method development should be accompanied by in-house reference standards and validated procedures where applicable.

Always refer to the item’s CoA/SDS for quality attributes and handle solely within non-clinical research environments.

Physical Properties

Item-specific physicochemical specifications are not provided in the Product Data.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
• BP/MP/Density/Refractive Index: Not specified for this item; refer to CoA/Spec Sheet.
• UV cutoff/Extinction: Not specified for this item; refer to CoA/Spec Sheet.
• Water/peroxide/metal limits: Not specified for this item; refer to CoA/Spec Sheet.

General/literature expectations for ibrutinib-derived small molecules (not item-specific):

• Typically nonvolatile solids with moderate-to-high lipophilicity; sparingly soluble in water; readily soluble in DMSO, and often soluble in DMF, acetonitrile, or mixed aqueous-organic systems with co-solvent.
• Stock solutions commonly prepared at 10–50 mM in anhydrous DMSO, then diluted into assay buffers to low micromolar or nanomolar concentrations.
• Compounds bearing an acrylamide warhead can show slow hydrolysis in basic/aqueous media; stability is generally improved in dry, neutral organic solvents at low temperature.

Practical note: For experimental planning, verify exact solubility and stability of this SKU using a small-scale test (serial dilution, visual inspection, and LC–MS). Rely on the product CoA for authoritative, item-specific values.

Quality and Grades

Item-specific grade and purity are not listed in the provided Product Data.

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

Context for small-molecule library compounds (general, not item-specific):

• Library members intended for screening are often supplied at high chemical purity (e.g., ≥95%) by HPLC with LC–MS identity confirmation; however, this should not be assumed. Always check the CoA for the exact purity, analytical method, and any stabilizers.
• If stabilizers or salt forms are used (e.g., TFA salt), these impact mass calculations, solubility, and storage; item-specific disclosure is required on the CoA.
• For analytical use (e.g., reference standards), users typically require: HPLC chromatogram, HRMS/ESI spectra, and where relevant, NMR confirmation. Request these documents if needed for regulated workflows.

Recommendations:

• Upon receipt, record lot number and CoA purity in LIMS/ELN.
• If long-term studies are planned, consider verifying identity/purity by orthogonal methods (LC–MS, 1H NMR) to establish an internal baseline and monitor any degradation on storage.

Reaction and Applications

Focus: This product is positioned as a small-molecule tool rather than a synthetic reagent. Applications emphasize biochemical/chemical biology studies. No manufacturer application text was provided; the following expands on typical uses of ibrutinib-derived probes (general literature, not item-specific):

• Covalent inhibition of BTK: Ibrutinib chemotype contains an acrylamide Michael acceptor that can form a covalent bond with Cys481 of BTK. Useful in enzymology to characterize time-dependent inhibition (kobs, kinact/KI).
• Target engagement assays: Competitive binding vs. a known covalent probe; thermal shift (CETSA) or NanoBRET displacement to quantify cellular target occupancy.
• Chemoproteomics: If the MPEA appendage functions as a tag/handle (not confirmed for this item), derivatives can enable affinity capture or click-chemistry enrichment; verify structure before planning such workflows.
• Selectivity profiling: Test against Tec-family kinases and off-target cysteine-containing kinases using kinase panels or activity-based profiling.
• Mechanistic studies: Determine time- and concentration-dependent inhibition, influence of reducing agents (DTT/βME), and competition with cysteine scavengers (e.g., glutathione) to infer covalency.

Practical notes:

• Prepare fresh DMSO stocks; minimize aqueous residence time before assays to limit hydrolysis of electrophilic warheads.
• Include appropriate vehicle controls and irreversible inhibitor controls to benchmark covalent kinetics.

Reminder: The exact functionalization implied by “MPEA” is not specified for this item; confirm structural features on the CoA before designing capture/enrichment experiments.

