Pentosidine TFA , CAS No.225784-09-8

CAS: 225784-09-8 Cat. No.: P1442343 Fórmula: C₁₉H₂₇F₃N₆O₆ Peso molecular: 492.45

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Descripción general

Pentosidine TFA is an advanced glycation end product (AGE) and cross-linked substance with fluorescent properties. Pentosidine TFA is present in various human tissues and can serve as a biomarker for diabetes, aging, uremia, protein accumulation damage, and non-enzymatic modification of long-lived proteins in the Maillard reaction. It aids in gaining a deeper understanding of the overall role of the Maillard reaction in aging and disease.

Specifications

Condiciones de almacenamiento de almacenamiento

Store at -20°C

Enviado en

Ice chest + Ice pads

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Nombres e identificadores

• Peso molecular: 492.45

Application Protocols

Item-specific, tested applications: Not specified for this item; refer to CoA/Spec Sheet.

General example protocols (literature; adapt to your method)

• Preparation of a primary stock: Equilibrate vial to room temperature in the dark. Dissolve an accurately weighed amount in water with 0.05–0.1% formic acid to a convenient concentration (e.g., mM-range). Vortex to mix; filter (0.2 µm) if needed. Aliquot into amber vials and store at -20°C.
• HPLC–FLD calibration curve: Prepare serial dilutions in mobile phase A. Inject in duplicate/triplicate. Monitor Ex ≈ 335 nm / Em ≈ 385 nm. Verify linearity and lack of carryover. Include a mid-level QC in each sequence.
• LC–MS/MS: Prepare standards in 0.1% formic acid in water. Use matrix-matched calibration when quantifying in complex samples. Monitor characteristic MRM transitions established during method development. Assess matrix effects by post-column infusion or post-extraction spike experiments.
• Spike–recovery assessment: Spike known amounts into pre-extracted or pre-digested matrix. Process alongside samples to determine recovery and method precision.

Notes

• Protect from light at all stages. Use low-binding plastics or silanized glass if adsorption is observed.

Biological Roles

General biology (literature; no medical claims)

• Pentosidine is a structurally defined advanced glycation end-product (AGE) that forms in proteins via nonenzymatic reactions between lysine and arginine side chains and reactive carbonyl species derived from pentoses (e.g., ribose). It introduces covalent crosslinks into long-lived extracellular matrix proteins such as collagen and elastin.
• Chemical features: an imidazolium-based crosslink that is intrinsically fluorescent, facilitating its detection in biological matrices without derivatization.
• Formation pathways: Maillard chemistry progressing from Schiff bases to Amadori products and subsequent oxidative and dehydrative steps that yield crosslinking AGEs; pentoses accelerate formation relative to hexoses (literature).
• Biochemical impact: Crosslinking can stiffen protein matrices, alter proteolytic susceptibility, and modify receptor interactions; pentosidine serves as a quantitative marker for cumulative glycation and oxidative stress burden in tissues and food matrices (literature).
• Analytical significance: Because of its defined structure and fluorescence, pentosidine is widely used as a surrogate indicator of total AGE load in experimental systems, enabling normalization across studies.

Notes for researchers

• Matrix binding and co-extracted salts can quench or enhance fluorescence; internal standards and matrix-matched calibration are recommended (literature).
• Avoid clinical interpretation within research-use-only scope; use pentosidine levels strictly as experimental readouts.

Buffer Applications

Applicability

• Pentosidine TFA is not a buffering agent. However, buffer selection is important for preparing stable, reproducible analytical standards and samples.

Practical guidance (literature)

• Stock solutions: Prepare in water acidified with ~0.05–0.1% formic acid or dilute mineral acid (e.g., 0.01–0.1 M HCl) to enhance stability and prevent adsorption to glassware. Exact concentrations and recipes should be determined by method requirements.
• Working solutions: Use the same buffer composition as your chromatographic mobile phase (minus organic content when appropriate) to minimize injection solvent effects.
• pH considerations: Maintain acidic pH (≈2–4) for RP-HPLC or LC–MS to improve peak shape and reduce on-column secondary interactions for this highly polar, basic analyte.
• Additives: Avoid primary amine-containing buffers (e.g., Tris) that may interact with detection or the analyte. Volatile acids (formic/acetic) are preferred for LC–MS compatibility.

Notes

• For fluorescence plate assays, phosphate buffer at mildly acidic pH can be used if compatible with the optical readout; validate for background fluorescence.
• Always filter and degas buffers; prepare fresh or store aliquots refrigerated and protected from light to maintain fluorescence integrity (general lab practice).

