8-Br-7-CH-ADPR , CAS No.1011457-95-6

CAS: 1011457-95-6 Cat. No.: B1437914 Fórmula: C₁₆H₂₃BrN₄O₁₄P₂ Peso molecular: 637.22

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Descripción general

8-Br-7-CH-ADPR (8-Bromo-7-deazaadenosine-5'-O-diphosphoribose) is a specific TRPM2 antagonist that inhibits TRPM2 activation by binding to the NUDT9 homology domain of the TRPM2 channel, thereby controlling the influx of cations through the cell membrane channel. 8-Br-7-CH-ADPR can be used to study the role of TRPM2 in pathological processes such as cell death, neurodegenerative diseases, myocardial infarction, and diabetes.

Especificaciones

Condiciones de almacenamiento de almacenamiento

Store at -20°C

Enviado en

Ice chest + Ice pads

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

Tipo de acción

ANTAGONIST

Nombres e identificadores

Peso molecular

637.22

Application Protocols

No tested applications or protocols are provided in the Product Data for SKU B1437914.

General example workflows for ADP‑ribose analogs (for planning only; not validated for this item):

• Enzyme inhibition or binding assays: Prepare serial dilutions in assay buffer (e.g., 10 mM HEPES, 150 mM NaCl, pH 7.5). Include appropriate controls (vehicle, known ligand). Incubate with purified protein and detect by activity readout, fluorescence polarization, ITC, or SPR.
• Ion channel assays (e.g., TRPM2 gating studies): Prepare fresh aqueous stocks; apply to inside-out patches or whole-cell configurations as per lab SOPs, controlling free Mg2+ and Ca2+ levels. Validate concentration–response curves anew for each analog.
• LC–MS reference standard use: Prepare accurately weighed standards, correct for counterion/water of hydration as needed, and generate calibration curves under your chromatographic conditions.

Important: These are generic, literature-style outlines. They are not item-validated protocols. For this specific SKU, consult your internal methods and the CoA/Spec Sheet for any supplier recommendations.

Biological Roles

Item-specific biological activity data are not provided for this SKU. The following is general, literature-based context for ADP‑ribose and its analogs, not specific claims about this item.

General context:

• ADP‑ribose is a pivotal metabolite in cellular signaling and DNA damage response, serving as a building block for poly(ADP‑ribose) chains synthesized by PARP enzymes and recognized/processed by macrodomains and hydrolases (e.g., PARG, ARH family).
• ADPR can gate specific ion channels (notably TRPM2) and participates in calcium signaling pathways. Structural modifications on the adenine ring (e.g., 8‑halogenation) are often explored to tune binding affinity and selectivity in vitro.
• Cyclic ADP‑ribose (cADPR) is a separate messenger with distinct activity; however, linear ADP‑ribose analogs can be valuable as tools to probe binding versus catalytic turnover across ADP‑ribose–recognition proteins.

Experimental implications:

• Purine substitutions can alter hydrogen bonding/π‑stacking within binding pockets, influencing Kd and catalytic efficiency; hydrophobic substitutions at positions 7/8 sometimes increase affinity for hydrophobic subpockets while decreasing catalytic turnover (case-dependent).
• Phosphate integrity: Enzymatic assays can be sensitive to phosphate masking and metal ion content. Validate buffer composition and ionic strength for your target system.

For this specific product, consult primary literature or the CoA for any documented protein targets or potency metrics if available.

Buffer Applications

This product is a small-molecule nucleotide analog rather than a buffer reagent. Therefore, it is not typically used to prepare buffering systems.

Practical handling in buffers (general guidance for ADP‑ribose analogs):

• Preferred matrices: Neutral pH aqueous buffers such as HEPES, MOPS, Tris, or phosphate-buffered saline are commonly used for enzyme and binding assays involving nucleotide analogs.
• pH considerations: Maintain pH 7.0–7.8 to balance compound stability (phosphate ester hydrolysis is faster at high pH) and protein compatibility. Avoid prolonged exposure to pH <5 or >9 unless stability has been validated.
• Ionic strength: Moderate ionic strength (50–200 mM salt) can improve solubility and protein assay robustness; adjust according to target protein requirements.
• Metal ions: Divalent cations (Mg2+, Ca2+) can be essential cofactors in some assays but may also influence stability; include or exclude intentionally.

Item-specific buffer compatibility or stock solution guidance is not provided; refer to the CoA/Spec Sheet or develop conditions empirically for your assay.

Green Alternatives

For highly polar nucleotide analogs such as ADP‑ribose derivatives, “green alternative” considerations primarily concern solvent choices and waste minimization rather than substituting the active reagent.

