DSPE-PEG-CH2COOH, MW 5000 , CAS No.D1445792

CAS: D1445792 Cat. No.: D1445792 Poids moléculaire: 5000(Average)

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Vue d’ensemble

DSPE-PEG-CH2COOH, MW 5000 is a PEG-based PROTAC linker that can be used in the synthesis of PROTACs.

Spécifications

Conditions de stockage de stockage

Store at -20°C

Expédié en

Ice chest + Ice pads

Ce produit nécessite l'expédition en chaîne froide. Les services terrestres et autres services économiques ne sont pas disponibles.

Noms et identifiants

Poids moléculaire

5000(Average)

Application Protocols

No item-specific, vendor-validated protocols are provided in the Product Data. Refer to general procedures for:

• Thin-film hydration: Dissolve DSPE-PEG-CH2COOH with co-lipids in CHCl3:MeOH, evaporate to a thin film, desiccate, hydrate above bilayer Tm, and size by extrusion.
• Solvent injection: Inject an ethanolic lipid solution into pre-warmed buffer with stirring to form vesicles/micelles; remove solvent under reduced pressure.
• EDC/NHS conjugation: Activate the –COOH group in MES buffer (pH 5–6), then couple to the amine-bearing ligand at pH 7.2–8.0; purify by dialysis/SEC.

For detailed, application-specific SOPs (e.g., ligand density control, post-insertion), consult peer-reviewed literature and adapt to your instrumentation (extruders, microfluidics).

Biological Roles

This section provides general biochemical context for DSPE-PEG-terminated carboxylic acids; it does not imply therapeutic use.

• Biomimetic anchor: DSPE (distearoyl phosphatidylethanolamine) is a saturated phospholipid analog that integrates into lipid bilayers and vesicles, serving as a robust hydrophobic anchor in model membranes.
• PEG corona (literature): PEG chains form a hydrated steric barrier that reduces nonspecific adsorption and interparticle interactions in biological buffers, improving colloidal stability of liposomes and micelles used in research.
• Surface presentation of ligands: Carboxyl-terminated PEG allows site-selective conjugation to amines (e.g., lysines on proteins/peptides) to create ligand-presenting nanostructures for binding studies, targeting assays, or biosensing.
• Charge behavior: At neutral pH, the terminal –COOH is largely deprotonated, imparting a negative surface charge that can influence zeta potential, protein corona formation, and colloidal stability in buffered saline (literature observations).
• Membrane mechanics: Incorporation of PEGylated lipids modulates membrane curvature and reduces vesicle–vesicle fusion by steric stabilization; high mol% can destabilize bilayers or alter permeability, necessitating optimization in experimental designs.

These biological roles are typical of PEGylated phospholipids in vitro and in vivo model systems; specific performance depends on formulation variables (lipid composition, PEG mol%, ionic strength, and temperature).

Buffer Applications

DSPE-PEG-CH2COOH is not a classical buffering agent. It does not define a pH buffering range and is not used to maintain pH. Instead, it is formulated within buffers to assemble micelles or liposomes and to perform conjugation chemistry.

Practical guidance (literature):

• For EDC/NHS activation of the terminal –COOH: Use MES buffer (50–100 mM) at pH 5.0–6.0 to maximize O-acylisourea formation and NHS ester yield.
• For amide coupling to amines: After activation, adjust to pH 7.2–8.0 using phosphate or HEPES buffer to favor nucleophilic attack while minimizing ester hydrolysis.
• For hydration and dispersion: Use PBS or HEPES-buffered saline at ionic strengths typical for liposome work (e.g., 10–150 mM NaCl). Gentle heating above the bilayer transition temperature can aid dispersal.

Avoid high-pH (>9) or prolonged basic conditions that can hydrolyze ester linkages in the phospholipid backbone. Include antioxidants (e.g., small amounts of BHT) only if compatible with your analytical goals; verify absence/presence per CoA.

Green Alternatives

Greener handling of PEGylated lipids focuses on solvent choice and process intensification rather than replacing the active material.

