GRADE & PURITYMoligand™?Moligand™ — Aladdin's line of ligands and bioactive small molecules. Use for receptor, pathway, and binding studies needing defined small-molecule tools.
This compound belongs to the class of organic compounds known as naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
External Descriptors
Not available
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
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Application Protocols
No item-specific validated application protocols (e.g., assay formats, recommended concentrations, or positive-control conditions) are provided in the Product Data for SKU N612228.
General guidance for small-molecule screening use
Stock preparation: Dissolve in anhydrous DMSO to prepare a concentrated master stock; vortex and, if necessary, sonicate briefly. Filter or centrifuge to remove particulates.
Storage of stocks: Aliquot to avoid repeated freeze–thaw; store according to your lab’s DMSO-stock practices (e.g., −20 °C for long-term), and protect from light if your assay is light-sensitive.
Assay setup: Titrate compound to define active concentration ranges; maintain consistent vehicle (DMSO) across wells and include vehicle-only controls.
Data quality: Check for precipitation or edge effects; confirm hits with orthogonal assay formats to reduce false positives.
For authoritative, item-specific directions, consult the CoA/Spec Sheet or contact Aladdin Technical Support.
Biological Roles
Scope
For research use only. The following describes biochemical context from the scientific literature, not medical or clinical use.
Literature context
Netoglitazone is widely used in the literature as a thiazolidinedione-class modulator of nuclear receptor signaling. Compounds of this class engage peroxisome proliferator-activated receptor gamma (PPARγ), a ligand-activated transcription factor involved in adipogenic gene expression and lipid/glucose homeostasis in model systems.
In biochemical assays, TZDs commonly promote coactivator recruitment and receptor conformational changes detectable by TR-FRET, SPR, or reporter-gene readouts. Effects can be context- and cell-type–dependent.
Experimental implications
Researchers employ netoglitazone as a reference ligand in panels profiling receptor selectivity, potency, and pathway bias. It serves in structure–activity relationship (SAR) benchmarking for synthetic analogs and in chemogenomic studies.
Because hydrophobic nuclear receptor ligands often exhibit significant plasma protein binding and membrane partitioning, experimental designs should account for free fraction and adsorption to plastics. Use low-bind labware and albumin-containing media judiciously.
Assay considerations
Validate vehicle tolerance, ligand stability in assay buffers, and potential fluorescence interference. Orthogonal assays (e.g., binding vs. transcriptional activation) help deconvolute direct target engagement from downstream pathway effects.
No biological properties are implied for clinical/diagnostic purposes; all uses are limited to controlled laboratory research.
Buffer Applications
This product is a hydrophobic small-molecule research ligand rather than a buffering agent. It does not form defined buffer systems.
Practical note
If delivering the compound into aqueous buffers, prepare a concentrated DMSO stock and dilute into the buffer with vigorous mixing to avoid precipitation. Maintain final DMSO at a level compatible with your assay (commonly ≤0.1–0.5% v/v) and include matched vehicle controls.
For low-solubility challenges, consider co-solvent systems or minimal amounts of non-ionic surfactant, validating that buffer composition does not interfere with assay readouts.
No specific buffer recipes or pKa-based buffering ranges apply to this item.
Green Alternatives
As a solid research compound, netoglitazone itself is not a process solvent. Greener practice considerations center on the choice of handling solvents and waste minimization.
Preferred greener solvent choices (general)
Where feasible, replace DMF/DMF-rich mixtures with ethanol, isopropanol, or water–miscible greener co-solvents for cleaning and sample prep, ensuring solubility and assay compatibility.
For chromatographic purification or analytics, favor ethanol or ethyl acetate over chlorinated solvents when separation performance permits.
Practical greener workflow tips
Use DMSO stock solutions at higher concentrations to reduce solvent volumes shipped and disposed.
Employ microscale assay formats (384/1536 wells) to reduce reagent and solvent consumption.
Consolidate analytical runs and use shorter columns/greener mobile phases (e.g., ACN-to-ethanol substitution where validated) to lower solvent use.
Tradeoffs (balanced view)
While ethanol or ethyl acetate offer greener profiles, they may provide reduced solubilizing power compared to DMSO/DMF, potentially necessitating co-solvent strategies.