Greener handling strategies (general guidance):

• Prefer water-based systems: Conduct dissolution and assay work in aqueous buffers at neutral pH where feasible, minimizing use of organic solvents.
• DMSO minimization: If DMSO is required for stock solutions, use the smallest volume necessary and dilute promptly into water/buffer. Capture DMSO waste for appropriate disposal.
• Buffer selection: Choose Good’s buffers (e.g., HEPES, MOPS) with favorable environmental and compatibility profiles; avoid volatile amines when possible.
• Waste reduction: Scale experiments judiciously; combine compatible aqueous waste streams; neutralize and treat according to local regulations.

Comparison (general):

• Organic cosolvents (acetonitrile, DMF) vs water-based buffers: Water/buffer offers the best EHS profile, lowest flammability, and simpler waste handling; organic solvents may only be necessary for analytical calibration or special assays.

Trade-offs:

• Aqueous systems can limit solubility for hydrophobically substituted analogs; in such cases, minimal DMSO or ethanol cosolvent may be required. Balance assay tolerance with environmental and safety considerations.

Note: No greener chemical substitute is suggested here because the compound itself is the subject of study; optimization focuses on solvent and process choices.

Pharmaceutical Uses

No pharmacopeial or excipient information is provided for this SKU. This product is supplied strictly for research use only.

General notes for nucleotide analogs in a pharmaceutical development context (non-clinical, informational):

• Role: Such compounds are typically investigated as biochemical probes or as starting points for target validation in discovery biology; they are not conventional excipients.
• Formulation studies: When used in preclinical research, solutions are often prepared in sterile water or isotonic buffers; stability and sterility must be verified for the specific compound and application.
• Regulatory status: Absent USP/EP monographs, materials are treated as research reagents; any use beyond laboratory research requires additional qualification.

For this specific item, no therapeutic or formulation claims are made. Consult the CoA/Spec Sheet for any available quality attributes if you intend to use it in regulated method development.

Physical Properties

Item-specific physical constants are not provided in the Product Data.

Item-specific values:

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point, boiling point, density, refractive index, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility: Not specified for this item; refer to CoA/Spec Sheet.

General/literature expectations for ADP‑ribose analogs (not specifications):

• Physical state: Typically isolated as a solid (often as a salt); many nucleotide analogs are hygroscopic.
• Aqueous behavior: High polarity and multiple ionizable phosphate groups usually confer good solubility in water and buffered saline across pH 6–8.
• Organic solvents: Poor solubility in most nonpolar and many mid‑polarity organic solvents; limited solubility can sometimes be achieved in DMSO for stock solutions.
• pKa/logP: Polyprotic phosphate groups exhibit acidic pKa values (≈1–2 and 6–7 for dihydrogen phosphate/hydrogen phosphate equilibria, literature-general for phosphate esters); overall logP is expected to be very low (strongly hydrophilic), but exact values for this item are not specified.

Note: For experiment planning, verify the exact counterion, hydration state, and solubility for this SKU on the CoA/Spec Sheet and SDS.

Quality and Grades

Item-specific grade/purity details are not provided in the Product Data for SKU B1437914.

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

General guidance for nucleotide analogs in research use:

• Research-grade nucleotide analogs are typically characterized by HPLC/UPLC purity and are supplied as defined counterion salts (e.g., sodium, triethylammonium). The stated purity usually reflects area % by HPLC at a specific wavelength; trace salts and water of hydration may be present.
• If a stabilizer or counterion exchange is relevant, the CoA will note it. Stabilizers (e.g., small amounts of buffer salts) can influence solubility and mass balance.
• For analytical and biochemical work (e.g., enzyme assays or binding studies), low UV-background and defined salt content are desirable. If you require low bioburden or endotoxin specifications, confirm availability prior to purchase.
• Recommended verification on receipt: Inspect for a single, dominant HPLC peak; confirm identity by HRMS and/or NMR if your workflow demands trace-level certainty. For quantitative work, consider drying to constant weight under mild vacuum if permitted by the material’s stability (verify with CoA/SDS).

Reaction and Applications

Manufacturer applications: Not provided in the Product Data for this item.

General research applications for ADP‑ribose analogs (literature-based; not item-specific claims):

• Enzymology and binding studies: ADP‑ribose and analogs are widely used as ligands or substrates in in vitro studies of ADP‑ribosylation machinery (e.g., PARPs, PARGs, macrodomains), ADPR-sensitive ion channels (e.g., TRPM2), and ADP‑ribose transferases/hydrolases.
• Probe/antagonist development: Purine ring substitutions (e.g., at C8) modulate recognition by protein binding pockets; such analogs can serve as structure–activity relationship (SAR) tools to dissect binding determinants.
• Analytical standards: Employed as reference compounds for LC–MS quantification methods in nucleotide and ADP‑ribose metabolomics, subject to availability of authentic standards.

