NXY-059 (Disufenton sodium) - 10mM in DMSO , CAS No.168021-79-2

CAS: 168021-79-2 Cat. No.: N408727 분자식: C₁₁H₁₃NNa₂O₇S₂ 분자량: 381.33

등급 & 순도 10mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

개요

Information

NXY-059 (Cerovive, Disufenton Sodium) is a novel nitrone, shows efficacious neuroprotective effects. Phase 3.
In vitro

NXY-059 is more soluble than the spin trapping agent α-phenyl-N-tert-butyl nitrone (PBN). ^[1] In an in vitro blood-brain barrier (BBB) model, 250 mM of NXY-059 administered at the onset or up to 4 h after oxygen glucose deprivation (OGD) produces a significant reduction in the increased BBB permeability caused by OGD. Furthermore, OGD produces a huge influx of tissue plasminogen activator across the BBB, which is substantially reduced by NXY-059. ^[2]

In vivo

NXY-059 reduces infarct volume in rats subjected to 2 hours of middle cerebral artery occlusion in a dose-dependent manner. At equimolar doses (3.0 mg/kg for NXY-059 and 1.4 mg/kg for PBN), NXY-059 is more efficacious than PBN. Similar results are obtained when a recovery period of 7 days is allowed. The window of therapeutic opportunity for NXY-059 is 3 to 6 hours after the start of recirculation. ^[1] NXY-059, a free radical-trapping agent, has a substantial protective effect, lessening the disability caused by an experimentally induced stroke in a primate species. NXY-059 treatment reduces the overall amount of brain damage by >50% of saline-treatment values, with similar levels of protection afforded to both white and gray matter. ^[3] Treatment with NXY-059 (50 mg/kg subcutaneous plus 8.8 mg/kg/h for 3 days subcutaneous delivered via implanted osmotic pumps) significantly decreases neurological impairment following intracerebral hemorrhage in rat, and reduces the neutrophil infiltrate observed 48 hours post-hemorrhage in the vicinity of the hematoma, and the number of TUNEL-positive cells 48 hours post-hemorrhage at the hematoma margin. ^[4]
Cell Data

cell lines：

Concentrations：

Incubation Time：

Powder Purity:

사양

사양 및 순도

10mM in DMSO

생화학 및 생리적 메커니즘

Free radical trapping agent. Reduces infarct size and preserves brain function in several animal models of acute ischemic stroke. Neuroprotectant.

보관 조건

Store at -80°C

배송

Dry ice packs + Cold packs

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이름과 식별자

이성체 SMILES

CC(C)(C)/[N+](=C/C1=C(C=C(C=C1)S(=O)(=O)[O-])S(=O)(=O)[O-])/[O-].[Na+].[Na+]

분자량

381.33

Reaxy-Rn

11120616

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=11120616&ln=

Application Protocols

Below are generalized, literature-informed protocols for common research uses. Adjust to your system and consult primary references.

1. Aqueous stock preparation

• Dissolve the compound in sterile water or buffer to prepare a concentrated stock (e.g., 100–500 mM if solubility permits; determine empirically). Filter sterilize (0.22 µm). Aliquot and store at −80°C.

2. EPR spin-trapping assay (cell-free)

• Buffer: 50 mM phosphate, pH 7.4, 25°C; include 0.1 mM DTPA if minimizing metal catalysis.
• Prepare radical source (e.g., xanthine/xanthine oxidase or Fenton system) in buffer.
• Add NXY-059 to 0.5–5 mM final concentration.
• Mix rapidly; transfer to EPR capillary; record spectra immediately and over time to capture adduct formation/decay.
• Include controls: buffer only, radical source only, and co-solvent controls if applicable.

3. Cell-based oxidative stress modulation (exploratory)

• Prepare working solution in culture medium immediately before use; minimize DMSO.
• Typical starting range: 100–1000 µM; assess cytocompatibility in your model.
• Treat cells concurrently with oxidant challenge; monitor endpoints (e.g., ROS probes, viability) with appropriate controls.

Notes

• Avoid metal-contaminated containers; use plastic or passivated glass.
• Confirm that the compound does not interfere with assay readouts (fluorescence/absorbance quenching, redox cycling).

