PLGA3000-PEG2000-VS , CAS No.P1441226

CAS: P1441226 Cat. No.: P1441226 Fórmula: C₁₁H₁₈O₈S Peso molecular: 310.32

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Visão geral

PLGA3000-PEG2000-VS (PLGA3000-PEG2000-Vinylsulfone)is an amphiphilic polymer. Amphiphilic polymers can be used in drug delivery studies due to their ability to self-assemble into discrete aggregates.

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: 310.32

Application Protocols

Not applicable for immunoassay protocols (WB, IHC, IF, FC). No tested biological assay protocols are provided for this item. For general use, see Reaction Conditions for guidance on thiol–vinyl sulfone conjugation and nanoparticle formation (literature/general).

Biological Roles

This product is a synthetic biomaterials reagent and does not possess intrinsic biological activity in the sense of a small-molecule metabolite. The following notes describe general roles of its constituent polymers in research contexts (literature/general):

• PEG segment
  • Confers hydrophilicity and steric stabilization to assemblies, reducing nonspecific adsorption in vitro. PEGylation is widely used to modulate protein and nanoparticle interactions with biological media.
• PLGA segment
  • Hydrophobic, biodegradable polyester that undergoes hydrolysis to lactic and glycolic acids under aqueous conditions; degradation rate depends on composition, molecular weight, and morphology. Used in research on controlled release matrices and particles.
• Vinyl sulfone functionality
  • Enables site-selective conjugation to thiol-bearing biomolecules (e.g., cysteine-containing peptides), allowing the presentation of targeting ligands, dyes, or affinity handles on polymer assemblies.
• Self-assembly and interfacial behavior
  • The PLGA core can sequester hydrophobic probes, while PEG forms a corona in aqueous media; VS provides a means to add bioactive ligands after assembly, preserving ligand integrity.

Note: Any statements above are general literature descriptions for research use. This item is labeled For research use only and is not intended for diagnostic or therapeutic applications.

Buffer Applications

This material is not a buffer component. However, buffers are central to thiol–vinyl sulfone conjugations and to handling in aqueous media (literature/general):

• Recommended buffer systems for thiol coupling
  • Phosphate-buffered saline (PBS) or sodium phosphate, pH 7.0–7.8, optionally with 5–20% DMSO to aid solubility of the polymer.
  • HEPES (pH 7.0–7.5) as an alternative zwitterionic buffer with low nucleophilicity.
• Buffers/additives to avoid
  • Tris, glycine, cysteine, and other primary amine- or thiol-containing buffers which can consume VS.
  • Reducing agents (DTT, β-mercaptoethanol). If reduction is needed (e.g., to expose cysteines), use TCEP briefly and remove by desalting prior to conjugation.
• Ionic strength
  • Moderate ionic strength (e.g., 150 mM NaCl) can aid protein stability during conjugation.
• Practical hints
  • Degas buffers gently if oxygen-sensitive partners are used, though VS–thiol reactions are generally tolerant.
  • Maintain temperature at 20–25 °C for predictable kinetics; lower temperatures slow the reaction but may improve selectivity with delicate proteins.

Green Alternatives

Sustainability considerations focus on solvent selection and functional group choice, as the polymer itself is fixed.

• Solvent choices (literature/general)

  • Prefer water-rich systems with small co-solvent fractions (≤20% DMSO, ethanol, or acetone) for conjugations and nanoprecipitation to reduce reliance on chlorinated solvents.
  • Avoid DCM/chloroform when feasible; acetone or ethyl acetate can substitute for many film-casting or emulsification processes, with attention to evaporation rates and particle size control.

• Functional handle alternatives (comparative, literature/general)

  • Vinyl sulfone vs maleimide: VS offers greater hydrolytic and retro-Michael resistance, reducing byproducts; maleimide may react faster but is less stable and can undergo ring opening.
  • VS vs click chemistries (azide/alkyne): CuAAC provides orthogonality and green aqueous conditions but requires copper catalyst; SPAAC avoids metal but increases mass and cost of cyclooctyne reagents.

