Melanotan-2
From $27.00to $157.50
Synthetic melanocortin peptide Melanotan-2, 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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Published Certificates of Analysis for Melanotan-2. All released analytical records are preserved here. Pending and in-testing lots are reachable only through the QR printed on the vial.
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Research Data
Chemical & Structural Identifiers
- Chemical Name (IUPAC)
- N-acetyl-L-norleucyl-cyclo-(L-aspartyl-L-histidyl-D-phenylalanyl-L-arginyl-L-tryptophyl-L-lysine) amide
- CAS Registry Number
- 121062-08-6
- PubChem CID
- 57377830
- Molecular Formula
- C50H69N15O9
- Molecular Weight
- 1023.54 Da (1024.18 g/mol average)
- Sequence
- Ac-[Nle]-c[DH-[d-Phe]-RWK]-NH2
- SMILES
- CCCC[C@@H](C(=O)N[C@H]1CCC(=O)NCCCC[C@@H](C(=O)N)NC(=O)[C@H](CC2=CNC3=CC=CC=C32)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](CC4=CC=CC=C4)NC(=O)[C@H](CC5=CNC=N5)NC1=O)NC(=O)C
- InChIKey
- DFYBWASLHDAONQ-PZAWBLPDSA-N
- Salt / Counter-Ion
- Supplied as a high-purity lyophilized acetate (CH3COO-) or trifluoroacetate (CF3COO-) salt.
- Synonyms
- Melanotan-2, Melanotan II, MT-2, MT-II, Cyclo-[Nle4, Asp5, D-Phe7, Lys10]-α-MSH(4-10) amide.
- Cyclization Architecture: Intramolecular lactam (isopeptide) bond between the β-carboxyl side chain of Asp2 (native position 5) and the ε-amino side chain of Lys7 (native position 10).
Analytical & COA Specifications
- Analytical Purity (RP-HPLC)
- ≥ 98.5% by area normalization under UV detection at λ = 214 nm and 280 nm (tryptophan 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.
- Lactam Core Stability & Handling: The cyclic lactam ring confers enhanced stability against general laboratory endopeptidases; protect tryptophan (Trp6) from UV photo-oxidation by using amber containers, avoid vigorous high-shear vortexing, and store single-use aliquots at -20°C to eliminate degradation from repeated freeze-thaw cycles.
Mechanism & Literature
Synthetic cyclic heptapeptide analog of endogenous α-melanocyte-stimulating hormone (α-MSH). Functions as a potent, non-selective agonist across central and peripheral melanocortin receptor subtypes (MC1R, MC3R, MC4R, and MC5R).
Structural Engineering Rationale: Engineered to enforce a stable pseudocyclic β-turn conformation via a side-chain-to-side-chain lactam bridge between aspartic acid and lysine. This conformational constraint, paired with the substitution of D-phenylalanine (D-Phe7), significantly improves resistance to enzymatic degradation and increases receptor binding potency at both neural and peripheral melanocortin receptors compared to linear parent peptides.
Cellular Pathways Investigated: Evaluated in receptor-transfected cell lines (CHO/HEK293 expressing individual human MCR subtypes) and primary cell models to quantify Gαs-protein coupling, adenylyl cyclase activation, intracellular cyclic AMP (cAMP) accumulation, and downstream activation of Protein Kinase A (PKA) and CREB transcription cascades. Preclinical assays also model central neural circuit activation via MC3R/MC4R-dependent sympathetic signaling pathways.
References (3)
- Al-Obeidi, F., et al. (1989). Design, synthesis, and biological activities of a cyclic heptapeptide with potent melanotropic activity. Journal of Medicinal Chemistry, 32(12), 2555–2561.
- Dorr, R. T., et al. (1996). Evaluation of a superpotent cyclic melanotropic peptide in vitro and in preclinical models. Life Sciences, 58(20), 1777–1784.
- Hadley, M. E., et al. (1996). Discovery and development of novel melanogenic peptides. Journal of Investigative Dermatology, 107(3), 460–467.
Technical Laboratory FAQs
How does Melanotan-2 differ structurally from Melanotan-1 (Afamelanotide)?
Melanotan-2 is a truncated cyclic heptapeptide containing an intramolecular lactam bridge between Asp5 and Lys10 side chains, whereas Melanotan-1 is a 13-amino-acid linear peptide. The cyclic architecture of MT-2 locks the His-D-Phe-Arg-Trp pharmacophore into a rigid β-turn, altering its receptor selectivity and binding profile.
Which melanocortin receptor subtypes are activated by Melanotan-2 in vitro?
Melanotan-2 acts as a non-selective agonist that activates MC1R, MC3R, MC4R, and MC5R with low-nanomolar to sub-nanomolar EC50 values, stimulating Gαs-mediated adenylyl cyclase activity and intracellular cAMP synthesis across all four receptor subtypes.
What reconstitution vehicle is recommended for in vitro Melanotan-2 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 potential deamidation or oxidative degradation in cell culture stock preparation, a sterile 0.1% acetic acid solution is standard.
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.