Indirubin Derivative E804 - Moligand™, 10 mM in DMSO , CAS No.854171-35-0

CAS: 854171-35-0 Cat. No.: I1498808 Formula: C₂₀H₁₉N₃O₄ Molecular Weight: 365.38

GRADE & PURITY Moligand™, 10 mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Indirubin Derivative E804 is a potent inhibitor of Insulin-like Growth Factor 1 Receptor (IGF1R) , with an IC 50 of 0.65 μM for IGF1R.

Specifications

Specifications & Purity

Moligand™, 10 mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

INHIBITOR

Product Properties

pKa

pKa: 10.55 (Predicted)

Names and Identifiers

Isomeric SMILES

C1=CC=C2C(=C1)C(=C(N2)O)C\3=NC4=CC=CC=C4/C3=N\OCCC(CO)O

Molecular Weight

365.38

Reaxy-Rn

61524917

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=61524917&ln=

Chemical and Physical Properties

• x_refractive_index: n20D1.70 (Predicted)
• x_boil_point_char: 719.8° C at 760 mmHg (Predicted)
• x_melt_point_char: 262.70° C (Predicted)

Application Protocols

No validated, product-specific protocols are provided for this SKU. The following are general, non-validated practices for small-molecule ligands in biochemical/cellular assays:

• Stock preparation: Dissolve in anhydrous DMSO to prepare a concentrated stock (e.g., 10–50 mM). Vortex and gently warm if needed; avoid prolonged heating. If particulates persist, sonicate briefly and/or sterile-filter through 0.2 µm PTFE for cell-based work.
• Aliquoting: Dispense single-use aliquots (e.g., 10–50 µL) in amber vials or plates to minimize freeze–thaw and light exposure.
• Dosing: Titrate into assay buffer or media to achieve final DMSO ≤0.1–1% v/v depending on assay tolerance. Mix thoroughly and allow equilibration if slow-binding behavior is suspected.
• Controls: Include vehicle controls at matched DMSO, and appropriate positive/negative controls for the assay modality. Use detergent-containing buffers when counterscreening for aggregation artifacts.

These guidelines are for research use only and are not product performance specifications.

Biological Roles

General background (literature/general for indirubin family):

• Indirubin is a naturally occurring bis-indole constituent related to indigo fermentation products. Numerous indirubin derivatives have been reported as modulators of protein kinases, notably cyclin-dependent kinases (CDKs) and glycogen synthase kinase-3 (GSK-3), impacting cell-cycle and Wnt/β-catenin signaling in research contexts.
• The scaffold’s lactam (oxindole) and indole NH provide H-bonding capacity, while the extended π-system supports binding in ATP pockets of kinases in many reported studies. Substituent patterns strongly influence selectivity, potency, and cell permeability across the series.
• Additional biochemical interactions described in the literature include casein kinase, Src-family kinases, and other signaling enzymes, though activity profiles are highly substitution-dependent.

Caveat for this SKU:

• Target specificity, potency, and selectivity of Indirubin Derivative E804 are not specified here. Researchers should consult the primary literature and the product’s CoA or any provided technical note for target annotations, and independently verify activity under their assay conditions.

Research use only: No clinical or diagnostic claims are made or implied.

Buffer Applications

This product is a small-molecule ligand and is not a buffering agent. It is not typically used to prepare pH buffer systems.

Practical note for assay buffers (general):

• When dosing from DMSO stocks into biological buffers (e.g., HEPES, Tris, PBS), maintain a consistent final DMSO percentage across all wells. To reduce precipitation, add the compound stock last with thorough mixing and consider low levels of nonionic detergent if assay-compatible.

For actual buffer preparation guidance, refer to dedicated buffering reagents.

Green Alternatives

Context: “Green alternatives” typically refer to choosing safer solvents or reagents. For a discrete small-molecule ligand like Indirubin Derivative E804, there is no direct “greener substitute” for the compound itself without altering experimental outcomes.

