This compound belongs to the class of organic compounds known as polypeptides. These are peptides containing ten or more amino acid residues.
External Descriptors
Not available
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.
Certificats (CoA, COO, BSE/TSE et tableau d'analyse)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propriétés chimiques et physiques
Poids moléculaire
1382.500 g/mol
XLogP3
Hydrogen Bond Donor Count
17
Hydrogen Bond Acceptor Count
17
Rotatable Bond Count
33
Exact Mass
1381.66 Da
Monoisotopic Mass
1381.66 Da
Topological Polar Surface Area
512.000 Ų
Heavy Atom Count
100
Formal Charge
0
Complexity
2760.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
9
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
2
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Application Protocols
Item-specific, validated application data are not provided in the Product Data. The following are general, literature-informed examples to guide method setup; optimize for your system.
Ligand binding assay (membrane preparation):
Prepare serial dilutions (e.g., 10 pM–1 µM) in binding buffer (50 mM HEPES, 1 mM CaCl2, 5 mM MgCl2, 0.1% BSA, pH 7.4).
Incubate with membranes expressing GnRHR and a radiolabeled/fluorescent GnRH probe; determine displacement to estimate Ki.
Functional Ca2+ assay (cell-based):
Load cells with a Ca2+ indicator (e.g., Fluo-4 AM). Stimulate with Nafarelin at 0.1 nM–100 nM and record fluorescence changes; include vehicle and known agonist controls.
LC–MS reference standard:
Prepare 0.1–1.0 mg/mL stock in water or 10% ACN with 0.1% formic acid. Create calibration curves via serial dilution. Store aliquots at −20°C; avoid repeated freeze–thaw.
Adsorption control:
Use low-bind tubes and 0.1% BSA in assay buffers at sub-nanomolar concentrations to minimize surface losses.
Note: These are general templates, not validated protocols for this product lot.
Biological Roles
Literature/general information (not a medical claim):
Mechanistic role: Nafarelin is a synthetic agonist of the gonadotropin-releasing hormone (GnRH) receptor, a class A GPCR primarily coupling to Gq/11. Agonism activates phospholipase Cβ, elevates IP3 and intracellular Ca2+, and can engage downstream PKC/MAPK pathways.
Structural pharmacology: Incorporation of D-2-naphthylalanine at position 6 increases metabolic stability against endopeptidases and enhances receptor affinity relative to native GnRH. The N-terminal pyroglutamyl cap and C-terminal Gly–NH2 are conserved features critical for receptor recognition.
In vitro outcomes: Sustained or high-efficacy agonism can trigger receptor internalization and desensitization, enabling studies of receptor trafficking and homologous desensitization dynamics.
Assay relevance: Serves as a tool compound for dissecting GnRH signaling kinetics, biased agonism, and structure-activity relationships among GnRH analogs.
Physicochemical context: As a polar decapeptide, it exhibits limited passive permeability; cellular effects in intact systems typically result from receptor activation at the cell surface rather than intracellular target engagement.
Item-specific note: No biological testing data for this catalog item are provided in the Product Data; consult primary literature and your internal controls for benchmarking activity.
Buffer Applications
This product is not a buffer reagent. However, appropriate buffer selection is crucial for its handling in assays.
Practical buffer guidance (general):
Common media: PBS (pH 7.2–7.4), HEPES (10–25 mM, pH 7.2–7.6), or acetate buffer (pH 4.5–5.5) depending on assay requirements and peptide stability.
Additives to reduce adsorption: 0.01–0.1% BSA or 0.01–0.05% Tween-20 can diminish losses to plastics and glass; verify that additives do not interfere with your readout.
Metal sensitivity: Not typically metal-chelating; EDTA is generally compatible if needed for enzymatic assays.
Filtration: Use 0.22 µm low-protein-binding membranes for sterilization prior to cell-based assays.
Stability notes (general):
Avoid prolonged exposure at extreme pH (<3 or >9) to limit backbone/side-chain degradation.
Maintain chilled conditions for long incubations; prepare fresh working solutions when possible.
Item-specific: No buffer recipes or pKa values are provided in the Product Data for this item.
Green Alternatives
For peptide research materials like Nafarelin acetate, the key “green” levers are solvent selection, process minimization, and waste management rather than substituting the compound itself.
Greener solvent choices (general guidance):
Prefer aqueous buffers and water where compatible with assay and stability.
Use ethanol or isopropanol for cleaning over chlorinated solvents when feasible.