Biological Roles

Research context (literature): NXY-059 (disufenton sodium) is widely referenced as a nitrone free-radical trap used to modulate and probe oxidative stress in biological systems.

• Mechanism of action (biochemistry): Nitrones undergo 1,3-dipolar addition to carbon- and oxygen-centered radicals to yield nitroxide adducts. This reduces steady-state radical concentrations and can intercept chain-propagating species.
• Reactive species addressed: Superoxide-derived radicals (via secondary chemistry), hydroxyl radicals (•OH), carbon-centered radicals from lipid peroxidation, and certain nitrogen-centered radicals; selectivity and rate constants vary by system.
• Use in enzymology and cell-free systems: Employed to dissect contributions of enzymatic vs non-enzymatic ROS generation; controls include catalase/SOD and metal chelators.
• Cell and tissue models: Utilized as a tool compound to adjust redox tone in vitro; uptake is limited by anionic character, making extracellular scavenging predominant unless transport mechanisms or permeabilization are used (literature generality).
• Analytical synergy: Pairing with EPR spectroscopy, fluorescence ROS probes (e.g., DCFH-DA, Amplex Red), and LC-MS adduct analysis enhances mechanistic insight.

Note: This section summarizes general literature roles of disulfonated nitrones. No medical or clinical claims are made. Users should tailor concentrations and exposure times to their specific biological model and confirm lack of interference with assay readouts.

Buffer Applications

This product is not a buffering agent per se. However, its use is tightly linked to aqueous buffer systems that maintain pH and ionic strength for radical-trapping studies.

Practical guidance (general):

• Common media: Phosphate-buffered saline (PBS), HEPES, or Tris buffers at pH 7.2–7.8 are frequently used for biochemical assays; confirm buffer compatibility with the readout (e.g., Tris can chelate metals weakly and may affect some reactions).
• Metal control: Incorporate chelators (e.g., 0.1 mM DTPA) to suppress Fenton-type background radical generation when desired.
• Ionic strength: Maintain physiological ionic strength for cell-facing assays; high salt does not typically precipitate disulfonate salts but verify solubility at intended concentrations.
• Filtration: Sterile filtration (0.22 µm) is recommended for cell-based experiments.
• Light/air: Routine lab lighting is acceptable, but minimize prolonged exposure to intense light/air if unintended photo/redox processes are a concern; use freshly prepared solutions for sensitive measurements.

Recipe hints (non-specific):

• Prepare a concentrated aqueous stock (e.g., in water or buffer) and dilute into the working buffer immediately prior to use.
• Avoid strong acids/bases that could compromise nitrone integrity; keep buffering capacity adequate to resist pH drift during radical generation assays.

Green Alternatives

As a research reagent used for radical trapping rather than as a process solvent, “green alternatives” focus on minimizing solvent burden and selecting benign auxiliaries in assays.

Strategies (general, literature):

• Prefer aqueous buffers over organic media where possible; NXY-059’s high water solubility supports purely aqueous systems, reducing VOC use.
• If organic co-solvent is unavoidable, use minimal DMSO and confirm that it does not confound radical chemistry.
• Choose alternative spin traps tailored to your endpoints to improve efficiency (lower loading), such as DMPO/DEPMPO/EMPO, potentially reducing overall chemical use.

Comparison snapshot (literature, qualitative):

• NXY-059 vs PBN: NXY-059 is more water-compatible (fewer organic solvents), improving EHS profile in aqueous assays.
• NXY-059 vs nitroxide scavengers (e.g., TEMPO): Different mechanisms; nitrones typically form adducts with transient radicals, while nitroxides may catalytically disproportionate radicals. Selection can lower required quantities.

Operational greening tips:

• Employ microplate-scale assays to minimize reagent volumes.
• Recycle/segregate aqueous waste streams to avoid mixing with chlorinated organics.
• Validate minimal effective concentration to reduce mass intensity (MI) and E-factor in screening workflows.

Pharmaceutical Uses

This item is provided strictly for research use. No therapeutic or clinical claims are made.