Practical considerations (general):

• Solvent choice: Prefer DMSO over DMF/NMP in bioassay stock preparation due to lower worker exposure concerns and better biocompatibility at low percentages. When feasible, minimize organic cosolvents in aqueous assay buffers.
• Waste minimization: Prepare concentrated stocks to reduce total solvent volumes; pool and segregate DMSO waste for appropriate disposal.
• Assay miniaturization: Use low-volume plates and acoustic dispensing to cut solvent and compound usage while maintaining data quality.

Comparison (general solvent context):

• DMSO vs DMF: DMSO offers lower volatility and better aqueous miscibility; DMF is generally less preferred in biological contexts due to toxicity concerns.
• Ethanol as cosolvent: Can assist with dissolution but may perturb cells; use sparingly and validate.

Bottom line: Green chemistry levers for this product lie in solvent and process choices rather than the molecule itself.

Pharmaceutical Uses

This product is supplied strictly for research use and is not an API, excipient, or GMP material. It is not listed with pharmacopeial monographs.

Discovery and pre-formulation context (general):

• Compounds of the indirubin class are commonly used as reference inhibitors or tool compounds in early discovery screening and mechanistic studies. Any formulation-like handling is limited to preparing analytical or bioassay-compatible solutions (e.g., DMSO stocks and subsequent dilutions) rather than clinical formulations.

No clinical, therapeutic, or diagnostic use is claimed or supported for this SKU.

Physical Properties

Item-specific properties:

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point, boiling point, density, refractive index: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility: Not specified for this item; refer to CoA/Spec Sheet.
• LogP, pKa: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general for indirubin-class small molecules (for context only):

• Physical state: typically a colored, crystalline solid owing to the extended conjugation of the bis-indole core.
• Solubility profile: poor water solubility; commonly soluble in polar aprotic organic solvents (e.g., DMSO, DMF) and in some chlorinated solvents; limited solubility in alcohols is frequent. These are general observations and may not apply to E804.
• Acid/base behavior: multiple heteroatoms yield H-bond donors/acceptors; most indirubin analogs are neutral or weakly acidic due to the oxindole NH; specific pKa values vary with substitution.

Practical note: For experimental planning, determine the exact solubility and any hygroscopic or polymorphic behavior from the item’s CoA/SDS prior to preparing stocks.

Quality and Grades

• Grade/Purity: Moligand™. This denotes a screening-ligand grade suitable for discovery biology and medicinal chemistry workflows, emphasizing identity confirmation and suitability for high-throughput screening and cell-free assays.

What Moligand™ typically implies (general explanation; not a specification):

• Emphasis on structural identity and cleanliness for biochemical assays, commonly supported by orthogonal characterization (e.g., LC–MS, NMR). Exact acceptance criteria for this SKU are not specified here—refer to CoA/Spec Sheet.
• Focus on reproducible performance in ligand-binding or enzyme inhibition assays rather than chromatographic-grade solvent specifications.

Item-specific notes:

• UV cutoff, trace metal content, water/peroxide levels, and stabilizers: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance and purity percentage: Not specified for this item; refer to CoA/Spec Sheet.

Recommendation:

• For assay-critical work, document lot-specific purity/identity from the CoA and consider verifying concentration of DMSO stocks by UV/Vis or quantitative NMR if your assay requires precise dosing.

Reaction and Applications

Primary application domain: This product is intended as a research ligand/small-molecule tool rather than as a general-purpose synthetic reagent.

Research use (general, literature-based for indirubin derivatives):

• Widely explored as chemical probes in kinase-centric signaling research (e.g., CDKs, GSK-3) and related pathways. E804, as an indirubin derivative, may serve as a reference or screening hit/lead in biochemical assays, target profiling, or phenotypic screens. Specific target data for this SKU are not provided here.
• Typical laboratory workflows include: target engagement assays (enzyme inhibition, binding), cellular pathway modulation studies, and structure–activity relationship (SAR) campaigns using related analog panels.

Practical tips:

• Prepare fresh aliquots to minimize freeze–thaw; verify solubilization by visual inspection and, if critical, by analytical HPLC.
• For enzymology, pre-incubation with the target protein may be necessary to reach equilibrium if the compound exhibits slow-binding behavior; maintain consistent DMSO across all wells.
• Include orthogonal counterscreens to detect aggregation or redox cycling; employ detergent-containing buffers where appropriate to mitigate nonspecific aggregation.

