Nafarelin, Agonist of GnRH 1 receptor, CAS No.76932-56-4, Agonist of GnRH 1 receptor

CAS: 76932-56-4 Cat. No.: N287275 Fórmula: C₆₆H₈₃N₁₇O₁₃•xC₂H₄O₂ Peso molecular: 1322.47+x(60.05) Número EC: 686-425-8

GRADE & PURITY Moligand™, ≥98%

Specifications

Product Name

Nafarelin, Agonist of GnRH 1 receptor, CAS No.76932-56-4

Sinónimos

1X0094V6JV | EPA Pesticide Chemical Code 071401 | Nafarelinum | HS-2018 | NAFARELIN [MI] | NAFARELIN | Nafarelina | Nafarelinum (Latin) | CCG-270673 | Nafareline | (S)-1-(((R)-2-((S)-2-((S)-2-((S)-2-((S)-3-(1H-imidazol-4-yl)-2-((S)-5-oxopyrrolidine-2-carb

Grado

Moligand™

Especificaciones y pureza

Moligand™, ≥98%

Mecanismos bioquímicos y fisiológicos

Synthetic gonadotropin-releasing hormone (GnRH) agonist that stimulates secretion of luteinizing hormone (LH) and follicle-stimulating hormone (FSH). Repeated administration causes desensitization of pituitary GnRH receptors resulting in inhibition of gon

Secuencia

XEHWSYXLRPG(Modifications: X-1 = Glp, X-2 = 2-Nal, Gly-10 = C-terminal amide)

Tipo de acción

AGONIST

Mecanismo de acción

Agonist of GnRH 1 receptor

CAS

76932-56-4

Tipo de molécula

Peptide

Almacenamiento y envío

Condiciones de almacenamiento de almacenamiento

Store at -20°C,Desiccated

Enviado en

Ice chest + Ice pads

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic Polymers
    • Clase Polypeptides

• Kingdom: Organic compounds
• Superclass: Organic Polymers
• Clase: Polypeptides
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Polypeptides
• Alternative Parents: Peptides Tyrosine and derivatives Phenylalanine and derivatives Histidine and derivatives Leucine and derivatives N-acyl-alpha amino acids and derivatives Proline and derivatives Alpha amino acid amides Serine and derivatives Tryptamines and derivatives Amphetamines and derivatives Naphthalenes 3-alkylindoles N-acylpyrrolidines Pyrrolidinecarboxamides 1-hydroxy-2-unsubstituted benzenoids Pyrrolidine-2-ones Substituted pyrroles N-acyl amines Tertiary carboxylic acid amides Heteroaromatic compounds Imidazoles Secondary carboxylic acid amides Guanidines Primary carboxylic acid amides Lactams Propargyl-type 1,3-dipolar organic compounds Carboximidamides Azacyclic compounds Hydrocarbon derivatives Primary alcohols Carbonyl compounds Organopnictogen compounds Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Polypeptide - Alpha peptide - Tyrosine or derivatives - Phenylalanine or derivatives - Histidine or derivatives - Leucine or derivatives - N-acyl-alpha amino acid or derivatives - Proline or derivatives - Alpha-amino acid amide - Triptan - Serine or derivatives - 3-alkylindole - N-substituted-alpha-amino acid - Naphthalene - Amphetamine or derivatives - Alpha-amino acid or derivatives - Indole - Indole or derivatives - N-acylpyrrolidine - Pyrrolidine carboxylic acid or derivatives - Pyrrolidine-2-carboxamide - Phenol - 1-hydroxy-2-unsubstituted benzenoid - Fatty amide - N-acyl-amine - Monocyclic benzene moiety - Fatty acyl - Benzenoid - Pyrrolidone - 2-pyrrolidone - Substituted pyrrole - Pyrrole - Tertiary carboxylic acid amide - Heteroaromatic compound - Pyrrolidine - Imidazole - Azole - Primary carboxylic acid amide - Secondary carboxylic acid amide - Guanidine - Lactam - Carboxamide group - Carboximidamide - Organoheterocyclic compound - Propargyl-type 1,3-dipolar organic compound - Carboxylic acid derivative - Azacycle - Organic 1,3-dipolar compound - Organic nitrogen compound - Organic oxide - Hydrocarbon derivative - Carbonyl group - Alcohol - Organonitrogen compound - Organopnictogen compound - Organic oxygen compound - Organooxygen compound - Primary alcohol - Aromatic heteropolycyclic compound
• Descripción: 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

