SN-38-CM2 , CAS No.2376127-86-3

CAS: 2376127-86-3 Cat. No.: S1454166 Formule: C₃₄H₃₆N₂O₉ Poids moléculaire: 616.66

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Vue d’ensemble

SN-38-CM2 is a split esterase, and shows >95% conversion to SN-38 within 5 min in vitro. SN-38-CM2 induces protein-protein interactions (PPI)-dependent esterase to mediate cell death in MDA-MB-231 cells.

Specifications

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: 616.66

Application Protocols

No tested application protocols are provided in the Product Data for this item. The following generic practices are commonly used for SN-38-type small molecules in research (not item-specific; verify experimentally):

• Stock preparation: Dissolve in anhydrous DMSO to a convenient concentration (e.g., 10–20 mM). Filter-sterilize through 0.22 µm PTFE if required for cell-based assays.
• Working solutions: Dilute the DMSO stock into pre-warmed media or assay buffer with vigorous mixing; keep final DMSO content low (≤0.1–1% v/v as system allows). Inspect for precipitation.
• Stability controls: Prepare fresh aliquots just before use; include vehicle controls and, if relevant, an SN-38 reference standard to benchmark release or activity in mechanistic assays.
• Analytics: Monitor integrity by HPLC/LC–MS at time zero and end of assay. Track any release of SN-38 from the conjugate.

These suggestions are provided as general guidance. For SN-38-CM2, consult the CoA/Spec Sheet or contact technical support for any product-specific instructions.

Biological Roles

Item-specific biological data are not provided. The following is general background for SN-38-type molecules in research contexts. No medical or clinical claims are made.

• Mechanistic role (literature, general): SN-38 is a potent topoisomerase I poison that stabilizes the covalent Topo I–DNA cleavage complex, leading to replication-associated DNA damage. Activity is highly dependent on the intact lactone E-ring and the phenolic substituent pattern.
• Derivatization rationale: Masking or modifying the 10-hydroxyl of SN-38 via linkers (e.g., carbonate/carbamate) can tune aqueous solubility, plasma stability, and controlled release (enzymatic or chemical) of the active phenol under specific conditions.
• Conjugate systems: SN-38 derivatives are commonly investigated as payloads in macromolecular conjugates (antibodies, peptides, polymers, lipids) to study targeted delivery and controlled payload liberation in cell-based or biochemical assays.
• Assay considerations: In vitro systems often require low DMSO percentages, carrier proteins or surfactants to maintain dispersion, and careful time-course sampling to separate prodrug, linker-intermediates, and released SN-38 by LC–MS.

Note: The exact biological role, release mechanism, and potency of SN-38-CM2 will depend on its specific linker chemistry and substitution pattern, which are not provided here. Consult the product’s documentation for any tested in vitro behavior or control assays.

Buffer Applications

This product is a specialized small-molecule research reagent and is not a conventional buffering agent. No buffer capacity, pKa set, or recipe guidance is applicable.

• Practical note: If using SN-38-CM2 in biological buffers, maintain low organic co-solvent percentages, avoid basic pH (to preserve a camptothecin lactone, in general), and verify compound solubility/stability by analytical HPLC.
• For actual buffer preparation guidance, refer to dedicated buffering reagents (HEPES, PBS, Tris, MES, etc.).

Green Alternatives

Because this product is a specialized SN-38 derivative used at small scale in research, the main “green chemistry” leverage points are solvent choice and process minimization. Item-specific details are not provided; the guidance below is general.

• Prefer greener solvents for workup/handling when feasible:

  • Replace DMF/NMP with safer polar aprotics such as Cyrene or propylene carbonate where compatible (test stability against carbonate media if carbonate linkers are present).
  • Use ethanol or isopropanol instead of chlorinated solvents for precipitation/washes when they do not induce degradation.
  • Limit dichloromethane and acetonitrile use; consider ethyl acetate or 2-MeTHF for extractions/chromatography when solubility permits.

• Micro-scale and in-line analytics:

  • Use microscale reactions and HPLC/UPLC to optimize coupling conditions before any scale-up, reducing waste.

• Light and moisture control:

  • Prevent degradation to avoid rework and waste—store properly, work quickly, and use dry reagents.

Illustrative comparison (general, not item-specific):

• DMSO vs DMF: DMSO often offers similar solvating power with better worker/environmental profile; however, some linkers may undergo exchange in strongly nucleophilic solvents—verify case-by-case.
• Ethyl acetate vs DCM: EtOAc is less hazardous and often adequate for extractions; check compound partitioning and stability.