Minimize use of HFIP/TFA; substitute with acetic or formic acid for LC–MS sample prep when possible.
Comparison (general, literature):
| Use case | Conventional option | Greener alternative | Trade-offs |
|---|---|---|---|
| LC sample acidifier | 0.1% TFA | 0.1% formic or acetic acid | Slightly broader peaks; improved MS sensitivity |
| Initial dissolution | Neat DMSO | Water with mild heating/sonication | May not reach high stock concentrations |
| Column cleaning | Acetonitrile-heavy gradients | MeOH/H2O gradients where compatible | Viscosity/backpressure changes |
Operational practices:
Prepare concentrated stocks to reduce total solvent volumes; aliquot to extend shelf life and limit waste.
Use low-bind consumables to avoid repeated re-preparations due to adsorption losses.
No therapeutic or clinical claims are made. The following pertains to laboratory and manufacturing support contexts.
Item-specific pharmacopeial status: Not specified for this item; refer to CoA/Spec Sheet and applicable compendia.
General laboratory/manufacturing support uses (literature/practice):
Reference standard: Employed as a qualitative/quantitative reference for method development and system suitability in QC labs (e.g., peptide mapping, assay specificity, impurity profiling).
Process development: Model GnRH analog for studying adsorption, filtration recovery, and stability during upstream/downstream handling.
Formulation research: Tool compound for exploring peptide solubilization strategies, counterion effects (acetate vs others), and excipient screening (tonicity agents, antioxidants) in early-stage studies.
Documentation and compliance:
For GMP or regulated use, source a lot with appropriate documentation (CoA, traceability, impurity data) and qualify it per your internal procedures.
Verify counterion content and water/solvent residuals when such attributes are critical to your method or stability specifications.
Item-specific limitations: No grade or certification details are provided in the Product Data; suitability for regulated applications must be determined by the end user.
Physical Properties
Note: No item-specific specifications (e.g., exact MW, elemental analysis, water content) are provided in the Product Data.
Item-specific:
Appearance: 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 properties for Nafarelin (informational, not product specifications):
Physical state: Typically a white to off-white peptide solid (literature).
Solubility: Readily soluble in water, dilute acetic acid, and polar aprotic solvents such as DMSO; limited solubility in nonpolar solvents (literature).
Acid/base behavior: Multiple basic (Arg, His) and acidic/neutral functional groups; acetate counterions present in salt forms (literature).
Hygroscopicity: Peptide acetate salts can be mildly hygroscopic; handle quickly in ambient air and reseal promptly (general peptide handling guidance).
Partitioning: Highly polar, expected low logP; strong preference for aqueous media (literature expectations for decapeptides).
Practical handling notes (general):
Prepare concentrated stocks (e.g., 1–5 mM) in sterile water or DMSO, then dilute into assay buffers.
If foaming occurs during dissolution, gently vortex or sonicate briefly to aid wetting.
For analytical work (LC–MS), avoid strong TFA in sample diluent when possible to minimize ion suppression; low % formic or acetic acid is commonly preferred (literature practice).
Quality and Grades
Item-specific quality information:
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers: Not specified for this item; refer to CoA/Spec Sheet.
Interpreting peptide quality (general guidance):
Purity reporting: Peptide materials are commonly reported by HPLC area % with complementary identity confirmation by MS. If present, the CoA/Spec Sheet will indicate the HPLC method (column, gradient, detection wavelength) and acceptance criteria.
Counterion content: “Acetate” denotes neutralization with acetic acid; the exact acetate stoichiometry can vary with protonatable sites (e.g., Arg, His). Counterion quantitation may be listed as % acetate or via ion chromatography in detailed CoAs.
Residual solvents and water: Peptide lots may list residual solvent (e.g., water, acetonitrile) content by KF/GC. Absent item-specific values, consult the CoA for your lot.
Identity testing: Typical methods include ESI-MS or MALDI-TOF for molecular mass, and, where applicable, amino acid analysis or peptide mapping.
Impurities: Epimerization, deletion sequences, and protecting group remnants are typical peptide-related impurities monitored by analytical HPLC and MS. For bioassays or analytical standards work, consider lots with higher HPLC purity and narrow MS envelope.
Reaction and Applications
This product is primarily used as a research ligand/standard rather than as a synthetic reagent.
Research applications (literature/general):
Receptor pharmacology: Potent GnRH receptor agonist used in binding and functional assays (e.g., intracellular Ca2+ mobilization, IP3 turnover) to characterize receptor activity and signaling bias.