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

Objetivos asociados (humanos)

GNRHR Tclin Gonadotropin-releasing hormone receptor (0 Activities)

Discover Target: GNRHR

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Información genética

• Alternate Names: 1X0094V6JV | EPA Pesticide Chemical Code 071401 | Nafarelinum | HS-2018 | NAFARELIN [MI] | NAFARELIN | Nafarelina | Nafarelinum (Latin) | CCG-270673 | Nafareline | (S)-1-(((R)-2-((S)-2-((S)-2-((S)-2-((S)-3-(1H-imidazol-4-yl)-2-((S)-5-oxopyrrolidine-2-carb
• Reference:
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  • 23. Variations in folate pathway genes are associated with unexplained female infertility., Fertility and sterility, Altmäe, Signe S and 7 more authors.
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  • 30. Integrative predictive model of coronary artery calcification in atherosclerosis., Circulation, McGeachie, Michael M and 13 more authors.
  • 31. Cystathionine beta-synthase 844Ins68 polymorphism is not associated with the levels of homocysteine and cysteine in an Indian population., Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals, Kumar, Jitender J, Garg, Gaurav G, Karthikeyan, Ganesan G and Sengupta, Shantanu S.
  • 32. The expression and activity of cystathionine-γ-lyase and 3-mercaptopyruvate sulfurtransferase in human neoplastic cell lines., Amino acids, Jurkowska, Halina H, Placha, Wojciech W, Nagahara, Noriuki N and Wróbel, Maria M.
  • 33. Ancient origin of the CTH alelle carrying the c.200C>T (p.T67I) variant in patients with cystathioninuria., Clinical genetics, Espinós, C C and 8 more authors.
  • 34. Variation at the NFATC2 locus increases the risk of thiazolidinedione-induced edema in the Diabetes REduction Assessment with ramipril and rosiglitazone Medication (DREAM) study., Diabetes care, Bailey, Swneke D SD and 11 more authors.
  • 35. Maternal genes and facial clefts in offspring: a comprehensive search for genetic associations in two population-based cleft studies from Scandinavia., PloS one, Jugessur, Astanand A and 12 more authors.
  • 36. [Expression of cystathionine-γ-lyase/hydrogen sulfide pathway in CVB3-induced myocarditis in mice]., Zhongguo dang dai er ke za zhi = Chinese journal of contemporary pediatrics, Hua, Wang W and 6 more authors.
  • 37. Folate-metabolizing gene variants and pregnancy outcome of IVF., Reproductive biomedicine online, Laanpere, M M and 5 more authors.
  • 38. Specificity protein-1 as a critical regulator of human cystathionine gamma-lyase in smooth muscle cells., The Journal of biological chemistry, Yang, Guangdong G, Pei, Yanxi Y, Teng, Huajian H, Cao, Qiuhui Q and Wang, Rui R.
  • 39. Phylogenetic-based propagation of functional annotations within the Gene Ontology consortium., Briefings in bioinformatics, Gaudet, Pascale P, Livstone, Michael S MS, Lewis, Suzanna E SE and Thomas, Paul D PD.
  • 40. Expression of cystathionine β-synthase and cystathionine γ-lyase in human pregnant myometrium and their roles in the control of uterine contractility., PloS one, You, Xing-Ji XJ and 8 more authors.
  • 41. MicroRNA-21 represses human cystathionine gamma-lyase expression by targeting at specificity protein-1 in smooth muscle cells., Journal of cellular physiology, Yang, Guangdong G, Pei, Yanxi Y, Cao, Qiuhui Q and Wang, Rui R.
  • 42. H2S-Induced sulfhydration of the phosphatase PTP1B and its role in the endoplasmic reticulum stress response., Science signaling, Krishnan, Navasona N, Fu, Cexiong C, Pappin, Darryl J DJ and Tonks, Nicholas K NK.
