Laquinimod - Moligand™, 10mM in DMSO , CAS No.248281-84-7

CAS: 248281-84-7 Cat. No.: L408638 Formule: C₁₉H₁₇ClN₂O₃ Poids moléculaire: 356.8 Numéro CE: 692-155-1

GRADE & PURITY Moligand™, 10mM in DMSO

Synonyms

ABR-215062, LAQ | 5-chloro-N-ethyl-4-hydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Vue d’ensemble

Information

Laquinimod Laquinimod (ABR-215062, LAQ) is a potent immunomodulator . Phase 3.
In vitro

Laquinimod treatment at 0.1-1 μM does not affect the viability of peripheral blood mononuclear cells (PBMC). By performing the large-scale gene expression microarray analysis in PBMC from healthy subjects or relapsing-remitting multiple sclerosis (RRMS) patients, Laquinimod is shown to induce suppression of genes related to antigen presentation and corresponding inflammatory pathways. Laquinimod induces activation of Th2 response in CD14+ and CD4+ cells and suppression of proliferation in CD8+ cells. Laquinimod displays significant effects on immune modulation related to the suppression of antigen presenting mechanism followed by a decrease of chemotaxis and adhesion, and exhibits potent anti-inflammatory potency through the suppression of the NF-κB pathway that concordantly leads to the activation of apoptosis of immuno-competent cells.

In vivo

Administration of Laquinimod (0.16-16 mg/kg/day) dose-dependently inhibits the incidence of experimental autoimmune neuritis (EAN) in Lewis rats, ameliorates clinical signs and inhibits P0 peptide 180-199-specific T cell responses as well as the inflammation and demyelination in the peripheral nerves, suggesting that Laquinimod may mediate its effects by regulation of Th1/Th2 cytokine balance. Laquinimod significantly inhibits the development of murine acute experimental autoimmune encephalomyelitis (EAE), being approximately 20 times more potent than the immunomodulator roquinimex. Laquinimod treatment inhibits the development of experimental autoimmune encephalomyelitis (EAE) in the Lewis rat in a dose-dependent manner, and shows better disease inhibitory effects as compared to roquinimex (Linomide). Laquinimod potently inhibits the development of chronic experimental autoimmune encephalomyelitis (chEAE) in IFN-beta k.o. mice and wild type mice. Laquinimod reduces clinical signs, inflammation, and demyelination in C57BL/6 mice with active EAE induced with MOG(35-55) peptide, and down-regulates VLA-4-mediated adhesiveness and pro-inflammatory cytokines such as IL-17. The study of Laquinimod in the mice model of EAE using a conditional BDNF knockout strain lacking BDNF expression in myeloid cells and T cells (LLF mice) indicates Laquinimod also modulates autoimmune demyelination via induction of brain-derived neurotrophic factor (BDNF).
Cell Data

cell lines：Rat cardiac fibroblasts cell lines

Concentrations：Dissolved in PBS, final concentrations ~1 μM

Incubation Time：24 hours

Powder Purity:≥99%

Specifications

Synonymes

ABR-215062, LAQ | 5-chloro-N-ethyl-4-hydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide

Spécifications et pureté

Moligand™, 10mM in DMSO

Mécanismes biochimiques et physiologiques

Laquinimod (ABR-215062, LAQ) is a potent immunomodulator. Phase 3.

Conditions de stockage de stockage

Store at -80°C

Expédié en

Dry ice packs + Cold packs

Ce produit nécessite l'expédition en chaîne froide. Les services terrestres et autres services économiques ne sont pas disponibles.

Grade

Moligand™

Noms et identifiants

Isomères SMILES

CCN(C1=CC=CC=C1)C(=O)C2=C(C3=C(C=CC=C3Cl)N(C2=O)C)O

Poids moléculaire

356.8

Reaxy-Rn

9650600

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=9650600&ln=

Application Protocols

No tested applications or recommended dilutions are provided in the product data for this SKU.

General guidance for small-molecule screening (research-only):

• Stock preparation: Dissolve in anhydrous DMSO to a convenient concentration (e.g., 10 mM). Vortex, sonicate, and warm gently if needed; filter (0.22 µm PTFE) to remove particulates.
• Plating: Dispense to assay plates using calibrated liquid handlers; maintain consistent DMSO percentages across wells.
• Dose–response: Use serial half-log dilutions (e.g., 10 points) to establish potency curves; include vehicle and, if available, positive control compounds.
• Data quality: Monitor Z′ factor, signal window, and potential compound interference (autofluorescence/absorbance in reporter channels).

These are general best practices and not product-specific performance claims.

Biological Roles

Laquinimod belongs to the quinoline-3-carboxamide chemical class, a scaffold broadly explored in research settings for immunology- and neurobiology-related pathways. The notes below are provided as general chemical biology context and do not constitute medical or clinical claims.