Reaction Conditions

As a bioactive small molecule, "reaction conditions" are typically assay/incubation conditions rather than synthetic transformations. Item-specific conditions are not provided; the following are general literature practices for covalent kinase inhibitor studies (not item-specific):

• Stock preparation: 10–50 mM in anhydrous DMSO; filter if necessary (PTFE, 0.2 µm). Store aliquots at −80°C.
• Biochemical BTK inhibition assays: Incubate enzyme with inhibitor at 0.1–10 µM for 15–60 min at 25–37°C in HEPES buffer (pH 7.4), 0.01–0.05% Tween-20, 1–5 mM MgCl2, with ATP at Km. Time-dependent inhibition analysis to extract kinact/KI.
• Covalent labeling confirmation: LC–MS of intact protein or tryptic peptides after incubation (e.g., 1–5 µM inhibitor, 30–60 min, 25–37°C). Include glutathione/βME competition controls.
• Cellular target engagement: Treat cells with 0.01–1 µM compound for 1–4 h; quantify BTK phosphorylation status or use NanoBRET competition where available. Maintain DMSO ≤0.1–0.5% v/v.
• Thermal shift (CETSA): Dose cells/lysates, heat gradient (e.g., 42–64°C), immunoblot BTK to assess stabilization; irreversible binders may show distinct profiles.

Notes:

• Excess free thiol (e.g., DTT) can compete with covalent labeling; use sparingly unless intentionally probing mechanism.
• Validate all conditions empirically for this SKU; exact potency/selectivity depend on its specific structure (not disclosed here).

Safety and Handling

Safety classification provided for this item is incomplete; consult the SDS prior to use.

• Signal Word: Not specified for this item; refer to SDS.
• H-Statements: Not specified for this item; refer to SDS.
• GHS Classification/Pictograms: Not specified for this item; refer to SDS.
• Research Use: For research use only.

General laboratory guidance (not item-specific):

• Use in a chemical fume hood with standard PPE: lab coat, safety glasses, and appropriate gloves (e.g., nitrile). Avoid inhalation, ingestion, and skin/eye contact.
• Potential hazard rationale (literature-based for covalent kinase ligands): acrylamide-containing electrophiles can be skin/respiratory sensitizers and irritants; avoid prolonged exposure. Prevent aerosolization and dust formation.
• Incompatibilities: Strong bases/acids may promote hydrolysis; strong nucleophiles (amines, thiols) can react with Michael acceptors. Avoid oxidizers unless controlled for synthesis.
• First aid overview: In case of contact, rinse affected area with plenty of water; remove contaminated clothing. If inhaled, move to fresh air. If ingested, rinse mouth and seek medical attention. Always follow SDS instructions.
• Waste: Collect organics and aqueous rinses containing DMSO/DMF/ACN in appropriate halogen-free organic waste per institutional and regulatory requirements.

Always defer to the product-specific SDS and institutional EHS policies for authoritative safety measures.

Solvent Selection

This product is a small-molecule library compound; solvent choice primarily supports stock solution preparation and assay compatibility.

• Item-specific solubility: Not specified for this item; verify experimentally and consult CoA.

General guidance for ibrutinib-derived molecules (literature, not item-specific):

• Primary stock solvent: Anhydrous DMSO (typical 10–50 mM stocks); minimizes hydrolysis of acrylamide moieties.
• Alternative solvents: DMF, acetonitrile, or mixtures with water containing surfactant or protein (e.g., 0.1–1% BSA) to mitigate adsorption in low-µM work.
• Aqueous buffers: Dilute DMSO stocks into assay buffers (e.g., HEPES, PBS) keeping final DMSO ≤0.5–1% v/v to preserve enzyme/cell assay performance.

Selection tips:

• For biochemical BTK assays, prefer HEPES or Tris buffers with added reducing agent (e.g., 1–2 mM DTT) only if compatible with covalent kinetics studies; note that excess thiol can compete with cysteine labeling.
• For cell-based assays, test a DMSO tolerance curve (0–1% v/v) and include vehicle controls.

Small comparison (general):

• DMSO: highest solvating power; hygroscopic; broadly compatible with enzymology and cell work at ≤0.5–1%.
• DMF/ACN: useful for intermediate stocks or analytical injections; assess biological compatibility carefully before use in live-cell systems.

Storage and Reconstitution

Item-specific conditions provided:

• Storage Conditions: Store at −80°C.
• Shipped In: Dry ice packs + Cold packs.

