ARRY 520 trifluoroacetate - ≥98%(HPLC) , CAS No.1781834-99-8

CAS: 1781834-99-8 Cat. No.: A287172 Formula: C₂₂H₂₃F₅N₄O₄S Peso molecolare: 534.50 PubChem CID: 90488964

GRADE & PURITY ≥98%(HPLC)

Synonyms

Filanesib | (2S)-2-(3-Aminopropyl)-5-(2,5-difluorophenyl)-N-methoxy-N-methyl-2-phenyl-1,3,4-thiadiazole-3(2H)-carboxamide trifluoroacetate | Filanesib TFA | ARRY-520 TFA

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Specifications

Sinonimi

Filanesib | (2S)-2-(3-Aminopropyl)-5-(2,5-difluorophenyl)-N-methoxy-N-methyl-2-phenyl-1,3,4-thiadiazole-3(2H)-carboxamide trifluoroacetate | Filanesib TFA | ARRY-520 TFA

Specifiche e purezza

≥98%(HPLC)

Meccanismi biochimici e fisiologici

Potent kinesin spindle protein (KSP) inhibitor (IC50= 6 nM); selective for KSP over >250 other receptors and kinases at a concentration of 10μM. Displays robust antitumor activity in bortezomib-resistant xenografts either alone or in combination with bort

Condizioni di conservazione di stoccaggio

Store at -20°C

Spedito in

Ice chest + Ice pads

Questo prodotto richiede spedizione a catena fredda. I servizi di terra e altri servizi economici non sono disponibili.

Tipo di azione

INHIBITOR

Purezza

≥98%(HPLC)

Nomi e identificatori

Sorrisi canonici

CN(C(=O)N1C(SC(=N1)C2=C(C=CC(=C2)F)F)(CCCN)C3=CC=CC=C3)OC.C(=O)(C(F)(F)F)O

IUPAC Name

(2S)-2-(3-aminopropyl)-5-(2,5-difluorophenyl)-N-methoxy-N-methyl-2-phenyl-1,3,4-thiadiazole-3-carboxamide;2,2,2-trifluoroacetic acid

InChIKey

CIJUJPVFECBUKG-BDQAORGHSA-N

INCHI

1S/C20H22F2N4O2S.C2HF3O2/c1-25(28-2)19(27)26-20(11-6-12-23,14-7-4-3-5-8-14)29-18(24-26)16-13-15(21)9-10-17(16)22;3-2(4,5)1(6)7/h3-5,7-10,13H,6,11-12,23H2,1-2H3;(H,6,7)/t20-;/m0./s1

Isomeri SMILES

CN(C(=O)N1[C@](SC(=N1)C2=C(C=CC(=C2)F)F)(CCCN)C3=CC=CC=C3)OC.C(=O)(C(F)(F)F)O

PubChem CID

90488964

Peso molecolare

534.50

Proprietà chimiche e fisiche

• Solubilità: Solvent:DMSO, Max Conc. mg/mL: 31.54, Max Conc. mM: 75; Solvent:ethanol, Max Conc. mg/mL: 31.54, Max Conc. mM: 75

Application Protocols

• Item-specific (from Product Data)
  • No tested applications, assay types, or recommended dilutions are provided for this item.
• General handling (non-specific guidance)
  • Prepare a concentrated stock in anhydrous DMSO under inert, dry conditions if possible. Vortex to dissolve fully; gentle heating (≤37 °C) and brief sonication can aid dissolution if compatible with stability.
  • Filter sterilize (0.22 µm) if sterile applications are required and the compound is stable under the conditions.
  • Dilute into pre‑warmed assay medium with thorough mixing; add stock as the final component to minimize precipitation. Maintain consistent vehicle percentage in controls.
  • Establish concentration ranges empirically (e.g., serial dilutions spanning orders of magnitude) and include time‑matched vehicle controls.
• Note
  • These are general best practices for small‑molecule tool compounds and are not item‑validated protocols. Consult your institutional SOPs.