  • 43. Characterization of hydrogen sulfide and its synthases, cystathionine β-synthase and cystathionine γ-lyase, in human prostatic tissue and cells., Urology, Guo, Hui H and 5 more authors.
  • 44. Sp1 is involved in regulation of cystathionine γ-lyase gene expression and biological function by PI3K/Akt pathway in human hepatocellular carcinoma cell lines., Cellular signalling, Yin, Peng P and 12 more authors.
  • 45. H₂S protects against pressure overload-induced heart failure via upregulation of endothelial nitric oxide synthase., Circulation, Kondo, Kazuhisa K and 14 more authors.
  • 46. Reduced cystathionine γ-lyase and increased miR-21 expression are associated with increased vascular resistance in growth-restricted pregnancies: hydrogen sulfide as a placental vasodilator., The American journal of pathology, Cindrova-Davies, Tereza T and 5 more authors.
  • 47. Dysregulation of hydrogen sulfide producing enzyme cystathionine γ-lyase contributes to maternal hypertension and placental abnormalities in preeclampsia., Circulation, Wang, Keqing K and 14 more authors.
  • 48. Regulation of cystathionine γ-lyase in mammalian cells by hypoxia., Biochemical genetics, Wang, Maoxian M, Guo, Zhanyun Z and Wang, Shilong S.
  • 49. A genome-wide association study of chemotherapy-induced alopecia in breast cancer patients., Breast cancer research : BCR, Chung, Suyoun S and 6 more authors.
  • 50. [Cystathionine γ-lyase]., Postepy higieny i medycyny doswiadczalnej (Online), Jurkowska, Halina H, Kaczor-Kamińska, Marta M, Bronowicka-Adamska, Patrycja P and Wróbel, Maria M.
  • 51. Decreased cystathionine-γ-lyase (CSE) activity in livers of type 1 diabetic rats and peripheral blood mononuclear cells (PBMC) of type 1 diabetic patients., The Journal of biological chemistry, Manna, Prasenjit P, Gungor, Neslihan N, McVie, Robert R and Jain, Sushil K SK.
  • 52. Hydrogen sulfide (H2S)/cystathionine γ-lyase (CSE) pathway contributes to the proliferation of hepatoma cells., Mutation research, Pan, Yan Y and 5 more authors.
  • 53. The cystathionine γ-lyase/hydrogen sulfide system maintains cellular glutathione status., The Biochemical journal, Lee, Zheng-Wei ZW, Low, Yi-Lian YL, Huang, Shufen S, Wang, Tianxiao T and Deng, Lih-Wen LW.
  • 54. The binding site for the transcription factor, NF-κB, on the cystathionine γ-lyase promoter is critical for LPS-induced cystathionine γ-lyase expression., International journal of molecular medicine, Wang, Maoxian M, Guo, Zhanyun Z and Wang, Shilong S.
  • 55. Regulation of cystathionine gamma-lyase/H₂S system and its pathological implication., Frontiers in bioscience (Landmark edition), Zhao, Kexin K, Li, Hongzhu H, Li, Shuangshuang S and Yang, Guangdong G.
  • 56. Dysregulation of hydrogen sulphide metabolism impairs oviductal transport of embryos., Nature communications, Ning, Nannan N and 5 more authors.
  • 57. Wnt/β-catenin signaling induces the transcription of cystathionine-γ-lyase, a stimulator of tumor in colon cancer., Cellular signalling, Fan, Kun K and 7 more authors.
  • 58. miRNA-30 family inhibition protects against cardiac ischemic injury by regulating cystathionine-γ-lyase expression., Antioxidants & redox signaling, Shen, Yaqi Y and 7 more authors.
  • 59. Role of the cystathionine γ lyase/hydrogen sulfide pathway in human melanoma progression., Pigment cell & melanoma research, Panza, Elisabetta E and 11 more authors.
  • 60. A proteome-scale map of the human interactome network., Cell, Rolland, Thomas T and 69 more authors.
  • 61. Neurodegeneration in Huntington's disease involves loss of cystathionine γ-lyase., Cell cycle (Georgetown, Tex.), Paul, Bindu D BD and Snyder, Solomon H SH.
