Teneligliptin-d8 , CAS No.1391012-95-5

CAS: 1391012-95-5 Cat. No.: T646291 Formula: C₂₂H₂₂D₈N₆OS Peso molecolare: 434.63

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Panoramica

Teneligliptin-d 8 is a deuterium labeled Teneligliptin (MP-513). Teneligliptin is a potent, orally available, competitive, and long-lasting DPP-4 inhibitor.

IC50& Target:DPP-4

Specifications

Meccanismi biochimici e fisiologici

Teneligliptin-d 8 is a deuterium labeled Teneligliptin (MP-513). Teneligliptin is a potent, orally available, competitive, and long-lasting DPP-4 inhibitor.

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.

Nomi e identificatori

• Sorrisi canonici: O=C([C@H]1NC[C@@H](N2C([2H])([2H])C([2H])([2H])N(C3=CC(C)=NN3C4=CC=CC=C4)C([2H])([2H])C2([2H])[2H])C1)N5CSCC5
• Peso molecolare: 434.63

Application Protocols

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

General note: No validated, item-specific protocols (e.g., tested assay conditions, recommended dilutions) are provided in the Product Data. Users should develop and qualify protocols appropriate to their matrix and instrumentation.

Biological Roles

General/literature context (not item-specific claims)

• Molecular target: Teneligliptin is a competitive inhibitor of dipeptidyl peptidase-4 (DPP-4; CD26), a serine exopeptidase that cleaves N-terminal dipeptides from peptides with penultimate proline/alanine (e.g., incretin hormones). The d8 isotopologue retains the same binding interactions; deuteration does not materially change target engagement under typical conditions.
• Research utility:
  • Probe for DPP-4 biochemistry, including active-site interactions and structure–activity relationships using MS-based assays.
  • Internal standard for quantifying teneligliptin in complex biological matrices, supporting pharmacokinetic and metabolism research in preclinical systems.
• Metabolism and disposition (parent compound, literature):
  • Teneligliptin undergoes oxidative metabolism and conjugation; deuteration at selected positions can help track isotope effects or exchange.
• Selectivity considerations:
  • Parent compound is characterized for DPP-4 selectivity over related peptidases (e.g., DPP-8/9) in the literature; such profiles inform assay design but should not be imputed to this specific SKU without supporting data.

Important note: This product is for research use only. No medical, diagnostic, or therapeutic use is intended or implied.

Buffer Applications

This product is a small-molecule analytical standard and is not used as a buffering agent. If incorporated into biochemical assays, it is typically dissolved in organic solvent (DMSO, MeOH, ACN) and then diluted into pre-existing buffers (e.g., formate/acetate or ammonium-based mobile phases for LC–MS, assay buffers for enzyme studies). Select buffer systems based on your analytical method rather than on this compound’s properties.

Green Alternatives

While Teneligliptin-d8 itself is a specialized analytical standard (no direct “greener” substitute), greener choices can be made in its use, especially in sample preparation and chromatography.

Greener solvent choices (general guidance)

• Prefer ethanol or isopropanol over acetonitrile/methanol where ionization and solubility permit; however, ACN/MeOH often deliver superior chromatographic performance for basic heterocycles.
• Use aqueous mobile phases with lower organic content where resolution and sensitivity allow; consider UHPLC to reduce total solvent consumption.
• Replace formic acid with ammonium bicarbonate for MS-compatible, mildly basic methods when appropriate, noting volatility and separation impacts.

Mini comparison (general)

• Acetonitrile: Excellent MS performance, low viscosity; derived from petrochemical sources; higher EHS burden.
• Methanol: Good MS performance; toxic but biodegradable; often a practical compromise.
• Ethanol: Renewable, lower toxicity; higher viscosity and sometimes poorer ESI performance for hydrophobic analytes.

Operational strategies

• Scale down: microflow/nanoflow LC–MS to cut solvent use and waste.
• Solid-phase extraction (SPE) with water-wettable sorbents can reduce organic volumes versus protein-precipitation methods.
• Consolidate batches and use multi-analyte panels to minimize runs.

Trade-offs: Greener solvents may modestly reduce sensitivity or alter selectivity; verify with system suitability tests.