Formulation and development context (general, literature):

• Tool compound in preformulation: Due to high water solubility as a disulfonate, NXY-059 can serve as a model for studying formulation effects on highly ionized small molecules (e.g., stability, compatibility with excipients, container interactions).
• Analytical standards: May be used as a system suitability or spike-in control for redox-related analytical methods (EPR, LC-UV/LC-MS) during method development.
• Stability studies: Supports investigations into nitrone stability across pH, ionic strength, and temperature; data can inform handling of related chemotypes.

Pharmacopeial status, excipient roles, and cGMP manufacturing considerations: Not specified for this item; refer to CoA/Spec Sheet and assess per project requirements if considering use in regulated contexts (not supplied as GMP material).

Physical Properties

Item-specific specifications (BP/MP/density/UV cutoff/metal limits) 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.
• Solubility (literature, qualitative): Highly water-soluble due to presence of disulfonate sodium salt groups; limited solubility in nonpolar organic solvents. Readily prepares neutral aqueous buffers and cell-compatible media.
• Ionization (literature): Strongly anionic at physiological pH via sulfonate groups; nitrone nitrogen is neutral/part of N-oxide imine functionality. No conventional pKa associated with sulfonate (very strong acid; fully deprotonated in water).
• Partitioning (literature, qualitative): Expected low logP and high logD(7.4) negativity, favoring aqueous phase; minimal permeability across hydrophobic matrices relative to non-sulfonated nitrones (e.g., PBN).
• Hygroscopicity: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point/decomposition: Not specified for this item; refer to CoA/Spec Sheet.

Practical handling note (general): As a highly water-soluble disulfonate salt, solutions are typically prepared in water or buffered saline; filtration (0.22 µm) is recommended for sterility. Avoid extended heating of solutions (nitrones can undergo slow decomposition in the presence of strong nucleophiles or metals; literature generality).

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Intended use: For research use only (per Product Data). Not for human or veterinary use.

Discussion and implications:

• In the absence of a stated grade (e.g., BioXtra, USP, HPLC, or screening library grade), users should consult the Certificate of Analysis for assay purity, residual solvents, water content, and chromatographic identity.
• Screening-library compounds (category indicates inclusion in a small-molecule/compound library) are commonly provided at high chemical purity (e.g., ≥95% by HPLC), but this is not specified here; verify on the CoA.
• Stabilizers/Inhibitors: None specified. Many nitrones are supplied neat as salts without stabilizers; if stabilizers are present, they will be disclosed on the CoA/SDS.
• UV profile/LC-MS suitability: Not specified. If intended for HTS, confirm low nonvolatile residue and predictable ionization in the selected MS method.

Best practices to ensure quality in use:

• Record lot-specific purity/identity data from the CoA in ELNs to ensure reproducibility.
• Perform quick incoming QC (e.g., 1H NMR in D2O, LC-UV) where critical.
• For screening, prepare DMSO or aqueous master stocks using volumetric methods, and confirm concentration by UV or qNMR when needed.

Reaction and Applications

This compound is primarily used as a free-radical trapping agent and antioxidant probe in chemical and biochemical systems.

Key application areas (literature):

• Radical trapping: The nitrone moiety forms persistent nitroxide adducts with carbon-, oxygen-, and nitrogen-centered radicals, enabling kinetic quenching and detection.
• EPR spin trapping: Generation of EPR-detectable nitroxide adducts allows identification of radical type and lifetime. Often used in conjunction with controlled radical sources (e.g., xanthine/xanthine oxidase, Fenton systems).
• Oxidative stress models: Employed to modulate ROS/RNS in in vitro assays, redox enzymology, and materials degradation studies.

Practical notes:

• Degassing/oxygen: Oxygen competes in radical reactions; for mechanistic work, rigorously degas solutions (argon sparge) or define O2 content.
• Metal ions: Transition metals catalyze radical generation/decay; include metal chelators (e.g., DTPA) when appropriate, and avoid metal-rich glassware if uncontrolled.
• Concentration windows: Literature use commonly spans ~0.1–10 mM, adjusted to radical flux; validate by titration and EPR/UV readouts.
• Matrix effects: Buffers and co-solvents (notably DMSO, ethanol) can themselves scavenge radicals—use matched controls.

