75921-69-6

Basic information

• Product Name: Melanotan-1
• Synonyms: [NLE4,D-PHE]ALPHA-MELANOCYTE STIMULATING HORMONE;(NLE4,D-PHE7)-ALPHA-MSH;[Nle4,D-Phe7]α-MSH;Ac-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;N-Ac-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;[Nle4,DPhe7] a-MSH, amide;[Nle4,DPhe7] a-MSH, amide:Melanotan Ⅰ;[Nle4, D-Phe7]-α-MSH, amide
• CAS NO: 75921-69-6
• Molecular Formula: C₇₈H₁₁₁N₂₁O₁₉
• Molecular Weight: 1646.85
• EINECS: 211-519-9
• Product Categories: Ion Channel Modulating Peptides;Melanocyte Stimulating Hormones (MSH);Obesity Research;Peptides for Cell Biology;Pituitary Hormones;Peptide;ImmunomodulatorsHormones;Melanocyte Stimulating Hormone (MSH)Peptides and Proteins;α-Melanocyte Stimulating Hormone (α-MSH)Peptides for Cell Biology;Cytokines Growth Factors and Hormones (Obesity)
• Mol File: 75921-69-6.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Density: 1.46 g/cm³
• Refractive Index: 1.674
• Storage Temp.: −20°C
• PKA: 4.43±0.10(Predicted)
• CAS DataBase Reference: Melanotan-1(CAS DataBase Reference)
• NIST Chemistry Reference: Melanotan-1(75921-69-6)
• EPA Substance Registry System: Melanotan-1(75921-69-6)

Safety Data

• WGK Germany: 3
• RTECS: OS1830200
• Hazardous Substances Data: 75921-69-6(Hazardous Substances Data)

Usage

Description

Melanotan-1 is a synthetic peptide hormone that is a modified version of α-Melanocyte Stimulating Hormone (α-MSH). It is designed to increase melanin production in the skin, which provides a natural tan and protects against harmful UV radiation.

Uses

Used in Pharmaceutical Industry:
Melanotan-1 is used as a pharmaceutical agent for promoting tanning and skin protection. It stimulates melanin production in the skin, providing a natural tan and reducing the risk of sunburn and skin damage caused by UV radiation.
Used in Research Applications:
Melanotan-1 is used as a research tool to study its effects on various physiological processes. It has been used to investigate its impact on oxygen consumption and carbon dioxide production in mice, as well as its influence on leptin secretion in primary cultures of differentiated adipocytes. This research helps to better understand the potential therapeutic applications of Melanotan-1 and its underlying mechanisms of action.

Features

Afamelanotide is a potent, linear synthetic analog of the naturally occurring peptide hormone α-melanocyte-stimulating hormone (α-MSH).Modified to have a stronger binding affinity to melanocortin- 1 receptor (MC1R) and a smaller disassociation constant, afamelanotide has a longer half-life and subsequently exerts longer pharmacologic activity than its parent hormone.

Biochem/physiol Actions

[Nle4, D-Phe7]-α-melanocyte stimulating hormone is 100 times more potent than α-MSH in stimulating melanoma tyrosinase, which is a rate limiting enzyme in melanin biosynthesis and is 26 times as potent as α-MSH in S91adenylate cyclase assay. α –MSH has an essential role to play in melanin production in animals. It also regulates development of several skin diseases, including cutaneous inflammation and hyper-proliferative skin diseases.

InChI:InChI=1/C78H111N21O19/c1-5-6-19-52(91-75(116)61(41-101)97-72(113)57(34-46-24-26-49(103)27-25-46)94-74(115)60(40-100)88-44(4)102)68(109)92-54(28-29-64(105)106)70(111)96-59(36-48-38-83-42-87-48)73(114)93-56(33-45-16-8-7-9-17-45)71(112)90-53(22-14-31-84-78(81)82)69(110)95-58(35-47-37-85-51-20-11-10-18-50(47)51)67(108)86-39-63(104)89-55(21-12-13-30-79)77(118)99-32-15-23-62(99)76(117)98-65(43(2)3)66(80)107/h7-11,16-18,20,24-27,37-38,42-43,52-62,65,85,100-101,103H,5-6,12-15,19,21-23,28-36,39-41,79H2,1-4H3,(H2,80,107)(H,83,87)(H,86,108)(H,88,102)(H,89,104)(H,90,112)(H,91,116)(H,92,109)(H,93,114)(H,94,115)(H,95,110)(H,96,111)(H,97,113)(H,98,117)(H,105,106)(H4,81,82,84)/t52-,53-,54-,55-,56+,57-,58-,59-,60-,61-,62-,65-/m0/s1