• Chemical biology context (literature-level): Quinoline-3-carboxamides have been investigated as modulators of immune signaling pathways and glial/neuronal responses in preclinical research. Specific molecular targets and mechanisms can vary among analogs and depend on substitution patterns and assay systems.
• Assay deployment considerations:
  • Implement appropriate negative/vehicle controls (e.g., matched DMSO) and, where applicable, orthogonal assay readouts to confirm on-target effects vs assay interference.
  • Pay attention to compound aggregation or nonspecific effects at high micromolar concentrations; include detergent or use lower compound concentrations with kinetic monitoring as needed.
  • Record full dosing histories and solvent percentages; replicate across cell lines or biochemical formats to establish robustness.
• ADME/physicochemical expectations (general for class): moderate lipophilicity, heteroaromatic UV absorbance, and limited aqueous solubility; permeability can be favorable in many cell models. Item-specific data are not provided in this listing.

Target specificity for this SKU is not specified in the product data; users should consult primary literature and perform in-house profiling appropriate to their research question.

Buffer Applications

This compound is not a buffering agent and is not used to prepare defined pH buffer systems. For biological experiments, it is typically dosed into pre-made buffers or media from an organic stock solution (commonly DMSO).

Practical notes:

• Prepare concentrated DMSO stocks and dilute into assay buffers (e.g., PBS, HBSS, culture media) while maintaining a controlled final co-solvent fraction.
• To mitigate precipitation upon dilution, add stock slowly with mixing; inclusion of 0.01–0.05% nonionic surfactant can help for hydrophobic compounds.

For buffer recipes and pH control, refer to dedicated buffering agents (e.g., HEPES, phosphate, Tris).

Green Alternatives

Green chemistry considerations for this item relate primarily to solvent and process choices during assay preparation and any optional synthetic manipulations, as the molecule itself is fixed.

• Prefer greener solvents for solution preparation when compatible with your assay:
  • Water-buffer systems with minimal DMSO where possible.
  • Bio-based or safer polar organics (e.g., propylene carbonate, ethyl lactate) are sometimes viable for intermediate dissolutions; validate assay tolerance.
• Minimize solvent volumes via higher-concentration DMSO stocks followed by precise aqueous dilutions to reduce waste.
• Use microscale formats (384/1536-well) and acoustic dispensing to reduce both compound and solvent consumption.

Illustrative comparison (general, not item-specific):

• DMSO vs DMF/NMP: DMSO generally ranks more favorably in EHS profiles than DMF/NMP and is typically preferred for stock solutions.
• Ethanol/isopropanol vs chlorinated solvents: Alcohols present lower environmental impact and are more acceptable for biological systems than dichloromethane or chloroform.

Waste and lifecycle:

• Collect DMSO- and DMF-containing waste for appropriate disposal; avoid drain disposal.
• Consider reformatting aliquots to reduce freeze–thaw and spoilage, lowering overall chemical usage.

Note: No changes to the molecular structure are implied; these recommendations address handling choices around the compound.

Pharmaceutical Uses

This product is provided strictly for research use only. No medical, diagnostic, or therapeutic use is intended or implied.

Formulation-related context for research workflows (non-clinical):

• Dosing vehicles in preclinical labs often employ DMSO or ethanol co-solvent with aqueous buffers and solubilizers (e.g., PEG-400, polysorbate 80); selection depends on institutional approvals and model requirements.
• For in vitro studies, plate-ready aliquots in DMSO (e.g., 10 mM) support automated liquid handling and minimize freeze–thaw cycles.

No pharmacopeial status, excipient role, or clinical formulation information is provided for this item. For any work beyond basic research, institution-specific review and approvals are required.

Physical Properties

Item-specific physicochemical specifications are not listed in this catalog entry. Consult the item’s CoA/Spec Sheet for definitive values.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point: Not specified for this item; refer to CoA/Spec Sheet. (Do not use literature values as specifications.)
• Boiling point: Not applicable; decomposition expected before boiling for most heteroaromatic carboxamides (general/literature note).
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (general laboratory guidance, not a spec):
  • Organic: typically soluble in polar aprotic solvents (DMSO, DMF, NMP) and in some alcohols; solubility improves with gentle warming and sonication.
  • Aqueous: low intrinsic water solubility expected for quinoline carboxamides; aqueous use commonly via DMSO stock dilution into buffered media with surfactant or co-solvent.
• LogP/logD: Not specified for this item; refer to CoA/Spec Sheet. Quinoline amides generally exhibit moderate-to-high lipophilicity (literature-class trend).
• pKa: Not specified for this item; refer to CoA/Spec Sheet. Quinoline nitrogen is weakly basic (literature-class trend).
• UV-Vis: Not specified for this item; refer to CoA/Spec Sheet. Quinoline chromophore typically absorbs in near-UV (literature observation).