• Solvent alternatives (literature guidance):

  • Replace chloroform/DCM with ethanol or isopropanol for solvent injection methods when feasible; these have preferable environmental and safety profiles.
  • Use 2-methyltetrahydrofuran (2-MeTHF) instead of DCM for certain film-casting steps, acknowledging different evaporation rates and solubility behavior.
  • Employ aqueous micellization with minimal co-solvent, leveraging the amphiphilicity of DSPE-PEG to avoid halogenated solvents.

• Process measures:

  • Closed-loop solvent recovery and rotary evaporation with cold traps to minimize emissions.
  • Lower temperature hydration using brief heating just above phase transition, reducing energy use compared with prolonged high-temperature cycles.
  • High-shear mixing or microfluidics to reduce solvent volumes and improve encapsulation efficiency in formulation steps.

Comparison (general):

• Chloroform/DCM: Excellent solubility and film quality; high toxicity and environmental burden.
• Ethanol/IPA: Safer, renewable routes available; may require process optimization for complete dissolution and uniform films.
• Aqueous-first methods: Safest; limited by cargo solubility and may yield broader size distributions without microfluidic control.

Trade-offs: Greener choices can affect micelle size, encapsulation, and bilayer order; validate by DLS, cryo-TEM, and DSC for each process change.

Pharmaceutical Uses

No clinical or therapeutic claims are made for this product. The following describes common research/formulation roles for PEGylated phospholipids (general literature context):

• Excipient role in research formulations: DSPE-PEG5k is widely used in laboratory-scale liposomes, mixed micelles, and LNPs to enhance colloidal stability via steric repulsion and to modulate surface charge through its carboxyl terminus.
• Conjugation handle: The –CH2COOH group allows amide coupling to targeting ligands, peptides, or polymers to create functionalized nanocarriers for binding or uptake studies in vitro.
• Process utility: Facilitates post-insertion techniques, where DSPE-PEG-ligand conjugates are inserted into pre-formed vesicles to adjust surface functionality without re-formulation.
• Reference standards: Employed as a model PEGylated lipid in method development for chromatography, DLS, and SEC-MALS characterization of nanoformulations.

Pharmacopeia status, residual solvent limits, and excipient monographs are not specified for this item; refer to the CoA/Spec Sheet and applicable regulatory references when designing translational studies. For GMP or clinical applications, source materials with documented compliance and full traceability.

Physical Properties

• Appearance: Not specified for this item; refer to CoA/Spec Sheet. (Typically supplied as a white to off-white solid or lyophilized powder, literature)
• Molecular weight: PEG nominal MW 5000 Da (polymer average; lot-specific dispersity). Overall conjugate average MW is greater than 5000 Da (literature note).
• Melting/phase transition (literature): DSPE-based PEGylated lipids exhibit gel–liquid crystalline transitions often in the 55–70 °C range depending on PEG length, hydration, and formulation. The PEG segment softens well below room temperature, but bilayer transitions are governed by the DSPE tails.
• Solubility (literature):
  • Water/buffer: Dispersible; forms micelles or integrates into liposomes above a critical aggregation concentration. True molecular solubility is low; behaves as a surfactant.
  • Organic: Soluble in chloroform, dichloromethane; soluble in alcohols (methanol/ethanol) and mixtures with chloroform; limited in pure hydrocarbons.
• Critical micelle concentration (CMC, literature): Typically low micromolar or below for DSPE-PEG5k in saline; depends strongly on temperature, ionic strength, and co-lipids.
• LogP (conceptual): Not applicable as a single value due to amphiphilicity and polymeric nature (literature note).
• pKa (literature): Terminal –COOH pKa typically ~4–5 in aqueous media; apparent pKa can shift with micellization and local environment.
• Refractive index/density: Not specified for this item; refer to CoA/Spec Sheet.

Notes: Because this is a polymer-conjugated lipid, many physical properties are distributions and formulation-dependent. Values above are general literature guidance, not product specifications.