Always verify that proposed “greener” conditions do not compromise the integrity of the camptothecin lactone or the specific linker used in SN-38-CM2.

Pharmaceutical Uses

No pharmacopeial status, excipient role, or formulation grade is specified for this item; it is supplied for research use only.

General context (not item-specific; no therapeutic claims):

• SN-38 derivatives are often evaluated in formulation research to explore solubilization strategies (e.g., cyclodextrins, micelles, lipid-based systems) or as payloads in conjugate platforms. These studies focus on release kinetics, stability profiling, and compatibility with delivery vehicles.
• For conjugate manufacture research, parameters include linker stability in formulation buffers, prevention of lactone hydrolysis, and control of residual solvents.

Important:

• This product is labeled: For research use only. Not for diagnostic or clinical use.
• If pursuing preclinical or CMC-oriented studies, obtain full specifications (purity assay, residual solvents, water, polymorph/solvate form, counterion) from the CoA and qualify the lot under your internal quality system.

Physical Properties

Item-specific physico-chemical data were not supplied in the Product Data. Do not infer values from related compounds; consult the CoA/Spec Sheet.

• Melting point: Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point: Not applicable/Not specified for this high-MW organic (likely decomposes); refer to CoA/Spec Sheet.
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility: Not specified for this item; refer to CoA/Spec Sheet.
• LogP/logD: Not specified for this item; refer to CoA/Spec Sheet.
• pKa(s): Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index: Not applicable for solids; Not specified for this item; refer to CoA/Spec Sheet.

General/literature context for SN-38-type conjugates (not item-specific):

• Many SN-38 derivatives exhibit very low aqueous solubility and are typically handled as DMSO stock solutions; hydrolyzable carbonate/carbamate/ester linkages may be moisture sensitive.
• The camptothecin lactone tends to hydrolyze to a less active carboxylate in basic or aqueous conditions; organic, slightly acidic, and anhydrous environments favor the lactone form. Exact stability for SN-38-CM2 is unknown; verify with item documentation.

Practical note:

• When no properties are specified, perform a small-scale solubility screen (e.g., anhydrous DMSO, DMF, MeCN, EtOAc) and monitor integrity by analytical HPLC/LC–MS to confirm compatibility.

Quality and Grades

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

Interpretation and guidance (general for high-value research reagents):

• If an assay purity is provided on the CoA (e.g., HPLC ≥95–98%), it typically refers to area% by HPLC/UPLC with UV detection; confirm the detection wavelength and method to compare across lots.
• For payload/linker-type molecules, additional quality criteria may include: residual solvents, water content (KF), identity by HRMS and NMR, and specific impurity profiles (e.g., lactone/carboxylate ratio for camptothecin cores). None are specified here; consult documentation.
• Stabilizers: Not specified for this item; refer to CoA/Spec Sheet. If stabilizers are present (e.g., ascorbate, acid modifiers), consider their impact on downstream reactions and analytics.
• Lot-to-lot consistency: For conjugate chemistry, small changes in counterions, solvate content, or polymorph can affect solubility and coupling efficiency—verify by quick analytical checks (HPLC retention, LC–MS) upon receipt.

Recommendations:

• Request and retain CoA/SDS for your lot.
• If performing regulated studies, qualify the lot internally (identity, purity, potency where applicable) and document analytical methods.
• If low-UV solvents or special grades are required for photometric assays, ensure compatibility since the grade for this item is not specified.

Reaction and Applications

Manufacturer application details were not provided for this specific item. The points below summarize common research applications of SN-38-based conjugates, offered as general context (not item-specific):

• As a payload intermediate: SN-38 derivatives equipped with linkers are used to prepare bioconjugates (e.g., antibody- or polymer-drug conjugates) through carbonate, carbamate, ester, or click-compatible functional handles.
• Prodrug studies: Linker-masked phenols/carboxyls can modulate solubility, stability, and release kinetics; enzymatically or chemically cleavable linkers are often explored.
• Analytical standards and method development: Used in LC–MS/MS method validation for camptothecin-related analytes and release products.

Practical considerations (general):

• Maintain the camptothecin lactone: Avoid basic conditions during coupling/cleanup to reduce E-ring opening. Slightly acidic, anhydrous conditions are preferred.
• Moisture/light control: Use amber glassware and desiccated atmospheres; minimize residence time in protic solvents.
• Monitoring: HPLC with dual-wavelength UV (e.g., 254/370 nm) or fluorescence detection is common; LC–MS to confirm mass of conjugates.

