MitoPerOx (cis- and trans- mixture) - ≥95% , CAS No.1392820-50-6

CAS: 1392820-50-6 Cat. No.: M275561 Fórmula: C₄₂H₃₈BF₂N₃OP • Br Peso molecular: 760.5

GRADE & PURITY ≥95%

Synonyms

2-(3-(5,5-difluoro-7-((1E,3E)-4-phenylbuta-1,3-dien-1-yl)-5H-5λ4,6λ4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-3-yl)propanamido)ethyl)triphenylphosphonium, monobromide (cis- and trans- mixture)

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Visão geral

Store at -20°C long term. Store In the Dark.

Specifications

Sinónimos

2-(3-(5,5-difluoro-7-((1E,3E)-4-phenylbuta-1,3-dien-1-yl)-5H-5λ4,6λ4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-3-yl)propanamido)ethyl)triphenylphosphonium, monobromide (cis- and trans- mixture)

Especificações e pureza

≥95%

Mecanismos bioquímicos e fisiológicos

Ratiometric, fluorescent, mitochondria-targeted lipid peroxidation probe

Condições de armazenamento de armazenamento

Protected from light,Store at -20°C

Enviado em

Ice chest + Ice pads

Este produto requer transporte de cadeia fria. Serviços terrestres e outros serviços econômicos não estão disponíveis.

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.

Pureza

≥95%

Nomes e identificadores

Peso molecular

760.5

Propriedades químicas e físicas

• Solubilidade: Soluble in DMSO to 25 mM
• Sensibilidade: Moisture sensitive;Light sensitive

Application Protocols

No tested application protocols, recommended dilutions, or instrument settings are provided in the Product Data for SKU M275561. Please consult the product datasheet/CoA for any validated procedures.

Important reminders:

• Follow your institution’s method development practices to optimize concentration, incubation time, washing, and imaging/reading parameters.
• Maintain consistent solvent content, temperature, and light exposure across control and experimental wells.

For research use only (as stated in Product Data).

Biological Roles

Nature of product: This is a synthetic small-molecule fluorescent probe; it is not a metabolite or natural cofactor.

Relevant biological context (general literature):

• Mitochondrial lipid peroxidation is a central event in oxidative stress, impacting membrane integrity, respiratory efficiency, and signaling pathways. Polyunsaturated phospholipids in the inner mitochondrial membrane are particularly susceptible to ROS/RNS-driven peroxidation.
• Probes of this class are designed to accumulate in mitochondria and undergo an oxidation-dependent spectral change that correlates with lipid peroxides. This enables ratiometric or intensity-based readouts in live cells and isolated mitochondria.
• Applications include studying the impact of electron transport chain inhibitors, antioxidants, iron metabolism/ferroptosis modulators, and fatty acid composition on mitochondrial redox balance.

Limitations and controls (general):

• Accumulation can be membrane potential–dependent; depolarized mitochondria may load differently, complicating interpretation.
• Probe oxidation reports a net balance of ROS generation, antioxidant defenses, and probe distribution; parallel assays (e.g., membrane potential dyes, ROS scavengers) improve mechanistic insights.

Note: No therapeutic or diagnostic use is intended or implied. For research use only (as stated in Product Data).

Buffer Applications

This product is not a buffering agent. However, buffer choice influences performance in imaging/assay workflows (general guidance):

• Use phenol red–free buffers/media (e.g., HBSS, PBS, HEPES-buffered saline) to minimize background and pH-dependent spectral shifts.
• Maintain physiological pH 7.2–7.4 and osmolarity for live-cell studies; HEPES (10–25 mM) can stabilize pH in open dishes during microscopy.
• Serum proteins can bind hydrophobic probes and alter distribution; consider serum-free loading followed by wash and recovery in complete media.

No item-specific buffer recipes or pKa values are provided in the Product Data; consult the product datasheet for any validated buffer systems.

Green Alternatives

Context: The probe itself is the analyte; “greenness” considerations focus on solvent choices, waste minimization, and safer alternatives for redox assays.

Greener handling strategies (general best practices):

• Prefer aqueous buffers for dilutions; keep DMSO/EtOH ≤0.1–0.2% v/v in final media where feasible.
• Use micro-volume stocks (aliquoted) to reduce freeze–thaw and waste.
• Implement amber, reusable glassware and minimize disposable plastics where compatible with sterility.

Alternative assay approaches (trade-offs, literature-level):

• Genetic redox reporters (e.g., mitochondria-targeted roGFP-based sensors) reduce chemical waste but require transfection/viral delivery and specialized calibration.
• Non-mitochondrial lipid peroxidation probes (e.g., membrane-inserting ratiometric dyes without mitochondrial targeting) may reduce potential perturbation of membrane potential but lose organelle specificity.
• Bulk biochemical assays (lipid hydroperoxide kits) avoid live-cell dye use but sacrifice spatial resolution.

Comparison (general):

• Small-molecule probe (this item): rapid deployment, no genetic manipulation; generates organic solvent/dye waste; requires light/oxidant care.
• Genetically encoded sensors: minimal chemical waste post-establishment; higher setup complexity; potential expression artifacts.

