BODIPY FL-C16 , CAS No.158757-82-5

CAS: 158757-82-5 Cat. No.: B1450796 Fórmula: C₂₇H₄₁BF₂N₂O₂ Peso molecular: 474.43

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Visão geral

BODIPY FL-C16 is a fluorescent probe that combines BODIPY FL dye and a sixteen-carbon fatty acid chain, and it can be used for lipid metabolism-related research.

Specifications

Condições de armazenamento de armazenamento

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.

Nomes e identificadores

• Peso molecular: 474.43

Application Protocols

Validated, item‑specific protocols and recommended dilutions are not provided for this catalog entry. Refer to primary literature and your institutional SOPs for method development.

General considerations (not product‑validated):

• Stock solutions: Prepare in anhydrous DMSO or chloroform. Store aliquots protected from light at −20°C.
• Working concentrations: Determine empirically for your instrument and biology; include vehicle controls and titrate to minimize background while maintaining sufficient signal.
• Imaging/flow settings: Use excitation filters near ~500 nm and collect emission near ~510–530 nm appropriate for green‑fluorescent channels; verify against your optics.
• Controls: Include unlabeled cells, competition with excess unlabeled fatty acid, and no‑probe controls to assess specificity and background.

Note: The above are general literature practices and are not specific recommendations for this product lot. For precise instructions, consult peer‑reviewed publications using BODIPY FL‑C16 and validate in your system.

Biological Roles

BODIPY FL‑C16 is a research probe that functionally mimics a long‑chain saturated fatty acid and reports on lipid handling in biological systems via fluorescence. It does not possess an endogenous biological role but is used to interrogate lipid biology.

Literature/typical research uses:

• Uptake pathways: Assesses activity of fatty‑acid transport and binding proteins at the plasma membrane through time‑dependent accumulation and localization of the fluorescent analog.
• Intracellular trafficking: Enables visualization of movement into endomembrane compartments, ER, and lipid droplets; distribution can be quantified by microscopy or flow cytometry.
• Metabolic fate: Partitioning into neutral lipids or phospholipids can be profiled post‑labeling using extraction and chromatographic separation coupled to fluorescence detection, providing a non‑radioactive readout of metabolic routing.
• Membrane biophysics: Serves as a hydrophobic fluorophore to probe bilayer domains, vesicle fusion, and diffusion processes in model membranes.

Considerations (general):

• Probe behavior may not be identical to native palmitate due to the dye’s steric and photophysical properties; control experiments with unlabeled fatty acids and vehicle are recommended.
• Phototoxicity/photobleaching should be minimized by reducing light exposure and using appropriate filters.

All uses are for laboratory research only; not for diagnostic, therapeutic, or in vivo clinical applications.

Buffer Applications

This product is not a buffering reagent. However, buffer composition can influence performance when using this lipophilic fluorescent probe.

General guidance (literature/practice):

• Aqueous buffers: Due to limited intrinsic aqueous solubility, include a small fraction of a water‑miscible organic co‑solvent (e.g., DMSO ≤0.1–0.5% v/v) or carriers such as fatty‑acid–free BSA to facilitate delivery to cells or liposomes.
• pH effects: BODIPY fluorescence is typically less sensitive to pH in the physiological range, but ionization of linkers or carboxylates (if present) can modestly affect partitioning; maintain physiological pH (7.2–7.4) for cell assays.
• Additives: Nonionic surfactants (e.g., low concentrations of Tween 20) can aid dispersion for some in vitro assays but may alter membrane interactions—validate carefully.

If you require a true buffering agent for your workflow, consider selecting from dedicated buffer salts/systems (e.g., PBS, HEPES); this product is a fluorescent probe and not intended to set or control pH.

Green Alternatives

While BODIPY FL‑C16 itself is a specialized probe, greener practice considerations focus on solvent choice and replacing hazardous tracers.

Greener practice opportunities (general):

• Replace radiolabeled fatty acids: Using fluorescent fatty‑acid analogs avoids radioisotopes, reducing hazardous waste and exposure risks while enabling live‑cell imaging (tradeoff: photobleaching and potential probe‑induced perturbations).
• Solvent selection: Prefer ethanol or isopropanol as co‑solvents where assay‑compatible, replacing chlorinated solvents for routine stock preparation (tradeoff: may require higher percentages to maintain solubility and can affect cells at higher concentrations).
• Minimize DMSO content: Keep working concentrations ≤0.1–0.5% v/v to reduce solvent load; validate cell compatibility.
• Process changes: For lipid film methods, use rotary evaporation with solvent recovery and nitrogen blow‑down traps to minimize emissions.