Biological Roles

• General/literature context (non-clinical, not item specifications)
  • ARRY‑520 (filanesib) is widely cited as a selective small‑molecule inhibitor of the mitotic kinesin Eg5 (also known as KSP, KIF11), a motor protein essential for bipolar spindle formation during cell division.
  • Inhibition of Eg5 disrupts centrosome separation and spindle bipolarity, leading to characteristic monopolar spindles and mitotic arrest in proliferating cells—a phenotype commonly used as a readout of target engagement.
  • As a chemical probe, ARRY‑520 supports studies of mitotic mechanics, checkpoint signaling, and synthetic‑lethal interactions with DNA damage responses in cell lines.
• Experimental considerations (general)
  • Cellular uptake and activity can depend on serum binding and efflux transporter expression; titration curves and time‑course experiments are recommended.
  • Phenotypic confirmation typically involves immunofluorescence microscopy of microtubules/centrosomes, mitotic index quantification, or live‑cell imaging of spindle dynamics.
  • Orthogonal validation may use genetic knockdown/knockout of KIF11 or alternative Eg5 inhibitors to confirm on‑target effects.
• Important notes
  • All uses are for research only; no medical, diagnostic, or therapeutic use is implied.
  • Specific activity values, EC50/IC50, and selectivity panels vary by cell line and assay format and are not specified for this item; consult primary literature for context and determine parameters empirically in your system.

Buffer Applications

• Applicability statement
  • This product is a small‑molecule research tool rather than a buffering agent. It does not form classical buffer systems and is not used to control solution pH.
• Practical notes for assay buffers (general)
  • When preparing working solutions, use physiologically relevant buffers/media (e.g., PBS, HBSS, or cell culture media) and keep final organic solvent content low and consistent across treatments.
  • If aqueous solubility is limited, modest acidification (e.g., adding a small fraction of acidic buffer) or inclusion of tolerated cosolvent can help maintain the TFA salt in solution.

Green Alternatives

• Context
  • As a small‑molecule research tool, the main environmental footprint arises from solvent use in preparation and assay workflows rather than from the compound itself.
• Greener solvent choices (general guidance)
  • Prefer aqueous buffers with minimal DMSO where feasible; consider pH adjustment or formulation aids (e.g., hydroxypropyl‑β‑cyclodextrin) to reduce organic solvent percentage.
  • If an organic cosolvent is required, ethanol is generally considered a greener alternative to DMF or acetonitrile for biological applications.
• Comparative considerations (general)
  • DMSO: High solvency; relatively low volatility; acceptable toxicity profile in small volumes but not classified as “green.”
  • Ethanol: Renewable feedstock and lower toxicity; may have lower solvency and can impact cells at higher percentages.
  • Aqueous buffer: Greenest option; may require careful pH control to maintain the TFA salt in solution.
• Practical steps to improve sustainability
  • Use concentrated stocks to minimize solvent volumes added to assays.
  • Standardize stock concentrations to reduce waste from repeated dilutions.
  • Dispose of halogenated waste streams (if any arise from analytical work) separately to facilitate appropriate treatment.
• Note
  • No alternative “green” chemical replacement exists for the biological activity of ARRY‑520; sustainability efforts should focus on solvent minimization and responsible waste management.

Pharmaceutical Uses

• Applicability statement
  • Supplied strictly for research use only. No medical, diagnostic, or therapeutic use is intended or implied.
• Formulation context (general, non-claim)
  • In preclinical research settings, small‑molecule TFA salts are often formulated for in vitro studies in DMSO stocks and for in vivo model research (where permitted) in aqueous vehicles containing suitable cosolvents/surfactants (e.g., PEG, Cremophor, or cyclodextrins). Specific vehicle compositions and dosing regimens are not provided for this item and must be developed and approved under relevant institutional protocols.
  • No pharmacopeial monograph is cited here for ARRY‑520 TFA.
• Manufacturing/analytical considerations (general)
  • Counterion identity and stoichiometry should be verified for dose normalization to free‑base equivalents.
  • Stability‑indicating methods (e.g., HPLC with UV/fluorescence or LC–MS) are recommended to monitor degradation in formulated matrices.
• Note
  • All handling and formulation should comply with local regulations for laboratory research chemicals.

Physical Properties

• Item-specific (from Product Data)
  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Literature/general values and expectations (not item specifications)
  • Physical state: Typically an off‑white to light solid for small‑molecule TFA salts; exact appearance depends on lot and hydration.
  • Solubility (typical practice): Readily soluble in DMSO; often soluble to working stocks (e.g., millimolar range) in anhydrous DMSO; sparingly to moderately soluble in aqueous buffers depending on pH and cosolvent content. Actual solubility for this item is not specified; confirm experimentally.
  • pKa (qualitative): Presence of a basic amine implies protonation under physiological pH; salt formation with TFA reflects basicity of the cation. Numerical pKa not stated here.
  • Partitioning: Aromatic, cationic salts often show higher aqueous compatibility than the free base at acidic pH; logP/logD are formulation‑dependent and not provided here.
  • Melting point, boiling point, density, refractive index, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
• Practical notes
  • Stock solutions are commonly prepared in dry DMSO and diluted into assay media immediately before use to minimize precipitation.
  • The TFA counterion can influence hygroscopicity; minimize exposure to humid air to avoid water uptake that can change apparent mass concentration.