Comparison (general tendencies)

• VS–thiol: aqueous, no metal, good stability; moderate rate; avoid thiol-containing buffers.
• Maleimide–thiol: very fast; less hydrolytically stable; potential exchange with thiols.
• CuAAC (azide–alkyne): robust, tolerant; needs Cu catalyst and ligand; excellent for modular assembly.

Implement greener processing by using microfluidic or continuous nanoprecipitation (reduced solvent volumes) and solvent recycling where possible.

Pharmaceutical Uses

No pharmacopeial grade or clinical use is indicated for this catalog item. For research use only.

General formulation roles for related materials (literature/general):

• Excipient/functionality
  • Amphiphilic PLGA–PEG block copolymers are investigated as matrix materials for controlled release, micelles, and nanoparticles. The PEG corona improves colloidal stability, while the PLGA core controls encapsulation and release of hydrophobic payloads.
  • Vinyl sulfone end groups enable post-formulation attachment of targeting ligands, fluorescent labels, or affinity tags under mild, aqueous conditions.
• Considerations when translating to regulated applications
  • Detailed control of Mn/Mw, lactide:glycolide ratio, residual solvents, catalysts, and endotoxin would be required. Specific pharmacopeial monographs exist for some grades of PLGA and PEG, but not for this particular block copolymer and functionality.

This SKU is not supplied as GMP or pharmacopeial grade; consult the CoA/Spec Sheet for quality attributes and restrict to non-clinical research.

Physical Properties

Item-specific physicochemical specifications are not provided for this SKU. The following are general/literature properties for related PLGA–PEG–VS materials; do not treat as specifications.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet. (Typically off-white to light tan solid for similar materials.)
• Average molecular weights: Name indicates nominal PLGA block ~3000 and PEG block ~2000; overall Mn depends on linker and block ratio (literature/general).
• Dispersity (Đ, PDI): Often 1.1–1.5 for well-controlled syntheses (literature/general).
• Thermal transitions (literature/general)
  • PLGA glass transition (Tg): typically ~40–60 °C depending on lactide:glycolide ratio and end-group chemistry.
  • PEG2000 melting transition (Tm): ~50–55 °C; PEG segment may crystallize and influence thermal behavior of the block copolymer.
• Solubility/miscibility (literature/general)
  • Good solubility in polar aprotic organics (DMSO, DMF, NMP, acetone, acetonitrile).
  • Dispersible/soluble in water due to PEG block; hydrophobic PLGA promotes micellization and nanoparticle formation above a critical concentration.
  • Soluble in chlorinated solvents (e.g., DCM, CHCl3) when VS stability is considered.
• Density, refractive index, logP, pKa: Not applicable or not meaningfully defined for polydisperse copolymers; Not specified for this item; refer to CoA/Spec Sheet if reported.

Note: Vinyl sulfone is hydrolytically stable relative to maleimide but can undergo Michael addition with nucleophiles; avoid prolonged exposure to strong base or amines when unconjugated (literature/general).

Quality and Grades

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

How to interpret quality for PLGA–PEG–VS materials (general guidance):

• Key macromolecular attributes typically reported on a CoA
  • Number-average molecular weight (Mn) and/or weight-average molecular weight (Mw) for each block and for the conjugate; dispersity (Đ, PDI).
  • Lactide:glycolide molar ratio in PLGA (e.g., 50:50, 75:25) determined by NMR; not specified for this item.
  • PEG chain length distribution (nominal 2 kDa) and end-group identity (e.g., methoxy vs hydroxyl) at the distal terminus.
  • Functionality: extent of vinyl sulfone substitution (f ≈ 1.0 is ideal for mono-functional conjugates), residual unreacted end-groups.
  • Residual solvents, monomers, catalysts, and water content (Karl Fischer) where relevant.
  • Bioburden/endotoxin for bio-oriented grades; not specified for this item.
• Typical analytical methods
  • 1H/13C NMR for composition and end-group verification; ATR-FTIR for functional groups (VS S=O stretches, ester C=O).
  • GPC/SEC (often with multi-angle light scattering) in DMF, THF, or HFIP for Mn/Mw/Đ.
  • UV–Vis to verify VS presence (weak chromophore) and to quantify thiol capacity after reaction.
• Stabilizers/Additives
  • Not specified for this item; refer to CoA/Spec Sheet. VS-functional polymers are commonly supplied without stabilizers and kept dry/inert.