Choose the approach that balances data needs (spatiotemporal resolution, ratiometry), lab capabilities, and environmental footprint.

Pharmaceutical Uses

This material is supplied strictly for research use only and is not intended for human or veterinary use in drugs, diagnostics, or clinical procedures.

Formulation/manufacturing context (general information):

• Small-molecule fluorescent probes like this are occasionally used in pharmaceutical R&D labs for mechanistic studies, phenotypic screening, and mitochondrial toxicity assessments in cell culture. They are not excipients and have no compendial (USP/EP) status for therapeutic products.
• If used in high-throughput screening, attention to DMSO handling, plate material (low-autofluorescence, black-walled), and consistent incubation conditions is critical for assay reproducibility.

No pharmacopeial monograph, excipient role, or clinical formulation data are provided for SKU M275561.

Physical Properties

Item-specific specifications:

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

Storage/handling from Product Data:

• Store at −20°C, protected from light. Shipped cold (ice chest + ice pads).

General/literature expectations for this probe class (for planning only; not product specifications):

• Physical state: typically a colored or dark solid supplied in milligram quantities and light-sensitive.
• Solubility: commonly soluble in anhydrous DMSO and anhydrous ethanol to prepare concentrated stocks; poor aqueous solubility without co-solvent or carrier.
• Photophysics: mitochondria-targeted lipid peroxidation probes are often designed for visible excitation/emission with ratiometric response upon oxidation in lipid phases; exact λex/λem and quantum yields are probe-specific and must be taken from the item CoA or vendor datasheet.
• Stability: stock solutions are generally stable for weeks to months at −20°C protected from light; repeated freeze–thaw and moisture/oxygen exposure can degrade performance.

Note: Do not treat the above as specifications. For experimental method development, verify exact optical and physicochemical values against the certificate of analysis for SKU M275561.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Item-specific notes:
  • The listing explicitly indicates a “cis- and trans- mixture.” For fluorescent performance, isomer ratios can influence spectral response and partitioning; the actual ratio for this lot should be verified on the CoA if critical to your application.
  • No stabilizers, counter-ions, or residual solvent levels are provided in the Product Data. If such details (e.g., TFA salt content, water, residual metals) are critical, request the current Certificate of Analysis.

What grade means for this product class (general guidance):

• Research-grade fluorescent probes are typically purified to high HPLC area % and assessed by MS/HRMS and 1H/13C NMR. For imaging and plate-reader assays, low levels of fluorescent impurities and defined counter-ions are important to minimize background.
• If designated “analytical” or “HPLC grade” for solvents used in formulation, that indicates low UV absorbance and minimal non-volatile residues—however no such designation is provided here for the probe itself.

Recommendations:

• For quantitative ratiometric studies, confirm batch-to-batch reproducibility (HPLC trace, isomer distribution, and optical constants). Retain CoA with your datasets for method traceability.

Reaction and Applications

This item is a research probe for analytical/imaging applications rather than a synthetic reagent.

Research applications (literature-level, for planning; verify with your assay system):

• Mitochondrial lipid peroxidation monitoring: Probe accumulates in mitochondria and responds to lipid peroxides, enabling evaluation of oxidative stress, ferroptosis-related lipid ROS, or antioxidant interventions in mitochondrial membranes.
• Live-cell and fixed-cell fluorescence readouts: Often used in confocal microscopy or plate-reader assays. Ratiometric response (reduced vs. oxidized forms) improves robustness to loading and probe concentration.
• Mechanistic studies: Time-resolved monitoring of peroxidation during respiratory chain inhibition, fatty acid supplementation, or pro-oxidant treatments.

Practical tips (general):

• Optimize loading concentration and incubation time to balance mitochondrial accumulation with minimal perturbation. Typical exploratory ranges are in the low nM to low µM in literature, but exact values should be determined empirically for your system.
• Control experiments: include vehicle-only, antioxidant-treated (e.g., lipophilic radical scavengers), and positive oxidant controls (e.g., cumene hydroperoxide) to define dynamic range.
• Validate mitochondrial localization with a counterstain when necessary, and confirm membrane potential dependence if interpretation requires it.

Note: No manufacturer application specifics were provided for SKU M275561; consult the product datasheet/SDS and your instrument settings for definitive protocols and spectral parameters.

Reaction Conditions

Not applicable for this catalog item as a chemical probe; it is not intended for use as a reagent in chemical synthesis.

Assay-condition considerations (general/literature-level) that may aid experimental planning:

• Temperature: live-cell loading typically at room temperature to 37°C depending on cell type; avoid thermal stress.
• Atmosphere/light: minimize oxygen super-saturation and ambient light during preparation to reduce premature oxidation/photobleaching.
• Timing: loading/incubation and wash steps should be empirically optimized; monitor signal stability over the experimental window.

These are operational suggestions rather than reaction conditions, and are not item-specific specifications.

Safety and Handling

Authoritative safety data: Not specified in Product Data; consult the product SDS for definitive classifications.