Quality and Grades

• Item-specific (from Product Data)
  • Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
• How to interpret grade/purity when provided (general guidance)
  • For small‑molecule research tools, vendors may report HPLC area % purity, residual solvent content, counterion content, and water (Karl Fischer). A higher HPLC purity (e.g., ≥98%) is typically preferred for biological assays to reduce confounding off‑target effects from impurities.
  • Trifluoroacetate salt form: The counterion content can be quantified (e.g., by 19F NMR, ion chromatography) and may vary slightly between lots; this affects mass‑based dosing. If your assay is sensitive to exact molarity, consider normalizing by free‑base equivalent based on the counterion stoichiometry provided on the CoA.
  • UV/HPLC suitability: If HPLC grade or LC–MS suitability is claimed in documentation, expect low baseline and well‑resolved main peak; otherwise, verify with your own method development.
• Recommendations
  • Request and review the CoA for: HPLC chromatogram, assay/purity, residual solvents, water content, and TFA stoichiometry. Adjust dosing to free‑base equivalents when comparing across lots or suppliers.

Reaction and Applications

• Item-specific (from Product Data)
  • Manufacturer application text: Not provided.
• Applicability statement
  • ARRY 520 trifluoroacetate is a small‑molecule research tool and is not typically used as a reagent or catalyst in synthetic organic reactions. Therefore, conventional “reaction families” (e.g., cross‑coupling, reductions) are not applicable to this product.
• Research usage (general, non-clinical)
  • Employed as a biochemical probe of mitotic kinesin function in cell and molecular biology experiments, including target engagement studies, mechanism‑of‑action assays, and phenotypic screenings where modulation of mitotic spindle dynamics is desired.
  • Often used alongside orthogonal tool compounds and negative controls to validate pathway dependence in cellular models.
• Practical notes
  • Prepare fresh working solutions immediately before dosing to maintain solubility and consistency.
  • Include vehicle controls matched for DMSO/ethanol content.
  • Consider time‑course and washout experiments to probe reversibility and cell‑cycle phase specificity.

Reaction Conditions

• Applicability statement
  • Not applicable. This product is not intended for use as a reagent or catalyst in chemical synthesis, so there are no recommended reaction temperatures, catalysts, or solvent systems.
• Practical notes for research use (general)
  • For solution preparation and biological assays, see Solvent Selection and Storage & Reconstitution sections for guidance on stock preparation, dilution, and handling.

Safety and Handling

• Item-specific (from Product Data)
  • Storage: Store at −20 °C.
  • Shipping: Ice chest + ice pads.
  • GHS classification, signal word, pictograms, and H‑statements: Not specified for this item; refer to SDS.
• General laboratory safety (defer to the SDS for authoritative guidance)
  • Handle in a certified chemical fume hood to avoid inhalation of dust or aerosols from fine organic solids/salts.
  • Personal protective equipment (PPE): lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Avoid skin/eye contact and ingestion.
  • Avoid generating dust; use antistatic precautions and weigh with care. Wash thoroughly after handling. Do not pipette by mouth.
  • Incompatibilities (general): Strong oxidizers, strong acids/bases may lead to degradation; avoid prolonged exposure to moisture which can alter the TFA salt stoichiometry.
  • First aid overview (general): If inhaled—move to fresh air; seek medical attention if symptoms persist. 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; seek medical advice.
  • Spill response: Avoid dust; carefully collect solids with disposable tools, wipe residues with dampened absorbent, and dispose according to institutional and local regulations.
  • Fire safety: Combustible organic solid; use dry chemical, CO2, or foam extinguishers. Thermal decomposition may produce irritating/toxic fumes (e.g., HF from TFA residues under severe conditions).

