TAPI-2 - ≥98% , CAS No.187034-31-7

CAS: 187034-31-7 Cat. No.: T275536 Fórmula: C₁₉H₃₇N₅O₅ Peso molecular: 415.5 PubChem CID: 10093303

GRADE & PURITY ≥98%

Synonyms

TNF Protease Inhibitor 2

Storage

Protected from light,Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Descripción general

Store at -20°C (desiccating conditions).

Specifications

Sinónimos

TNF Protease Inhibitor 2

Especificaciones y pureza

≥98%

Mecanismos bioquímicos y fisiológicos

TAPI-2 (TNF Protease Inhibitor 2) is a broad-spectrum inhibitor of matrix metalloprotease (MMP), tumour necrosis factorα-converting enzyme (TACE) and a disintegrin and metalloproteinase (ADAM), with an IC50 of 20 μM for MMP. TAPI-2 blocks the entry of inf

Condiciones de almacenamiento de almacenamiento

Protected from light,Store at -20°C,Desiccated

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Nota

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Pureza

≥98%

Nombres e identificadores

Sonrisas canónicas

CC(C)CC(CC(=O)NO)C(=O)NC(C(=O)NC(C)C(=O)NCCN)C(C)(C)C

IUPAC Name

N-[(2S)-1-[[(2S)-1-(2-aminoethylamino)-1-oxopropan-2-yl]amino]-3,3-dimethyl-1-oxobutan-2-yl]-N'-hydroxy-2-(2-methylpropyl)butanediamide

InChIKey

LMIQCBIEAHJAMZ-RMTCENKZSA-N

INCHI

1S/C19H37N5O5/c1-11(2)9-13(10-14(25)24-29)17(27)23-15(19(4,5)6)18(28)22-12(3)16(26)21-8-7-20/h11-13,15,29H,7-10,20H2,1-6H3,(H,21,26)(H,22,28)(H,23,27)(H,24,25)/t12-,13?,15+/m0/s1

Isómeros SMILES

C[C@@H](C(=O)NCCN)NC(=O)[C@H](C(C)(C)C)NC(=O)C(CC(C)C)CC(=O)NO

PubChem CID

10093303

Peso molecular

415.5

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Clase Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Peptides
          • Level6 Dipeptides

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Clase: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Peptides
• Direct Parent: Dipeptides
• Alternative Parents: Valine and derivatives N-acyl-alpha amino acids and derivatives Alpha amino acid amides Alanine and derivatives N-acyl amines Secondary carboxylic acid amides Hydroxamic acids Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Alpha-dipeptide - Valine or derivatives - N-acyl-alpha amino acid or derivatives - Alpha-amino acid amide - Alanine or derivatives - N-substituted-alpha-amino acid - Alpha-amino acid or derivatives - Fatty acyl - Fatty amide - N-acyl-amine - Amino acid or derivatives - Secondary carboxylic acid amide - Carboxamide group - Hydroxamic acid - Organic nitrogen compound - Primary aliphatic amine - Organonitrogen compound - Organooxygen compound - Primary amine - Carbonyl group - Hydrocarbon derivative - Amine - Organic oxide - Organic oxygen compound - Aliphatic acyclic compound
• Descripción: This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
• External Descriptors: Not available

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

Propiedades químicas y físicas

• Solubilidad: Soluble in water to 50 mM
• Sensibilidad: Moisture、Light sensitive
• Peso molecular: 415.500 g/mol
• XLogP3: -0.100
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 12
• Exact Mass: 415.279 Da
• Monoisotopic Mass: 415.279 Da
• Topological Polar Surface Area: 163.000 Ų
• Heavy Atom Count: 29
• Formal Charge: 0
• Complexity: 574.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

Item-specific

• No tested applications or recommended dilutions are provided for this item. Refer to your laboratory’s validated protocols and the primary literature.

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

• Biochemical assays: Prepare serial dilutions from a concentrated DMSO stock (e.g., 10–50 mM) into assay buffer containing detergent/protein as required; include vehicle controls.
• Cell-based assays: Add compound from DMSO stock to pre-warmed media to achieve target concentration with minimal DMSO (≤0.1–0.5% v/v when possible). Preincubate as required by the assay design.
• Readouts: Quantify substrate accumulation or shed ectodomains by ELISA, immunoblotting, or fluorogenic substrates; confirm viability to exclude nonspecific toxicity.
• Data quality: Employ duplicates/triplicates, full dose–response curves, and appropriate statistical methods. Always protect solutions from light exposure during extended incubations.