Practical considerations:

• Purity and counterion: The presence of inorganic salts and water of hydration impacts mass-based dosing; use molar dosing whenever possible.
• Solution handling: Prepare fresh aqueous or DMSO stocks; avoid repeated freeze–thaw of working solutions to minimize hydrolysis of phosphate esters.
• Metal sensitivity: Trace divalent cations can catalyze phosphate cleavage in some contexts; if necessary, include chelators (e.g., EDTA) consistent with your assay design.

Note: For this specific SKU, consult the CoA/Spec Sheet and SDS for any item-validated applications or test conditions, if available.

Reaction Conditions

No item-specific reaction or assay conditions are provided in the Product Data.

General conditions for handling ADP‑ribose analogs in biochemical assays (literature-based guidance, not specifications):

• Stock solutions: Prepare in water or buffer at neutral pH; if necessary, dissolve in minimal DMSO (e.g., 10–50 mM stocks) and dilute into assay buffer to a final DMSO content typically ≤1–2%, ensuring assay compatibility.
• Temperature: Most assays run at 20–37 °C. Avoid prolonged heating; phosphate esters can hydrolyze faster at elevated temperature and extreme pH.
• Light sensitivity: Purine nucleotides can show some UV sensitivity; protect solutions from strong light during long incubations.
• Metals: For enzyme assays that do not require divalent cations, consider adding 0.1–1 mM EDTA to minimize adventitious metal effects; omit chelators where Mg2+/Mn2+ are needed.
• Typical ranges: Binding/enzymatic assays often employ 0.1–1000 µM concentrations depending on affinity and assay format. Determine exact ranges empirically for the target system.

Analytical characterization:

• Monitor integrity by HPLC/UPLC with UV at 254–260 nm and confirm by MS if possible. Track any degradation products (e.g., phosphate cleavage) during storage/use.

For this product, consult the CoA/Spec Sheet for any validated conditions if available.

Safety and Handling

GHS and hazard information (item-specific):

• Signal Word: Not specified for this item; refer to SDS.
• H‑Statements: Not specified for this item; refer to SDS.
• GHS Classification: Not specified for this item; refer to SDS.
• Pictograms: Not specified for this item; refer to SDS.

General safety guidance for nucleotide analogs (not a substitute for the SDS):

• Likely hazards: Many nucleotides are of low volatility and present low acute inhalation risk; however, dust generation should be minimized. Sensitization and specific organ toxicity data may be limited—handle as a chemical of unknown hazard.
• PPE: Use lab coat, safety glasses, and appropriate disposable gloves (e.g., nitrile). Employ dust control practices; handle solutions in a fume hood if aerosolization or acid/base treatment is anticipated.
• Incompatibilities: Strong acids/bases may hydrolyze phosphate esters; avoid prolonged exposure to elevated temperatures and metal-catalyzed oxidative conditions. Avoid contact with oxidizing agents.
• First aid (general): If inhaled, move to fresh air. On skin contact, wash with soap and water. If in eyes, rinse cautiously with water for several minutes and remove contact lenses if present and easy to do. If ingested, rinse mouth and seek medical advice. Consult the SDS for definitive measures.
• Environmental: Prevent release to the environment without appropriate treatment; dispose of aqueous solutions and solids according to institutional and local regulations.

Always consult the product-specific SDS prior to use.

Solvent Selection

Item-specific solubility and solvent recommendations are not provided for this SKU.

General solvent guidance for ADP‑ribose analogs (literature-based expectations):

• Aqueous media: Typically the preferred solvent system due to high polarity and multiple ionic phosphate groups. Use deionized water or biological buffers (e.g., HEPES, phosphate-buffered saline) at neutral pH.
• DMSO: Often used to prepare concentrated stock solutions (e.g., 10–100 mM) for biochemical assays when water solubility is limiting; then dilute into buffer immediately before use. Verify compatibility with your assay components.
• Alcohols/other organics: Methanol and ethanol can sometimes dissolve small amounts but may not be practical for concentrated stocks; solubility in acetonitrile, acetone, and nonpolar solvents is typically poor.

Polarity/miscibility (general):

• Strongly hydrophilic; expected to be fully miscible with water; immiscible with nonpolar solvents.

Practical tips:

• Adjust ionic strength and pH to enhance dissolution; gentle warming (≤30 °C) and brief sonication can help, avoiding prolonged heating.
• Filter sterilize aqueous stocks (0.22 µm) if sterility is required for biological assays.

Note: Confirm the precise solubility and any counterion/cocrystal specifics for this item on the CoA/Spec Sheet before preparing stocks.