Additional best practices (general, not item-specific):

• On receipt, keep the container frozen (−80°C). Allow to equilibrate to room temperature in a desiccator before opening to prevent moisture condensation.
• Prepare concentrated DMSO stocks (e.g., 10–20 mM) under dry conditions. Filter if necessary (PTFE 0.2 µm). Dispense into single-use aliquots to minimize freeze–thaw.
• Short-term handling: Keep solutions on ice and minimize time in aqueous buffers before use to limit hydrolysis of electrophilic warheads.
• Light/air sensitivity: If degradation is suspected, work under reduced light and inert gas (N2/Ar) during stock prep.
• Stability monitoring: Periodically check by LC–MS/HPLC after storage. Discard aliquots showing new impurity peaks or loss of potency.

Reconstitution notes:

• Solubility is not specified for this item; start with DMSO and, if needed, add co-solvent (ACN, DMF) or gentle heating (<40°C) and sonication. Avoid strong base or nucleophiles during dissolution.

Always refer to the product’s CoA/Spec Sheet and SDS for definitive instructions and item-specific stability information.

Structure and Identity

Brief overview: Ibrutinib-MPEA is listed as a small-molecule library member related to ibrutinib. Item-specific identifiers are incomplete in the provided data.

• SKU: I656407
• Product Name: Ibrutinib-MPEA
• CAS: 1710768-30-1
• PubChem CID: 59799011
• Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.

Structural features (general literature context, not item‑specific):

• Compounds named “ibrutinib‑X” typically derive from ibrutinib, a covalent Bruton’s tyrosine kinase (BTK) ligand bearing an acrylamide Michael acceptor and a diarylamine/pyrazolopyrimidine core. Modifications (here “MPEA”) often append a linker/handle for probe chemistry or solubility tuning.
• Expected 2D motif (literature, not item-specific): heteroaromatic kinase-recognition core, secondary anilide/amino connections, and an electrophilic acrylamide side chain capable of reaction with cysteine.

Important note: Because the exact structure, stereochemistry, and linker identity for “MPEA” are not provided in the Product Data, do not assume precise atom connectivity. Consult the CoA/Spec Sheet or contact Aladdin Scientific for definitive identifiers and structure files (SDF/MOL, SMILES, InChI).

Synthetic Utility

This SKU is intended as a finished small-molecule tool; it is not typically used as a general synthetic reagent.

General structural/reactivity discussion for ibrutinib-class compounds (literature, not item-specific):

• The acrylamide warhead functions as a Michael acceptor toward thiols (e.g., protein cysteine), enabling covalent target engagement; it can also undergo conjugate addition with small-molecule thiols under forcing conditions.
• The heteroaromatic core (e.g., pyrazolopyrimidine-like) and anilide linkages offer diversification points via nucleophilic aromatic substitution, Buchwald–Hartwig amination, or amide coupling in analog synthesis.
• If “MPEA” denotes an appended linker/handle (exact nature not specified), it may provide a site for conjugation (click chemistry, amide formation) to craft probes or immobilized ligands.

Use in retrosynthesis (conceptual):

• Late-stage installation of the electrophilic acrylamide is often employed to avoid premature side reactions.
• Protecting-group strategies and chemoselective couplings are chosen to preserve the warhead during assembly.

Caution: Do not assume specific reactivity or functional groups for this SKU without the CoA/structure. If you intend derivatization, obtain the exact structure and verify stability of the warhead under planned conditions.

Target Specificity

Item-specific target profile is not provided in the Product Data.

• Confirmed (item-specific) antigen/target, epitope, clone/isotype: Not applicable; no biological reagent metadata supplied for this small molecule.

General literature context (not item-specific):

• Ibrutinib-class covalent inhibitors are designed to target BTK via covalent modification of Cys481 in the ATP-binding site.
• Off-target engagement can occur for kinases with a homologous cysteine near the ATP site (e.g., other Tec-family kinases), depending on scaffold and warhead orientation.

Action items:

• Determine specificity for this SKU experimentally using kinase activity panels, cellular phospho-BTK readouts, or chemoproteomic profiling.
• Consult the CoA or supplier technical notes for any available target-binding data specific to Ibrutinib‑MPEA.

Preguntas frecuentes

How should this product be stored?

Store at ?80 °C. Ultra-low temperature storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships frozen with dry ice and cold packs. Unpack on arrival and transfer it to the storage condition stated above; handle dry ice with insulated gloves in a ventilated area.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 1710768-30-1, the molecular formula is C32H39N9O2, and the molecular weight is 581.71 g/mol.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.