Biological Roles

Literature/general (for research context; no clinical claims)

• Primary target class: zinc-dependent metalloproteases, notably ADAM (a disintegrin and metalloproteinase) family members such as ADAM17/TACE, and various matrix metalloproteinases (MMPs). TAPI-2 is commonly categorized as a hydroxamate-based inhibitor that chelates the catalytic Zn2+ ion in the active site.
• Functional consequence: Inhibition of proteolytic ectodomain shedding of membrane-bound substrates. This can attenuate the release of soluble factors (e.g., certain cytokine precursors and growth factor ligands) and modulate receptor activation/turnover, with system-dependent outcomes.
• Use in mechanistic studies: Serves as a probe to dissect shedding-dependent signaling pathways, validate protease involvement, and differentiate contributions of ADAM vs. MMP activities using complementary assays and orthogonal inhibitors.
• Selectivity considerations: Hydroxamate inhibitors can exhibit cross-reactivity across multiple metalloproteases. Experimental designs typically include dose–response curves, temporal profiling, and counter-screens against unrelated proteases to confirm on-target effects.
• Assay modalities: Employed in enzymatic activity assays (fluorogenic peptide substrates), ELISA/Western blot detection of shed ectodomains, reporter assays sensitive to ligand availability, and surface protein measurements by flow cytometry.
• Caveats: Off-target metal chelation at high concentrations, potential effects on cell adhesion and extracellular matrix turnover, and DMSO carrier effects require careful control.

Note: Target specificity and potency parameters are assay- and source-dependent; verify with primary literature or vendor CoA/Tech Sheet for the lot in hand.

Buffer Applications

Not typically applicable.

• TAPI-2 is not a buffering agent. It is a bioactive inhibitor used in biochemical and cell-based assays.
• Practical guidance: Prepare concentrated stock in DMSO and dilute into your assay buffer immediately before use. Maintain consistent buffer composition and DMSO percentage across controls and treated samples to avoid confounding effects.

Green Alternatives

Applicability

• This product is a specialized bioactive inhibitor used at micromolar concentrations in research assays. “Green solvent” substitution concepts apply primarily to stock-solution preparation and cleaning, not to the compound itself.

Considerations (general)

• Preferred solvent: DMSO is standard for bioactive stocks; while not “green,” it is low-volatility, fully water-miscible, and used at very low final concentrations, limiting environmental burden.
• Alternative co-solvents: Ethanol or aqueous buffer with minimal co-solvent may be acceptable if solubility permits, reducing reliance on higher-toxicity solvents.
• Waste minimization: Prepare minimal-volume stocks at concentrations aligned to experimental needs; aliquot to avoid discard from freeze–thaw degradation.
• Process scale: Given typical micro- to milligram research use, the green-chemistry impact is dominated by solvent handling and lab practices rather than synthesis or use-phase of the compound.

Comparison (general)

• DMSO: high solubilizing power; low vapor pressure; widely accepted in bioassays.
• Ethanol: lower toxicity and more renewable sourcing; may limit achievable concentration and stability.
• Aqueous buffers: greenest medium but often incompatible with required solubility; risk of precipitation and variable bioavailability.

Recommendation

• Use the least hazardous solvent that achieves required solubility and assay performance; scale down and segregate waste appropriately. No item-specific green alternatives are defined.

Pharmaceutical Uses

Scope and limitations

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

Formulation and development context (general/literature)

• Role in R&D: Utilized as a reference standard or tool compound in early discovery studies to interrogate metalloprotease biology, establish structure–activity relationships, and benchmark new chemical entities targeting ADAMs/MMPs.
• Form factors: Typically provided as a dry solid for storage stability; users commonly prepare DMSO stock solutions for in vitro testing.
• Excipient considerations: For in vitro work, co-solvents such as DMSO and carriers like serum proteins can influence apparent potency and availability; careful control of vehicle and protein content is recommended.
• Analytical characterization: Identity/purity may be verified by HPLC, MS, and NMR; for formulation research, additional tests (e.g., solubility screening across pH, stability-indicating methods) may be performed by the end user.

Item-specific notes

• No pharmacopeial grade or compendial status is specified for this item. Consult the CoA/Spec Sheet for any lot-specific analytical data.

Physical Properties

Item-specific (from Product Data)

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

Literature/General values and handling expectations (not item specifications)

• Physical state: typically an off-white to light-colored solid for many lots from various suppliers (literature/general observation).
• Solubility (literature): sparingly soluble in aqueous buffers; readily soluble in polar aprotic organics such as DMSO; limited to moderate solubility in ethanol or methanol; poor solubility in nonpolar solvents.
• Acid/base properties: hydroxamic acids are weakly acidic (pKa of the N–OH generally ~8–9, literature-general for hydroxamates), which influences ionization and aqueous solubility with pH.
• Partitioning: hydroxamate-containing inhibitors often show moderate lipophilicity (exact logP for this item not provided; refer to databases/CoA).
• Thermal properties (BP/MP): Not specified for this item; refer to CoA/Spec Sheet.
• Density, refractive index, UV-Vis cutoff: Not specified for this item; refer to CoA/Spec Sheet.

