DM1-MCC-PEG3-biotin - ≥95% , CAS No.2183472-94-6

CAS: 2183472-94-6 Cat. No.: D596514 Fórmula: C₆₅H₉₅ClN₈O₁₈S₂ Peso molecular: 1376.1

GRADE & PURITY ≥95%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Descripción general

DM1-MCC-PEG3-biotin is a biotin-attached DM1 molecule.

Specifications

Especificaciones y pureza

≥95%

Condiciones de almacenamiento de almacenamiento

Store at -20°C

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Pureza

≥95%

Nombres e identificadores

Peso molecular

1376.1

Propiedades químicas y físicas

• Solubilidad: Solubility in DMSO, DCM, DMF

Application Protocols

Not specified for this item; refer to CoA/Spec Sheet and SDS for any available usage notes.

General protocols, tested applications, recommended dilutions, and positive controls are not provided in the product data for this SKU. Users should develop and qualify in‑house procedures appropriate to their assay format (e.g., streptavidin‑based pull‑downs, ELISA‑like detection, or biosensor immobilization) and validate performance with suitable controls.

Biological Roles

Item-specific biological annotations are not provided for this product. The following context is general literature information for the components of DM1‑MCC‑PEG3‑biotin (research only):

• DM1 (maytansinoid) moiety: binds to the vinca site of tubulin and inhibits microtubule polymerization, disrupting mitotic spindle dynamics in proliferating cells (literature). This biochemical activity underlies the widespread use of maytansinoids as payloads in antibody–drug conjugate research.
• MCC linker: a non‑cleavable maleimidocaproyl group that forms a stable thioether with thiols; in conjugates, intracellular processing must release the active catabolite via proteolysis rather than linker scission (literature concept). In this construct, MCC is already coupled to DM1.
• PEG3 spacer: improves aqueous compatibility and reduces nonspecific binding/aggregation while introducing minimal steric bulk.
• Biotin terminus: affords femtomolar‑range binding to streptavidin/avidin, enabling capture, immobilization, and signal amplification in biochemical assays.

Use cases in biochemistry (non-clinical):

• Affinity capture/pull‑down of interacting proteins or complexes on streptavidin beads for proteomic or mechanistic studies.
• Surface presentation on streptavidin‑coated biosensors (BLI/SPR) to quantify binding of tubulin or tubulin‑binding ligands in competition formats.

All uses are for research laboratories only. No claims are made regarding therapeutic, diagnostic, or in vivo applicability.

Buffer Applications

This product is not a buffering agent and does not form a defined conjugate acid/base pair for pH control. Consequently, it is not typically used to make buffer systems.

Practical note: In biochemical assays, it is commonly handled in standard buffers (e.g., PBS, HEPES) with a small percentage of a water‑miscible organic solvent such as DMSO to aid solubilization. Select the buffer that best matches your biological system, accounting for potential interactions of the hydrophobic DM1 moiety with serum proteins or detergents.

Green Alternatives

Sustainability considerations revolve around solvent use and assay design, since the molecule itself is a specialized probe.

• Preferred greener solvents for handling: where feasible, use water‑rich buffers with minimal DMSO (≤1–2% v/v) while maintaining solubility and assay performance. Replace DMF with DMSO or ethanol (if compatible) to improve EHS profiles. Note: efficacy must be verified experimentally.
• Resource‑efficient immobilization: employ reusable streptavidin matrices with validated regeneration protocols (e.g., mild acidic/basic cycles compatible with biotinylated ligands) to reduce consumables.
• Microscale workflows: miniaturize assays (384/1536‑well formats) to reduce solvent and reagent consumption without sacrificing data quality.

Illustrative comparison (general; not item specs):

• DMF vs DMSO: DMSO has lower vapor pressure, lower acute toxicity profile, and superior water miscibility; DMF is reprotoxic and should be minimized.
• Acetonitrile vs ethanol for chromatography: ethanol is greener but increases viscosity and backpressure; MeCN remains common for LC but should be captured and recycled when possible.

Waste and exposure minimization:

• Given the potency of maytansinoid payloads, apply closed‑loop liquid handling, dedicated cytotoxic waste streams, and adsorbent pads to capture drips. Implement solvent recycling where permitted.

Balance green choices with assay fidelity; prioritize operator safety and data integrity.

Pharmaceutical Uses

No pharmacopeial/excipient role is specified for this product. Not for clinical or therapeutic use.

