Afamelanotide is a first-in-class, synthetic, 13-amino acid peptide analogue of the endogenous alpha melanocyte-stimulating hormone (α-MSH). It differs structurally from its endogenous counterpart by only two amino acids - these structural differences improve biological efficacy by imparting a greater affinity for its target and a longer biological half-life.
CAT No: R1512
CAS No:75921-69-6
Synonyms/Alias:Melanotan I;Melanotan-1;75921-69-6;NDP-alpha-MSH;4-Nle-7-phe-alpha-msh;CUV1647;afamelanotida;CUV 1647;CUV-1647;QW68W3J66U;Melanotan-I;scenesse;(Nle4,D-Phe7)-alpha-MSH;[Nle4,D-Phe7]-alpha-MSH;AC-Ser-Tyr-Ser-Nle-Glu-His-D-Phe-Arg-Trp-Gly-Lys-Pro-Val-NH2;Msh, 4-nle-7-phe-alpha-;Afamelanotide [INN];alpha-Msh, nle(4)-phe(7)-;AFAMELANOTIDE [MI];Afamelanotide [USAN:INN];AFAMELANOTIDE [USAN];[Nle4,D-Phe7]--MSH;(nle4,d-phe7)-.alpha.-msh;AFAMELANOTIDE [WHO-DD];alpha-Melanotropin, 4-L-norleucine-7-D-phenylalanine-;SCHEMBL22463810;AFAMELANOTIDE [ORANGE BOOK];DA-48757;(Nle4,D-Phe7)-alpha-MSH trifluoroacetate salt;Afamelanotide; MT-I; [Nle4,D-Phe7]-alpha-MSH;EN300-18527915;.ALPHA.-MELANOTROPIN (SWINE), 4-L-NORLEUCINE-7-D-PHENYLALANINE-;N-acetyl-L-seryl-L-tyrosyl-L-seryl-L-norleucyl-L-alpha-glutamyl-L-histidyl-D-phenylalanyl-L-arginyl-L-tryptophylglycyl-L-lysyl-L-prolyl-L-valinamide;N-acteyl-L-Ser-L-Tyr-L-Ser-L-Nle-L-Glu-L-His-D-Phe-L-Arg-L-Trp-Gly-L-Lys-L-Pro-L-Val-NH2;
Chemical Name:(4S)-4-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-acetamido-3-hydroxypropanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-hydroxypropanoyl]amino]hexanoyl]amino]-5-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-6-amino-1-[(2S)-2-[[(2S)-1-amino-3-methyl-1-oxobutan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxohexan-2-yl]amino]-2-oxoethyl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
Afamelanotide is a synthetic peptide analogue of alpha-melanocyte-stimulating hormone (α-MSH), engineered to mimic and enhance the activity of endogenous melanocortins. As a linear peptide composed of thirteen amino acids, it demonstrates high affinity for the melanocortin 1 receptor (MC1R), a key regulator of melanogenesis and pigmentary processes in mammalian cells. Due to its potent melanotropic properties and resistance to enzymatic degradation, afamelanotide has become a valuable tool in biochemical research focused on pigmentation pathways, receptor pharmacology, and peptide signaling mechanisms. Its structural stability and functional specificity make it particularly relevant for studies dissecting the molecular dynamics of melanocortin systems and their broader physiological roles.
Pigmentation research: Afamelanotide serves as a powerful probe in the elucidation of melanogenesis, the complex biochemical pathway responsible for melanin synthesis in melanocytes. By selectively activating MC1R, it enables researchers to investigate the downstream signaling cascades, such as cAMP-mediated pathways, that drive pigment production and distribution. This peptide is frequently employed in cell-based assays and ex vivo skin models to quantify the effects of melanocortin stimulation on melanin content, gene expression profiles, and cellular morphology, supporting the development of new insights into skin biology and pigmentary regulation.
Receptor pharmacology: The compound is widely utilized in studies aimed at characterizing the pharmacodynamics and ligand-binding properties of melanocortin receptors, especially MC1R. Its high receptor selectivity and defined structure allow for detailed kinetic and affinity analyses, which are essential for mapping receptor activation, desensitization, and downstream effector engagement. In vitro and in silico investigations using afamelanotide facilitate the exploration of receptor-ligand interactions, contributing to the broader understanding of G protein-coupled receptor (GPCR) biology and the design of novel receptor modulators.
Peptide signaling pathway studies: As a stable α-MSH analogue, afamelanotide is instrumental in dissecting the roles of peptide hormones in cell signaling networks. Researchers leverage its resistance to proteolytic degradation to perform extended time-course experiments, enabling the study of both acute and sustained signaling events. Applications include the analysis of cross-talk between melanocortin pathways and other cellular networks, such as oxidative stress responses, inflammatory signaling, and DNA repair mechanisms, thereby broadening the scope of peptide hormone research.
Peptide synthesis and analytical validation: Afamelanotide's defined sequence and bioactivity make it a reference standard in peptide synthesis protocols and quality control assays. Synthetic chemists and analytical laboratories use it to optimize solid-phase peptide synthesis (SPPS) methodologies, validate chromatographic separation techniques, and calibrate mass spectrometric detection systems. Its application in these contexts ensures the accuracy and reproducibility of peptide production workflows, supporting both research and industrial-scale manufacturing of bioactive peptides.
Photobiology and UV response models: The peptide is frequently incorporated into experimental models designed to study cellular responses to ultraviolet (UV) radiation and environmental stressors. By modulating melanin synthesis, afamelanotide enables controlled investigations of melanin's protective roles against UV-induced DNA damage, oxidative stress, and cellular apoptosis. These studies are central to understanding the adaptive mechanisms of skin cells, facilitating the identification of molecular targets for photoprotection and the assessment of environmental risk factors in skin biology research.
2. Adipose tissue is a key organ for the beneficial effects of GLP-2 metabolic function
3. Immune responses to homocitrulline-and citrulline-containing peptides in rheumatoid arthritis
4. SERS spectrum of the peptide thymosin‐β4 obtained with Ag nanorod substrate
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