Solvent Selection

• Item-specific (from Product Data)
  • No solvent recommendations specified for this item; see general guidance below.
• General/literature guidance for ARRY‑520 TFA and similar small‑molecule salts
  • Primary stock solvent: DMSO (anhydrous) is the default due to high solvating power for aromatic, cationic drug‑like molecules and compatibility with most biochemical assays at ≤0.5% v/v.
  • Aqueous compatibility: The TFA salt can improve water compatibility, but precipitation may occur upon dilution if the free base forms at neutral pH. Use co‑solvents (DMSO, ethanol) and/or pH control to maintain solubility.
  • Alternative solvents: Ethanol or methanol can dissolve many TFA salts; for cell‑based work, ethanol is often preferred over methanol. DMF may be used for preparative dissolution but is less favored in live‑cell assays.
  • Buffering strategy: Dilute concentrated organic stock into pre‑warmed media/buffer while vortexing; add stock last to well‑mixed solutions to minimize local supersaturation.
• Comparison (general)
  • DMSO: Highest solvency; broad assay compatibility; hygroscopic and can carry water—store dry.
  • Ethanol: Biologically tolerated at low %; lower solvency; volatile—allows quick evaporation for coating.
  • Aqueous buffer: Most biocompatible; may require acidic pH or cyclodextrin/formulation aids for sufficient solubility.
• Practical tips
  • Filter sterilize final working solutions (0.22 µm) if sterility is required and the compound is stable.
  • Avoid repeated freeze–thaw of DMSO stocks to prevent concentration drift from moisture uptake.

Storage and Reconstitution

• Item-specific (from Product Data)
  • Storage: Store at −20 °C.
  • Shipping: Ice chest + ice pads.
• Reconstitution and aliquoting (general best practices)
  • Open containers only after equilibrating to room temperature in a desiccator to prevent condensation. Minimize exposure to ambient humidity to avoid changes in TFA stoichiometry.
  • Reconstitute in anhydrous DMSO to prepare a concentrated stock. The exact solubility and recommended stock concentration are not specified for this item; refer to CoA/Spec Sheet and determine empirically.
  • After dissolution, prepare single‑use aliquots in low‑bind tubes to avoid repeated freeze–thaw cycles. Flush headspace with dry inert gas (e.g., nitrogen or argon) if long‑term storage is anticipated.
  • Store DMSO stocks at −20 °C or below in tightly sealed vials; protect from light if the compound is light‑sensitive (not specified here).
• Stability notes
  • Long‑term stability, degradation pathways, and retest intervals are not specified for this item; monitor by HPLC/LC‑MS as appropriate.
  • Avoid repeated freeze–thaw; thaw on ice or at room temperature just before use and immediately return unused aliquots to cold storage.

Structure and Identity

• Item-specific (from Product Data)
  • SKU: A287172
  • Product name: ARRY 520 trifluoroacetate
  • CAS: 1781834-99-8
  • PubChem CID: 90488964
  • InChIKey: 44997 (as provided)
  • 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.
• General/literature context (non-specification)
  • ARRY‑520 (also known in literature as filanesib) is a small‑molecule inhibitor typically supplied as a trifluoroacetate (TFA) salt to improve handling and solubility.
  • As a TFA salt, the material is a protonated amine-containing organic compound paired with trifluoroacetate anion; no polymeric or macromolecular features are expected.
  • Structural features reported in the literature for ARRY‑520 include multiple aryl/heteroaryl rings and a basic amine that forms the salt with TFA; stereochemistry may be present in the free base depending on the specific scaffold.
• 2D structural description (general)
  • The cationic portion consists of a polycyclic/aryl-rich, nitrogen‑containing framework bearing at least one basic tertiary/secondary amine center; the anion is CF3CO2−. The salt form is expected to be a discrete ion pair under anhydrous conditions and partially dissociated in polar protic/aqueous media.

Synthetic Utility

• Applicability statement
  • ARRY 520 trifluoroacetate is an end‑use small‑molecule probe and is not typically employed as a reagent, catalyst, or building block in synthetic chemistry.
• Recommendations
  • If derivatization or analog synthesis is of interest, consult primary medicinal chemistry literature on ARRY‑520/filanesib scaffolds for SAR and late‑stage functionalization strategies. Such work generally begins from the documented intermediates rather than from the final TFA salt.
  • For analytical characterization during any exploratory derivatization, orthogonal methods (1H/13C/19F NMR, HRMS, HPLC) are advised to quantify counterion content and confirm purity.
• Non-applicable details
  • Named reaction conditions, protective group strategies, and reagent compatibility are not provided here because the compound is not intended for use as a synthetic reagent.

Target Specificity

• Item-specific (from Product Data)
  • No target, antigen, clone, or species reactivity information has been provided for this item.
• Statement of limitation
  • Target specificity details are not specified for this item; refer to CoA/Spec Sheet and primary literature for context appropriate to your study design.