Research/manufacturing context (general, non-clinical):

• Reference material: may be used as a research‑grade standard or control in analytical methods that profile non‑cleavable DM1–linker catabolites or assess stability under simulated processing conditions.
• Affinity probe in process analytics: the biotin tag allows immobilization on streptavidin supports to evaluate binding interactions or to build model systems for conjugation process development (e.g., studying off‑target binding in complex matrices).
• Device/assay development: useful for creating surface‑bound test articles on streptavidin‑functionalized sensors (e.g., BLI/SPR) for method qualification.

Any application must remain strictly in vitro/instrumental and within research and development environments. There are no claims of GMP status, compendial listing, or suitability for human/animal administration.

Physical Properties

Item-specific specifications (this product):

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Purity/grade: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• Other physicochemical specs (mp/bp, water/peroxide/metals, UV cutoff, refractive index): Not specified for this item; refer to CoA/Spec Sheet.

General/literature expectations for DM1–linker–biotin conjugates (informational, not specifications):

• Physical state: typically solid or film; may be amorphous; decomposes on strong heating.
• Solubility: good in polar aprotic organics (DMSO, DMF, N‑methyl‑2‑pyrrolidone). PEG3 and biotin units can improve miscibility in aqueous buffers when pre‑dissolved in DMSO (e.g., 1–10% v/v cosolvent) (literature/practice).
• Aqueous behavior: limited intrinsic water solubility for the DM1 core; overall construct can form colloidal solutions depending on concentration, buffer ionic strength, and presence of carrier proteins/detergents (literature).
• LogP: expected high apparent lipophilicity from DM1, partially offset by PEG3/biotin (qualitative, literature).
• pKa: multiple ionizable groups may be present (e.g., phenolic/amide environments), but dominant behavior is neutral to weakly polar; exact values vary by analog and are not standardized (literature).
• Stability: thioether (DM1–MCC) is generally robust; ester/acetal motifs in the maytansinoid can be sensitive to strong base/acid and prolonged aqueous exposure at elevated temperature (literature).

Always verify exact values and solution behavior for your lot via the CoA and small‑scale pretests.

Quality and Grades

• Grade/purity for this specific item: Not specified for this item; refer to CoA/Spec Sheet.
• Research use note: For research use only (as provided). Not for human or veterinary use, clinical diagnostics, or household use.

How to interpret grades for bioconjugate reagents (general guidance):

• Analytical/research grade: suitable for discovery workflows, assay development, and mechanistic studies; may include trace residual solvents/byproducts not impacting typical in‑vitro applications. Verify by LC–MS/HPLC where critical.
• Conjugation-ready or probe grade (if stated on CoA): indicates identity/purity suitable for affinity assays, pull‑downs, or as positive controls/standards. Low nonvolatile residue and defined counter‑ions are beneficial.
• Stabilizers: none are listed for this item. If a stabilizer is present on the CoA (e.g., antioxidants), consider downstream assay compatibility.

Verification practices:

• Identity confirmation by exact mass (ESI‑MS), isotopic pattern, and diagnostic fragment ions of DM1/MCC/biotin motifs.
• Purity by HPLC/UPLC with diode‑array/MS detection; monitor for maleimide‑related hydrolysis products (not expected here because maleimide is consumed) and DM1 epimerization/hydrolysis products (literature).

Always defer to the item’s CoA/Spec Sheet for lot‑specific acceptance criteria and analytical methods.

Reaction and Applications

This construct is designed primarily as a biochemical probe/affinity handle rather than a small‑molecule coupling reagent.

Representative research applications (general, literature-based):

• Affinity capture and target engagement: the biotin terminus enables high‑affinity binding to streptavidin/avidin matrices for pull‑down of interacting proteins or for immobilization in enzyme/cell‑free assays. The DM1 moiety provides a defined microtubule‑active pharmacophore for competition or binding studies.
• Assay development: use as a biotinylated positive control in ELISA‑like formats or SPR/BLI surfaces functionalized with streptavidin, enabling kinetic or displacement measurements against tubulin‑interacting ligands.
• Mechanistic ADC research: serves as a reference standard to study non‑cleavable DM1–linker behavior, stability of the thioether (DM1–MCC), and impact of PEG spacing on binding/solubility (in vitro models).
• Imaging and localization (indirect): after immobilization, detect with labeled streptavidin (HRP/fluorophore) in microplate or blot formats; or assemble multicomponent complexes on streptavidin scaffolds.