Conclusion: Use the CoA to match Mn values and functionality to your application (e.g., stoichiometric thiol conjugation).

Reaction and Applications

Principal utility of PLGA3000-PEG2000-VS arises from its terminal vinyl sulfone, enabling selective thiol conjugation, combined with the self-assembly of the PLGA–PEG architecture.

• Thiol–Michael addition (literature/general)
  • VS reacts chemoselectively with thiols (e.g., cysteine residues, thiolated ligands) at pH ~7–8.5 to form stable thioether linkages. Reaction is less reversible than maleimide conjugation and shows improved hydrolytic stability.
  • Suitable for conjugating peptides, proteins, antibodies (after controlled reduction), small-molecule thiols, and surface thiols on nanoparticles.
• Materials and nanoformulations (literature/general)
  • Amphiphilic block copolymer enables micelle formation, polymersomes, and core–shell nanoparticles with PLGA cores and PEG coronas for stealth behavior. VS offers post-assembly surface functionalization.
  • Use in nanoprecipitation, emulsion–solvent evaporation, or microfluidic mixing to encapsulate hydrophobic cargos in the PLGA domain.
• Surface and hydrogel chemistry (literature/general)
  • VS can crosslink with multi-thiol components to yield hydrogels or surface grafts on thiol-bearing substrates (e.g., gold–thiol SAMs followed by VS coupling to present PEGylated PLGA).
• Practical tips
  • Maintain pH 7.0–8.0; avoid thiol-scavenging buffers (Tris, cysteine) and free reducing agents (DTT, βME). Use TCEP sparingly and remove before conjugation.
  • Control stoichiometry to achieve near-quantitative consumption of VS; monitor by Ellman’s assay (for thiol) or SEC shift of macromolecule.
  • For nanoparticle work, preform particles then functionalize via VS to minimize loss of functionality during organic processing.

Reaction Conditions

General literature guidance for thiol–vinyl sulfone conjugation and for forming assemblies with PLGA–PEG block copolymers. These are not item-specific specifications.

• Thiol–VS conjugation (bioconjugation)
  • Solvent: Aqueous buffer (PBS or HEPES) at pH 7.0–8.0, optionally with 5–20% DMSO or DMF to aid solubility.
  • pH: 7.0–8.5; higher pH accelerates reaction but may risk ester hydrolysis and side reactions.
  • Temperature: 20–25 °C typical; 4 °C for sensitive proteins (slower kinetics), up to 37 °C for robust ligands (faster kinetics).
  • Stoichiometry: 1.1–1.5 equivalents of thiol per VS to drive completion while minimizing crosslinking.
  • Time: 1–16 h depending on reactant concentration (10 µM–5 mM range) and pH.
  • Catalysts: Generally not required; mild base (e.g., triethylamine) can accelerate in organic media, but avoid excess base in water.
  • Quench/unreacted VS: Cap by adding a small excess of 2-mercaptoethanol or cysteine after desired coupling to consume residual VS, then purify.
• Nanoparticle formation (block-copolymer self-assembly)
  • Nanoprecipitation: Dissolve polymer in acetone/ACN/DMSO (5–20 mg/mL), inject into stirring water (5–20× volume) at room temperature; size tuned by solvent choice, addition rate, and polymer concentration.
  • Emulsion–solvent evaporation: Dissolve in DCM or ethyl acetate, emulsify in aqueous surfactant (e.g., PVA), then evaporate solvent; VS best preserved by minimizing high pH and prolonged heating.
• Analytical monitoring
  • SEC/GPC for size shift; Ellman’s assay to track free thiol; 1H NMR to verify disappearance of vinyl protons.