Pharmaceutical Uses

Formulation/manufacturing context (no therapeutic claims)

• Role: Deuterated analogue used as a reference standard/internal standard in analytical methods for assay, content uniformity, stability-indicating methods, and impurity profiling of teneligliptin-containing research materials.
• Compendial status: Not specified for this item; refer to CoA/Spec Sheet and relevant pharmacopeial monographs for the non-deuterated parent when designing methods.
• Typical applications (general):
  • Stability studies: Monitor degradation pathways of teneligliptin with co-injected d8 standard to correct for variability.
  • Process development: Track recovery during purification steps using isotope-dilution mass spectrometry.
  • Cleaning validation: Spike-and-recover protocols using d8 as a surrogate to assess method performance.
• Advantages of isotopic internal standards:
  • Co-elute with analyte and behave similarly through extraction and ionization, improving quantitation robustness compared to structural analogues.

Item-specific information such as exact salt form, assay, and impurity limits is not provided and should be confirmed on the CoA/Spec Sheet.

Physical Properties

Item-specific properties

• 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.

General/literature guidance (not item specifications)

• Physical state: Teneligliptin analogues are typically crystalline solids at ambient conditions.
• Ionization: Basic nitrogen centers; protonation expected in acidic media; useful for LC–MS positive ESI.
• Solubility tendencies: Often sparingly soluble in water as a free base; soluble in polar aprotic organic solvents (DMSO, DMF, acetonitrile) and in aqueous media upon acidification or as salts (literature).
• Partitioning: Moderately lipophilic with ionizable functionality; actual logP/logD depends on ionization state and counterion (literature, parent compound data trends).
• Thermal behavior: Stable under normal lab conditions; avoid prolonged heating above typical drying temperatures to prevent degradation or isotopic exchange in protic media (general guidance).

Note: Where precise numeric values (mp, bp, density, pKa, logP, refractive index) are required for method development or regulatory documentation, obtain them from the item’s CoA/Spec Sheet or determine experimentally under your conditions.

Quality and Grades

Item-specific quality

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Isotopic enrichment (d8 content), residual unlabeled analogue, and residual solvents: Not specified for this item; refer to CoA/Spec Sheet.

Interpreting typical quality attributes for deuterated reference standards (general guidance)

• Isotopic purity: High d8 incorporation (with minimal d0–d7) is critical for use as an LC–MS internal standard to avoid interference with the analyte channel. Verify isotopologue distribution by high-resolution MS on the CoA.
• Chemical purity: HPLC/UPLC purity is commonly reported; low levels of process impurities improve baseline stability and quantitation accuracy.
• Counterion/form: Some teneligliptin materials are supplied as salts (e.g., hydrobromide) or as free base. The form impacts solubility and mass calculation; confirm on the CoA.
• Water/volatile content: Karl Fischer (water) and residual solvent data inform stability and accurate weighing; consult the CoA.
• Spectral identity: 1H/13C NMR (with attenuated 1H signals at labeled sites), HRMS, and IR typically support identity; for deuterated compounds, 2H NMR or MS isotopic pattern is informative.

Practical notes

• For quantitative bioanalytical work, match the matrix preparation and chromatographic conditions to minimize differential ionization between analyte and internal standard.
• Always cite the exact lot-specific specifications from the CoA in your methods.

Reaction and Applications

This item is primarily an analytical/biochemical tool rather than a synthetic reagent. Key research applications (general/literature):

• LC–MS/LC–MS/MS internal standard:
  • Serves as a stable isotopically labeled internal standard (SIL-IS) for quantification of teneligliptin in research matrices (plasma, tissue homogenate, microsomes). The +8 Da mass shift enables clear chromatographic co-elution with mass-channel separation.
  • Benefits: compensates for extraction recovery, matrix effects, and ion suppression; improves accuracy and precision of calibration and QC samples.
• Metabolic and stability studies:
  • Tracer in in vitro metabolic stability (microsomes/hepatocytes) to distinguish parent vs labeled compound and to probe isotope effects or exchange liabilities.
• Mechanistic enzymology and target engagement:
  • Supports studies of DPP-4 binding and displacement in biochemical assays where MS readouts are employed.
• Method development tips (general):
  • Match retention time with analyte; confirm no unexpected MRM cross-talk due to natural isotopic tails of the analyte or incomplete deuteration of the IS.
  • Optimize collision energies for distinct precursor→product transitions for d8 vs d0 when needed.
  • Validate linearity over the intended dynamic range; assess carryover and autosampler stability.