Comparison (general, illustrative):

• Chloroform vs. Ethanol: CHCl3 provides superior solubility for co‑dissolving lipids and dye but is toxic and environmentally persistent; ethanol is safer but may not fully dissolve lipids/dye without heating or co‑solvents.
• DCM vs. Ethyl acetate: DCM dissolves well but is a chlorinated solvent; EtOAc offers a greener profile yet may have limited solubility for very hydrophobic constructs.

Note: Any change in solvent system should be re‑qualified for spectral properties and biological performance.

Pharmaceutical Uses

This material is supplied strictly for research use only and is not intended for human or veterinary use, drug substance, or excipient applications.

General/industry context (non‑clinical):

• Discovery research: Utilized in preclinical, in vitro workflows to visualize lipid uptake/trafficking in cell lines or primary cells, supporting target validation and mechanism studies.
• Formulation screening (laboratory): As a fluorescent tracer within lipid‑based carriers (e.g., liposomes, emulsions) to monitor incorporation, leakage, or stability during formulation development—strictly in research settings.

Regulatory and compendial status for this item: Not specified; no pharmacopoeial monograph applicability claimed.

Any consideration of use beyond basic research would require comprehensive toxicological assessment, GMP manufacturing, and regulatory qualification, none of which are implied for this catalog product.

Physical Properties

Item-specific physicochemical specifications are not provided for this catalog entry. Consult the CoA/Spec Sheet for definitive values relevant to your lot.

Literature/general properties for BODIPY FL–type fatty‑acid probes (not item‑specific):

• Appearance: typically a dark solid or powder; intensely colored/green fluorescent (literature).
• Solubility profile: good solubility in DMSO, DMF, dichloromethane, chloroform, and other nonpolar/medium‑polarity organic solvents; limited solubility in aqueous buffers without carrier (literature).
• Photophysical (BODIPY FL in common organic media):
  • Excitation maximum: ~500–505 nm (typical ~503 nm) (literature).
  • Emission maximum: ~510–515 nm (typical ~512 nm) (literature).
  • High fluorescence quantum yield and extinction coefficient in non‑protic, low‑polarity solvents (literature).
• Partitioning: strongly lipophilic due to C16 chain; tends to associate with membranes, micelles, or lipid vesicles (literature).
• Melting point, boiling point, density, logP, pKa, refractive index: Not specified for this item; refer to CoA/Spec Sheet. Where needed, determine experimentally under your conditions.

Practical notes (general): Prepare concentrated stocks in anhydrous DMSO or chloroform; avoid prolonged exposure to light and moisture. Filter or centrifuge if particulates remain after dissolution.

Quality and Grades

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

General guidance for fluorescent probes:

• Research grade: Suitable for in vitro and cell‑based research. Typical expectations include high chemical purity (to reduce background), low inorganic residue, and minimal fluorescent impurities that could broaden emission. Absence of stabilizers or specific counterions should be verified on the CoA if critical to your assay.
• Dye quality considerations:
  • Spectral purity: Narrow, well‑defined absorption/emission bands are important for quantitative imaging or flow cytometry; impurities can introduce shoulders or background.
  • Residual solvents/water: Can affect solubility and photophysics; check CoA for residual solvent content if necessary.
  • Lot‑to‑lot consistency: Verify excitation/emission maxima and dye content by UV‑Vis to ensure assay comparability.
• Stabilizers/Additives: Not specified for this item; refer to CoA/Spec Sheet. If present, they may affect solubility or cell compatibility.

Recommendation: For sensitive quantitation (e.g., kinetic fatty‑acid uptake), run a quick quality check (UV‑Vis spectrum in your solvent, fluorescence emission at working concentration) on receipt to benchmark lot performance.

Reaction and Applications

This product is primarily an analytical/biological probe rather than a synthetic reagent. Accordingly, its most relevant “applications” are in fluorescence‑based lipid research, not as a reactant.