Storage and Reconstitution

Storage (item-specific from Product Data):

• Store at −20 °C.
• Shipped in an ice chest with ice pads.

General handling and reconstitution guidance for nucleotide analogs (not specifications):

• Upon receipt: Allow the sealed container to equilibrate to room temperature in a desiccator before opening to avoid moisture condensation if the material is hygroscopic.
• Reconstitution: If item is supplied as a solid, dissolve in sterile water or appropriate buffer at neutral pH. If solubility is limited, prepare a concentrated DMSO stock and dilute into buffer immediately before use. Filter sterilize (0.22 µm) if sterility is required.
• Working solutions: Store on ice during use. For short-term storage (hours to a day), keep at 2–8 °C protected from light. Avoid repeated freeze–thaw cycles—aliquot stock solutions and freeze at −20 °C or below.
• Stability: Phosphate esters can hydrolyze under acidic or basic conditions and at elevated temperatures. Validate stability in your chosen buffer by analytical HPLC.
• Documentation: For exact solvent, counterion, concentration limits, and long-term stability of this SKU, refer to the CoA/Spec Sheet and SDS.

Research Use Note: For research use only.

Structure and Identity

Overview: 8-Br-7-CH-ADPR is described as a substituted ADP‑ribose analog. The name suggests an ADP‑ribosyl nucleotide built on an adenosine scaffold bearing an 8‑bromo substitution on the purine base and an additional hydrophobic substituent associated with the 7‑position of the adenine ring (inferred from the name). Item-specific identifiers are not provided below unless explicitly stated.

Item-specific identifiers (from Product Data):

• CAS: 1011457-95-6
• Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

Structural features (general, literature-based inference):

• Core: Adenine-derived nucleobase linked to ribose(s) with a diphosphate moiety characteristic of ADP‑ribose analogs.
• Functional groups: Polyol ribose hydroxyls; pyrophosphate (diphosphate) functionality; halogen substituent at the 8‑position of the purine; an additional hydrophobic group associated with the 7‑position (designation “7‑CH” in the name; exact identity not specified for this item).
• Ionization: Multiple anionic sites at physiological pH due to diphosphate; expected to form sodium or other counterions in isolated salts (general information).

2D structure (verbal description, general): A purine ring (adenine-like) bearing an 8‑bromo substituent and a 7‑position hydrophobic substituent, N9‑linked to a ribose; the ribose 5′‑position carries a diphosphate chain connected to a terminal ribose (ADP‑ribosyl motif). Exact substitution pattern for this specific item is not specified; consult CoA/Spec Sheet for definitive structure.

Synthetic Utility

As a specialized ADP‑ribose analog, 8‑Br‑7‑CH‑ADPR is primarily a biochemical probe rather than a general synthetic building block. Item-specific reactivity data are not provided.

General synthetic context for nucleotide analogs (literature-based):

• Protecting group chemistry: Synthesis typically involves stepwise protection of ribose hydroxyls and phosphate installation via phosphoramidite or phosphorochloridate chemistry, followed by coupling to generate the diphosphate and final deprotection under carefully controlled conditions.
• Base modification: 8‑halogenation of adenine and further substitution at C7/C8 are common tactics to alter electronics and steric profile for SAR studies; cross-coupling on 8‑halo purines (e.g., Suzuki, Sonogashira) can be used at the nucleoside stage prior to phosphorylation (general strategy; not specific to this SKU).
• Salt form/counterion exchange: Post-synthesis ion-exchange methods are employed to deliver defined counterion salts (e.g., Na+, TEA) suitable for biochemical work.

Utility in synthesis:

• While not typically used as a reagent, ADPR analogs can serve as authentic standards to validate enzymatic synthesis of ADP‑ribosylated products or to calibrate LC–MS methods for ADP‑ribosylation workflows.

Note: For practical synthetic handling of this exact compound, refer to primary literature or the supplier’s CoA for structure-specific conditions, if available.

Target Specificity

This product is a small-molecule nucleotide analog, not a biological macromolecule (e.g., antibody). No item-specific target, epitope, clone, or species reactivity information is provided in the Product Data.

General note (literature context, not item-specific claims): ADP‑ribose analogs are often employed to probe proteins that bind, transfer, or hydrolyze ADP‑ribose (e.g., PARP family, macrodomains, TRPM2). However, target specificity varies widely with substitution pattern and must be established experimentally for each analog.

For definitive target information, binding constants, or inhibition/activation profiles for this SKU, please refer to primary literature or request the CoA/Spec Sheet if available.

Preguntas frecuentes

How is this product shipped?

This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.

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

The CAS Number is 1011457-95-6, the molecular formula is C16H23BrN4O14P2, and the molecular weight is 637.22 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.