Validate and optimize conditions on small scale before committing valuable ligands or payloads.

Safety and Handling

• GHS classification, signal word, pictograms, H/P statements: Not specified for this item; refer to the SDS for authoritative safety information.
• General hazards (literature/general)
  • Vinyl sulfone end groups are electrophilic Michael acceptors and may be irritating and sensitizing upon contact; avoid skin/eye exposure and inhalation of dust/aerosols.
  • PLGA–PEG backbone is generally regarded as low acute toxicity in research settings; nonetheless, handle as a chemical of unknown toxicity.
• Recommended PPE and engineering controls
  • Lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Handle powders in a fume hood or ventilated enclosure to minimize dust.
• Incompatibilities and stability (literature/general)
  • Avoid strong nucleophiles (excess primary amines, thiols) unless performing intended conjugation; VS can react.
  • Avoid strong bases and prolonged high pH which can accelerate ester hydrolysis of PLGA and side reactions at VS.
  • Moisture can hydrolyze ester linkages over time; keep material dry. Oxygen is not a specific concern; inert atmosphere is good practice for long-term stability.
• First-aid overview (general)
  • Skin/eye contact: Rinse with water for at least 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 advice.
• Spill/leak response
  • Avoid creating dust; collect mechanically and place in appropriate waste. Decontaminate surfaces with suitable solvent (e.g., ethanol or water) followed by detergent.

Always consult the product SDS for definitive guidance before use.

Solvent Selection

Given its amphiphilic block structure, PLGA3000-PEG2000-VS exhibits dual solubility behavior.

• Polarity and miscibility (literature/general)
  • PEG block imparts hydrophilicity; PLGA block provides hydrophobicity. The polymer dissolves well in polar aprotic organic solvents (DMSO, DMF, NMP, acetone, acetonitrile) and in chlorinated solvents (DCM, chloroform). In water and buffered saline, it may dissolve or self-assemble into micelles/nanoparticles depending on concentration and temperature.
• Selecting solvents by task
  • Thiol conjugation to biomolecules: Use aqueous buffers (pH 7.0–8.0) with a modest fraction of DMSO or DMF (5–20%) to aid solubilization while maintaining protein integrity; avoid thiol-containing buffers (DTT, βME) and primary amine buffers that can consume VS.
  • Nanoparticle formation: Employ water-miscible organics (acetone, acetonitrile, ethanol, DMSO) for nanoprecipitation into water; or DCM/acetone for emulsion–solvent evaporation.
  • Film casting or coating: Use DCM, chloroform, acetone, or HFIP as appropriate, mindful of VS stability.
• Comparison notes (literature/general)
  • DMSO vs DMF: DMSO is highly solvating and biocompatible with aqueous media; DMF offers lower viscosity but is more cytotoxic—prefer DMSO for bioconjugation setups.
  • Acetone/ACN: Good for nanoprecipitation due to rapid diffusion into water; VS remains reasonably stable near neutral pH.

Always confirm polymer solubility and VS integrity by small-scale trials and analytical checks (e.g., SEC, NMR).