  • 62. The importance of MTHFR, MTR, MTRR and CSE expression levels in Caucasian women with preeclampsia., European journal of obstetrics, gynecology, and reproductive biology, Seremak-Mrozikiewicz, Agnieszka A and 6 more authors.
  • 63. The importance of rs1021737 and rs482843 polymorphisms of cystathionine gamma-lyase in the etiology of preeclampsia in the Caucasian population., Ginekologia polska, Mrozikiewicz, Przemysław M PM and 8 more authors.
  • 64. Cystathionine γ-lyase, a H2S-generating enzyme, is a GPBAR1-regulated gene and contributes to vasodilation caused by secondary bile acids., American journal of physiology. Heart and circulatory physiology, Renga, Barbara B and 9 more authors.
  • 65. Correlation between the cystathionine-γ-lyase (CES) and the severity of peptic ulcer disease., African health sciences, Chen, Xiong X, Wan, Ying-Chun YC, Guo, Tao T, Xu, Can-Xia CX and Wang, Fen F.
  • 66. MPST but not CSE is the primary regulator of hydrogen sulfide production and function in the coronary artery., American journal of physiology. Heart and circulatory physiology, Kuo, Maggie M MM and 10 more authors.
  • 67. Transcriptional Regulation of Cystathionine-γ-Lyase in Endothelial Cells by NADPH Oxidase 4-Dependent Signaling., The Journal of biological chemistry, Mistry, Rajesh K RK and 8 more authors.
  • 68. LPS Up-Regulates Cystathionine γ -Lyase Gene Expression in Primary Human Macrophages via NF-κB/ERK Pathway., Inflammation & allergy drug targets, Badiei, Alireza A, Gieseg, Steven S, Davies, Sian S, Izani Othman, Mohd M and Bhatia, Madhav M.
  • 69. Radiation Exposure Promotes Hepatocarcinoma Cell Invasion through Epithelial Mesenchymal Transition Mediated by H2S/CSE Pathway., Radiation research, Pan, Yan Y, Zhou, Cuiping C, Yuan, Dexiao D, Zhang, Jianghong J and Shao, Chunlin C.
  • 70. Cystathionine γ-lyase(CSE)/hydrogen sulfide system is regulated by miR-216a and influences cholesterol efflux in macrophages via the PI3K/AKT/ABCA1 pathway., Biochemical and biophysical research communications, Gong, Duo D and 15 more authors.
  • 71. MicroRNA-186 promotes macrophage lipid accumulation and secretion of pro-inflammatory cytokines by targeting cystathionine γ-lyase in THP-1 macrophages., Atherosclerosis, Yao, Yan Y and 9 more authors.
  • 72. Cystathionine γ-lyase is expressed in human atherosclerotic plaque microvessels and is involved in micro-angiogenesis., Scientific reports, van den Born, J C JC and 5 more authors.
  • 73. Dichotomous effects of isomeric secondary amines containing an aromatic nitrile and nitro group on human aortic smooth muscle cells via inhibition of cystathionine-γ-lyase., Biochimie, Ji, Yajing Y and 6 more authors.
  • 74. Distinctive expression pattern of cystathionine-β-synthase and cystathionine-γ-lyase identifies mesenchymal stromal cells transition to mineralizing osteoblasts., Journal of cellular physiology, Gambari, Laura L and 6 more authors.
  • 75. Age-Dependent Allergic Asthma Development and Cystathionine Gamma-Lyase Deficiency., Antioxidants & redox signaling, Wang, Peipei P and 6 more authors.
  • 76. Augmented H2S production via cystathionine-beta-synthase upregulation plays a role in pregnancy-associated uterine vasodilation., Biology of reproduction, Sheibani, Lili L and 7 more authors.
  • 77. Total sulfane sulfur bioavailability reflects ethnic and gender disparities in cardiovascular disease., Redox biology, Rajpal, Saurabh S and 12 more authors.
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Application Protocols