Since the exact reactive handle(s) on SN-38-CM2 are not specified, do not assume compatibility with any particular coupling chemistry. Review the product’s CoA/Spec Sheet or contact technical support for the linker identity and recommended conjugation strategies.

Reaction Conditions

No item-specific reaction conditions are provided. Below are general guidelines for transformations involving SN-38 phenolic derivatives and linker installation (literature-based, not specific to SN-38-CM2):

• Carbonate formation (general):

  • Reagents: p-nitrophenyl chloroformate or triphosgene/CdI2; or CDI to form imidazolyl carbonate.
  • Solvent: anhydrous DCM, THF, or MeCN; 0–25°C; catalytic DMAP in minimal amounts.
  • Notes: Strictly limit base equivalents; short contact times; exclude moisture to protect the lactone.

• Carbamate formation (general):

  • Reagents: CDI pre-activation of the phenol followed by amine coupling; or use of chloroformates.
  • Solvent: DCM or MeCN; 0–25°C; monitor by TLC/HPLC.

• Click conjugation (when azide/alkyne handles are present):

  • CuAAC: CuSO4/sodium ascorbate, t-BuOH/H2O or DMF/H2O co-solvent; room temp. For lactone-sensitive systems, minimize aqueous content and time.
  • SPAAC: neat or in DMSO/aqueous mixtures—no copper, milder but requires strained alkyne.

• Purification:

  • Prefer normal-phase or reverse-phase flash/HPLC with acidified eluents (e.g., 0.1% formic acid) to retain the lactone; avoid basic modifiers.

• Stability checks:

  • Analyze pre- and post-reaction samples by LC–MS and 1H NMR promptly. Watch for lactone-opened carboxylate signals.

Use these as starting points only; adjust based on the actual functional groups present in SN-38-CM2 per its CoA/Spec Sheet.

Safety and Handling

Safety information specific to this item was not provided in the Product Data. Always consult the product SDS for authoritative guidance.

• GHS/CLP (item-specific):
  • Signal word: Not specified for this item; refer to SDS.
  • Hazard statements (H-codes): Not specified for this item; refer to SDS.
  • Pictograms: Not specified for this item; refer to SDS.

General safety context for camptothecin/SN-38 derivatives (literature; not item-specific):

• Potential hazards: cytotoxicity, reproductive toxicity, and organ toxicity have been reported for camptothecin-class agents in research settings. Avoid inhalation, ingestion, skin, and eye contact. Handle in a fume hood or designated cytotoxic work area.
• PPE: lab coat, double nitrile gloves (change frequently), splash goggles/face shield as appropriate. Use closed containers and absorbent pads to control contamination risk.
• Incompatibilities: avoid strong bases (can open the camptothecin lactone), strong oxidizers, and prolonged exposure to moisture/light that may promote degradation of labile linkages.
• First-aid overview (general): remove contaminated clothing, rinse affected skin/eyes with water for at least 15 minutes, seek medical attention. If inhaled, move to fresh air; if ingested, do not induce vomiting—seek immediate medical attention.
• Waste: collect cytotoxic/chemotherapy-type organic waste according to institutional hazardous waste procedures. Decontaminate surfaces with appropriate organic solvents and detergent, dispose of wipes as hazardous waste.

Note: The above is general guidance. Follow your institution’s EHS procedures and the SDS for SN-38-CM2.

Solvent Selection

Item-specific solubility data are not provided. The following is general guidance for handling SN-38-type derivatives in research workflows (not item-specific; verify with small-scale tests and the CoA):

• Likely solvent preferences (general):

  • Anhydrous DMSO: commonly used for stock solutions of camptothecin derivatives due to high solvating power and inertness toward many linkages.
  • DMF or NMP: alternative polar aprotic solvents if DMSO is unsuitable for downstream applications.
  • Acetonitrile, dichloromethane, ethyl acetate: may dissolve certain derivatives; test empirically.
  • Aqueous buffers: typically poor without co-solvent or cyclodextrin; risk of lactone hydrolysis in neutral/basic media.

• Polarity and miscibility (general):

  • Expect poor water miscibility; DMSO stock (e.g., 10–20 mM) then dilute into assay medium with vigorous mixing, keeping final DMSO ≤0.1–1% v/v depending on system tolerance.