Analytical readouts:

• EPR: Hyperfine splitting patterns of adducts inform radical identity.
• LC-MS/LC-UV: Detection and quantification of adducts and parent compound degradation products.

Note: This section reflects general literature behavior of disulfonated nitrones; confirm conditions for your specific system.

Reaction Conditions

Typical usage conditions below are provided as general literature guidance for nitrone-based radical trapping and EPR studies with water-soluble disulfonated nitrones; optimize for your system.

• Concentration: Commonly 0.1–10 mM depending on radical flux; start with 1 mM and titrate.
• Solvent: Aqueous buffer (PBS, HEPES). Limit organic co-solvent; if required, ≤1–2% DMSO v/v with appropriate controls.
• pH: Neutral to mildly basic (pH 7.0–8.0) to preserve nitrone integrity and biological compatibility.
• Temperature: 20–37°C for biochemical assays; maintain constant temperature to ensure reproducible kinetics.
• Metal control: Add 0.05–0.1 mM DTPA when suppression of metal-catalyzed background is desired.
• Atmosphere: Ambient air for biological relevance, or degassed (argon/nitrogen) for mechanistic kinetic studies.
• Reaction time: Seconds to hours depending on radical generation rate and detection method; monitor in real time by EPR or quench and analyze by LC-MS/UV.

Expected outcomes (literature):

• Formation of nitroxide adducts with characteristic EPR spectra; adduct stability varies with radical type and substituents.
• Decrease in observable radical-dependent probe signals (e.g., inhibited lipid peroxidation markers) proportional to nitrone concentration.

Caveats:

• Co-scavengers (e.g., DMSO, ethanol) confound kinetics.
• High ionic strength or extreme pH may alter reactivity and detection.

Safety and Handling

Authoritative safety information must be taken from the product’s SDS. No GHS details are specified in the Product Data.

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

General laboratory precautions (good practice):

• Personal protective equipment: lab coat, safety glasses, and appropriate gloves (e.g., nitrile). Handle powders in a fume hood to avoid inhalation of dust/aerosols.
• Avoid contact with strong oxidizers or reducing agents that may undesirably transform nitrone functionality; minimize exposure to transition metal contaminants that can catalyze radical chemistry.
• Nitrones are free-radical traps; while often of low acute hazard, they may cause irritation upon contact or ingestion—consult SDS for specific hazard classes.
• Solution preparation: Use clean, preferably metal-ion–free plasticware or pre-passivated glassware to limit adventitious redox processes. Filter sterilize if using in cell-based research.

First-aid overview (consult SDS for definitive guidance):

• Inhalation: Move to fresh air; seek medical attention if symptoms persist.
• Skin/eye contact: Rinse with water for several minutes; remove contaminated clothing; seek medical advice if irritation continues.
• Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.

Fire and spill response (general):

• Not known to be highly flammable as an inorganic-rich salt; use water spray, CO2, or dry chemical appropriate for surrounding materials. For spills, avoid dust formation; collect with inert absorbent and dispose per local regulations.

Solvent Selection

Solvent choice for NXY-059 is dominated by its disulfonate sodium salt character and nitrone functionality.

• Polarity class (literature, qualitative): Highly polar/ionic; best handled in water or aqueous buffers (e.g., PBS, HEPES).
• Miscibility profile (literature): Freely soluble in water; limited solubility in nonpolar solvents. Solubility in highly polar organic media (e.g., methanol) may be moderate but generally inferior to water for the disodium salt. DMSO can solubilize many salts, but confirm compatibility.
• pH considerations: Sulfonate groups remain ionized across typical pH ranges; maintain neutral to mildly basic pH to preserve nitrone integrity. Avoid strong acid/base which can promote hydrolysis or rearrangement.
• When to choose water vs DMSO:
  • Water/buffer: Preferred for biological assays, EPR spin-trapping, and ROS/RNS scavenging studies.
  • DMSO: Use sparingly if required for concentrated stocks; DMSO itself is a radical scavenger—control experiments are essential.

Comparison (literature, qualitative):

• Versus PBN (N-tert-butyl-α-phenylnitrone): NXY-059 is far more water-soluble, facilitating aqueous assays without co-solvent.
• Versus DMPO/DEPMPO spin traps: These are also water-soluble nitrones/nitroxides; selection depends on target radical specificity and EPR adduct stability.