No item-specific, validated application protocols are provided in the Product Data.

General starting points (research use only):

• Stock preparation: Prepare a sterile 1–10 mM stock in water with 0.1% acetic acid or in DMSO. Vortex gently; avoid foaming. Filter sterilize (0.22 µm) if aqueous and assay requires sterility.
• Calcium flux assay (outline): Plate GnRHR-expressing cells, load with Ca2+ dye (e.g., Fluo-4 AM), stimulate with serial dilutions of ligand, record fluorescence changes in real time. Include vehicle controls to account for DMSO.
• IP1/Second-messenger assays: Use commercial HTRF/IP-One kits following manufacturer instructions; generate concentration–response curves for EC50 estimation.
• Radioligand binding (outline): If using radioiodinated Tyr-containing peptide, perform saturation and competition binding on membranes or intact cells at 4°C to RT, with rapid filtration through GF/C filters and gamma counting.

These are literature-style templates only; optimize conditions (ligand concentrations, incubation times, temperatures) for your specific system.

Biological Roles

General literature context (no medical/clinical claims):

• Target: Gonadotropin-releasing hormone receptor (GnRHR), a class A GPCR predominantly coupling to Gq/11.
• Mode of action: Nafarelin is an agonist that mimics endogenous GnRH. Acute exposure activates GnRHR, engaging PLCβ, generating IP3/DAG, mobilizing intracellular Ca2+, and activating PKC/MAPK cascades. Sustained exposure typically induces receptor desensitization and downregulation.
• Structural pharmacology: The D-2-naphthylalanine substitution at position 6 enhances receptor affinity and confers resistance to peptidases, increasing duration of action in experimental systems.
• Experimental uses:
  • Probe for receptor activation kinetics, internalization, and β-arrestin recruitment.
  • Benchmark ligand for antagonist/partial-agonist pharmacology profiling.
  • Tool to dissect pulsatile vs sustained GnRH signaling in endocrine cell models (e.g., pituitary gonadotrophs) by modulating exposure paradigms.
• Downstream readouts (examples): Calcium imaging, IP1 accumulation, ERK phosphorylation, LH/FSH secretion in ex vivo pituitary preparations, gene-expression signatures of GnRH-responsive genes.

Note: All uses are for laboratory research only. Potency, efficacy, and signaling bias can vary with cell type, receptor expression level, and assay configuration.

Buffer Applications

This product is a peptide ligand and is not itself a buffer component. However, buffer choice is critical for reproducible bioassays (general guidance):

• Common assay buffers: HEPES- or Tris-based physiological buffers (e.g., HBSS, DPBS, 10–25 mM HEPES, pH ~7.2–7.4) with Ca2+/Mg2+ for functional assays involving GPCR signaling.
• Additives: 0.1% BSA or similar carrier proteins can reduce peptide adsorption to plastics; 0.01–0.05% non-ionic surfactant (e.g., Pluronic F-68) may help in some cell assays.
• pH/ionic strength: Maintain near-physiological conditions unless the experiment requires otherwise; extreme pH can induce peptide degradation or aggregation.
• Sterility: Filter working solutions through 0.22 µm membranes for cell-based assays.

Item-specific buffer recipes or stability ranges are not provided in the Product Data; consult CoA/Spec Sheet or perform small-scale pretests.

Green Alternatives

As a peptide ligand, Nafarelin is not a process solvent or bulk reagent. Green-chemistry considerations focus on dissolution media and handling (general guidance):

• Prefer aqueous buffers over organic solvents whenever solubility and assay design permit.
• If an organic co-solvent is required, DMSO is commonly used due to its miscibility with water and comparatively favorable safety/biodegradability profile relative to DMF or NMP.
• Minimize solvent volumes and prepare concentrated stocks to reduce waste.
• Use low-temperature storage and single-use aliquots to extend shelf life and reduce repeat preparations and solvent consumption.

Illustrative comparison (general):

• DMSO vs DMF/NMP: DMSO offers lower toxicity and better environmental profile; DMF/NMP are reproductive hazards and typically avoided in bioassays.
• Aqueous buffers with mild acid (e.g., 0.1% acetic acid) can improve initial dissolution of peptide salts, enabling predominantly water-based systems.

Waste reduction:

• Plan experiments to use aliquoted stocks fully within stability windows, limiting disposal of expired solutions.

Pharmaceutical Uses

No pharmacopeial status or excipient role is provided in the Product Data. This product is supplied strictly for research use only.

Research/formulation context (general, non-clinical):

• Can serve as a reference peptide in preformulation studies (solubility, stability, adsorption to containers) to develop handling practices for GnRH-like peptides.
• May be used as a model active in device compatibility or extraction studies (e.g., interaction with elastomers, plastics) under research conditions.

Note: No therapeutic, diagnostic, or clinical uses are claimed or supported for this listing.