Research applications (general, literature):

• Lipid uptake and trafficking: Tracks incorporation of a palmitate‑like moiety into cells; used to visualize membrane association, vesicular transport, and subcellular lipid distribution by fluorescence microscopy or flow cytometry.
• Metabolism studies: Serves as a non‑radioactive alternative to radiolabeled fatty acids for monitoring uptake kinetics and partitioning among lipid pools (e.g., neutral lipids vs. phospholipids) after extraction and TLC/HPLC with fluorescence detection.
• Model membranes: Doping of liposomes, micelles, or supported bilayers to examine membrane phase behavior, lateral diffusion (FRAP), and partitioning between liquid‑ordered/disordered phases.
• High‑content screening: Reporter for modulators of fatty‑acid transporters or β‑oxidation pathways in cell‑based assays (research use only).

Practical tips:

• Prepare fresh working dilutions immediately before use; protect from light.
• Minimize final organic solvent to avoid perturbing lipid processes; include vehicle controls.
• Adsorption losses: Hydrophobic probes can adsorb to plastic; pre‑rinse or use low‑binding plastics or glass vials.
• Validate spectral settings: Excite near ~500 nm and collect emission near ~510–530 nm (literature, adjust to instrument filters).

Reaction Conditions

This product is not intended for use as a reagent in chemical transformations; therefore, conventional reaction condition guidance (solvent, temperature, catalysts, yields) is not generally applicable.

Practical laboratory conditions for use as a probe (general, literature):

• Stock preparation: Dissolve in anhydrous DMSO or chloroform at 1–10 mM; protect from light. Warm gently and vortex/sonicate if needed; avoid prolonged heating.
• Working solutions: Dilute into assay buffer or media to low micromolar to nanomolar levels as compatible with your detection system; keep final organic solvent ≤0.1–0.5% v/v. Validate that the vehicle does not affect your biology.
• Temperature: Use at ambient to physiological temperatures (e.g., 20–37°C) according to the biological assay.
• Light: Minimize exposure; use amber vials and subdued lighting during setup.

For any chemical modification or conjugation, consult the verified structure on the CoA/Spec Sheet and standard coupling literature appropriate to the functional groups present.

Safety and Handling

Follow standard precautions for handling lipophilic fluorescent dyes.

• GHS/Classification: Not specified for this item; refer to the SDS for authoritative information.
• Signal word / Hazard statements / Pictograms: Not specified for this item; refer to the SDS.
• Primary hazards (general for organic dyes and DMSO stocks):
  • May cause skin/eye irritation; DMSO can facilitate dermal absorption of solutes.
  • Dust may be combustible; avoid generating dust and ignition sources for dry powders.
  • Environmental persistence possible for hydrophobic dyes; prevent release to drains.
• PPE: laboratory coat, nitrile gloves (change regularly when working with DMSO), safety glasses or face shield when handling solutions or weighing powders.
• Handling: work under dim light or amber conditions to minimize photobleaching. Use clean, dry glassware; avoid prolonged exposure to air and moisture for solutions. Cap vials promptly.
• Incompatibilities (general): strong oxidizers, strong acids/bases for extended periods (may degrade chromophore or linkage). Avoid halogenating agents. Keep away from sources of UV/visible light.
• First aid (summary; see SDS): rinse eyes/skin with water for ≥15 min upon contact; remove contaminated clothing. If inhaled, move to fresh air. If ingested, rinse mouth; seek medical attention.
• Spill/Disposal: absorb with inert material; collect as hazardous organic waste per institutional and local regulations.

Solvent Selection

BODIPY FL‑C16 is highly lipophilic and typically prepared as concentrated stocks in aprotic organic solvents.

• Polarity/miscibility (literature, general):
  • Readily soluble: DMSO, DMF, dichloromethane, chloroform, THF, toluene, ethyl acetate.
  • Limited solubility: water and aqueous buffers without carriers; solubility can improve with surfactants, serum albumin, cyclodextrins, or co‑solvent systems.
• Practical solvent choices by use case:
  • Cell labeling/uptake assays: Prepare 1–10 mM stocks in anhydrous DMSO; dilute into serum‑containing media with final DMSO ≤0.1–0.5% v/v to limit solvent effects (general guidance; validate for your system).
  • Liposome/micelle work: Chloroform or CHCl3:MeOH for lipid film preparation; evaporate solvent under nitrogen, then hydrate to incorporate the probe (general method).
  • Spectroscopy: Low‑polarity aprotic solvents minimize nonradiative quenching; record solvent and concentration to ensure reproducibility.
• Comparison notes (general):
  • DMSO: convenient, miscible with water; may alter membranes at higher %.
  • Chloroform: excellent solubility for co‑dissolving lipids; volatile and toxic—use in fume hood.
  • Ethanol/IPA: intermediate option; higher percentages may be needed to keep dye in solution.

