Sulfane sulfur probe 4 , CAS No.1810731-98-6

CAS: 1810731-98-6 Cat. No.: S1450979 Formula: C₃₄H₂₀O₇S₂ Peso molecolare: 604.65

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Panoramica

Sulfane sulfur probe 4 (SSP4) is a fluorescent probe used to detect sulfane sulfur species (E x /E m =494/515 nm). Sulfane sulfur probe 4 exhibits high sensitivity in detecting sulfane sulfur, even in the presence of other substances such as homocysteine, methionine, cysteine, glutathione, N-acetyl-L-cysteine, glycine, tyrosine, tryptophan, arginine, and metal ions (Fe 2+ , Fe 3+ , Mg 2+ , Ca 2+ , and Zn 2+ ).

Specifications

Condizioni di conservazione di stoccaggio

Store at -20°C

Spedito in

Ice chest + Ice pads

Questo prodotto richiede spedizione a catena fredda. I servizi di terra e altri servizi economici non sono disponibili.

Nomi e identificatori

Peso molecolare

604.65

Application Protocols

Item-specific, tested applications and recommended protocols (e.g., microscopy, flow cytometry, plate reader settings, working concentrations) are Not specified for this item; refer to CoA/Spec Sheet.

Note on literature practices (for context only; not product instructions)

• Researchers commonly prepare concentrated DMSO stocks and dilute into buffered media immediately before measurements, maintaining low organic content and protecting from light. Exact concentrations, incubation times, and instrument settings vary by cell type, assay format, and instrumentation and must be optimized by the user.

Biological Roles

Literature/general background (not product-specific claims)

• Sulfane sulfur species (persulfides, polysulfides) are emerging redox-active metabolites in sulfur biology. They can arise from enzymatic pathways involving cystathionine β-synthase (CBS), cystathionine γ-lyase (CSE), and 3-mercaptopyruvate sulfurtransferase (3-MST), as well as from non-enzymatic transformations of hydrogen sulfide (H2S) and thiosulfate.
• Functional roles: Sulfane sulfur acts as a potent nucleophile and electrophile in different contexts, enabling protein persulfidation (S-sulfhydration) that modulates enzymatic activity, signaling, and antioxidant capacity. Polysulfides can also directly modify cysteine residues, influencing cellular redox homeostasis.
• Compartmentalization: Mitochondria and the cytosol are common sites for sulfane sulfur generation and turnover; local pH and thiol pools (e.g., GSH) affect speciation.

Role of SSP-class probes (general)

• Mechanistic readout: Fluorescence turn-on correlates with the presence/flux of electrophilic sulfane-sulfur pools rather than free H2S, enabling discrimination among sulfur species under defined conditions.
• Experimental considerations: Cellular uptake, esterase activity (if applicable), and intracellular pH can influence probe response. Ratiometric calibration is generally not inherent to SSP-type probes, so parallel controls with known donors/inhibitors are recommended.

For this specific item, no biological validation data are provided in the listing. Users should consult the primary literature on SSP4 and verify performance under their exact experimental conditions.

Buffer Applications

Not a buffering reagent. However, buffers are central to using sulfane-sulfur probes effectively (literature/general guidance):

• Common systems: PBS (pH 7.2–7.6), HEPES (pH 7.2–7.5), or Tris (pH 7.4) support robust reactivity and fluorescence for fluorescein-like probes after activation.
• pH considerations: Maintain near-neutral pH to balance probe stability with phenolate fluorescence after activation; acidic pH can suppress fluorescence, while strong basic conditions may cause hydrolysis of masking groups.
• Additives: Keep metal chelators (e.g., EDTA) low unless needed, as some transition metals can catalyze polysulfide decomposition. Avoid high concentrations of free thiols that may quench or compete depending on the assay design.
• Organic cosolvent: Limit DMSO/ethanol to ≤0.5–1% v/v in cell-based assays. In purely chemical assays, higher organic content may be acceptable but can shift fluorescence baselines.

Item-specific buffer recommendations, working concentrations, and recipes are Not specified for this item; refer to CoA/Spec Sheet and primary literature.

Green Alternatives

Context

• Fluorescent small-molecule probes are typically used at micromolar levels in aqueous buffers with trace organic cosolvent. The main environmental considerations are the choice and volume of organic solvents and the lifecycle of single-use plastics.