Green Alternatives

Context

• As an analyte/standard rather than a process solvent or bulk reagent, the green-chemistry focus is on solvent systems and sample preparation choices used with Pentosidine TFA.

Greener choices (literature/guidance)

• Mobile phase modifiers: Prefer formic acid or acetic acid over TFA for LC–MS workflows to reduce ion suppression and facilitate lower solvent usage by improving sensitivity.
• Solvent selection: Favor water-rich mobile phases and ethanol (where compatible) over acetonitrile/methanol when fluorescence-only detection is used and separation performance remains acceptable.
• Sample prep: Employ microscale workflows (µSPE, on-line cleanup) and miniaturized hydrolysis/digestion to cut down acid/solvent consumption. Consider enzymatic digestion at mild conditions in place of strong-acid hydrolysis when fit-for-purpose.

Trade-offs

• Replacing acetonitrile with ethanol/water can increase viscosity and backpressure and may compromise resolution.
• Avoiding TFA can slightly broaden peaks for very polar analytes on certain columns; optimization of column chemistry (e.g., embedded polar groups, HILIC) often compensates.

Implementation tips

• Validate greener methods with side-by-side precision/accuracy and detection-limit comparisons.
• Use column chemistries designed for aqueous-rich conditions to allow higher water fractions without performance loss.

Pharmaceutical Uses

Scope

• This product is supplied for research use only. It is not intended for human or veterinary use, diagnostic procedures, or as an active pharmaceutical ingredient.

Formulation-related context (literature/general)

• Pentosidine is not used as an excipient. Its role in pharmaceutical or bioprocess contexts is confined to analytical reference material for characterizing glycation levels in biomaterials or protein-based formulations under forced degradation or stability studies.
• Reference standard usage: Can be employed to develop and validate analytical methods that monitor AGE formation in protein therapeutics during stress testing (e.g., heat/light exposure, oxidative conditions), provided appropriate containment and documentation are maintained.

Regulatory considerations

• No pharmacopeial monograph is known for pentosidine; if methods are intended for GMP environments, qualify the reference material internally (identity, purity, stability) and establish chain-of-custody and storage controls consistent with quality system requirements.

Operational guidance

• Maintain traceable records of lot numbers and CoAs.
• Where quantitative results inform process decisions, confirm concentration by an orthogonal method (e.g., qNMR), and bracket calibration over the expected range of analyte in samples.

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.

Literature/general properties for pentosidine (base or salt; indicative, not item specifications)

• Physical state: typically isolated as a solid; highly polar and hygroscopic behavior is common for AGE standards (literature).
• Solubility: readily soluble in water and aqueous acids; miscible at analytical concentrations in polar protic solvents; DMSO stock solutions are commonly used (literature).
• Acid–base: contains multiple basic nitrogens; forms stable salts with strong acids such as TFA, increasing water solubility (literature).
• Spectroscopy: intrinsically fluorescent AGE; typical excitation ≈ 325–335 nm and emission ≈ 380–400 nm depending on medium, pH, and matrix (literature).
• Partitioning: expected very low logP and strong retention on HILIC; poor retention on purely hydrophobic phases without ion-pairing (literature).

Not provided for this specific item (do not infer; see CoA/SDS)

• Melting point, boiling point, density, refractive index, water/peroxide/metal limits, UV cutoff, exact pKa values.

Practical notes

• Prepare and store solutions under low light to minimize photobleaching of the fluorophore (literature).
• Filtration through low-protein-binding membranes (e.g., PVDF, PTFE) is advisable prior to chromatographic use (general lab practice).

Quality and Grades

Item-specific (from Product Data)

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

General guidance (literature/industry practice)

• Reference-standard use: Pentosidine TFA is commonly supplied as a research/analytical standard for AGE quantification in complex matrices (e.g., collagen digests, tissue hydrolysates). For such use, low levels of residual inorganic salts, minimal moisture, and well-defined counterion content are advantageous.
• Identity confirmation: Typical quality control includes HRMS, 1H/13C NMR in D2O or DMSO-d6, and purity assessment by HPLC/UPLC with UV/fluorescence detection and/or LC–MS.
• Counterion considerations: As a TFA salt, the exact TFA stoichiometry can influence calculated concentrations and LC–MS ionization. The CoA should report counterion content or provide molecular weight for the salt form used in assay calculations.
• Chromatography-grade expectations: For fluorescence/HPLC applications, low UV background and minimal fluorescent impurities are important to maintain assay linearity and detection limits.

Recommendation

• Use the supplied CoA to derive the precise molecular weight for concentration calculations. If performing quantitative work, prepare gravimetric primary stocks and verify by an orthogonal assay (e.g., qNMR) when method validation requires it.