Quality and Grades

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

How to interpret quality for PEGylated lipids (general guidance):

• Polymer dispersity: PEG components are provided as averages (e.g., 5 kDa) with inherent molecular weight distributions. CoA typically reports Mn/Mw or an SEC profile. This affects hydrodynamic size and CMC in formulations.
• Residual solvents and volatiles: High-purity lipid-PEGs are often dried under high vacuum and tested for residual chloroform/methanol; consult CoA.
• Functional end-group integrity: For –CH2COOH products, acid number or titration may be provided on CoA to quantify end-group fidelity. End-group capping efficiency is critical for predictable coupling yields.
• Oxidation profile: Unsaturated lipids can oxidize; DSPE is fully saturated (stearoyl), which improves oxidative stability. Peroxide values may still be monitored; consult CoA.
• Low-UV/analytical grade considerations: For analytical uses (e.g., HPLC of conjugates), low baseline absorbance and minimal impurities are preferred; verify by HPLC/UPLC traces when provided.

Item-specific storage and shipping

• Storage: Store at −20 °C (from Product Data). Protect from light and moisture.
• Shipping: Ice chest + ice pads (from Product Data), limiting thermal excursions to maintain material integrity.

For lot-release specifications, including assay method, residual solvent limits, moisture, and functional group analysis, refer to the item’s CoA/Spec Sheet.

Reaction and Applications

Primary application domains (research/manufacturer context):

• Surface functionalization: Terminal –CH2COOH enables carbodiimide-mediated coupling (EDC/NHS) to primary amines on peptides, proteins, or small molecules, producing amide-linked DSPE-PEG-ligand constructs that anchor into lipid bilayers.
• Nanocarriers: Incorporation into liposomes, micelles, and lipid nanoparticles (LNPs) to tune stealth properties (PEG corona), colloidal stability, and circulation behavior in research models. Carboxyl termini permit post-insertion or pre-insertion ligand attachment.
• Self-assembly: Amphiphilic character drives formation of micelles and stabilizes liposomes; PEG length (~5 kDa, literature) is commonly chosen for dense brush regimes on vesicle surfaces.
• Surface coatings: Adsorption/insertion on hydrophobic surfaces or vesicle fusion to introduce carboxylate functionality on colloids for further coupling.

Practical tips (literature):

• For EDC/NHS activation, maintain pH ~5.0–6.0 (MES buffer) during O-acylisourea formation; add NHS or sulfo-NHS to form stable NHS esters. Couple to amines at pH ~7.2–8.0. Control stoichiometry to minimize crosslinking between micelles/vesicles.
• Incorporation methods: Thin-film hydration above Tm, ethanol or solvent injection, or post-insertion (incubate pre-formed vesicles with DSPE-PEG at elevated temperature to allow insertion).
• Analytical verification: Use 1H NMR in CDCl3/CD3OD mixtures, MALDI-TOF/SEC-MALS (polymer distributions), and phosphate assay or FTIR to confirm incorporation and conjugation.

Note: No medical/clinical claims are implied; applications are for research use only.

Reaction Conditions

General literature guidance for coupling the –CH2COOH terminus to primary amines (optimize per system):

• Activation (EDC/NHS method):

  • Solvent: Aqueous MES buffer (50–100 mM), pH 5.0–6.0. Optional co-solvent: DMF or DMSO up to ~10–20% to aid solubilization.
  • Reagents: EDC (0.5–2.0 equiv per –COOH) and NHS or sulfo-NHS (1–3 equiv) to form the NHS ester.
  • Temperature/time: 20–25 °C for 15–60 min (monitor to limit hydrolysis). Protect from excess heat.

• Coupling to amines:

  • Adjust pH to 7.2–8.0 with phosphate or HEPES buffer.
  • Add amine nucleophile (1.2–5 equiv). Gentle agitation; maintain colloidal stability.
  • Temperature/time: 20–25 °C for 1–4 h or at 4 °C overnight for sensitive biomolecules.

• Purification: Dialysis (MWCO chosen above cargo), size-exclusion chromatography, or ultrafiltration to remove small-molecule reagents/byproducts.

