cIAP1 Ligand-Linker Conjugates 16 , CAS No.2143956-63-0

CAS: 2143956-63-0 Cat. No.: C1448730 Fórmula: C₂₉H₃₇N₉O₅S Peso molecular: 623.73

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Visão geral

cIAP1 Ligand-Linker Conjugates 16 is an E3 ligase ligand-linker conjugate that can be used in the synthesis of PROTACs.

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

623.73

Application Protocols

Only item-specific, tested protocols should be listed; none are provided in the Product Data.

Not specified for this item; refer to CoA/Spec Sheet.

General guidance (for planning purposes; not product-validated)

• Stock preparation: Dissolve in anhydrous DMSO at high concentration (e.g., 10–50 mM), sonicate gently if needed, and filter (0.22 µm PTFE) for sterile applications. Record exact concentration by weight and volume.
• Dosing to cells/assays: Add DMSO stock slowly to media with mixing to reach the desired final concentration while keeping DMSO typically ≤0.5% v/v or per assay tolerance.
• Controls: Include vehicle controls and, where available, a non-binding analog of either the POI ligand or the cIAP1 recruiter to control for off-target effects.
• Verification: Confirm compound integrity by LC–MS before critical assays; assess solubility/precipitation visually and by light scattering.

For validated, product-specific protocols, consult the CoA/Spec Sheet.

Biological Roles

General biological context (no medical claims)

• cIAP1 (cellular inhibitor of apoptosis protein 1) is an E3 ubiquitin ligase containing BIR domains that recognize IAP-binding motifs such as the AVPI sequence from SMAC/DIABLO. Binding of SMAC mimetics to BIR domains can modulate ubiquitination pathways and signaling complexes linked to TNF/NF-κB regulation (literature/general info).
• Small-molecule cIAP1 ligands mimic SMAC’s interaction, displacing endogenous partners from BIR domains. In degrader design, the cIAP1 ligand functions as a recruiter to form ternary complexes with a POI-ligand conjugate, positioning the POI for ubiquitination and subsequent proteasomal processing (literature/general info).
• Linker engineering influences cellular permeability, ternary complex cooperativity, and degradation kinetics. Parameters include linker length, rigidity, polarity (e.g., PEG vs alkyl vs aryl), and exit vector relative to the cIAP-binding pharmacophore (literature/general info).

For this specific item

• No item-specific binding constants (Kd), selectivity versus XIAP/cIAP2, or cellular outcomes are provided in the Product Data. Consult literature methods appropriate to cIAP1 recruiters for characterization (e.g., FP/BLI/SPR for binding; cellular ubiquitination readouts) and the CoA/Spec Sheet for any available testing notes.

Buffer Applications

This product is not a buffering reagent and is not typically used to control solution pH. It is a bioactive small-molecule conjugate component intended for chemical biology and degrader assembly.

Practical note (general)

• When dosing into biological buffers, prepare concentrated DMSO stocks and add gradually to the buffer or cell media with mixing to prevent precipitation. If aqueous delivery is challenging, consider solubilization aids (e.g., serum proteins, cyclodextrins) as compatible with the assay.

There are no buffer recipes or pH ranges applicable to this item.

Green Alternatives

Context: While DMSO is widely used for assay stocks, synthetic assembly and purification of ligand–linker conjugates can leverage greener solvents and practices. The guidance below is general and not item-specific.

Potential greener choices (literature/general)

• Reaction solvents: 2-Methyltetrahydrofuran (2-MeTHF), cyclopentyl methyl ether (CPME), and propylene carbonate can replace DMF/DMF-like dipolar aprotics in some coupling steps, offering lower toxicity and improved recyclability.
• Workup/extraction: EtOAc or Me-THF instead of chlorinated solvents when feasible; heptane/MTBE mixtures for normal-phase chromatography.
• Coupling conditions: Aqueous micellar catalysis (e.g., TPGS-750-M) for amide couplings and click reactions can reduce organic solvent usage.
• Purification: Switch from normal-phase to reversed-phase chromatography using water/MeOH or water/ACN with volatile buffers to reduce halogenated waste.

Illustrative comparison (general)

• DMF vs 2-MeTHF: 2-MeTHF has a better environmental profile and is easily recoverable; however, its lower polarity may limit solubility of highly polar intermediates.
• DCM vs CPME: CPME provides a wider liquid range and lower peroxide tendency than many ethers; but watch for azeotrope behavior and peroxidation over long storage.