Physical Properties

Item-specific specifications are not provided in the Product Data. For definitive specifications, consult the CoA/Spec Sheet.

• 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.
• Melting point: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (general, literature guidance for GnRH peptides):
  • Often soluble in aqueous buffers (e.g., dilute acetic acid, dilute HCl, or basic buffers) and polar aprotic solvents (DMSO). High-concentration stocks are commonly prepared in DMSO or water with 0.1% acid, then diluted into assay buffer.
  • Peptide solubility may be sequence- and counterion-dependent; gentle warming and sonication may assist dissolution.
• LogP/logD, pKa, refractive index, density: Not typically reported for peptides of this class; not specified for this item.

Notes:

• Hygroscopicity: Peptide salts can be hygroscopic; handle rapidly at room temperature and return to cold storage to avoid moisture uptake (general peptide handling practice).
• Counterion effects: The acetate form can influence solubility and pH upon dissolution (literature/general).

Quality and Grades

• Grade/Purity (from Product Data): Moligand™.

Interpretation and context:

• Moligand™ (general description): Designates materials suitable for molecular screening, ligand discovery, and chemical-biology workflows where identity and purity are controlled for research applications. It emphasizes suitability as a ligand/probe candidate rather than compliance with pharmacopoeial monographs. Exact assay purity, residual solvents, counterion content, water, and metal levels are not specified here; refer to the CoA/Spec Sheet for item-specific data.
• Identity confirmation: For peptides, identity is typically supported by high-resolution MS and, where applicable, peptide mapping or analytical HPLC (general practice). Documentation specific to this lot should be obtained from the CoA.
• UV/HPLC use: If intended for analytical assays (e.g., as a reference ligand), customers should verify UV background and purity by running a scouting gradient; low-UV absorbance background is not implied unless stated on the CoA.
• Stabilizers: Not specified for this item; refer to CoA/Spec Sheet. No stabilizers should be assumed unless explicitly listed.

Recommendations:

• Upon receipt, verify lot-specific purity/identity data on the CoA before critical experiments.
• For screening libraries, prepare master stocks under anhydrous, sterile conditions and perform QC (LC–MS) after dissolution to confirm integrity.

Reaction and Applications

This product is supplied as a bioactive research peptide/ligand rather than a synthetic reagent. Accordingly, its primary applications are in biochemical and cell-based studies (general/literature context):

• GPCR ligand studies: Nafarelin is a potent agonist of the gonadotropin-releasing hormone (GnRH) receptor. It is widely used as a tool compound to interrogate GnRH receptor signaling, receptor desensitization/internalization, and downstream pathways (e.g., Gq/PLC/IP3/Ca2+ mobilization) in recombinant or native systems.
• Endocrine axis research: Employed to probe hypothalamic–pituitary–gonadal (HPG) axis mechanisms in vitro and ex vivo models, measuring LH/FSH release from pituitary cells (research context; no clinical claims).
• Assay development: Reference agonist in radioligand binding, fluorescence-based functional assays, and label-free impedance assays to benchmark receptor activity and antagonist potency.
• Structural/biophysical: Used to study peptide–receptor interactions via NMR, SPR, ITC, and computational docking, aided by the D-2-naphthylalanine modification that enhances hydrophobic contacts.

Notes:

• Not typically used as a reagent in organic synthesis. If chemical modification is intended (e.g., labeling), see “Synthetic Utility” for general peptide-derivatization strategies.

Reaction Conditions

This product is not intended for use as a reagent in synthetic reactions. For laboratory handling and optional derivatization (general guidance):

• Reconstitution (see also Storage & Reconstitution): Dissolve in sterile water, dilute acid (e.g., 0.1% acetic acid), or DMSO before further dilution into assay buffer. Gentle vortexing and brief sonication may assist dissolution.
• Radiolabeling of Tyr (general): Iodination with Iodogen, Chloramine-T, or Bolton–Hunter reagents under mild conditions (ice-cold to room temperature, minutes) followed by rapid purification to minimize peptide oxidation.
• Assay incubation: Functional GPCR assays commonly run at 20–37°C with ligand exposures from seconds (calcium flux) to hours (gene expression). Optimize concentration ranges empirically (e.g., 0.1 nM–1 µM) depending on system sensitivity (general literature range; not item-specific).
• Stability considerations: Avoid prolonged exposure to strong light and oxidants; include antioxidants (e.g., 0.1 mM methionine) if compatible with the assay when iodination or photo-oxidation is a concern.