• Controls/analytics:

  • Monitor by 1H NMR (disappearance of carboxylate signals is indirect), UV/Vis if chromophores present, TNBS/OPA assays for free amines, and DLS for size stability.

• Yields: Reported conjugation efficiencies often range widely (40–90%, literature) depending on crowding on the PEG corona, ligand size, and stoichiometry.

Cautions: Avoid high pH and prolonged heating that can hydrolyze ester linkages in the lipid. Oxygen exposure can lead to slow oxidation; use inert gas blanket where practical.

Safety and Handling

• 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 handling (good practice):

• Avoid inhalation of dust/aerosols; handle powders in a fume hood or ventilated enclosure. Wear appropriate PPE: lab coat, safety glasses, and nitrile gloves.
• Incompatibilities: Strong oxidizers and strong bases/acids can degrade the lipid or PEG; carbodiimides/active esters may prematurely react with the terminal –COOH if present during storage.
• Thermal considerations: Prolonged exposure above the lipid phase transition can promote oxidation or hydrolysis. Process expediently when warming for dissolution; re-cool after use.
• Hygroscopicity: PEG segments can absorb moisture; keep tightly closed under inert atmosphere if possible to minimize hydrolysis and oxidation of the fatty acyl chains.
• First aid overview (general): In case of contact, rinse skin/eyes with water for several minutes; remove contaminated clothing. If inhaled, move to fresh air. If ingested, rinse mouth. Seek medical attention if irritation persists. Defer to the SDS for authoritative guidance.
• Waste: Dispose according to institutional and local regulations for organic polymeric/lipid waste; avoid drain disposal.

Always consult the product SDS for definitive hazard, exposure limits, and emergency response instructions.

Solvent Selection

As an amphiphilic PEGylated phospholipid, DSPE-PEG-CH2COOH dissolves best in moderately polar organics and can be dispersed in aqueous buffers.

• Preferred solvents (literature/practice):

  • Chloroform or CHCl3:MeOH (2:1 to 9:1 v/v) for thin-film hydration and lipid film casting.
  • Dichloromethane (DCM) for rapid dissolution and rotary evaporation; avoid prolonged exposure to prevent acid-catalyzed hydrolysis.
  • Ethanol or isopropanol for solvent injection methods into aqueous buffers.
  • Water/PBS: Forms micelles or incorporates into liposomes upon hydration and agitation; solubility is colloidal.

• Miscibility/polarity: PEG segment confers good compatibility with polar solvents; hydrocarbon tails favor apolar phases. Binary mixtures help achieve homogeneous films for liposome preparation.

• Selection tips:

  • For liposome prep by thin-film hydration: Use CHCl3:MeOH to co-dissolve with other lipids (e.g., DSPC, cholesterol), dry thoroughly, then hydrate with buffered saline above the highest Tm component.
  • For ligand conjugation (EDC/NHS): Perform in aqueous MES or phosphate buffer (pH 5–6 for activation) containing surfactant-compatible conditions; organic co-solvent (≤10–20% DMF/DMSO) can aid solubilization of hydrophobic amines.
  • For micelle formation: Hydrate in buffer and sonicate or heat gently to achieve clear dispersions.

• Avoid: Strongly basic aqueous media for extended periods (risk of ester hydrolysis) and neat acetone/ethers (limited solubility).

Storage and Reconstitution

• Storage conditions (item-specific): Store at −20 °C (from Product Data). Keep tightly sealed, desiccated, and protected from light. Minimize freeze–thaw cycles by aliquoting.
• Shipping (item-specific): Shipped in an ice chest with ice pads (from Product Data) to limit thermal exposure during transit.

Reconstitution (general guidance):

• For organic stock: Dissolve the material in chloroform or CHCl3:MeOH (2:1 v/v) to 5–20 mg/mL for film casting. Store aliquots under inert gas at −20 °C; warm to room temperature briefly before opening to avoid condensation.
• For aqueous dispersions: Hydrate thin films with pre-warmed buffer (e.g., PBS or HEPES) above the bilayer transition temperature. Sonicate or extrude to the desired size. For micelles, direct dissolution with gentle heating and vortexing may suffice.
• For conjugation stocks: Prepare freshly in MES buffer for activation; avoid long pre-activation to limit hydrolysis. Remove activating reagents post-reaction by dialysis/SEC.