Tradeoffs

• Solubility constraints of complex conjugates may still necessitate polar aprotics. A hybrid approach (green solvent where possible; minimal use of DMF/NMP) often yields the best balance of performance and sustainability.

Pharmaceutical Uses

Scope

• This product is supplied for research use only. It is not an excipient, API, or a pharmacopeial standard, and it is not intended for human or veterinary use.

Research/manufacturing context (general)

• In preclinical discovery, cIAP1 ligand–linker conjugates can serve as intermediates for assembling heterobifunctional degraders used in target validation workflows, SAR programs, and mechanistic studies of ubiquitin–proteasome–mediated protein turnover (literature/general info).
• Formulation for in vitro studies commonly relies on DMSO stocks with careful control of final vehicle concentration to ensure assay compatibility. For in vivo enabling studies, bespoke formulation strategies are required and are outside the scope of this product listing.

Regulatory status

• No pharmacopeial status or compendial monograph is provided for this item. Any cGMP-related use would require separate qualification and is not covered by this research-use product.

Item-specific claims

• None provided; purity grade, residual solvent limits, and other specifications are Not specified for this item; refer to CoA/Spec Sheet.

Physical Properties

Item-specific properties

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point: Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point: Not applicable/Not measured for this class; complex organics typically decompose before boiling under ambient pressure (general comment).
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility: Not specified for this item; refer to CoA/Spec Sheet.
• LogP/logD, pKa, refractive index: Not specified for this item; refer to CoA/Spec Sheet.

General/literature guidance for cIAP ligand–linker conjugates (not item-specific)

• Physical form: Usually off-white to light-colored solids; hygroscopicity varies with linker composition (literature/general info).
• Solubility practice: Stocks are commonly prepared in anhydrous DMSO (e.g., 10–50 mM) due to typical limited aqueous solubility of higher-MW conjugates; subsequent dilution into assay media requires gradual titration with vigorous mixing to avoid precipitation (literature/general info).
• Stability: Many conjugates are stable when stored dry and protected from light at low temperature; hydrolysis may occur at amide/ester/carbonate linkages under strongly acidic or basic conditions (literature/general info).

Important

• Do not treat the above generalities as specifications. For precise property values of this specific SKU (C1448730), refer to the CoA/Spec Sheet.

Quality and Grades

Item-specific grade/purity

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

Interpretation and typical QC for research-use ligand–linker conjugates (general)

• Research-use only: Supplied for laboratory investigation, screening, and method development; not for human or veterinary use.
• Common characterization packages may include HPLC/UPLC purity, LC–MS or HRMS identity confirmation, and, where feasible, 1H/13C NMR. Chiral/stereochemical assignment may be provided for stereodefined ligands (general info).
• Purity designation (if present on CoA):
  • “≥95% (HPLC)” supports use in SAR and screening; lower impurity background aids target engagement interpretation.
  • Residual solvents, water, and salts may be reported; for exact limits consult the CoA.
• Stabilizers/inhibitors: Not specified for this item; if present, the CoA will note stabilizers or counter-ions and their implications for assays.

Practical notes

• For cell-based assays, verify lot-specific purity and impurity profile to assess potential off-target effects.
• For conjugation chemistry, confirm counter-ion/salt form, as it can influence coupling efficiency and stoichiometry.

For definitive quality data of SKU C1448730, consult the CoA/Spec Sheet.

Reaction and Applications

Research applications (general for cIAP1 ligand–linker conjugates)

• Degrader/PROTAC assembly: Serves as the E3 ligase–recruiting module by binding cIAP1 BIR domains; the pre-installed linker and terminal handle enable modular coupling to a protein-of-interest (POI) ligand to create heterobifunctional degraders (literature/general info).
• Biochemical probes: Can be incorporated into affinity reagents for studying IAP-ligase engagement, ternary complex formation, or for pull-down/chemoproteomics applications once coupled to reporter tags (general info).
• SAR exploration: Varying linker length/chemotype from the “Conjugates” series allows systematic assessment of degradation efficiency and selectivity across targets (general info).

Typical chemistries for downstream coupling (general)

• Amide bond formation (COOH ↔ amine) using carbodiimides (EDC/HOBt), uronium reagents (HATU/HBTU), or activated esters.
• Urea/carbamate formation via isocyanate/chloroformate or CDI-mediated protocols.
• Click chemistry: Cu(I)-catalyzed azide–alkyne cycloaddition (CuAAC) when azide/alkyne handles are present; strain-promoted variants for metal-free conditions.

