Melanotan-1
From $27.00to $157.50
Melanotan-1 (afamelanotide), lyophilized reference standard for in vitro laboratory research.
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Price
$27.00
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Quantity
In Stock · 100 Units Available
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Certificate of Analysis & Specifications
Documentation will be published once this lot completes third-party analytical release.
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Research Data
Chemical & Structural Identifiers
- Chemical Name (IUPAC)
- N-acetyl-L-seryl-L-tyrosyl-L-seryl-L-norleucyl-L-glutamyl-L-histidyl-D-phenylalanyl-L-arginyl-L-tryptophylglycyl-L-lysyl-L-prolyl-L-valinamide
- CAS Registry Number
- 75921-69-6
- PubChem CID
- 92432
- Molecular Formula
- C78H111N21O19
- Molecular Weight
- 1645.83 Da (1646.88 g/mol average)
- Sequence
- Ac-SYS-[Nle]-EH-[d-Phe]-RWGKPV-NH2
- SMILES
- CCCC[C@H](NC(=O)[C@H](CO)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CO)NC(=O)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](Cc2c[nH]cn2)C(=O)N[C@@H](Cc3ccccc3)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](Cc4c[nH]c5ccccc45)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N6CCC[C@H]6C(=O)N[C@@H](C(C)C)C(=O)N
- InChIKey
- VORLPRMQGQJWNX-KXAMVRLASA-N
- Salt / Counter-Ion
- Supplied as a high-purity lyophilized acetate (CH3COO-) or trifluoroacetate (CF3COO-) salt.
- Synonyms
- Melanotan-1, MT-1, MT-I, Afamelanotide, NDP-α-MSH, [Nle4, D-Phe7]-α-MSH, CUV1647.
Analytical & COA Specifications
- Analytical Purity (RP-HPLC)
- ≥ 98.5% by area normalization under UV detection at λ = 214 nm and 280 nm (tyrosine and tryptophan chromophore detection).
- Identity Confirmation (RP-HPLC RT + UV vs. reference)
- Main peak retention time and UV spectrum conform to the reference standard.
- Physical Characterization
- Dense, white to off-white lyophilized solid cake/powder.
Handling & Stability
Storage. Store dry solid desiccated at -20°C to -80°C, protected from atmospheric moisture and direct light.
Solubility. Soluble in sterile laboratory-grade deionized water (≥ 10 mg/mL), sterile Phosphate-Buffered Saline (PBS, pH 7.4, ≥ 5 mg/mL), or dilute sterile 0.1% acetic acid for stock stabilization in in vitro assay applications.
- Photostability & Handling Parameters: Contains UV-sensitive aromatic residues (Tyr2, Trp9); prepare concentrated working stocks under amber lighting conditions, avoid high-shear vortexing, and store single-use aliquots at -20°C to eliminate degradation from repeated freeze-thaw cycles.
Mechanism & Literature
Synthetic linear tridecapeptide analog of endogenous α-melanocyte-stimulating hormone (α-MSH). Acts as a non-selective, high-affinity agonist across melanocortin receptor subtypes (MC1R, MC3R, MC4R, MC5R), demonstrating sub-nanomolar binding potency (Ki ≈ 0.1--0.5 nM) at the Melanocortin 1 Receptor (MC1R).
Structural Engineering Rationale: Replaces endogenous methionine at position 4 with norleucine (Nle4) to eliminate susceptibility to oxidative degradation, and substitutes L-phenylalanine with D-phenylalanine (D-Phe7), conferring resistance against proteolytic cleavage by endopeptidases and prolonging receptor binding kinetics in in vitro models.
Cellular Pathways Investigated: Evaluated in cultured mammalian melanocytes and melanoma cell models (e.g., B16-F10 and primary human melanocytes) to quantify Gαs-protein activation, adenylyl cyclase stimulation, intracellular cyclic AMP (cAMP) accumulation, Protein Kinase A (PKA) activation, downstream phosphorylation of CREB, and transcriptional induction of Microphthalmia-associated transcription factor (MITF) and Tyrosinase (TYR) activity.
References (3)
- Sawyer, T. K., et al. (1980). [Nle4, D-Phe7]-alpha-melanocyte-stimulating hormone: a highly potent alpha-melanotropin with ultralong biological activity. Proceedings of the National Academy of Sciences (PNAS), 77(10), 5754–5758.
- Hunt, G., et al. (1995). NDP-MSH stimulates melanogenesis and tyrosinase expression in cultured human melanocytes in vitro. Journal of Cell Science, 108(4), 1651–1657.
- Abdel-Malek, Z., et al. (2006). Melanocortin 1 receptor: its role in regulating human melanocyte function and response to UV radiation in vitro. Cell Cycle, 5(4), 434–439.
Technical Laboratory FAQs
What structural modifications differentiate Melanotan-1 from native α-MSH?
Melanotan-1 incorporates two substitutions into the tridecapeptide backbone: norleucine at position 4 (Nle4) and D-phenylalanine at position 7 (D-Phe7), providing stability against oxidative stress and enzymatic degradation by laboratory proteases.
How does Melanotan-1 (NDP-α-MSH) activate intracellular signaling cascades in cell culture?
Melanotan-1 binds MC1R, stimulating Gαs-mediated adenylyl cyclase activity to elevate intracellular cAMP, activating PKA and driving CREB-mediated transcription of MITF and associated melanogenic enzymes in vitro.
What reconstitution conditions are recommended for in vitro Melanotan-1 stock assays?
Sterile deionized water or sterile PBS (pH 7.4) provides rapid dissolution at concentrations ≥ 5 mg/mL. For long-term stock stabilization against hydrolysis in cell culture media, a weakly acidic buffer (such as sterile 0.1% acetic acid) provides maximum solution integrity.
For Research Use Only. Not for human or animal administration. Not intended to diagnose, treat, cure, or prevent any disease. Sold for laboratory research purposes only.