Stability notes (general): Avoid prolonged exposure to temperatures above 40–50 °C and to strong light/oxygen. If long-term storage is needed, consider storing under inert gas with antioxidants if compatible with downstream use. Always refer to the CoA/SDS for lot-specific handling and stability information.

Research Use: For research use only (from Product Data).

Structure and Identity

DSPE-PEG-CH2COOH (MW 5000) is an amphiphilic lipid–polymer conjugate comprised of a phospholipid anchor and a poly(ethylene glycol) chain terminating in a carboxymethyl group.

• Item-specific identifiers

  • SKU: D1445792
  • Product name: DSPE-PEG-CH2COOH, MW 5000
  • CAS: 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.
  • Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Nominal molecular weight: PEG segment 5000 Da (nominal, polymeric distribution). Overall conjugate mass is higher due to the DSPE-PE anchor; exact average is lot-dependent (polymer dispersity).

• Structural features (general/literature)

  • Lipid anchor: DSPE = 1,2-distearoyl-sn-glycero-3-phosphoethanolamine (two C18:0 stearoyl chains on glycerol; zwitterionic phosphoethanolamine headgroup when not derivatized).
  • PEG spacer: linear poly(ethylene glycol), ca. 5 kDa average, covalently attached to the ethanolamine nitrogen or phosphoethanolamine moiety (supplier-specific linkage chemistry; typically amide or carbamate in DSPE-PEG reagents).
  • Terminal group: –CH2–COOH (carboxymethyl), providing a reactive carboxyl for carbodiimide couplings to primary amines.
  • 2D description: A hydrophobic tail domain (two parallel C18 chains) attached to a polar phosphodiester–ethanolamine junction, extended by a flexible PEG coil terminating in a small carboxylic acid head. The molecule is amphiphilic and can insert into bilayers or form micelles.

• Stereochemistry (general): Natural sn-glycero backbone at the phospholipid; PEG segment is atactic (no defined stereocenters).

Synthetic Utility

DSPE-PEG-CH2COOH serves as a multifunctional building block for constructing amphiphilic conjugates and surface-presenting ligands.

Functional group reactivity (general):

• Terminal –COOH: Amenable to carbodiimide (EDC/DIC) activation, forming NHS esters for coupling to primary amines on biomolecules or small molecules. Alternative activations include CDI (to imidazolides) or mixed anhydrides for specialized couplings.
• PEG chain: Provides spacing and solvation; can reduce steric hindrance near the bilayer surface and improve aqueous compatibility of hydrophobic ligands.
• Lipid anchor: Ensures membrane insertion and retention; two stearoyl chains confer low critical desorption rates from bilayers.

Use cases:

• Synthesis of DSPE-PEG–ligand conjugates (peptides, antibodies fragments, dyes) for incorporation into liposomes/micelles.
• Preparation of carboxyl-functionalized vesicles for subsequent surface grafting via EDC/NHS in situ.
• Fabrication of supported lipid bilayers or polymer–lipid hybrid particles with carboxylate-bearing coronas.

Practical considerations:

• Conduct couplings in buffered aqueous media with controlled co-solvent (DMF/DMSO ≤20%) to maintain colloidal stability.
• Quantify conjugation by TNBS assay (amine consumption), UV/Vis if chromophores are present, or by SEC to monitor shifts in hydrodynamic size.
• Thoroughly remove activating reagents and byproducts (ureas, NHS) by dialysis or SEC to prevent downstream interference.

Target Specificity

Not applicable. This product is a chemical/lipid reagent, not an antibody, enzyme, or affinity reagent with defined biological target specificity. Any target-binding properties arise only after conjugation of specific ligands to the –CH2COOH terminus.

Foire aux questions

How should this product be stored?

Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.

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 D1445792, and the molecular weight is 5000(Average) 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.