Practical tips (general)

• Maintain anhydrous conditions and inert atmosphere for moisture-sensitive couplings.
• Minimize excessive heat and strong base that may degrade the IAP-binding pharmacophore or labile linkers (e.g., esters/carbonates).
• After conjugation, verify retention of cIAP1 binding via biophysical assays (e.g., FP, ITC) before cell testing.

Note: Item-specific reactive handle and conditions are not provided; consult the CoA/Spec Sheet for exact functional group details.

Reaction Conditions

General literature guidance for coupling cIAP1 ligand–linker conjugates (not item-specific)

• Amide coupling: HATU (1.1–1.5 equiv), DIPEA (2–4 equiv) in DMF or 2-MeTHF at 0–25°C for 1–4 h; monitor by LC–MS. EDC·HCl (1.5–2.0 equiv) with HOAt/HOBt/NHS in DMF/DCM alternatives. Typical isolated yields are highly substrate-dependent.
• Urea/carbamate formation: CDI activation in anhydrous THF/DMF (0–25°C), then reaction with amines/alcohols; or use NHS carbonates/chloroformates for carbamate installation.
• CuAAC click: CuSO4/sodium ascorbate with TBTA ligand in t-BuOH/H2O or DMF/H2O (rt to 40°C, 0.5–4 h). For sensitive systems, use Cu(I) sources with rigorous degassing; strain-promoted variants run neat or in aqueous media without metal.
• Protecting groups: Boc (acid-labile) and Fmoc (base-labile) are commonly used for orthogonal protection of amines on multi-functional linkers; remove under mild, warhead-compatible conditions.
• Purification: RP-HPLC with water/ACN (0.1% volatile acid/base as needed) or flash chromatography using polar modifiers for highly functionalized conjugates.

Cautions

• Avoid strong base and prolonged heating that may compromise the cIAP-binding pharmacophore or labile linkers (esters/carbonates).
• Validate reaction completion by LC–MS and check for epimerization if chiral centers are present.

Item-specific conditions, if any, are Not specified for this item; refer to CoA/Spec Sheet.

Safety and Handling

Item-specific safety data

• GHS Classification: Not specified for this item; refer to SDS.
• Signal Word: Not specified for this item; refer to SDS.
• H-Statements: Not specified for this item; refer to SDS.
• Pictograms: Not specified for this item; refer to SDS.

General safety considerations for bioactive small molecules (literature/best practice)

• Handle in a chemical fume hood with appropriate PPE: lab coat, safety glasses, and nitrile gloves. Avoid inhalation of dust/aerosols and skin contact.
• Assume potential acute toxicity and environmental hazard until SDS confirms otherwise; minimize exposure and prevent release to drains.
• Solvent handling: When preparing DMSO or DMF stocks, avoid dermal exposure—these solvents can enhance dermal absorption of solutes.
• Incompatibilities: Strong acids/bases and oxidants may degrade common linkers (esters, carbonates) and heterocycles. Avoid prolonged exposure to moisture if the compound bears moisture-sensitive handles (general guidance).
• First aid (overview; defer to SDS): In case of skin/eye contact, rinse with water for ≥15 minutes; remove contaminated clothing. If inhaled, move to fresh air. If ingested, rinse mouth; do not induce vomiting; seek medical advice.
• Waste: Collect organic solutions and solids as hazardous chemical waste per institutional and local regulations.

Always consult the product-specific SDS for authoritative hazard and response information.

Solvent Selection

Applicability: As a cIAP1 ligand–linker conjugate, this product is typically handled as a small-molecule solid prepared in organic stock solutions for biochemical and cellular assays.

General guidance (literature/common practice; not item-specific specs)

• Primary stock solvent: Anhydrous DMSO is most commonly used due to broad solubilizing power for higher-MW, heteroatom-rich conjugates.
• Alternative solvents/co-solvents: DMF, NMP, or mixtures with ethanol/acetonitrile may be used for intermediate stocks; subsequent dilution into aqueous buffers requires slow titration with vigorous mixing.
• Aqueous delivery: To minimize precipitation on dilution, add the DMSO stock to pre-warmed media dropwise while vortexing; final DMSO content of 0.1–1% v/v is typical for cell assays, subject to cell line tolerance (general practice).
• Polarity and miscibility: Such conjugates often display amphiphilic character (polar warhead + flexible linker) yet remain poorly water-soluble at neutral pH; consider cyclodextrin or serum-protein aided delivery if required (general practice).

Comparison (general)

• DMSO vs DMF: DMSO offers better biological compatibility at low percentages; DMF can be harsher on cells and plastics.
• ACN/EtOH: Useful for analytical injections or rapid drying, but limited in aqueous miscibility at high loads.