• Practical tips:

  • Use dry, oxygen-poor conditions for long manipulations; protect from light.
  • If precipitation occurs upon aqueous dilution, increase surfactant/carrier protein (for biological assays) or co-solvent fraction; pre-warm and vortex/sonicate briefly.

• Comparison to alternatives:

  • For light- and moisture-sensitive camptothecin conjugates, DMSO and acetonitrile typically offer better stability than alcoholic solvents, which may transesterify labile linkers. Confirm for SN-38-CM2 specifically before scale-up.

Storage and Reconstitution

• Storage conditions (from Product Data): Store at -20°C.
• Shipping (from Product Data): Shipped in ice chest + ice pads.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

General handling guidance for SN-38-type derivatives (not item-specific):

• Protect from light and moisture. Store tightly sealed under inert gas or in a desiccator when possible.
• Avoid repeated freeze–thaw cycles: aliquot upon first opening. Typical small aliquots (e.g., 1–5 mg or pre-dissolved DMSO stocks) help maintain integrity.

Reconstitution (general recommendation; verify experimentally):

• Solvent: anhydrous DMSO is commonly suitable for initial dissolution. If needed, follow with dilution into compatible organic solvent or buffer system.
• Concentration: prepare concentrated stocks (e.g., 10–20 mM) to minimize aqueous exposure during dilution steps.
• Post-reconstitution stability: store DMSO stocks at −20°C or below in amber vials; use within days to weeks depending on analytical stability checks. Discard if HPLC indicates significant degradation or if precipitation persists after warming.

Labeling note: The product is for research use only. For definitive instructions on storage limits, re-test intervals, and any stabilizers or counterions, consult the lot-specific CoA/Spec Sheet.

Structure and Identity

Brief overview: SN-38-CM2 is listed under life-science research reagents and appears to be an SN-38 (camptothecin-derived) conjugate or derivative. Item-specific identifiers are minimal in the provided data; therefore definitive structural assertions cannot be made here.

• Item-specific identifiers (from Product Data)

  • SKU: S1454166
  • CAS: 2376127-86-3
  • Product name: SN-38-CM2
  • 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 description (general, literature context for “SN-38” derivatives; not item-specific)

  • SN-38 is the active metabolite of camptothecin analogs and contains a pentacyclic camptothecin core with a lactone E-ring, a phenolic OH at C-10, and an ethyl substituent at C-7.
  • Conjugates labeled “SN-38-…(linker)” typically feature a cleavable or stable linker appended to the phenolic oxygen (C-10) or via carbonate/carbamate/ester motifs, preserving the intact lactone where possible.
  • Stereochemistry (for the camptothecin scaffold, literature): chiral centers at C-20 (E-ring junction) and others fixed by the fused ring system; stereochemical integrity is important for activity.

• Notes

  • Without an item-specific structure or formula, assume nothing about linkage site, protecting groups, or counterions. Consult the product CoA/Spec Sheet for the definitive structural representation and exact identity.

Synthetic Utility

Item-specific functional handles for SN-38-CM2 are not disclosed in the Product Data. The following outlines general synthetic roles of SN-38 derivatives with linkers (not item-specific):

• Payload precursor: SN-38 phenolic OH at C-10 can be derivatized as carbonates, carbamates, ethers, or esters to install cleavable/stable linkers. Common strategies include p-nitrophenyl carbonate activation or CDI-mediated carbonate formation followed by coupling to amines/PEGs.
• Orthogonality: Protecting group choices and linker chemistry must preserve the camptothecin lactone (acidic, anhydrous conditions preferred). Base-labile linkers can be problematic.
• Conjugation handles: Azides/alkynes (for CuAAC or SPAAC), maleimides (thiol-selective), NHS esters (amine-selective), or hydrazides/aldehydes (oxime/hydrazone formation) are widely used motifs in the literature.
• Analytical control: Track reactions by LC–MS and HPLC at two wavelengths; monitor for lactone opening and over-acylation.

Retrosynthetic perspective (general):

• Divide into camptothecin core (SN-38) and linker module (CM2). Assemble the linker under conditions that tolerate sensitive motifs, then perform late-stage coupling to the phenolic site with minimal base exposure and short reaction times.

Because SN-38-CM2’s exact linker (CM2) is not defined here, verify functional group compatibility before attempting any coupling or deprotection steps.

Target Specificity

Not applicable. This product is a small-molecule research reagent and not a biological affinity reagent (e.g., antibody, ligand protein). No target specificity, clone, isotype, or species reactivity data are provided for this item.