• GHS classification, signal word, pictograms, H-statements: Not specified for this item; refer to SDS.
• Principal hazards (general for lipophilic, cationic fluorescent probes):
  • May be harmful if swallowed, inhaled, or absorbed through skin; can cause eye/skin irritation.
  • Light-sensitive; photodegradation products may differ in hazard profile.
  • Organic solvent carriers (e.g., DMSO, ethanol) facilitate dermal absorption—avoid skin contact.
• PPE and engineering controls:
  • Wear lab coat, nitrile gloves, and safety glasses; handle solutions in a chemical fume hood.
  • Use amber vials/syringes and minimized ambient light exposure during handling.
• Incompatibilities and precautions:
  • Avoid strong oxidizers/reductants unless intended experimentally.
  • Prevent contact with acids/bases that may degrade dye structures; keep away from moisture.
  • Do not autoclave solutions; heat and light accelerate decomposition.
• First-aid overview (general guidance; defer to SDS):
  • Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention as needed.
  • Inhalation: Move to fresh air; obtain medical attention if symptoms occur.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Waste: Collect dye-containing organic solutions as hazardous chemical waste per institutional and local regulations.

Solvent Selection

Applicability: This product is a hydrophobic fluorescent probe rather than a reaction solvent. Solvent considerations here address stock preparation and working solutions.

General/literature guidance for mitochondria-targeted lipid peroxidation probes:

• Primary stock solvents:
  • Anhydrous DMSO: common, high solubility; prepare 1–10 mM stocks. Minimize water uptake and frequent freeze–thaw.
  • Anhydrous ethanol or anhydrous DMF: alternatives when DMSO is undesirable; confirm compatibility with cells/assay.
• Aqueous handling:
  • Dilute small aliquots of stock into pre-warmed, serum-free buffer/media with vigorous mixing to keep final organic co-solvent ≤0.1–0.2% v/v for live-cell work (literature best practice; adjust per your system).
  • Use HBSS, PBS, or phenol-red–free imaging buffers as appropriate. Include fatty-acid–free BSA if needed to modulate membrane partitioning.
• Light and oxygen management:
  • Use amber glassware and reduced ambient light. Prepare fresh working dilutions immediately before use.

When to choose different solvents (comparison, literature-level):

• DMSO vs ethanol: DMSO offers higher solubility and stability; ethanol can be less perturbing to some cells but has lower solubility and faster evaporation.
• Aqueous vehicles with surfactants (e.g., Pluronic F-127) can aid delivery but may alter mitochondrial membrane potential—validate rigorously for quantitative assays.

Storage and Reconstitution

Item-specific storage/shipping (from Product Data):

• Storage conditions: Store at −20°C, protected from light.
• Shipping: Shipped in an ice chest with ice pads to maintain cold chain.

Reconstitution:

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

General handling notes (non-binding guidance):

• Keep container tightly closed. Work quickly under low light when opening to prepare aliquots.
• Avoid repeated freeze–thaw cycles by preparing single-use aliquots upon first opening.
• Allow cold vials to equilibrate to room temperature in the dark before opening to minimize condensation.

Always defer to the product label and CoA for lot-specific instructions.

Structure and Identity

• Product name: MitoPerOx (cis- and trans- mixture)
• CAS: 1392820-50-6
• Category: Small-molecule research probe (mitochondria-focused; mixture of geometric isomers)
• 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 description, not item-specific):

• MitoPerOx is widely described as a lipophilic, cationic, mitochondria-accumulating small-molecule fluorescent probe designed to report on lipid peroxidation in mitochondrial membranes. The commercial material is often provided as a cis/trans isomeric mixture.
• Typical designs in the literature couple a mitochondria-targeting moiety to a peroxidation-responsive fluorophore, yielding a ratiometric or intensity-change signal upon oxidation in lipid environments. Exact substituents and stereochemistry can vary by supplier/batch; consult the CoA for definitive structural identifiers applicable to this SKU.

2D structure (verbal, literature-level):

• A conjugated fluorescent core bearing hydrophobic substituents is linked through a spacer to a permanently charged, lipophilic group that favors accumulation across the mitochondrial membrane potential; the probe embeds in lipid bilayers where peroxide-driven reactions alter the fluorophore’s electronic properties.

Synthetic Utility

Not typically applicable. MitoPerOx is an analytical/imaging probe and is not generally employed as a building block or reagent in synthetic chemistry.

General note for chemists:

• If derivative synthesis or conjugation is desired (e.g., probe modification, linker exchange), consult primary literature for compatible coupling strategies and protect the fluorophore from light/oxidation. However, such transformations are outside the scope of this catalog item, and no reactivity specifications are provided.

Target Specificity

This section typically applies to antibodies/biologics (antigen, clone, isotype). For SKU M275561, a small-molecule probe, no antibody target information is applicable or provided.

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

General comment: Mitochondria-directed probes often accumulate in mitochondria based on physicochemical properties and membrane potential rather than binding a discrete protein epitope; verify localization in your biological system with appropriate counterstains.