All numerical ranges above are general literature practices for peptide ligands and are not item-specific specifications.

Safety and Handling

Always consult the SDS for authoritative safety information.

• GHS classification, signal word, H-statements, pictograms: Not specified for this item; refer to SDS.
• Likely hazards (general peptide handling): Solid, non-volatile peptide; low inhalation volatility but avoid dust formation. May cause irritation upon contact or inhalation of dust.
• PPE (best practice):
  • Lab coat, nitrile gloves, and safety glasses as minimum PPE.
  • Handle powders in a clean, low-draft area; for weighing, use a fume hood or balance enclosure to minimize airborne particulates.
• Handling guidance:
  • Avoid repeated freeze–thaw of reconstituted solutions; prepare single-use aliquots.
  • Use sterile, low-binding polypropylene tubes to reduce adsorption.
  • For bioassays, filter sterilize (0.22 µm) when compatible.
• Incompatibilities (general): Strong oxidizers may degrade peptides; prolonged exposure to strong acids/bases can lead to hydrolysis or side-chain modifications.
• First-aid (general):
  • Skin/eye contact: Rinse with plenty of water for several minutes; remove contaminated clothing; seek medical attention if irritation persists.
  • Inhalation: Move to fresh air; seek medical attention if symptoms occur.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Waste: Dispose of peptide-containing solutions and consumables as chemical waste per institutional and regional regulations.
• Research use only: Not for human or veterinary use.

Solvent Selection

Application-driven solvent choices for peptide ligands (general guidance; not item-specific specifications):

• Polarity class: Highly polar, polyfunctional peptide; typically favors protic or strongly polar aprotic media.
• Common solvent systems (literature/practice):
  • Water or aqueous buffers, often with 0.1% acetic acid or 0.1 M HCl for initial dissolution of acetate salts; adjust to assay buffer post-dissolution.
  • DMSO for concentrated stock solutions (e.g., 10–50 mM), then dilute into aqueous buffers just before use to limit DMSO in assays (<0.1–1% v/v).
  • Minimal volumes of DMF can assist dissolution before aqueous dilution if required.
• Miscibility/compatibility:
  • DMSO is miscible with water; avoid high DMSO fractions that can affect cell-based assays.
  • High ionic strength and extreme pH may induce peptide aggregation or hydrolysis; optimize buffer composition.
• When to choose which:
  • Bioassays: Prefer aqueous physiological buffers (PBS, HBSS, HEPES) with carrier proteins (e.g., 0.1% BSA) to reduce surface adsorption when compatible.
  • Biophysical assays (SPR/ITC): Use degassed buffers with low surfactant; include minimal DMSO matching between sample/reference if DMSO is present.
• Practical tips:
  • Filter sterilize final working solutions (0.22 µm) where sterility is required.
  • Prepare fresh before use or utilize single-use aliquots to avoid freeze–thaw degradation.

Storage and Reconstitution

• Storage conditions (from Product Data): Store at -20°C, desiccated. Shipments are made in an ice chest with ice pads.

• General handling recommendations for peptides (literature/best practice):

  • Upon arrival, allow the sealed container to equilibrate to room temperature before opening to prevent condensation.
  • For long-term storage, keep dry and protected from light. For storage beyond several months, consider -80°C for reconstituted aliquots.
  • Avoid repeated freeze–thaw cycles. Prepare single-use aliquots immediately after first dissolution.

• Reconstitution (general guidance; item-specific solvent not specified):

  • Use sterile water, 0.1% acetic acid, or DMSO to prepare a concentrated stock. Target concentration depends on planned use; Not specified for this item; refer to CoA/Spec Sheet.
  • Mix gently; brief sonication may help dissolution. If required, filter sterilize aqueous solutions through a 0.22 µm filter.
  • For working solutions, dilute into assay buffer immediately before use. Include carrier protein (e.g., 0.1% BSA) to minimize adsorption when compatible.