Note: No specific manufacturer application text was provided for this SKU; the above reflects common research uses of deuterated analogues.

Reaction Conditions

As an analytical standard, Teneligliptin-d8 is most often used in LC–MS workflows rather than in chemical reactions. The following are general, literature-informed method conditions for teneligliptin-class analytes; adapt as needed and verify experimentally. These are not item-specific specifications.

• Sample preparation (general):
  • Stock solutions: 1–10 mM in anhydrous DMSO or MeOH; store frozen in aliquots.
  • Biological matrices: Protein precipitation with ACN or MeOH (3–4× volume), vortex, centrifuge; supernatant diluted with aqueous mobile phase. Alternatively, SPE (mixed-mode cation exchange) for cleaner extracts.
• LC conditions (typical):
  • Column: C18 or phenyl-hexyl, 2.1 × 50–100 mm, 1.7–3 µm.
  • Mobile phase A: water + 0.1% formic acid (or 5–10 mM ammonium formate, pH ~3.0–3.5).
  • Mobile phase B: acetonitrile or methanol.
  • Gradient: 5–60% B over 3–6 min; adjust for retention/k′ matching of d0/d8.
  • Flow: 0.2–0.4 mL/min; temp 30–40°C.
• MS conditions (typical):
  • Ionization: ESI positive.
  • Acquire distinct MRM/PRM transitions for d8 vs d0 to avoid overlap with natural isotopic envelope. Optimize cone/fragmentor and collision energy empirically.
• Stability checks:
  • Assess bench-top (4–6 h), autosampler (4–24 h at 4–10°C), freeze–thaw (≥3 cycles), and long-term stability per your validation protocol.

Note: Confirm any labile deuterium positions by testing in aqueous acidic/basic conditions to rule out H/D back-exchange during sample prep.

Safety and Handling

Item-specific hazard information

• 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 safety (always defer to the SDS for authoritative guidance)

• PPE: Wear lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Use a fume hood during weighing, dissolution, and transfers to minimize inhalation exposure.
• Handling: Avoid generation of dust/aerosols. Prepare stock solutions with anhydrous solvents to minimize hydrolysis or isotopic exchange in strongly protic/acidic media.
• Incompatibilities (general): Strong oxidizers; strong acids/bases can promote degradation or isotopic H/D exchange. Avoid prolonged exposure to moisture if using the free base.
• First aid overview: If inhaled, move to fresh air; seek medical attention if symptoms occur. In case of skin or eye contact, rinse thoroughly with water for at least 15 minutes and remove contaminated clothing. If ingested, rinse mouth and seek medical advice. Provide the SDS to responders.
• Waste: Dispose of solutions and solids according to institutional guidelines for organic small molecules; do not discharge to drains. Segregate halogenated vs non-halogenated solvent waste appropriately.
• Transport/storage risks: Keep tightly closed, protected from light, at low temperature per storage guidance. Shipments for this item are prepared with cold packs as noted in Product Data.

Solvent Selection

Guidance for preparing and using Teneligliptin-d8 solutions (general/literature)

• Primary stock solvents:
  • DMSO (anhydrous): Excellent solubilizing power for basic, heteroaromatic drug-like molecules; compatible with LC–MS sample preparation at low v/v%.
  • Methanol or acetonitrile: Useful for LC–MS calibration solutions and working standards; low viscosity and good ESI compatibility.
  • Water with 0.1% formic acid: For aqueous working solutions when the compound is in a protonated state; avoid long exposure if isotopic exchange is a concern.
• Miscibility and polarity:
  • DMSO, MeOH, ACN are fully miscible with water, enabling straightforward serial dilution schemes for calibration curves.
• When to choose which:
  • DMSO for concentrated freezer stocks (e.g., 1–10 mM) due to stability and solubility.
  • MeOH/ACN for daily working solutions and LC–MS autosampler vials to reduce matrix effects and improve spray stability.
  • Buffered aqueous media (e.g., 0.1% FA or 10 mM ammonium formate) for final injection or spiking into biological matrices.
• Practical tips:
  • Filter or centrifuge to remove particulates before LC–MS.
  • Minimize water content and strong acids/bases during long-term storage to limit H/D back-exchange at labile positions.
  • Validate adsorption losses by using low-bind plastics or glass vials, especially at low ng/mL levels.