Note: No medical or diagnostic use is implied; this product is for research use only.

Reaction Conditions

Not specific to this SKU as a finished ligand. For researchers synthesizing indirubin analogs related to E804, the following literature-style conditions are commonly reported (general guidance only):

• Indirubin core assembly: Condense isatin with indoxyl acetate or related indoxyl donors in basic or Lewis-acidic media. Solvents include DMF, ethanol, acetic acid, or polar aprotics; temperatures range from ambient to reflux. Yields are substrate-dependent.
• Halogenation/electrophilic substitution: NBS/NCS in DMF or dichloromethane at 0 °C to room temperature can introduce halo substituents selectively; monitor to avoid over-halogenation.
• Cross-coupling: For aryl–aryl diversification, use Pd-catalyzed Suzuki–Miyaura with aryl boronates in mixed aqueous/organic solvents (e.g., dioxane/H2O, K2CO3 base, 60–100 °C). Protect sensitive NHs if necessary to maintain catalyst activity.
• Oxime formation (if targeted): Hydroxylamine hydrochloride with pyridine or acetate buffer in ethanol or methanol, 0–50 °C, affords oximes from ketone precursors.
• Purification: Reverse-phase preparative HPLC is often preferred due to strong coloration and close-running regioisomers on normal-phase silica.

Always validate conditions for the specific substitution pattern of interest; indirubin cores can isomerize or undergo decomposition under strongly basic or oxidative conditions.

Safety and Handling

Item-specific hazard information:

• Signal word: Not specified for this item; refer to SDS.
• GHS classification, pictograms, and H-statements: Not specified for this item; refer to SDS.

General handling guidance for indirubin-like research chemicals (not product-specific):

• PPE: lab coat, nitrile gloves, and safety glasses as a minimum. Avoid inhalation of dust and contact with skin/eyes.
• Engineering controls: handle powders in a fume hood or ventilated enclosure; minimize aerosol/dust generation.
• Storage incompatibilities: segregate from strong oxidizers and strong acids/bases until compatibility is confirmed. Avoid prolonged light exposure that can accelerate degradation of conjugated systems.
• First aid (overview; defer to SDS): rinse skin/eyes with water for several minutes if contacted; if inhaled, move to fresh air; if ingested, seek medical attention—do not induce vomiting unless directed by medical personnel.
• Spill response: gently cover with inert absorbent, avoid dust, collect for disposal as hazardous chemical waste.
• Thermal/light sensitivity: many conjugated indole systems can be photosensitive or air-sensitive to a degree; store cold and protected from light where possible.

Always consult the Aladdin SDS for authoritative, product-specific safety information before use.

Solvent Selection

Applicability: As a small-molecule ligand from the indirubin family, solvent choice is primarily about preparing concentrated stocks for biochemical or cell-based assays rather than using it as a reaction solvent.

General guidance (literature/general):

• Primary stock solvent: DMSO is commonly used due to the typically poor aqueous solubility of indirubin derivatives. Prepare concentrated stocks (e.g., 10–50 mM) and dilute into assay media, keeping final DMSO ≤0.1–1% v/v depending on assay tolerance.
• Cosolvent systems: For difficult dissolutions, mixtures such as DMSO:PEG-400, or DMSO with a small fraction of ethanol or DMF, can improve solubility. Filter through 0.2 µm PTFE if particulates persist.
• Aqueous compatibility: Expect limited water solubility; use surfactant-containing buffers (e.g., 0.01–0.05% Tween-20) cautiously if allowed by the assay protocol to mitigate precipitation upon dilution.
• Polarity/miscibility context: DMSO is miscible with water and many organics, easing titration into buffers; DMF and NMP are alternatives but are less favored in biological assays.

Item-specific solubility and maximum workable stock concentration are not specified for this SKU; confirm experimentally and consult the CoA/SDS.