Storage and Reconstitution

• Storage conditions (item-specific)
  • Store at -20 °C. Keep tightly closed in a dry, inert atmosphere to limit moisture and hydrolysis. Avoid repeated warming/cooling cycles.
  • Shipped in: Ice chest + Ice pads.
• Stability considerations (general)
  • Vinyl sulfone is reasonably stable at neutral to mildly acidic conditions; prolonged exposure to high pH or nucleophiles can lead to side reactions. PLGA ester linkages hydrolyze in the presence of water; maintain dryness for long-term storage.
• Reconstitution and handling (literature/general)
  • To prepare stock solutions, dissolve in anhydrous DMSO or DMF (e.g., 10–100 mg/mL) under inert gas, then dilute into buffer immediately before use. For fully aqueous use, dissolve with gentle stirring at room temperature; brief sonication may help. Filter (0.22 µm) if needed for bioconjugation.
  • For nanoprecipitation, prepare an organic solution (e.g., acetone or ACN) and add to water under stirring; remove organic solvent promptly.
  • Avoid buffers containing free thiols or primary amines unless intended for reaction with VS.
• Aliquoting and freeze–thaw
  • Aliquot dry polymer or concentrated solutions to minimize freeze–thaw cycles. Store solutions at ≤ –20 °C (anhydrous) for short periods; verify VS integrity before critical experiments.
• Shelf-life
  • Not specified for this item; refer to CoA/Spec Sheet. Periodically assess by NMR/SEC to confirm molecular weight and VS functionality after storage.

Research use only. Refer to the product SDS and CoA for batch-specific guidance.

Structure and Identity

PLGA3000-PEG2000-VS is a block copolymer comprising a poly(lactic-co-glycolic acid) (PLGA) segment (nominal Mn ~3000) covalently linked to a poly(ethylene glycol) (PEG) segment (nominal Mn ~2000), bearing a terminal vinyl sulfone (VS) electrophile for thiol-selective conjugation.

• Item-specific registry fields

  • CAS: P1441226 (catalog identifier)
  • Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet. (Name indicates nominal block sizes only.)
  • 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 description)

  • Architecture: Linear AB-type block copolymer with a hydrophobic PLGA block and a hydrophilic PEG block, end-functionalized with a vinyl sulfone.
  • Functional groups: Ester linkages (PLGA backbone), ether linkages (PEG backbone), terminal vinyl sulfone (–SO2–CH=CH2) as a soft Michael acceptor selective for thiols.
  • Stereochemistry: PLGA segment may contain isotactic/heterotactic lactic units; detailed tacticity and lactide:glycolide ratio are not specified for this item.
  • 2D structure (verbal): Repeating –[O–CH(CH3)–CO]– and –[O–CH2–CO]– units (lactic and glycolic esters) form the PLGA block attached via an ester or urethane linker to a –[CH2–CH2–O]n– PEG chain terminated by a –SO2–CH=CH2 vinyl sulfone group.

• Identity notes

  • Polydisperse material; exact Mn/Mw and Đ (PDI) are batch-specific and reported on CoA where applicable.

Synthetic Utility

As a macromolecular building block, PLGA3000-PEG2000-VS provides a versatile platform for constructing functional biomaterials (literature/general):

• End-group reactivity
  • Vinyl sulfone engages in Michael addition with thiols to form robust thioethers. Useful for site-specific attachment of peptides, proteins, thiolated DNA, dyes, or small-molecule ligands.
• Post-polymer modification
  • After assembly into nanoparticles or films, surface-accessible VS groups allow ligand grafting without reprocessing the bulk polymer, preserving encapsulated cargo.
• Multivalent constructs
  • Combining VS–thiol coupling with multi-thiol linkers enables crosslinking to form hydrogels, networks, or star-like architectures.
• Orthogonal strategies
  • VS is orthogonal to many click reactions (e.g., CuAAC) allowing sequential modifications when additional handles are present on the distal PEG end or on cargo.
• Retrosynthetic perspective
  • Starting from thiol-bearing ligands (R–SH), a single-step conjugation installs R onto the polymer terminus. Protecting groups on cysteine (e.g., Acm, StBu) can be used to control selectivity, followed by deprotection and conjugation.

Key advantages over other handles include aqueous compatibility and the formation of non-reversible linkages under physiological pH, simplifying purification and downstream stability.

Target Specificity

Not applicable. This product is a synthetic polymer reagent and is not an antibody or affinity reagent with defined biological target specificity.