Reaction and Applications

Scope for this product

• Pentosidine TFA is primarily used as an analytical reference standard and spike-in control rather than as a synthetic reagent.

Analytical applications (literature)

• Calibration standard: Construct external or internal calibration curves for pentosidine quantification by HPLC with fluorescence detection (typical Ex/Em ≈ 335/385 nm) or by LC–MS.
• Method validation: Assess accuracy, precision, recovery, matrix effects, LOD/LOQ in complex biological or food-derived matrices (e.g., collagen-rich hydrolysates).
• Spike–recovery and QC: Use to monitor sample prep efficiency (acid hydrolysis, enzymatic digestion, solid-phase extraction) and chromatographic performance over time.
• Chromatographic modes: Reverse-phase with aqueous acidic mobile phases; HILIC for enhanced retention of the highly polar analyte; ion-pairing is generally avoidable with optimized gradients (literature).

Complementary reactions/workflows

• Sample liberation: Pentosidine in proteins is commonly quantified after acid hydrolysis or enzymatic digestion of the protein matrix; exogenous standard enables absolute quantification (literature).
• Derivatization: Typically not required due to native fluorescence; nonetheless, pre-column derivatization can be used for multiplex AGE panels if methods demand unified detection parameters.

Practical considerations

• Maintain consistent pH and ionic strength across standards and samples to minimize fluorescence variability.
• Use amber vials and minimize exposure to intense UV/visible light.

Reaction Conditions

Analytical workflow conditions (literature; not item specifications)

• HPLC–FLD: Reverse-phase C18; mobile phase A: water + 0.05–0.1% formic acid; B: acetonitrile + 0.05–0.1% formic acid. Gradient with high aqueous content; detect at Ex ≈ 335 nm / Em ≈ 385 nm. Column temps 25–40°C commonly used.
• LC–MS/MS: Prefer volatile acids (formic/acetic). Multiple reaction monitoring of protonated molecular ion to characteristic fragments; minimize TFA to avoid ion suppression.
• HILIC: Amide or zwitterionic phases with acetonitrile-rich mobile phases (60–90% ACN) and low ionic strength buffers improve retention of very polar analytes like pentosidine.

Sample preparation

• Protein matrices: Acid hydrolysis (e.g., 6 M HCl, controlled temperature/time) or enzymatic digestion (e.g., pronase/collagenase cocktails) followed by desalting/SPE before analysis (literature). Spike pentosidine standard pre- or post-digestion depending on recovery study design.

Stability considerations

• Store solutions at low temperature, protected from light. Maintain acidic pH to limit degradation and fluorescence loss (literature).

Performance expectations

• Calibration curves are typically linear across low ng/mL to µg/mL ranges depending on detector sensitivity and matrix; validate LOD/LOQ and recovery for each method (literature guidance).

Safety and Handling

Item-specific (from Product Data)

• Storage: Store at -20°C.
• Shipping: Ice chest + ice pads.
• GHS classification, signal word, pictograms, H-statements: Not specified for this item; refer to SDS.

General safety guidance (literature/standard lab practice)

• Likely hazards: Organic salts of polyfunctional amines are commonly classified as irritants. In absence of item-specific classification, handle as a laboratory chemical of unknown toxicity.
• Personal protective equipment: lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Work in a fume hood when weighing powders or preparing solutions to avoid inhalation of dust/aerosols.
• Incompatibilities: Strong oxidizers and strong bases may degrade advanced glycation end-products; avoid prolonged exposure to elevated temperatures, high pH, or intense light which can diminish fluorescence (literature).
• Spill/accidental contact: For solids, avoid dust generation; collect mechanically. For solutions, absorb with inert material. Wash affected skin with soap and water; rinse eyes with water for several minutes. Seek medical attention per SDS guidance.
• Waste: Dispose according to institutional and local regulations for organic laboratory chemicals; do not discharge to drains.

Authoritative source

• Always consult the product-specific SDS for definitive hazards, first-aid measures, firefighting, and exposure controls. Where data are absent here, defer to the SDS and institutional EHS policies.

Solvent Selection

Applicability

• Pentosidine TFA is a highly polar, cationic organic salt. Solvent choice should prioritize solubility, chemical stability, and compatibility with analytical detection.

Preferred solvents (literature)

• Water and aqueous acids: Excellent solubility; 0.05–0.1% formic acid or 0.1 M HCl commonly used for stable stocks in LC–MS or fluorescence assays.
• Mixed aqueous-organic: Water/acetonitrile or water/methanol mixtures are compatible with HPLC. Slight acidification suppresses secondary interactions on silica-based phases.
• DMSO: Useful for preparing concentrated intermediate stocks; dilute promptly into aqueous media to working strength.