Greener handling options (general guidance)

• Reduce solvent load: Prepare higher-concentration DMSO stock (within solubility limits) to minimize total organic solvent introduced into assays; keep final DMSO ≤0.5% v/v.
• Prefer ethanol or PEG-400 over DMF where compatible with the assay; both have more favorable EHS profiles. Validate background fluorescence and solubility.
• Aqueous-first workflows: Where possible, dilute the probe into buffer immediately before use to limit organic solvent exposure and waste.
• Light management: Use amber vials and low-light handling to extend solution life and reduce the need for repeated solution preparation.

Comparison (general)

• DMSO: High solvency, widely accepted in bioassays; moderate EHS profile; dermal absorption risk—use care.
• Ethanol: Greener alternative; may affect cell membranes; higher volatility can aid solvent removal.
• PEG-400: Low volatility and good solvency for hydrophobic probes; viscosity can complicate pipetting; typically low cytotoxicity at ≤0.5% v/v.

Waste minimization

• Consolidate rinses, use microvolumes in high-density plates, and segregate fluorescent waste streams. While there is no direct “green substitute” for the probe itself, solvent and workflow choices can significantly improve sustainability.

Pharmaceutical Uses

This product is a research-use fluorescent probe and is not intended for use as a drug substance or excipient.

General context (not product-specific use claims)

• Analytical tool: Small-molecule fluorescent probes are occasionally used in pharmaceutical research settings for mechanistic studies, target engagement assays, or high-content imaging, but they are not typically components of finished dosage forms.
• Regulatory status: No pharmacopeial monograph is expected for specialty research probes of this type. Any use in regulated environments would require internal qualification (identity, purity, stability) and method validation tailored to the intended application.

For this specific item, no formulation/excipient roles or pharmacopeial statuses are provided. All uses are restricted to research and laboratory applications only.

Physical Properties

Item-specific (from Product Data)

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

Literature/general values for SSP-class fluorescein probes (not product specifications)

• Optical properties (typical, literature for fluorescein-type scaffolds after activation):
  • Excitation/Emission: green channel, often Ex ~480–500 nm / Em ~510–530 nm after reaction with sulfane sulfur, due to release of a fluorescein-like phenolate. Exact maxima depend on solvent, pH, and substituents.
  • pH dependence: fluorescence intensity generally increases in neutral to slightly basic buffers (phenolate form favored); acidic media can suppress emission.
• Solubility handling (typical): low aqueous solubility as-stock; readily soluble in aprotic polar organics such as DMSO or DMF for stock solutions; working solutions prepared by diluting into aqueous buffers with ≤1% organic cosolvent.

Not available for this specific item (consult CoA/SDS)

• Melting point, boiling point, density, logP, refractive index, water content, metal content, UV cutoff: 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.

How to interpret quality for fluorescent probes (general guidance)

• Identity confirmation: For small-molecule probes, NMR (1H/13C), HRMS, and HPLC purity are the core QC elements. Look for a sharp single peak in analytical HPLC/UPLC and matching HRMS for the molecular ion and key fragments.
• Purity metrics: HPLC/UPLC area % at relevant detection wavelengths (e.g., 254, 280, 488 nm) are commonly reported. Trace colored or fluorescent impurities can disproportionately affect imaging assays; therefore, probe-grade materials often exceed 95% area purity.
• Residual solvents and water: Karl Fischer and GC may be reported; these can influence shelf life and solubility when preparing concentrated DMSO stocks. For this item, specific limits are Not specified; refer to CoA/Spec Sheet.
• Stabilizers/additives: Some probes ship without stabilizers; others may contain trace antioxidants. For this item, Not specified; refer to CoA/Spec Sheet.
• Batch documentation: Request a Certificate of Analysis for exact purity, analytical chromatograms, and spectral data. When reproducing literature assays, match solvent, buffer pH, and excitation/emission settings to those used during QC to minimize variability.

Reaction and Applications

Item-specific (from Product Data)

• Manufacturer Applications: Not specified in the listing beyond the product name.