Practical notes

• Prepare concentrated DMSO stocks to overcome aqueous solubility limits.
• For biological assays, dilute DMSO stocks into buffer immediately before use to minimize precipitation; final DMSO typically kept ≤0.1–0.5% v/v depending on assay tolerance.

Quality and Grades

Item-specific

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

General guidance for this product class (literature/practice)

• Research-grade small-molecule inhibitors are commonly qualified by NMR, HPLC/UPLC purity, and MS. For analytical or screening applications, users often target ≥95% HPLC purity; for mechanistic enzymology or in vivo probe development (preclinical research only), higher purity and detailed impurity profiles may be preferred.
• Stabilizers: Not typically required for dry solids when stored desiccated and protected from light; solution stability depends on solvent and temperature. This listing does not indicate any stabilizer for the item.
• Documentation: For lot-specific assay data (e.g., HPLC trace, water content, residual solvents), consult the CoA/Spec Sheet. Where assay interference (e.g., metal chelation) is a concern, verify counterion/metal content if relevant to your study.
• Use-case alignment: For cell-based or biochemical assays targeting metalloproteases (e.g., ADAM17/TACE, MMPs), confirm purity and identity meet your lab’s acceptance criteria prior to screening or SAR comparisons.

Reaction and Applications

Scope note

• This product is a bioactive small-molecule inhibitor rather than a general synthetic reagent. Accordingly, classical organic reaction applications (e.g., catalysis, coupling) are not the primary use-case.

Research applications (literature/general; not item-specific)

• Enzyme inhibition studies: Widely used as a tool compound to inhibit ADAM17/TACE and related metalloproteases in biochemical assays to study ectodomain shedding of membrane proteins (e.g., TNF precursors, growth factor ligands). Mechanism involves zinc chelation by the hydroxamate moiety.
• Cell biology: Applied in cell-based assays to modulate shedding-dependent signaling pathways; time- and dose-dependent inhibition profiles are typically established to minimize off-target effects. Vehicle controls (DMSO) and rescue experiments (e.g., recombinant protease) are commonly employed.
• Protease panels: Utilized as a reference inhibitor in ADAM/MMP selectivity panels and to benchmark new metalloprotease inhibitors.

Practical tips

• Prepare fresh working solutions from concentrated DMSO stocks; avoid repeated freeze–thaw.
• Include appropriate controls: inactive analogs or orthogonal inhibitors; confirm on-target effect by complementary readouts (e.g., substrate accumulation, sAPP/sTNF release in supernatants by ELISA or immunoblot).
• Beware of general metalloprotease inhibition leading to pleiotropic effects; titrate to the lowest effective concentration compatible with assay readouts.

Note: No manufacturer application notes were provided for this specific item.

Reaction Conditions

Not typically applicable.

• As a bioactive small-molecule tool compound, TAPI-2 is not used as a reagent or catalyst in synthetic transformations. Consequently, there are no standard “reaction conditions” to report for chemical synthesis.

Assay-condition notes (literature/practice; not item-specific)

• Working concentration ranges in biological assays often fall in the low micromolar domain, with exact values determined empirically by enzyme or cell model.
• Vehicle: DMSO stocks diluted into aqueous assay buffers or culture media; maintain consistent vehicle percentages.
• Temperature and time: Incubations commonly at 25–37 °C for minutes to hours depending on assay kinetics; protect from light during prolonged incubations.
• These are general research-use practices and should be optimized per protocol.

Safety and Handling

Item-specific (from Product Data)

• GHS classification: Not specified for this item; refer to SDS.
• Signal word: Not specified for this item; refer to SDS.
• Hazard statements (H-Statements): Not specified for this item; refer to SDS.
• Pictograms: Not specified for this item; refer to SDS.
• Storage conditions: Protect from light; store at −20 °C; keep desiccated. Shipped in an ice chest with ice pads.

General laboratory safety guidance (literature/best practice; defer to SDS for authoritative information)

• Likely hazards: Small-molecule organic inhibitor; avoid inhalation of dust and contact with skin/eyes. Handle in a fume hood when weighing powders or preparing stock solutions.
• PPE: lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Use eye/face protection if splash risk exists.
• Incompatibilities: Avoid strong oxidizers and strong acids/bases that may degrade hydroxamate and amide functionalities. Minimize exposure to moisture to prevent hydrolysis.
• First aid (general): In case of skin/eye contact, rinse with water for several minutes; remove contaminated clothing. If inhaled, move to fresh air. If ingested, rinse mouth; seek medical attention as needed. Always consult the SDS.
• Spill response: Collect solids by gentle sweeping while avoiding dust generation; for solutions, absorb with inert material. Dispose of waste according to institutional and regulatory guidelines.
• Stability considerations: Protect from light and moisture; avoid repeated freeze–thaw of solutions to limit decomposition.