Note: Verify item-specific solubility, permissible vehicles, and assay compatibility on the CoA/Spec Sheet or by small-scale solubility screening.

Storage and Reconstitution

Item-specific conditions (from Product Data)

• Storage Conditions: Store at -20°C.
• Shipped In: Ice chest + Ice pads.

General best practices (not item-specific specs)

• Keep container tightly closed under inert atmosphere or dry air; use desiccant and protect from light to limit hydrolysis/oxidation of sensitive linkers.
• Allow to warm to room temperature in a desiccator before opening to minimize moisture condensation.
• Reconstitution: Prepare concentrated stocks in anhydrous DMSO. If required, co-solvents (DMF, ACN, EtOH) can be used for initial dissolution before final dilution into assay buffer.
• Aliquoting: Divide DMSO stock into single-use aliquots to avoid repeated freeze–thaw cycles. Store aliquots at -20°C or below.
• Freeze–thaw: Avoid repeated cycles; thaw on ice or at ambient temperature, mix gently, and promptly return unused portions to low-temperature storage.
• Stability: Item-specific stability, hygroscopicity, and light sensitivity are Not specified for this item; refer to CoA/Spec Sheet.

Research Use Note

• For research use only.

Structure and Identity

Brief description: This item is a cIAP1 ligand–linker conjugate intended as an E3 ligase–recruiting module for degrader/PROTAC research and related chemical biology.

Item-specific (from Product Data)

• SKU: C1448730
• Product Name: cIAP1 Ligand-Linker Conjugates 16
• CAS: 2143956-63-0
• 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.

General structural features (context, literature)

• cIAP1 ligands typically mimic the N‑terminal AVPI motif of SMAC/DIABLO and bind the BIR domains of IAPs. Small-molecule mimetics often incorporate heteroaromatic scaffolds and amide/urea motifs for key H-bonding interactions (literature/general info).
• “Ligand–linker conjugate” denotes a cIAP1-binding warhead pre-attached to a spacer bearing a terminal functional handle (e.g., amine, carboxyl, azide, alkyne) for downstream coupling to a target-binding moiety (literature/general info).
• 2D description (general): an IAP-binding pharmacophore core connected through a flexible or semi-rigid linker (alkyl/PEG/aryl) to a terminal reactive group for conjugation; multiple heteroatoms (N/O) are typical to maintain binding and solubility (literature/general info).

Notes

• Exact stereochemistry, ring systems, and functional group pattern for “Conjugates 16” are not provided in the Product Data. Consult the CoA/Spec Sheet for definitive structural identifiers.

Synthetic Utility

Role in synthesis (general)

• Acts as a pre-functionalized E3 ligase recruiter module. The built-in linker and terminal handle enable rapid assembly of heterobifunctional degraders by coupling to a ligand for the protein of interest (POI).

Common transformations applied downstream (general)

• Amide formation: Coupling the conjugate’s carboxyl (or amine) terminus with POI-ligand amines (or acids) using HATU/HBTU/EDC systems; micro-scale parallel chemistry expedites linker SAR.
• Click ligations: CuAAC when azide/alkyne handles are present; strain-promoted cycloadditions for metal-free conditions and live-cell compatibility of final constructs.
• Carbamate/urea linkages: CDI or triphosgene surrogates to install stable yet cleavable linkages as needed for ADME tuning.

Retrosynthetic value (general)

• Decouples optimization of the cIAP1-binding pharmacophore from POI-ligand SAR by providing a modular linker platform with defined exit vector.
• Facilitates rapid library generation for ternary complex cooperativity mapping by varying linker length and flexibility while holding recruiter and POI warheads constant.

Notes

• The specific reactive handle and protective groups for “Conjugates 16” are not provided in the Product Data. Verify functional groups and counter-ions on the CoA/Spec Sheet before planning couplings and purification.

Target Specificity

Only item-specific data may be listed here.

• Target/antigen, epitope, species reactivity, clone/isotype: Not applicable to small molecules and Not specified for this item.

General note

• As a small-molecule recruiter, the cIAP1 ligand component is designed to engage cIAP1 BIR domains (literature/general info). However, no item-specific affinity or selectivity data versus cIAP1/2/XIAP are provided in the Product Data. Consult CoA/Spec Sheet or perform in-house binding assays (e.g., FP, BLI, SPR) for quantitative characterization.

Perguntas frequentes

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 2143956-63-0, the molecular formula is C29H37N9O5S, and the molecular weight is 623.73 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.