Water-rich systems can cause precipitation for hydrophobic ligands; ensure adequate cosolvent fractions or employ solubilizers.
These recommendations are general sustainability practices for handling bioactive small molecules; no changes to the compound itself are implied.
Pharmaceutical Uses
This material is supplied strictly for research use only. No GMP status or pharmacopeial monograph is claimed.
Can serve as a reference standard in analytical method development (e.g., LC–MS/MS quantitation in discovery samples).
Useful for preclinical formulation feasibility studies (e.g., solubilization via DMSO/PEG/water cosolvents, cyclodextrin inclusion), provided appropriate safety controls are in place.
Employed in in vitro ADME assays (microsomal stability, protein binding, permeability) as a comparator compound in discovery research.
What is not covered
No claims for therapeutic use, clinical diagnosis, human or veterinary administration, or inclusion in commercial drug product manufacturing.
For any regulated applications, source a GMP-qualified material and follow appropriate pharmacopeial/ICH guidance. Consult the CoA for batch-specific purity and residual solvent information if needed for analytical standardization.
Physical Properties
Item-specific specifications
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
Typical physical behavior (general/literature guidance; not item specifications)
Physical state: Netoglitazone is commonly encountered as a crystalline organic solid.
Polarity: Moderately lipophilic with a polar imide (TZD) moiety; often exhibits poor aqueous solubility but dissolves in high-polarity aprotic organic solvents.
Solubility profile (literature/general): Readily soluble for screening use in DMSO; solubility can be improved in MeOH/EtOH or with co-solvent systems; limited solubility in water or phosphate buffers at neutral pH.
Acid/base character: The thiazolidinedione ring contains an acidic N–H (imide) capable of weak hydrogen bonding; no strong basic centers.
Partitioning: Expect elevated logP/logD typical of aryl–ether–TZD chemotypes; actual values vary by source and measurement method.
Optical/electronic characteristics (general)
Aromatic chromophores may contribute to UV absorbance in the 200–300 nm region, enabling HPLC–UV quantification; exact UV cutoff or extinction coefficients are not specified for this item.
For definitive, batch-specific constants (melting point, purity, water/peroxide/metal limits, refractive index, density), refer to the item’s CoA/Spec Sheet; such specifications are not provided here.
Quality and Grades
Grade provided: Moligand™ (item-specific)
Moligand™ designates compounds curated for small‑molecule screening, target engagement studies, and chemical biology. Emphasis is placed on identity confirmation and suitability for research use rather than pharmacopeial compliance.
What Moligand™ typically entails (general description of the grade)
Identity verification by appropriate spectroscopic/analytical methods (e.g., NMR, MS, HPLC/LC–MS) to ensure the intended structure is supplied for screening applications.
Purity appropriate for discovery workflows (typical small-molecule library expectations); exact purity thresholds, residual solvents, and related-substance profiles are batch-specific and should be confirmed on the CoA. Item-specific values are not provided here.
Packaging sized for medicinal chemistry and assay deployment, with attention to compatibility with DMSO dissolution and plate-based dispensing.
What is NOT implied
No claim of GMP manufacturing, pharmacopeial monograph compliance, or suitability for human or veterinary use.
No guarantee of low-UV “HPLC grade solvent” characteristics (not applicable; this is a solid compound, not a solvent).
How to use this information
For quantitative assays or structure–activity studies, request/review the CoA and, if needed, confirm purity/identity in-house prior to critical experiments.
If your workflow is sensitive to stabilizers/additives, verify on the CoA whether any excipients are present (none are specified for this item).
Reaction and Applications
Intended use per catalog category (item-specific context)
Supplied as a Moligand™ small-molecule for research use only, suitable for target engagement studies, assay development, SAR benchmarking, and as a reference compound in receptor/ligand panels.
Research application domains (general, non-clinical)
Chemical biology: probe the consequences of thiazolidinedione-based nuclear receptor modulation in cell-free or cellular models (e.g., reporter assays, coactivator recruitment, TR-FRET binding assays).
ADME/FA/WF: use as a comparator in in vitro metabolic stability, plasma protein binding, permeability (PAMPA/MDCK), and solubility assessments.