Practical tips:

• Ensure maleimide is not expected to be available—DM1‑MCC signifies a stable thioether adduct; do not plan thiol–maleimide coupling on this molecule.
• Pre‑block streptavidin surfaces to minimize nonspecific adsorption of hydrophobic DM1.
• Use low adsorption plastics and include carrier proteins (e.g., 0.1% BSA) when appropriate to reduce loss.
• Validate functional integrity after any drying or lyophilization by a small‑scale binding test to streptavidin beads.

Reaction Conditions

There are no manufacturer‑specified reaction conditions for this item. The following general, literature‑based guidance addresses common laboratory uses of biotinylated small‑molecule probes:

• Preparation of stock: dissolve in anhydrous DMSO or DMF to 1–10 mM. Vortex and sonicate briefly if needed. Avoid basic additives that can compromise maytansinoid integrity over time.
• Immobilization on streptavidin beads/plates: incubate the DMSO‑diluted solution (final DMSO ≤1–2% v/v) with streptavidin‑coated support for 15–60 min at room temperature with gentle mixing. Wash with assay buffer (e.g., PBS with 0.01–0.05% Tween‑20) to remove unbound material.
• Competition/binding assays: introduce tubulin or tubulin‑ligand analytes to immobilized probe in suitable buffer. Typical temperatures 20–25°C; equilibration 10–60 min depending on system. Readout may be enzymatic (HRP‑streptavidin), fluorescence, or label‑free (BLI/SPR).
• Stability checks: monitor by LC–MS after exposure to buffers at set pH (e.g., pH 6–8) and temperatures (4–37°C) to ensure structural integrity during assay durations. Avoid extended incubation >24 h at 37°C in aqueous media.

These conditions are provided as general research guidance only. Optimize parameters empirically for your assay format and instrument. Always verify compatibility of DMSO percentage with your biological system.

Safety and Handling

Authoritative safety information for this specific item (GHS, H‑statements, pictograms) is Not specified for this item; refer to SDS. Handle under institutional controls for potent bioactive research chemicals.

Best‑practice guidance (general; defer to SDS/inst. policies):

• Hazard profile: maytansinoids (DM1 class) are highly potent microtubule inhibitors in cells (literature). Treat as cytotoxic. Avoid inhalation, ingestion, skin contact, and sharps contamination.
• Engineering controls: work in a certified chemical fume hood or cytotoxic safety cabinet. Use closed microtubes; minimize aerosol generation.
• PPE: double nitrile gloves (frequent change), lab coat/gown, eye protection; consider sleeve covers. Use dedicated waste containers for cytotoxic solids/solutions.
• Incompatibilities: avoid strong acids/bases (hydrolysis risk for ester/acetal moieties), strong oxidizers, and prolonged exposure to aqueous buffers at elevated temperature.
• Handling tips: prepare concentrated DMSO stocks; dispense with positive‑displacement tips; wipe down external vial surfaces after use. Protect from light if possible.
• First aid (overview; follow SDS): skin—immediately wash with soap/water; eyes—rinse with water for 15 min and seek medical attention; inhalation—move to fresh air; ingestion—seek medical attention.
• Spill/cleanup: absorb with inert material, decontaminate surfaces with suitable solvent/detergent, then 10% bleach followed by water; dispose as cytotoxic chemical waste per local regulations.

Consult the product SDS for definitive hazard classification, exposure controls, and disposal instructions.

Solvent Selection

Role and polarity: DM1‑MCC‑PEG3‑biotin is amphiphilic—hydrophobic DM1 core with polar PEG3/biotin. It dissolves best in polar aprotic organics; aqueous buffers may require cosolvent.

Recommended choices (general guidance; not specifications):

• Primary solvents: anhydrous DMSO or DMF for stock solutions (e.g., 1–10 mM). These solubilize the macrocyclic DM1 moiety while accommodating PEG3/biotin.
• Cosolvent systems: 1–10% DMSO or DMF in PBS, HEPES, or assay buffers to achieve working concentrations, minimizing precipitation. Include 0.01–0.1% nonionic surfactant (e.g., Tween‑20) only if compatible with the assay.
• Aqueous media: direct dissolution into water or PBS is often incomplete; pre‑dissolve in DMSO then dilute to the desired final solvent composition.
• Volatile organics (MeCN, MeOH): can aid HPLC handling or lyophilization, but may be less efficient for preparing concentrated stocks.

Comparison notes (literature/practice):

• DMSO vs DMF: DMSO offers broader miscibility with water and is widely accepted in bioassays; DMF can be advantageous for lyophilization to remove DMSO background in MS.
• PEG3 enhances tolerance to aqueous dilution relative to non‑PEGylated maytansinoids, but precipitation can still occur near the solubility limit—evaluate visually and by light scattering if critical.