Less suitable

• Nonpolar solvents (e.g., hexanes, toluene) offer negligible solubility and are not recommended.

Comparative notes

• Formic acid vs TFA as mobile phase modifiers: Formic acid is generally preferred for LC–MS sensitivity, whereas TFA can improve peak shape on some columns but may suppress ESI response (literature).
• RP vs HILIC: Reverse phase (C18) can retain pentosidine under acidic, water-rich conditions; HILIC often provides stronger retention and better separation from hydrophilic interferents.

Practical tips

• Filter solutions through 0.2 µm membranes prior to injection.
• Protect solutions from strong light to preserve intrinsic fluorescence.
• Avoid high-pH buffers which can degrade AGE crosslinks over time (literature).

Storage and Reconstitution

Item-specific (from Product Data)

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

General guidance (literature/best practice)

• Protect from light and moisture. Allow the sealed container to warm to room temperature before opening to avoid condensation.
• Reconstitution: Dissolve in high-purity water or aqueous acidic solution (e.g., 0.05–0.1% formic acid or dilute HCl) to prepare stocks suitable for fluorescence or LC–MS. DMSO can be used for concentrated stocks, followed by dilution into aqueous media.
• Aliquoting: Prepare single-use aliquots in amber microvials to minimize freeze–thaw cycles.
• Freeze–thaw: Avoid repeated freeze–thaw; if unavoidable, limit to a small number of cycles and verify integrity by HPLC/LC–MS.
• Short-term storage of solutions: Refrigerate (2–8°C) protected from light for hours to a few days; for longer-term storage, freeze at -20°C or below. Confirm stability in your matrix and container system.
• Documentation: Record exact solvent, counterion assumptions, and concentration used to enable traceable quantitative work.

Disclaimer

• Where specific values or protocols are required, consult the product CoA and SDS. All uses are for research purposes only.

Structure and Identity

Item-specific (from Product Data)

• SKU: P1442343
• Product name: Pentosidine TFA (trifluoroacetate salt)
• CAS: 225784-09-8
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

General structural description (literature)

• Pentosidine is a well-characterized advanced glycation end-product (AGE) formed as a covalent crosslink between lysine and arginine residues mediated by a pentose-derived dicarbonyl pathway.
• Core motif: an aromatic imidazolium ring linking a lysine-derived amino group and an arginine-derived guanidino fragment through a pentose-derived bridge.
• Functionality highlights: guanidinium/secondary amine-derived nitrogens, multiple hydroxyls/carboxamide-like heteroatoms depending on tautomeric state; overall highly polar and cationic under acidic conditions.
• Salt form: the TFA (trifluoroacetate) counterion protonates the basic sites, typically enhancing aqueous solubility and stability during handling and chromatographic work.
• 2D description in words: a fused imidazolium-like heteroaromatic core bearing two aliphatic linkers that mimic segments of lysine and arginine side chains; multiple heteroatoms confer strong hydrogen-bonding capacity and high polarity.

Notes

• Exact stereochemistry and counterion stoichiometry of the supplied TFA salt are not specified for this item; consult the CoA for definitive structural identifiers.

Synthetic Utility

Relevance

• Pentosidine TFA is not commonly used as a building block or reagent in synthetic chemistry; its primary value is as a structurally defined analyte/standard.

Contextual utility (literature)

• Model compound: Serves as a model AGE crosslink for studies probing chemical reactivity of imidazolium-linked protein crosslinks toward reduction, cleavage, or remodeling by small molecules.
• Benchmarking reactivity: Useful for testing depolymerization/cleavage conditions (e.g., reductants, nucleophiles) aimed at reversing advanced glycation crosslinks in model systems, enabling mechanistic understanding without using complex protein matrices.
• Method development: Facilitates optimization of hydrolysis, extraction, and clean-up workflows intended to liberate and quantify protein-bound pentosidine.

Notes

• Because of its high polarity and multiple basic sites, derivatization strategies (e.g., silylation or acylation) can be explored for GC-based methods, although LC-based methods are generally preferred (literature).
• Any transformations should be validated by spectroscopic and chromatographic methods to confirm structural integrity due to potential for rearrangements of the imidazolium core under harsh conditions.

Target Specificity

Not applicable

• This product is a small-molecule reference standard, not an antibody or affinity reagent.
• No antigen, epitope, clone, isotype, or species-reactivity information applies.