Solvent Selection

Item-specific

• No item-specific solvent specifications are provided. Practical selection should follow the guidance below and your assay constraints.

Literature/practical guidance for TAPI-2 class inhibitors

• Primary stock solvent: DMSO is preferred due to high solvating power for hydroxamate-containing inhibitors and compatibility with biological assays at low final percentages.
• Secondary solvents: DMF can dissolve many hydroxamates but is less preferred in bioassays. Ethanol or methanol may dissolve limited amounts; aqueous buffers generally require co-solvent or pH adjustment.
• Aqueous handling: Prepare concentrated DMSO stocks (e.g., 10–50 mM), then dilute into buffered media immediately before use. Maintain final DMSO ≤0.1–0.5% v/v when possible.
• Polarity and miscibility (literature/general): DMSO (ε ≈ 47) is fully miscible with water and many organics, minimizing precipitation during titration. Ethanol is also water-miscible but may offer lower compound solubility.

Comparison (general)

• DMSO: maximum solubility, assay-compatible at low %; hygroscopic, can affect cells above ~0.5–1%.
• Ethanol: cleaner evaporation, but often lower solubility; biological tolerance varies.
• Aqueous buffer only: often insufficient solubility; risk of precipitation and adsorption losses.

Tips

• Warm and vortex DMSO stocks gently to ensure dissolution; avoid prolonged heating.
• Filter sterilize diluted working solutions when needed using low-binding membranes.

Storage and Reconstitution

Item-specific (from Product Data)

• Storage: Protect from light; store at −20 °C; keep desiccated.
• Shipping: Ice chest with ice pads.

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

• Solvent: Dissolve in anhydrous DMSO to prepare a concentrated stock (e.g., 10–50 mM), based on your assay’s working range and solubility limits.
• Technique: Allow vial to equilibrate to room temperature in a desiccator before opening to prevent moisture condensation. Add pre-warmed DMSO, vortex gently, and sonicate briefly if needed. Avoid prolonged heating.
• Aliquoting: Dispense single-use aliquots into low-bind tubes to avoid repeated freeze–thaw cycles.
• Storage of solutions: Store DMSO stocks at −20 °C or below, protected from light. Typical practice is to use within weeks to a few months; verify integrity by analytical check (e.g., HPLC) as needed.
• Handling cautions: Minimize exposure to moisture and air; recap promptly. When diluting into aqueous buffers, add stock last with rapid mixing to avoid local supersaturation and precipitation.

Research use note

• For research use only. Not for human or veterinary use. Consult the CoA and SDS for lot-specific guidance and safety before first use.

Structure and Identity

Item-specific (from Product Data)

• Product name: TAPI-2 (SKU: T275536)
• CAS: 187034-31-7
• PubChem CID: 10093303
• InChIKey: 203408 (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.

Literature/General characterization (for context; not item specifications)

• Compound type: small-molecule, hydroxamate-based metalloprotease inhibitor commonly used as a TACE/ADAM17 inhibitor and broad-spectrum MMP inhibitor tool compound.
• Key structural motif (literature): a hydroxamic acid functional group capable of chelating the catalytic Zn2+ of metalloproteases; additional amide linkages and hydrophobic substituents that enhance affinity and selectivity toward ADAM/MMP family enzymes.
• 2D structural features (qualitative, literature): contains one hydroxamate (–CONHOH), at least one tertiary/branched hydrophobic side chain, and peptide-like amide backbone elements that position the hydroxamate for active-site binding.

Notes

• The exact stereochemistry, ring/chain substitution pattern, and full line notation should be verified against the Certificate of Analysis (CoA) or official spectral data for this specific lot/item.

Synthetic Utility

Not a general building block.

• TAPI-2 is a finished small-molecule inhibitor and is not typically employed as a synthon or reagent in organic synthesis.

General chemistry note (literature)

• The hydroxamate functional group present in this inhibitor class is synthetically accessible via coupling of activated carboxylic acid derivatives with hydroxylamine and subsequent elaboration; however, such transformations pertain to the synthesis of TAPI-2 analogs rather than the use of TAPI-2 itself as a reagent.

Target Specificity

Item-specific

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

Literature/general context

• Commonly described as an inhibitor of ADAM17/TACE and related metalloproteases via zinc chelation by the hydroxamate moiety. Actual selectivity and potency are assay- and lot-dependent; consult primary literature and verify under your conditions.