Internalization/desensitization studies: Useful probe to investigate receptor trafficking and downregulation kinetics.
Analytical reference: Employed as a system suitability or calibration standard in LC–UV/LC–MS methods for peptide analysis; supports bioanalytical method development (retention behavior, ionization efficiency).
Stability studies: Model peptide for evaluating oxidative (e.g., Trp/Tyr), deamidation (Asn/Gln absent here), and racemization pathways under stress conditions.
Practical notes:
Adsorption control: Low-concentration working solutions may adsorb to plastics; precondition surfaces with 0.1% BSA or use low-bind polypropylene.
Oxidation mitigation: Prepare and store solutions under low light; include minimal antioxidant or degas buffers if oxidative artifacts are a concern (per lab SOPs).
Quantitation: For UV detection, aromatic residues (Trp, Tyr, naphthylalanine) provide strong absorbance near 280 nm; establish extinction coefficients experimentally for your matrix.
Not typically used for: Cross-coupling, Grignard, or other small-molecule synthetic reactions.
Reaction Conditions
Conventional chemical reaction conditions are not applicable to this product’s use. The following guidance concerns solution preparation and assay conditions (general literature/practice):
Stock solution preparation:
Water or buffer: Dissolve to 1–5 mM with gentle vortexing; if needed, sonicate briefly. Adjust pH to ~6–7.5 for stability unless your assay dictates otherwise.
DMSO co-solvent: For highly concentrated stocks (e.g., 10–50 mM), dissolve first in DMSO, then dilute into aqueous buffer while mixing to avoid precipitation; keep final DMSO ≤1–2% for biological assays.
Working solutions:
Prepare fresh daily or store aliquots at 2–8°C for short periods (hours to a day) to minimize degradation; protect from light.
Filter sterilize (0.22 µm, low protein-binding) for cell-based assays.
Environmental factors:
Temperature: Typical assays at 20–37°C; avoid unnecessary heating during dissolution.
Light/oxidation: Shield from strong light; minimize air exposure for extended incubations to limit aromatic oxidation (Trp/Tyr).
Analytical conditions (examples from general peptide practice):
RP-HPLC: C18, water/ACN with 0.05–0.1% formic or acetic acid; gradient elution over 10–30 min.
LC–MS: Prefer formic or acetic acid modifiers for improved ionization; monitor [M+H]+ and common multiply charged states.
Safety and Handling
Regulatory note: For research use only.
Item-specific hazard data:
Signal word: Not specified for this item; refer to SDS.
H-statements: Not specified for this item; refer to SDS.
GHS classification: Not specified for this item; refer to SDS.
Pictograms: Not specified for this item; refer to SDS.
General safety guidance for peptide solids (literature/practice):
Avoid inhalation of dust or aerosols; handle powders in a fume hood or with local exhaust ventilation.
Wear appropriate PPE: lab coat, nitrile gloves, and safety glasses; use respiratory protection if dust generation cannot be controlled.
Prevent cross-contamination between bioactive peptides; dedicate tools/areas where appropriate.
First aid overview: If inhaled—move to fresh air; if on skin—wash with soap and water; if in eyes—rinse with water for several minutes; if ingested—rinse mouth and seek medical advice. Always follow your institution’s protocols and consult the SDS.
Incompatibilities: Strong oxidizers may degrade peptide side chains; avoid prolonged exposure to strong acids/bases that can hydrolyze amide bonds.
Thermal/photostability: Peptides may undergo degradation under excessive heat or UV; protect from light where feasible and store as directed.
Spill response: Gently mist to suppress dust, collect with disposable towels or HEPA-filtered vacuum, and dispose of as laboratory chemical waste in accordance with local regulations.
Solvent Selection
Nafarelin acetate is a polar decapeptide salt; solvent choice prioritizes peptide stability, solubility, and downstream compatibility.
Moderately soluble: Methanol, ethanol (may need sonication).
Poorly soluble: Nonpolar solvents (e.g., hexanes, toluene) and many purely aprotic, low-polarity media.
Practical selection guidelines:
Bioassays/receptor studies: Use aqueous buffers (e.g., PBS, HEPES) with 0.1–0.5% carrier protein (BSA) if nonspecific adsorption is observed. Maintain pH ~6.5–7.5 unless assay dictates otherwise.
Analytical LC–MS: Prepare stocks in water or 10–20% ACN with 0.1% formic acid or acetic acid. Minimize TFA in the sample diluent to avoid ion suppression.