Important: Use literature values only for preliminary planning; verify with your in-house measurements or the product CoA where available.

Quality and Grades

• Grade/Purity for this catalog item: Moligand™ (screening collection grade).

What Moligand™ typically implies (general description):

• Intended use: research screening, target discovery, and probe development in biochemical, cellular, and phenotypic assays.
• Analytical identity: Lots are commonly confirmed by orthogonal analytical methods (e.g., LC–MS, NMR) for structure verification; exact tests and acceptance criteria are batch-dependent. Item-specific tests are not listed here—refer to the CoA.
• Purity: Not specified for this item; refer to CoA/Spec Sheet. Screening-grade materials often target high purity suitable for biological assays, but users should verify if their workflow (e.g., crystallography or in vivo models) requires additional purification.
• Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
• Water, residual solvents, metals, and UV-cutoff: Not specified for this item; refer to CoA/Spec Sheet.

Recommendations for users:

• For HTS or cell-based assays, confirm purity and identity against your internal thresholds via LC–MS/HPLC prior to large-scale campaigns.
• If ultra-low impurity profiles are required (e.g., for SAR, chemoproteomics), consider in-house recrystallization or preparative HPLC purification and document the new specifications in your ELN.
• Cite the SKU and batch/lot on publications to ensure traceability.

Reaction and Applications

This product is supplied as a finished small molecule for screening and probe development rather than as a general synthetic reagent.

• Not typically used as a solvent, ligand, catalyst, or stoichiometric reagent in preparative chemistry.
• Primary applications (research-only): chemical biology, phenotypic screening, and SAR exploration using the quinoline-3-carboxamide scaffold.

If using the compound in chemical synthesis (uncommon):

• Quinoline-3-carboxamides can, in principle, undergo late-stage functionalization on the aromatic ring (e.g., electrophilic substitution, metal-catalyzed C–H activation) or amide modifications (hydrolysis under forcing conditions), but such transformations are not the intended use of this catalog item.

For most users, see the “Biological Roles,” “Target Specificity,” and “Application Protocols” tabs for guidance relevant to screening and assay deployment. No manufacturer application notes are provided beyond research-use-only.

Reaction Conditions

Not applicable in the usual sense: this product is not sold as a reagent for performing chemical reactions.

For researchers undertaking independent synthesis or derivatization of quinoline-3-carboxamides (general literature guidance only):

• Amide couplings: DMF or DCM; EDC/HOBt, HATU, or CDI; base (DIPEA); 0–25 °C, 1–16 h.
• Aromatic substitutions/cross-couplings on halogenated quinolines: Pd-catalyzed Suzuki–Miyaura (Pd(PPh3)4, K2CO3, dioxane/H2O, 60–100 °C) or Buchwald–Hartwig amination (Pd2(dba)3/XPhos, NaOtBu, toluene or dioxane, 80–110 °C).
• Electrophilic substitutions: Nitration, sulfonylation, or Friedel–Crafts conditions tailored to ring electronics; protect amide if necessary.

These are generic conditions reported for the scaffold class and are not recommendations for altering this catalog item.

Safety and Handling

• GHS classification: Not specified for this item; refer to SDS for authoritative information.
• Signal word / H-statements / Pictograms: Not specified for this item; refer to SDS.

General laboratory precautions (good practice for small, lipophilic heteroaromatics):

• Engineering controls: Work in a chemical fume hood to avoid inhalation of dust or aerosols.
• PPE: Lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Avoid skin/eye contact and inhalation of powders.
• Handling: Minimize exposure to ambient humidity and light. Open vials at room temperature only after allowing to equilibrate from −80 °C to prevent condensation. For powdered solids, use antistatic tools and weigh boats with local exhaust.
• Incompatibilities (general): Strong oxidizers, strong acids/bases that may hydrolyze the amide under forcing conditions. Avoid prolonged heating in air.
• First aid (overview; defer to SDS):
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: Rinse with plenty of water for at least 15 minutes; remove contaminated clothing; seek medical advice if irritation persists.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Spill response: Avoid dust generation. Collect with inert absorbent or dampened wipes; dispose of as hazardous chemical waste per institutional guidelines.
• Waste: Treat as organic hazardous waste. Follow local regulations and institutional SOPs.

Always consult the product-specific SDS for definitive hazard classification, exposure limits, and emergency measures.

Solvent Selection

Laquinimod, as a quinoline-3-carboxamide analog, behaves as a moderately lipophilic, weakly basic heteroaromatic. Solvent handling in screening workflows focuses on preparing robust stock solutions and ensuring assay compatibility.