Synthetic route

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-Val-OH (68858-20-8) + Fmoc-Pro-OH (71989-31-6) + Fmoc-Ser(tBu)-OH (71989-33-8) + (S)-2-[{({9H-fluoren-9-yl}methoxy)carbonyl}amino]pentanedioic acid (104091-09-0, 136083-74-4, 121343-82-6) + Fmoc-Tyr(tBu)-OH (71989-38-3) + Fmoc-Lys-OH (105047-45-8) + Fmoc-D-Phe-OH (86123-10-6) + Fmoc-His(Trt)-OH (109425-51-6) + Fmoc-(S)-2-aminohexanoic acid (77284-32-3) + 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester (143824-78-6) + Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine → NDP-MSH (75921-69-6)

Conditions

Yield

Stage #1: Fmoc-Val-OH With 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 0.5h; Stage #2: With piperidine In N,N-dimethyl-formamide for 0.333333h; Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Pro-OH; Fmoc-Ser(tBu)-OH; (S)-2-[{({9H-fluoren-9-yl}methoxy)carbonyl}amino]pentanedioic acid; Fmoc-Tyr(tBu)-OH; Fmoc-Lys-OH; Fmoc-D-Phe-OH; Fmoc-His(Trt)-OH; Fmoc-(S)-2-aminohexanoic acid; 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine Further stages;

...Expand

NDP-MSH (75921-69-6) + [125I]2,3,5,6-tetrafluorophenyl 4-fluoro-3-iodobenzoate → [125I][Nle4, D-Phe7, FIB-Lys11]α-MSH

Conditions	Yield
With borate buffer In acetonitrile at 45℃; for 0.5h; pH=8;

NDP-MSH (75921-69-6) + [18F]2,3,5,6-tetrafluorophenyl 4-fluoro-3-iodobenzoate → [18F][Nle4, D-Phe7, FIB-Lys11]α-MSH

Conditions	Yield
With borate buffer In acetonitrile at 50℃; for 0.166667h; pH=8;

NDP-MSH (75921-69-6) + 2,3,5,6-tetrafluorophenyl 4-fluoro-3-iodobenzoate → C85H113FIN21O20

Conditions	Yield
With borate buffer In acetonitrile at 20℃; for 1.5h; pH=8.6;	0.18 mg

Upstream product

• 29022-11-5 N-(fluoren-9-ylmethoxycarbonyl)glycine 
• 68858-20-8 Fmoc-Val-OH 
• 71989-31-6 Fmoc-Pro-OH 
• 71989-33-8 Fmoc-Ser(tBu)-OH 
• 104091-09-0 (S)-2-[{({9H-fluoren-9-yl}methoxy)carbonyl}amino]pentanedioic acid 
• 71989-38-3 Fmoc-Tyr(tBu)-OH 
• 105047-45-8 Fmoc-Lys-OH 
• 86123-10-6 Fmoc-D-Phe-OH 
• 109425-51-6 Fmoc-His(Trt)-OH 
• 77284-32-3 Fmoc-(S)-2-aminohexanoic acid 
• 143824-78-6 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester 
• 187618-60-6 Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine 

Relevant articles and documents

Design of MC1R Selective γ-MSH Analogues with Canonical Amino Acids Leads to Potency and Pigmentation

Melanoma is a lethal form of skin cancer. Skin pigmentation, which is regulated by the melanocortin 1 receptor (MC1R), is an effective protection against melanoma. However, the endogenous MC1R agonists lack selectivity for the MC1R and thus can have side effects. The use of noncanonical amino acids in previous MC1R ligand development raises safety concerns. Here we report the development of the first potent and selective hMC1R agonist with only canonical amino acids. Using γ-MSH as a template, we developed a peptide, [Leu3, Leu7, Phe8]-γ-MSH-NH2 (compound 5), which is 16-fold selective for the hMC1R (EC50 = 4.5 nM) versus other melanocortin receptors. Conformational studies revealed a constrained conformation for this linear peptide. Molecular docking demonstrated a hydrophobic binding pocket for the melanocortin 1 receptor. In vivo pigmentation study shows high potency and short duration. [Leu3, Leu7, Phe8]-γ-MSH-NH2 is ideal for inducing short-term skin pigmentation without sun for melanoma prevention.