Sparingly soluble samples: Start with a small volume of DMSO to make a concentrated stock (e.g., 10–50 mM), then dilute into aqueous buffer while vortexing to keep final DMSO ≤1–2%.
Comparison (general):
Water vs DMSO: Water is preferred for biological compatibility; DMSO maximizes solubility for initial stock preparation.
Acetic acid (dilute) vs TFA: Both acidify to improve solubility; acetic acid is more MS-friendly, whereas TFA can sharpen HPLC peaks but suppress MS signal.
Storage and Reconstitution
Item-specific storage (from Product Data):
Storage conditions: Room temperature.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Reconstitution (general guidance for peptide acetates):
Solvents: Use sterile water, dilute acetic acid, or DMSO to prepare a concentrated stock. For biological assays, further dilute with compatible buffer (e.g., PBS, HEPES).
Concentration: Common stock concentrations are 1–5 mM in water or up to 10–50 mM in DMSO, subject to solubility and assay needs.
Mixing: Add solvent gradually along the vial wall, gently vortex; brief sonication may assist dissolution. Avoid vigorous foaming.
Aliquoting and stability (general):
After reconstitution, dispense single-use aliquots in low-bind tubes to avoid adsorption and freeze–thaw cycles.
Short-term storage of solutions: 2–8°C (hours to ≤1 day) is typical; for longer-term storage, freeze at −20°C or −80°C. Protect from light.
Freeze–thaw: Minimize cycles; thaw on ice and mix gently to ensure homogeneity.
Compatibility notes:
Avoid extended exposure to strong acids/bases or oxidants.
Verify container compatibility (glass or low-bind polypropylene) to reduce peptide loss.
Always consult the product’s CoA/SDS for lot-specific instructions and stability information.
Structure and Identity
Concise overview: Nafarelin acetate is a synthetic decapeptide analog of gonadotropin-releasing hormone (GnRH), typically supplied as an acetate salt for research use in receptor biology and analytical method development.
Item-specific (from Product Data):
SKU: N986601
Product name: Nafarelin Acetate
CAS: 76932-60-0
Storage conditions: Room temperature
Category: Small molecules and compound library (小分子和化合物库)
InChIKey: 111827 (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/structural description (general information, not item-specific specifications):
Structural class: Decapeptide GnRH analog containing one D–amino acid residue for enhanced metabolic stability.
Typical sequence motif: pGlu–His–Trp–Ser–Tyr–D-2Nal–Leu–Arg–Pro–Gly–NH2, where 2Nal = 3-(2-naphthyl)-alanine (literature).
Salt form: Commonly isolated as the acetate salt; number of acetate counterions depends on protonation state (literature, varies by supplier and conditions).
2D structure (verbal): A linear decapeptide with an N-terminal cyclic lactam (pyroglutamate), followed by aromatic and polar side-chains, a D-configured naphthylalanine at position 6 introducing a bulky aromatic moiety, and a C-terminal amidated glycine.
Synthetic Utility
Nafarelin acetate is a finished peptide ligand and is not typically used as a building block or reagent in synthetic chemistry.
Not typically applicable:
It does not serve as a coupling partner, catalyst, or protecting-group reagent in standard organic synthesis.
Related utility (general/research):
Benchmark analog: Serves as a reference in structure–activity relationship (SAR) studies of GnRH decapeptides, informing selection of position-6 substitutions and N-/C-terminal modifications during peptide design.
Analytical probe: Useful for validating peptide purification workflows (RP-HPLC), assessing column selectivity for aromatic-rich peptides, and optimizing gradient and ion-pairing conditions.
Retrosynthetic note (general):
Laboratory synthesis of Nafarelin typically proceeds via Fmoc solid-phase peptide synthesis (SPPS) using protected amino acids including Fmoc-D-2Nal-OH, followed by side-chain deprotection and cleavage; final salt exchange affords the acetate form. This is provided as context only; the catalog item is the final compound, not a precursor.
Target Specificity
Item-specific data: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general context:
Primary target: Gonadotropin-releasing hormone receptor (GnRHR, a class A GPCR).
Pharmacology: Agonist activity with high affinity reported for mammalian GnRHR in vitro; can be used as a positive control in receptor activation assays. Exact potency (Ki/EC50) values vary by assay system and are not specified for this item.
Note: No testing, clone, epitope, or species reactivity data are provided in the Product Data for this catalog entry.
Foire aux questions
How should this product be stored?
Store at room temperature.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 76932-60-0. InChIKey GUJYDLHACHDKAJ-CFWZQLQRSA-N.
What documentation is provided?
Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.
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