Literature/general applications of sulfane sulfur probe 4 (SSP-class)

• Analytical target: Selective detection of “sulfane sulfur” species, including persulfides (RSSH), polysulfides (RSSnR, H2Sn), and related electrophilic sulfur pools, distinct from H2S and thiols.
• Sensing mechanism: Nucleophilic attack by sulfane-sulfur species on sulfur-reactive masking groups triggers fragmentation to liberate a fluorescein-like phenolate, producing a large fluorescence turn-on in the green channel. This confers high signal-to-background in neutral aqueous buffers.
• Use cases:
  • Live-cell fluorescence microscopy or flow cytometry to visualize labile sulfane sulfur under physiological conditions (buffered saline, 37°C) (literature).
  • Plate-based kinetic or endpoint assays to quantify sulfane sulfur generated by enzymatic systems (e.g., 3-MST, CSE/CBS pathways) (literature).
  • Chemical validation with defined donors (Na2Sx mixtures, glutathione persulfide) to calibrate response and selectivity (literature).
• Selectivity considerations: SSP-class probes respond strongly to polysulfides/persulfides while showing modest response to simple thiols and H2S under optimized conditions; pH and buffer composition modulate selectivity profiles.
• Practical tips (general):
  • Prepare fresh, light-protected working solutions; avoid prolonged exposure to ambient light.
  • Maintain low DMSO content to minimize biological interference.
  • Include controls: no-analyte, thiol controls (GSH/Cys), and known polysulfide donors to verify probe performance.

Note: For this specific catalog item, consult the CoA/Spec Sheet for any validated application data and conditions.

Reaction Conditions

Item-specific conditions: Not specified for this item; refer to CoA/Spec Sheet and SDS.

Literature/general guidance for SSP-class probe activation assays

• Medium: Aqueous buffers (PBS, HEPES) at pH 7.2–7.6. Ionic strength near physiological (e.g., 1× PBS) supports reproducible fluorescence.
• Temperature: Room temperature to 37°C. Reaction with polysulfides/persulfides is typically fast (minutes), enabling kinetic reads.
• Concentrations: Probe often used at low micromolar levels; analyte donors (e.g., Na2Sx or glutathione persulfide) prepared freshly to avoid decomposition. Keep final organic cosolvent ≤0.5–1% v/v.
• Light: Protect from ambient light; measure with appropriate excitation/emission settings in the green channel. Allow short equilibration after dilution to stabilize baseline.
• Controls: Include blanks (buffer only), thiol controls (e.g., GSH, Cys) to assess selectivity, and known sulfane-sulfur donors for positive controls. A reducing agent (e.g., DTT) control can help confirm reversibility/irreversibility of signal under your conditions.
• Interferences: High concentrations of nucleophiles, strong bases, or oxidants can alter probe response. Transition metals may catalyze sulfur speciation changes; chelation may be beneficial.

Note: These are general literature conditions for SSP-type probes and are not specifications for this catalog item.

Safety and Handling

Item-specific (from Product Data)

• GHS classification, pictograms, hazard statements, signal word: Not specified for this item; refer to SDS.
• Storage conditions: Store at −20°C.
• Shipping: Ice chest + ice pads (to maintain cold chain).

General safety guidance for organic fluorescent probes (literature/general)

• PPE: Wear lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Handle powders/solids in a fume hood to avoid dust inhalation. Avoid contact with skin and eyes.
• Incompatibilities: Avoid strong oxidizers and strong bases/acids during storage. Protect from light to minimize photodegradation; many xanthene probes are light sensitive in solution and, to a lesser degree, as solids.
• Special risks: Fluorescent probes may be supplied with trace residual solvents. Concentrated DMSO stock solutions can facilitate dermal absorption—avoid skin contact.
• First aid (overview; defer to SDS):
  • Skin/eye contact: Rinse with water for ≥15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
  • Inhalation: Move to fresh air; seek medical attention if symptoms occur.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Waste: Collect solutions and contaminated disposables as hazardous chemical waste; do not discharge to drain. Photobleaching byproducts and sulfur adducts should be treated as laboratory chemical waste.

Always consult the product-specific SDS for authoritative hazard information and response measures.

Solvent Selection

Item-specific (from Product Data)

• No solvent recommendations are specified; refer to CoA/Spec Sheet.

Literature/general guidance for SSP-class sulfane-sulfur probes

• Stock solution solvent: DMSO is commonly used due to excellent solubility and chemical stability of xanthene-based probes. DMF or acetonitrile are secondary options.
• Working media: Aqueous biological buffers (PBS, HEPES, Tris) at pH 7.2–7.6 are typical for reactivity toward sulfane sulfur species, with organic cosolvent kept ≤0.5–1% v/v to mitigate cytotoxicity and fluorescence artifacts.
• Polarity and photophysics: After activation, fluorescein-type chromophores are highly polar (phenolate) and water-compatible; before activation, the masked probe is more hydrophobic, benefiting from a polar aprotic solvent for stock preparation.
• Degassing/light: Oxygen is generally not detrimental to SSP chemistry, but protect solutions from light to reduce baseline photobleaching and background signal.