• Primary stock solvent (practical guidance):
  • DMSO is the default for small-molecule libraries due to broad solvency, chemical compatibility, and assay interoperability.
  • Typical stock concentrations: 1–50 mM depending on downstream dilution limits and solubility (establish empirically).
• Alternative solvents (when DMSO is unsuitable):
  • DMF or NMP for difficult-to-dissolve samples (use with caution in biology due to cytotoxicity).
  • Ethanol or isopropanol for certain biochemical assays; pre-test for assay interference.
  • Aqueous buffers may require co-solvent (≤1–2% DMSO or ethanol) and surfactant (e.g., 0.01–0.05% Tween-20) to avoid precipitation.
• Miscibility and polarity (general):
  • DMSO is miscible with water and most organics, enabling straightforward serial dilutions.
  • Avoid nonpolar solvents (hexanes, toluene) for biological use; they offer limited benefit and complicate dosing.
• Practical tips:
  • Warm gently (25–40 °C) and sonicate to aid dissolution; filter 0.22 µm if particulate persists.
  • For plate-based work, pre-wet tips with DMSO stocks, and equilibrate to room temperature to minimize viscosity-induced pipetting error.
  • Track final co-solvent fraction in assays; cap DMSO at levels validated for your system (commonly ≤0.1–0.5% v/v).

Item-specific solubility data are not provided here; verify experimentally or consult the CoA if available.

Storage and Reconstitution

• Storage conditions (item-specific): Store at −80 °C.
• Shipping: Shipped on dry ice packs + cold packs.
• Research use note: For research use only.

Reconstitution and handling (general guidance, not a specification):

• Solvent: Use anhydrous DMSO for primary stocks. Alternative solvents (DMF, NMP, ethanol) may be used if validated for your assay.
• Concentration: Prepare concentrated stocks (e.g., 10–50 mM) based on solubility and assay needs. Document exact concentration by mass and volume.
• Thawing: Allow vials to equilibrate to room temperature in a desiccated environment before opening to prevent moisture condensation.
• Aliquoting: Split into single-use aliquots in inert vials or plated formats to avoid repeated freeze–thaw.
• Freeze–thaw: Minimize cycles; if unavoidable, keep thaw time short and avoid prolonged exposure to ambient humidity and light.
• Stability: Item-specific stability data are not provided; verify short-term bench stability empirically (e.g., LC–MS after 24–48 h at room temperature) before extended use.
• Aqueous dilutions: Add DMSO stock slowly to vigorously mixed buffer/media to prevent precipitation. Maintain a consistent final DMSO percentage across samples.

For definitive shelf-life and re-test intervals, consult the CoA/Spec Sheet and your institution’s QC protocols.

Structure and Identity

Laquinimod is a small-molecule quinoline-3-carboxamide analog supplied as part of Aladdin’s Moligand screening collection.

• SKU: L408638
• CAS: 248281-84-7
• Common name: Laquinimod
• Synonym class (literature): quinoline-3-carboxamide derivative (general scaffold description)
• 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-level description):

• Aromatic heterobicycle: a quinoline core (benzannulated pyridine) typical of the class.
• Carboxamide functionality at the 3-position of the quinoline ring (quinoline-3-carboxamide scaffold).
• Substituent pattern often includes halogen and phenyl/alkyl amide substitution in this chemical class; exact substitution for this lot is not specified here (refer to CoA/SDS for definitive identifiers).

2D structure description (general scaffold):

• A fused benzene–pyridine bicyclic ring (quinoline) bearing a carbonyl carbon (C=O) at C3 linked to an anilide/alkylamide nitrogen, producing an amide linkage orthogonal to the ring system. Additional ring substituents modulate electronics and lipophilicity (details not provided in this listing).

Synthetic Utility

Laquinimod is supplied as a finished bioactive small molecule; it is not positioned as a synthetic building block. Consequently, synthetic utility is limited in the context of this catalog item.

General retrosynthetic considerations for the quinoline-3-carboxamide scaffold (literature-level, not a directive for this SKU):

• Assembly of the quinoline core via Skraup, Doebner–Miller, Conrad–Limpach, or Friedländer syntheses, followed by installation of a carboxamide at C3.
• Amide diversification through coupling of 3-carboxylic acid derivatives (acid chloride/anhydride or modern peptide-coupling reagents) with anilines or alkyl amines.
• Late-stage functionalization on the quinoline ring (e.g., halogenation, metal-catalyzed cross-couplings) to adjust electronics and lipophilicity.

These notes are provided solely for chemists interested in the broader scaffold chemistry; they are not specific to modifications of the supplied compound.

Target Specificity

No target, pathway, or binding specificity is provided for this SKU in the product data.

• Target/protein: Not specified for this item; refer to CoA/Spec Sheet or primary literature relevant to your study design.
• Assay validation: Users should perform in-house profiling (e.g., biochemical binding, reporter assays, transcriptomics) to establish target engagement and selectivity under their experimental conditions.

All uses are for research only.