Always filter or centrifuge to remove undissolved particulates before sensitive measurements.

Storage and Reconstitution

• Storage conditions (item‑specific): Store at −20°C. Protect from light. Avoid repeated freeze–thaw cycles by aliquoting upon first opening.
• Shipping (item‑specific): Shipped in an ice chest with ice pads to maintain a low temperature during transit.
• Stability: Item‑specific stability data are not provided; refer to CoA/Spec Sheet. In general, dry dye solids are stable for extended periods at −20°C when protected from light and moisture.
• Reconstitution (general guidance):
  • Use anhydrous solvents (e.g., DMSO, chloroform) for initial dissolution; target 1–10 mM stocks depending on intended use.
  • Vortex/sonicate briefly if needed. Filter through a PTFE syringe filter or centrifuge to remove particulates for spectroscopy‑grade work.
  • Prepare small aliquots in amber vials or foil‑wrapped tubes; purge headspace with inert gas if long‑term storage is planned.
• Working solutions: Prepare immediately before use. Minimize light exposure and keep on ice or at room temperature per assay requirements. Discard unused diluted solutions; do not refreeze dilute aqueous stocks.

Always refer to the product’s CoA/Spec Sheet and SDS for definitive storage and handling instructions for your lot.

Structure and Identity

BODIPY FL‑C16 is a lipophilic fluorescent fatty‑acid analog comprising a BODIPY FL fluorophore covalently attached to a long C16 aliphatic chain (palmitate‐like). It is widely used as a probe for lipid uptake, trafficking, and metabolism studies in cells and membranes (research use only).

• Item-specific identifiers:
  • CAS: 158757-82-5
  • 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):
  • Contains a BODIPY (boron‑dipyrromethene) core with a difluoroboron chelate and two pyrrolic nitrogens embedded in a fused dipyrromethene framework.
  • The “FL” variant is a green‑fluorescent BODIPY with minimal Stokes shift and high quantum yield in many organic media.
  • A saturated C16 alkyl chain provides hydrophobic character and mimics palmitic acid; typical constructs use an amide or analogous linkage to the dye core (literature, vendor‑independent description).
• 2D structural description (general): planar BODIPY chromophore bearing substituents at the 3,5-positions, coordinated to BF2; a linear, unbranched 16‑carbon chain extends from the chromophore through a short linker, conferring membrane affinity.

Note: Exact stereochemistry is not applicable (all‑aliphatic chain, no stereocenters in the chromophore).

Synthetic Utility

BODIPY FL‑C16 is not typically used as a synthetic building block; it is an end‑use fluorescent probe. Nevertheless, understanding functional groups can inform conjugation strategies or immobilization in research setups.

General structural/reactivity notes (literature):

• BODIPY core: Aromatic, photostable chromophore with a BF2 chelate; generally resistant to mild bases and nucleophiles. Susceptible to strong oxidants and harsh acids.
• Fatty‑acid chain/linker: If a terminal carboxylate or amide is present (variant‑dependent), standard carbodiimide coupling (EDC/NHS) or active ester chemistry can be used to anchor the probe onto surfaces, polymers, or nanoparticles. Verify the exact functionality for this specific item via CoA before planning chemistry.
• Hydrophobic interactions: Noncovalent incorporation into hydrophobic matrices (e.g., polymers, lipid bilayers) is often preferred to preserve photophysics without chemical modification.

Use cases:

• Doping polymer films or nanoparticles to create fluorescent standards or tracers for diffusion and release studies.
• Embedding into lipid assemblies (liposomes, micelles) for visualization and leakage assays.

Caution: Do not assume specific reactive handles without confirming the exact structure and functional groups for this catalog item.

Target Specificity

Not an antibody or affinity reagent; no antigen/epitope target, clone, or species reactivity applies to this product.

Functional specificity (general, literature): The probe is designed to mimic a long‑chain fatty acid and preferentially partitions into lipid environments (membranes, lipid droplets). Apparent “specificity” thus arises from hydrophobic interactions and cellular lipid handling pathways rather than from molecular recognition of a discrete biomolecular epitope.