When to choose alternatives

• If DMSO is restricted, consider PEG-400 or ethanol for stock solutions; verify compatibility with your biological system and maintain low final organic fractions. For purely chemical (non-biological) assays, MeCN can provide cleaner baselines in spectroscopic measurements.

Quick comparison (general)

• DMSO: highest solvency; potential cellular effects at >0.5%.
• DMF/MeCN: good solvency; ensure minimal carryover into bioassays.
• Aqueous buffer only: often insufficient for concentrated stocks; use cosolvent.

Storage and Reconstitution

Item-specific (from Product Data)

• Storage: Store at −20°C.
• Shipping: Ice chest + ice pads (cold chain).

General guidance (literature/good practice)

• Light sensitivity: Store in amber vials or wrap containers in foil to minimize photodegradation. Minimize freeze–thaw by aliquoting on first use.
• Reconstitution: If supplied as a solid, dissolve a weighed portion in anhydrous DMSO to prepare a concentrated stock (e.g., millimolar range), then aliquot and refreeze at −20°C. If supplied in solution, keep tightly capped, under inert headspace if feasible, and avoid repeated warming cycles.
• Stability: Working aqueous solutions are best prepared fresh before use; prolonged storage in aqueous media can reduce signal due to hydrolysis or slow background activation. Avoid strong bases/acids and oxidants.
• Documentation: Record preparation date, solvent, and concentration on each aliquot. Verify concentration by UV–vis where possible using literature extinction coefficients for fluorescein-like chromophores after activation (for approximation).

For any lot-specific stabilizers, concentrations, or shelf-life claims: Not specified for this item; refer to CoA/Spec Sheet and SDS.

Structure and Identity

Item-specific (from Product Data)

• Product name: Sulfane sulfur probe 4 (SKU: S1450979)
• CAS: 1810731-98-6
• 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.

Literature/general description

• “Sulfane sulfur probe 4” (often abbreviated SSP4 in literature) refers to a turn-on fluorescent probe engineered to detect sulfane-sulfur species (e.g., persulfides RSSH, polysulfides RSSnR, H2Sn). Many reported SSP-class probes are built on a fluorescein-like xanthene chromophore whose fluorescence is unmasked upon specific reaction with electrophilic sulfane sulfur.
• Structural features (typical for this probe class): a masked xanthene core bearing sulfane-sulfur–reactive triggers on phenolic positions; after reaction, the free phenolate/xanthene is restored, yielding strong green fluorescence.

2D structure (descriptive, literature)

• Central xanthene ring system (anthracene-like tricyclic core with a bridging oxygen) fused to substituted phenyl units; phenolic sites derivatized with sulfur-reactive masking groups. No stereogenic centers are typically present in such xanthene-based probes.

Synthetic Utility

As a specialized fluorescent probe, this compound is not typically employed as a synthetic building block.

General synthetic/contextual notes (literature)

• Functional group logic: SSP-class probes incorporate sulfur-reactive masking groups on a xanthene/fluorescein scaffold. While not generally used in multistep synthesis, the underlying chemistry illustrates strategies for designing activity-based probes that unmask fluorophores upon reaction with target analytes.
• Analytical reagent role: In synthetic or mechanistic sulfur chemistry, the probe can serve as a selective indicator for the formation of polysulfides/persulfides in reaction mixtures, enabling rapid, qualitative monitoring by fluorescence.
• Retrosynthetic perspective: The probe scaffold demonstrates modular protection/deprotection on phenolic positions and late-stage installation of sulfane-sulfur–responsive motifs—useful design principles for chemists developing next-generation redox probes.

Item-specific synthetic transformations, reactivity toward standard organic functional groups, and derivatization guidance are Not specified for this item; consult primary literature on SSP4 for detailed synthetic pathways and intermediates.

Target Specificity

Item-specific, experimentally validated targets and selectivity panels are Not specified for this item; refer to CoA/Spec Sheet and any application notes provided with the lot.

Literature/general description

• SSP-class probes are designed to be selective for sulfane-sulfur species (persulfides, polysulfides) over thiols and H2S under optimized neutral aqueous conditions. Selectivity depends on buffer composition, pH, temperature, and competing nucleophiles.
• Users should verify specificity in their system using appropriate donor/competitor panels and orthogonal analytical methods where possible.