Analytical reference: develop and validate LC–MS/MS methods, system suitability, and retention-time locking in screening campaigns.
Practical tips (general)
Prepare and store DMSO stocks at controlled concentrations; thaw minimally and aliquot to avoid freeze–thaw cycles.
Filter or centrifuge solutions prior to assay loading to remove particulates and prevent false negatives due to precipitation.
When used in cellular assays, titrate vehicle content (commonly ≤0.1–0.5% DMSO v/v) and include vehicle controls.
No specific reaction chemistry manufacturing applications are claimed for this item; it is provided primarily as a bioactive small-molecule research tool.
Reaction Conditions
This product is not provided for use as a reaction solvent, reagent, or catalyst; it is a finished small-molecule ligand. Therefore, standard “reaction condition” parameters (e.g., temperature, equivalents, yields) are not typically applicable.
If pursuing analog synthesis or derivatization (general medicinal chemistry context)
N‑Alkylation of thiazolidinedione cores commonly employs mild base (e.g., K2CO3, Cs2CO3) in polar aprotic solvents (DMF, DMSO, acetone) at ambient to moderate temperatures; workups must carefully remove residual polar solvents.
Ether formation steps may use Williamson conditions (alkoxide in DMF/acetone, 0–60 °C) or Mitsunobu couplings (DEAD/DIAD, PPh3) where functional-group tolerance is needed.
Purification typically involves silica gel chromatography with gradients of EtOAc/hexanes or MeOH/DCM as dictated by polarity; final polishing by preparative HPLC for library quality.
These conditions are general literature guidance for the TZD chemotype and are not specifications or procedures for this catalog item as supplied.
Safety and Handling
GHS and hazard information (item-specific)
Signal word: Not specified for this item; refer to SDS.
H-statements: Not specified for this item; refer to SDS.
GHS classification/pictograms: Not specified for this item; refer to SDS.
General laboratory precautions (for organic small-molecule solids)
Avoid dust formation and inhalation; handle in a fume hood to minimize exposure.
Prevent ingestion and environmental release; dispose of waste according to institutional and local regulations.
Incompatibilities and stability (general)
Store in a tightly closed container away from strong oxidizers and strong bases that may promote degradation of imide/aryl ether motifs.
Protect from prolonged exposure to heat, light, and moisture. Follow “Room temperature” storage per Product Data and consult the SDS/CoA for any stability notes.
First-aid overview (general guidance; defer to SDS)
Inhalation: Move to fresh air; seek medical attention if symptoms occur.
Skin contact: Wash with soap and water; remove contaminated clothing.
Eye contact: Rinse cautiously with water for several minutes; remove contact lenses if present and easy to do.
Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
Always consult the product-specific SDS for authoritative hazard classification, exposure limits, and emergency procedures.
Solvent Selection
Netoglitazone is a lipophilic aryl–ether thiazolidinedione typically handled as a solid stock dissolved into organic solvents for screening.
Practical dissolution strategy (general best practices)
Primary solvent: DMSO is the standard vehicle for preparation of concentrated stocks (e.g., 10–50 mM) for HTS or cell-free assays.
Secondary solvents/co-solvents: DMF, methanol, ethanol, or acetonitrile can assist in intermediate dilutions; incorporate aqueous buffers last to avoid precipitation.
Aqueous solubility is typically limited; use surfactants (e.g., 0.01–0.05% Tween-20) or co-solvent systems if aqueous delivery is required, validating assay compatibility.
Polarity/miscibility considerations (general)
DMSO mixes completely with water, enabling final assay dilutions while maintaining compound in solution if kept below its kinetic/thermodynamic solubility limit.
Avoid high percentages of strong protic solvents in long-term storage vials to limit hydrolytic risk to the imide.
Quick comparison for screening vehicles (general)
DMSO: highest solvating power; widely compatible with biochemical assays up to 0.1–1% v/v.
DMF: strong solvent but less favored in biology-facing assays due to toxicity/volatility.
ACN/MeOH/EtOH: useful for HPLC sample prep and short-term dilutions; monitor precipitation upon aqueous mixing.
Item-specific solubility limits and UV characteristics are not specified; verify empirically and consult the CoA/Spec Sheet.