• Stability after reconstitution: Not specified for this item; refer to CoA/Spec Sheet. As a precaution, use freshly prepared solutions or store aliquots at -20 to -80°C and use within a few weeks, monitoring for loss of activity by assay readout.

• Research Use Note: For research use only.

Structure and Identity

Overview: Nafarelin is a synthetic decapeptide gonadotropin-releasing hormone (GnRH) receptor agonist commonly supplied as the acetate salt. It features an N-terminal pyroglutamyl residue and a C-terminal glycinamide, with a D-2-naphthylalanine (D-Nal(2)) substitution at position 6 that enhances receptor affinity and metabolic stability.

• Item-specific identifiers (from Product Data):

  • SKU: N287275
  • Product name: Nafarelin
  • CAS: 76932-56-4 (commonly associated with Nafarelin acetate)
  • CID: 25077405
  • InChIKey: 327789 (as provided; non-standard format—consult CoA/SDS for definitive identifier)
  • 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.

• Structural features (general peptide-chemistry description; literature):

  • Sequence motif: pGlu–His–Trp–Ser–Tyr–D-2-Nal–Leu–Arg–Pro–Gly–NH2 (GnRH analog with D-2-naphthylalanine at position 6)
  • Functional groups: multiple secondary amide bonds (peptide backbone), N-terminal cyclic lactam (pyroglutamyl), phenolic hydroxyl (Tyr), guanidinium (Arg), indole (Trp), and a naphthyl aromatic system (D-Nal).
  • Stereochemistry: L-configuration for natural residues; D-configuration at position 6 (D-Nal), contributing to proteolytic stability.
  • 2D description: a linear decapeptide capped N-terminus (lactam ring of pGlu), backbone of alternating amide carbonyl and NH linkages, with side chains including indole (Trp), phenol (Tyr), bulky naphthyl (D-Nal), aliphatic (Leu, Pro), basic guanidinium (Arg), and terminal primary amide (Gly–NH2).

Synthetic Utility

As provided, Nafarelin functions as a bioactive peptide ligand rather than a general synthetic building block. Nevertheless, for chemical-biology derivatization (general literature guidance):

• Labeling opportunities:
  • Tyrosine phenol: amenable to electrophilic radioiodination (I-125/I-131) or oxidative coupling strategies; also possible to install reporter tags via carbonate/carbamate chemistry in specialized workflows.
  • N-terminus is cyclized to pyroglutamyl (lactam), and C-terminus is amidated; these termini are not directly available for standard amide-coupling. Site-selective labeling typically targets side chains or proceeds via introduced linkers.
  • Arginine guanidinium is generally not used for covalent conjugation without prior protection/derivatization.
• Conjugation strategies:
  • Oxidative iodination for tracer generation in binding assays (radioligand studies).
  • Non-covalent immobilization on sensor chips (e.g., via amine-capture of a preinstalled linker or through hydrophobic capture) for SPR.
  • If analogs with additional handles (e.g., Lys or azido/alkyne tags) are synthesized, standard NHS-ester coupling or CuAAC can be used for fluorophore/biotin attachment.

Caveat: Site-selective modification of native Nafarelin requires careful method development to preserve receptor activity; verify activity post-derivatization.

Target Specificity

Item-specific, experimentally verified target details are not provided in the Product Data.

General literature context:

• Primary target: Gonadotropin-releasing hormone receptor (GnRHR; GNRHR). Nafarelin acts as an agonist at this receptor in mammalian systems.
• Off-targets: Comprehensive off-target profiling data for this specific item/lot are not provided; users should verify selectivity in their assay context.

For definitive, lot-specific potency/selectivity information, consult the CoA, internal validation data, or perform in-house profiling.

Preguntas frecuentes

What is the purity of this product?

This product is supplied at ≥98% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

What is Moligand??

Moligand? is one of Aladdin Scientific's premium product lines, formulated for high-purity applications across multiple workflows. Compared to standard grades in the same workflow, Moligand? products typically offer tighter specifications, more rigorous QC, and stronger lot-to-lot consistency.

How should this product be stored?

Store at ?20 °C, desiccated. Keep the container tightly closed with desiccant — the material is moisture-sensitive.

How is this product shipped?

This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 76932-56-4. InChIKey RWHUEXWOYVBUCI-ITQXDASVSA-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.