Storage and Reconstitution

Item-specific storage and shipping:

• Storage conditions: Store at -80 °C.
• Shipped in: Dry ice packs + Cold packs.

General handling guidance:

• Keep container tightly closed under inert headspace if possible and protected from light and moisture. Allow vials to equilibrate to room temperature in a desiccator before opening to prevent condensation.
• After first opening, promptly prepare DMSO stock solutions, aliquot into amber vials or plates, and refreeze at -80 °C. Avoid repeated freeze–thaw cycles.
• Reconstitution solvent: Not specified for this item; refer to CoA/Spec Sheet. In practice for indirubin derivatives, anhydrous DMSO is commonly used to prepare concentrated stocks.
• Stability: Not specified for this item; refer to CoA/Spec Sheet. As a precaution, use freshly thawed aliquots and discard if precipitation, color change, or degradation is observed by LC–MS/HPLC.

Research use only: Not for human or veterinary use.

Structure and Identity

• Product name: Indirubin Derivative E804 (SKU: I1498808)
• CAS: 854171-35-0; PubChem CID: 135398511
• 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 (literature/general):

• Indirubin derivatives are based on the indirubin scaffold, a bis-indole framework formally described as a 3,2′-biindolyl-2-one (an oxindole linked to an indole across a central C=C bond).
• Typical motifs: one oxindole ring (lactam) conjugated to an indole ring; frequent substitution on the indole/oxindole rings (e.g., halo, methoxy), and in some analogs oxime or other functionalities at the 3′-position.
• 2D description: two fused indole-type heteroaromatics aligned in a planar, conjugated system with one carbonyl (lactam) on the oxindole; multiple H-bond donor/acceptor sites (NH, C=O) and an extended π-system.

Note: Exact substitution pattern for E804 is not specified here; consult the CoA/Spec Sheet for definitive structure and identifiers.

Synthetic Utility

As a finished small-molecule ligand, Indirubin Derivative E804 is not typically used as a starting reagent in synthesis workflows. However, understanding the underlying chemistry of the indirubin scaffold can inform analog design and custom synthesis.

General synthetic considerations for indirubin derivatives (literature/general):

• Core construction: Condensation approaches between isatin (oxindole precursor) and indoxyl derivatives can furnish the indirubin backbone via C=C bond formation between the two indole units.
• Functional diversification: Electrophilic aromatic substitution (e.g., halogenation), nucleophilic substitutions on activated positions, and late-stage cross-couplings (Suzuki, Buchwald–Hartwig) from aryl halide handles are common to generate SAR arrays.
• Carbonyl/oxime chemistry: Some derivatives incorporate oxime or imine functionalities at the 3′-position; these are typically accessed via oximation of the corresponding ketone/aldehyde under mild conditions (hydroxylamine, buffered aqueous-alcoholic media).
• Protecting-group strategy: Indole/oxindole NH groups may require temporary protection (e.g., Boc, SEM) to direct selectivity in multi-step sequences.

For route design or customization of E804-related analogs, consult primary literature and perform small-scale route scouting to validate regioselectivity and stability.

Target Specificity

No target, enzyme, or receptor specificity is provided for Indirubin Derivative E804 in the current product data.

Notes:

• Many indirubin derivatives are studied as kinase modulators (literature/general), but activity profiles are highly substitution-dependent. Do not assume a target profile for this SKU without direct data.
• Consult the CoA/Spec Sheet or contact Aladdin Technical Support for any available lot-specific target annotations or references.

Frequently Asked Questions

What is Moligand??

Moligand? is one of Aladdin Scientific's premium product lines, formulated for high-purity applications across multiple workflows. Compared to standard grades in the same workflow, Moligand? products typically offer tighter specifications, more rigorous QC, and stronger lot-to-lot consistency.

How should this product be stored?

Store at ?80 °C. Ultra-low temperature storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships frozen with dry ice and cold packs. Unpack on arrival and transfer it to the storage condition stated above; handle dry ice with insulated gloves in a ventilated area.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 854171-35-0, the molecular formula is C20H19N3O4, and the molecular weight is 365.38 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.