Storage and Reconstitution
Item-specific storage
Storage Conditions: Room temperature (per Product Data). Keep tightly closed in a dry, well-ventilated place. Protect from excessive heat, moisture, and prolonged light exposure.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Reconstitution (general guidance for research use)
Solvent: Use anhydrous DMSO to prepare concentrated stock solutions suitable for screening. Document final stock concentration and date of preparation.
Aliquoting: Dispense into single-use or limited-use aliquots to minimize freeze–thaw and headspace moisture uptake.
Working solutions: Prepare just-in-time dilutions into assay-compatible media; add DMSO stocks last with vigorous mixing to mitigate precipitation.
Stability considerations (general)
Avoid extended exposure to aqueous media, strong bases, or oxidants that may compromise the thiazolidinedione core or aryl-ether linkages.
If long-term storage of DMSO stocks is required, consider −20 °C with desiccation and light protection; verify stability empirically by LC–MS/HPLC.
Research Use Note
For research use only. Not for human or veterinary use. Always consult the SDS and CoA for batch-specific handling and stability information.
Structure and Identity
Netoglitazone (SKU N612228) is provided as a member of Aladdin’s Moligand small-molecule library for research screening and chemical biology applications.
Item-specific identifiers (from Product Data)
CAS: 161600-01-7
SKU: N612228
Grade: Moligand™
Storage: Room temperature
CID: 204109
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Structural features (general chemistry description; literature)
Netoglitazone is a thiazolidinedione (TZD) scaffold bearing an aryl-oxyalkyl substituent on the TZD N-3 and a para-substituted phenyl ether side chain.
Key functional groups: a 1,3-thiazolidine-2,4-dione core (acidic imide; two carbonyls), aryl ether(s), lipophilic aryl motif(s).
Typical 2D description: a five-membered TZD ring fused through an N–alkyl linkage to an aryl ether chain terminating in a para-substituted phenyl ring; no defined stereocenters in the parent structure (literature).
Synonymy/context (literature)
Common research name: Netoglitazone (also known in literature as MCC-555).
Note: Precise line notation (SMILES) and InChIKey for this catalog item are not specified in the provided Product Data; consult the item’s CoA/Spec Sheet for definitive identifiers tied to this batch.
Synthetic Utility
Netoglitazone is primarily a finished, bioactive small molecule used as a reference ligand rather than a synthetic building block.
Retrosynthetic/synthetic perspective (general)
The molecule features a 1,3-thiazolidine-2,4-dione (TZD) core, which in synthetic routes is often assembled by cyclization of α-mercapto/thiourea derivatives or via condensation strategies forming the imide, followed by N-alkylation to append aryl–ether side chains.
Aryl–O–alkyl linkages are typically introduced via nucleophilic aromatic substitution or Mitsunobu/Williamson ether formations depending on substitution patterns.
Derivatization opportunities (general)
The TZD N–H (in intermediates) can be deprotonated for selective N-alkylations; aryl rings allow for late-stage diversification (e.g., halogenation, Suzuki/Buchwald couplings if appropriate handles are present in analogs).
Prodrug or solubility-enhancing analog design often targets the ether side chain or installs ionizable moieties.
Practical note
While insightful for medicinal chemistry, the above pertains to synthetic planning; the catalog item itself is intended for research assays as supplied, not as a routine synthon. If using as a starting material, verify compatibility and purity on the CoA and consider the cost-effectiveness versus de novo synthesis.
Target Specificity
Target specificity data (e.g., named protein targets, binding constants, selectivity panels) are not provided in the Product Data for this item. As such, no item-specific target annotations are made here.
Note: While netoglitazone is discussed in the literature within the context of nuclear receptor modulation, any specific target details, affinities, or selectivity profiles should be sourced from primary references and are not implied for this catalog entry.
Perguntas frequentes
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 room temperature.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 161600-01-7, the molecular formula is C21H16FNO3S, and the molecular weight is 381.42 g/mol. InChIKey PKWDZWYVIHVNKS-UHFFFAOYSA-N.
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.
Need help choosing the grade?
Our grade selection guide covers purity, stabilizer status, and application suitability for all variants in our catalog.
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