Practical tips:

• Prepare aqueous stocks, filter (0.22 µm), and aliquot. Avoid metal-contaminated water (use chelex-treated or ultrapure water if trace metals are problematic).

Storage and Reconstitution

Item-specific conditions per Product Data:

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

Reconstitution (general guidance for this class of compounds):

• Solvent: Use sterile water or suitable buffer (e.g., PBS, HEPES) to prepare concentrated stock solutions. If high concentrations are required and solubility allows, a minimal fraction of DMSO may be employed with controls.
• Technique: Allow the container to equilibrate briefly to reduce condensation; open under low-humidity conditions. Dissolve with gentle mixing; avoid vigorous vortexing that can introduce air.
• Filtration: For sterile applications, pass through a 0.22 µm filter.
• Aliquoting: Dispense into single-use aliquots to avoid repeated freeze–thaw.

Stability considerations (general):

• Freeze–thaw: Minimize cycles; store aliquots at −80°C protected from light. Thaw on ice and use promptly.
• Aqueous solution stability: Prepare fresh working solutions; prolonged storage at room temperature or elevated pH may promote nitrone degradation.
• Containers: Use polypropylene tubes or borosilicate glass; avoid reactive metals. For trace-metal–sensitive experiments, consider chelex-treated water.

Disposal: Dispose of unused solutions and materials according to institutional and local regulations for organic salts and laboratory chemicals.

Structure and Identity

NXY-059 (Disufenton sodium) is a small-molecule nitrone free-radical trapping agent supplied for research use.

• SKU: N408727
• Product Name: NXY-059 (Disufenton sodium)
• CAS: 168021-79-2
• PubChem CID: 6440181
• Synonyms (literature): NXY-059; disufenton sodium; nitrone spin trap derivative of PBN with sulfonate groups for aqueous solubility
• 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 (literature, non-spec):

• Contains a nitrone functional group (R1–CH=N+(O−)–R2), typically derived from N-tert-butylnitrone (PBN) chemistry.
• Aromatic ring bearing disulfonate groups (present as sodium salts) that confer high aqueous solubility and anionic character.
• Alkyl substituent on the nitrone nitrogen (classically tert-butyl in PBN analogs), providing steric bulk and modulating reactivity.
• 2D description: an anionic, disulfonated phenyl core attached to an N-oxide imine (nitrone) moiety; overall zwitterionic resonance but isolated as a disodium salt.

Note: Exact atom connectivity (SMILES/InChI) and empirical formula for this specific catalog item are not provided here; consult the product CoA/Spec Sheet for definitive identifiers.

Synthetic Utility

NXY-059 is primarily a final research reagent rather than a general-purpose synthetic building block.

• Reactivity (literature): Nitrones are 1,3-dipoles capable of [3+2] cycloadditions with alkenes/alkynes to form isoxazoline/isoxazolidine adducts. However, the presence of disulfonate sodium salts and an electron-deficient aromatic core biases the compound toward use as a radical trap in water rather than as a cycloaddition substrate in organic synthesis.
• Functional group compatibility: Stable under neutral aqueous conditions; strong acids/bases or nucleophiles can induce degradation or rearrangement of nitrone functionality over time.
• Retrosynthetic value: Limited, as the disulfonated, highly polar structure complicates downstream derivatization and isolation in non-aqueous settings.

If synthetic transformation is attempted (general guidance):

• Use polar protic or mixed aqueous-organic media; monitor by LC-MS.
• Control counterions and ionic strength to manage phase behavior.
• Expect challenges in extraction-based workups; resort to ion-exchange or lyophilization methods.

Target Specificity

This product is a small-molecule reagent, not a biological affinity reagent. No antigen/epitope/clone/isotype information applies.

• Target specificity (context): Reacts broadly with transient free radicals via nitrone trapping; selectivity among radical classes is governed by intrinsic reaction rates and environmental conditions rather than discrete molecular targets.

Item-specific immunochemical details: Not applicable.

자주 묻는 질문

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 168021-79-2, the molecular formula is C11H13NNa2O7S2, and the molecular weight is 381.33 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.