Always filter (0.2 µm PTFE) solutions intended for chromatography; for biological assays, avoid filters that bind hydrophobic payloads (test recovery).

Storage and Reconstitution

Manufacturer storage and shipping:

• Storage Conditions: Store at −20°C (as provided in Product Data). Minimize freeze–thaw cycling.
• Shipped In: Ice chest + ice pads.

Additional best practices (general guidance; verify with your CoA/SDS):

• Container: keep tightly sealed under inert headspace if possible; protect from light.
• Reconstitution: Not specified for this item; refer to CoA/Spec Sheet. Typical laboratory practice is to prepare concentrated stocks in anhydrous DMSO or DMF (e.g., 1–10 mM), aliquot into low‑adsorption tubes, and store at −20°C or below.
• Thawing/handling: thaw aliquots on ice, mix gently, and avoid introducing moisture. After dilution into aqueous buffer, use promptly; prolonged incubation at elevated temperature can promote degradation of sensitive motifs.
• Freeze–thaw: avoid repeated freeze–thaw; prepare single‑use aliquots sized for one experiment.
• Stability monitoring: confirm integrity by LC–MS or HPLC upon first use and periodically for long‑term stored stocks.

Always consult the item’s CoA and SDS for definitive storage limits, compatibility, and any stabilizers or counter‑ions specific to your lot.

Structure and Identity

Brief overview: DM1‑MCC‑PEG3‑biotin is a multifunctional bioconjugate comprising the microtubule‑active maytansinoid DM1 joined through a non‑cleavable MCC (maleimidocaproyl) linker to a short PEG3 spacer terminated with biotin for high‑affinity streptavidin capture.

• SKU: D596514
• CAS: 2183472-94-6
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• 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-based):

• DM1 fragment: a highly oxygenated macrocyclic maytansinoid bearing a reactive thiol in DM1 (used for conjugation in ADC chemistry); multiple ester, thioether, and acetal motifs are typical in this class (literature).
• MCC linker: a non‑cleavable maleimidocaproyl linkage; in DM1‑MCC adducts, the thiol–maleimide Michael addition forms a stable thioether (literature). For this construct, the maleimide is consumed and no longer reactive.
• PEG3 spacer: triethylene glycol providing hydrophilicity, reduced aggregation, and spatial separation between DM1 and biotin (literature).
• Biotin terminus: bicyclic ureido‑thiophene ring system enabling tight binding to avidin/streptavidin for affinity capture and immobilization (literature).

2D structure in words (conceptual): a central DM1 macrocycle linked via a thioether to a caproyl chain; this connects to a short PEG3 chain terminating in biotin through an amide/ureido linkage. The molecule is amphiphilic: a hydrophobic DM1 core balanced by PEG3/biotin polar functionality.

Synthetic Utility

Although supplied as a finished bioconjugate probe rather than a small‑molecule building block, DM1‑MCC‑PEG3‑biotin offers the following utility in chemical biology workflows:

• Stable thioether core: the DM1–MCC linkage is a robust thioether formed by Michael addition of a DM1 thiol to maleimide (literature). It provides a defined, non‑cleavable payload architecture for comparative studies versus cleavable linkers.
• Affinity handle: the terminal biotin enables noncovalent yet ultra‑strong attachment to streptavidin/avidin for immobilization, enabling surface‑based assays, pull‑downs, and directed presentation of the DM1 pharmacophore.
• PEG3 spacing: introduces hydrophilic separation that can reduce steric hindrance upon immobilization and modulate local microenvironment.

Transformations are generally not targeted at this molecule (no free maleimide remains). However, users sometimes:

• Assemble multicomponent constructs by docking the biotin end to streptavidin, then recruiting additional biotinylated partners to vacant binding sites (protein–small molecule complexes).
• Employ photoreactive or click‑enabled streptavidins to further derivatize the immobilized complex on solid supports.

For classical organic synthesis (amide couplings, cross‑couplings, etc.), this probe is not an efficient starting material; instead, use DM1 with an appropriate protected handle or a maleimide‑bearing linker prior to biotinylation.

Target Specificity

Item-specific target annotations (antigen/epitope/clone/isotype/species reactivity) are not applicable and not provided for this small‑molecule probe.

General note (literature context): the DM1 moiety interacts with tubulin at the vinca site in biochemical assays, but this product is not an antibody or biologic and has no defined immuno‑specificity parameters.