Storage and Reconstitution

Item-specific instructions from Product Data

• Storage conditions: Store at -20°C.
• Shipping: Shipped in ice chest with ice pads.

General handling and reconstitution guidance (not item-specific specs)

• Upon receipt: Allow the sealed container to equilibrate to room temperature before opening to prevent condensation.
• Reconstitution:
  • Prepare concentrated stock solutions in anhydrous DMSO or methanol (e.g., 1–10 mM). Vortex to dissolve fully.
  • For LC–MS calibration standards, dilute stocks with acetonitrile, methanol, or mobile phase containing volatile buffers (e.g., 0.1% formic acid or 5–10 mM ammonium formate).
  • Avoid strong acids/bases and prolonged exposure to aqueous media if H/D exchange is a concern.
• Aliquoting and freeze–thaw:
  • Dispense single-use aliquots to minimize freeze–thaw cycles. Store tightly sealed at -20°C (or lower if compatible with container) protected from light and moisture.
  • Use low-bind tubes/vials to reduce adsorption at low concentrations.
• Stability checkpoints:
  • Verify solution stability in your matrix (bench-top, autosampler, freeze–thaw, long-term) as part of method qualification.

Always defer to the product’s CoA and SDS for lot-specific guidance on stability, storage form (free base vs salt), and safe handling.

Structure and Identity

Brief description: Teneligliptin-d8 is the deuterium-labeled analogue (d8) of the DPP-4 inhibitor teneligliptin, intended for research and analytical applications (e.g., LC–MS internal standard). It preserves the parent scaffold and inhibitory profile while introducing eight deuterium atoms to enable isotopic discrimination.

• Chemical identity (item-specific):
  • 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.
  • CAS: 1391012-95-5 (for the d8 isotopologue; literature association, verify on CoA)
• Structural features (general/literature):
  • Core scaffold: fused heteroaromatic/heterocyclic framework bearing a secondary amine and a nitrile-containing side chain typical of teneligliptin.
  • Functional groups: tertiary/secondary amines (basic centers), nitrile (–C≡N), thiazolidine/imidazole-like heterocycles depending on depiction (literature, parent compound).
  • Isotopic labeling: eight protium positions in the parent teneligliptin are replaced with deuterium (2H), conferring an exact mass shift of +8.0005 u relative to the non-labeled analogue (literature/general isotopic principle).
  • Stereochemistry: Teneligliptin contains defined stereocenters in the parent structure; the d8 analogue maintains the same configuration (literature). Exact stereochemical specification for this item is not provided; consult CoA.
• 2D structure description (general): polycyclic, nitrogen- and sulfur-containing heterocycles linked to an amine-bearing side chain terminating in a nitrile; aromatic and saturated rings present; deuterium labels are typically placed on metabolically stable aromatic/benzylic positions (literature practice).

Synthetic Utility

Teneligliptin-d8 is not typically employed as a synthetic building block due to cost and specialized labeling. However, it can be relevant in method validation and mechanistic studies.

General notes (literature/practice)

• Isotope effect studies: Comparing reaction or degradation rates of d8 vs d0 analogues can reveal mechanistic insights (e.g., benzylic oxidation liability). Primary kinetic isotope effects are usually small for deuteration at non-labile positions in solution-phase transformations not involving C–H cleavage at the labeled sites.
• Degradation pathway mapping: Use under forced-degradation conditions (acid/base/oxidative, photolysis) to distinguish pathways and help assign fragment origins in MS/MS.
• Reference for impurity synthesis: When synthesizing impurities or metabolites of the parent, the d8 standard provides a mass-resolved internal calibrant for LC–MS structure confirmation.

If a synthetic transformation is intended using this material, carefully evaluate the risk of H/D exchange under acidic/basic or catalytic hydrogenation conditions. For preparative chemistry, unlabeled teneligliptin is generally more appropriate.

Target Specificity

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

Note: This SKU is a small-molecule standard rather than an antibody/biologic. Target-binding characteristics (e.g., DPP-4 inhibition parameters) are not provided for this item.