alpha-Melanocyte-stimulating hormone

α-Melanocyte-stimulating hormone (α-MSH) is an endogenous peptide hormone and neuropeptide of the melanocortin family, with a tridecapeptide structure and the amino acid sequence Ac-Ser-Tyr-Ser-Met-Glu-His-Phe-Arg-Trp-Gly-Lys-Pro-Val-NH₂. It is the most important of the melanocyte-stimulating hormones (MSHs) (also known as melanotropins) in stimulating melanogenesis, a process that in mammals (including humans) is responsible for pigmentation primarily of the hair and skin. It also plays a role in feeding behavior, energy homeostasis, sexual activity, and protection against ischemia and reperfusion injury.[1]

α-Melanocyte-stimulating hormone

Names
IUPAC name N-acetyl-L-seryl-L-tyrosyl-L-seryl-L-methionyl-L-α-glutamyl-L-histidyl-L-phenylalanyl-L-arginyl-L-tryptophylglycyl-L-lysyl-L-prolyl-L-valinamide
Other names alpha-MSH, α-melanocortin, α-melanotropin, α-intermedin; Ac-Ser-Tyr-Ser-Met-Glu-His-Phe-Arg-Trp-Gly-Lys-Pro-Val-NH2
Identifiers
CAS Number	581-05-5
ChEMBL	ChEMBL385886
ChemSpider	17289286
PubChem CID	16132636
UNII	OVF025LA77
CompTox Dashboard (EPA)	DTXSID50226430
InChI InChI=1S/C77H109N21O19S/c1-42(2)64(65(79)106)97-75(116)61-20-13-30-98(61)76(117)54(18-10-11-28-78)88-62(103)38-85-66(107)57(34-46-36-84-50-17-9-8-16-49(46)50)94-67(108)51(19-12-29-83-77(80)81)89-70(111)55(32-44-14-6-5-7-15-44)92-72(113)58(35-47-37-82-41-86-47)95-68(109)52(25-26-63(104)105)90-69(110)53(27-31-118-4)91-74(115)60(40-100)96-71(112)56(33-45-21-23-48(102)24-22-45)93-73(114)59(39-99)87-43(3)101/h5-9,14-17,21-24,36-37,41-42,51-61,64,84,99-100,102H,10-13,18-20,25-35,38-40,78H2,1-4H3,(H2,79,106)(H,82,86)(H,85,107)(H,87,101)(H,88,103)(H,89,111)(H,90,110)(H,91,115)(H,92,113)(H,93,114)(H,94,108)(H,95,109)(H,96,112)(H,97,116)(H,104,105)(H4,80,81,83) Key: WHNFPRLDDSXQCL-UHFFFAOYSA-N InChI=1/C77H109N21O19S/c1-42(2)64(65(79)106)97-75(116)61-20-13-30-98(61)76(117)54(18-10-11-28-78)88-62(103)38-85-66(107)57(34-46-36-84-50-17-9-8-16-49(46)50)94-67(108)51(19-12-29-83-77(80)81)89-70(111)55(32-44-14-6-5-7-15-44)92-72(113)58(35-47-37-82-41-86-47)95-68(109)52(25-26-63(104)105)90-69(110)53(27-31-118-4)91-74(115)60(40-100)96-71(112)56(33-45-21-23-48(102)24-22-45)93-73(114)59(39-99)87-43(3)101/h5-9,14-17,21-24,36-37,41-42,51-61,64,84,99-100,102H,10-13,18-20,25-35,38-40,78H2,1-4H3,(H2,79,106)(H,82,86)(H,85,107)(H,87,101)(H,88,103)(H,89,111)(H,90,110)(H,91,115)(H,92,113)(H,93,114)(H,94,108)(H,95,109)(H,96,112)(H,97,116)(H,104,105)(H4,80,81,83) Key: WHNFPRLDDSXQCL-UHFFFAOYAP
Properties
Chemical formula	C77H109N21O19S
Molar mass	1664.884 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

α-MSH is a non-selective full agonist of the melanocortin receptors MC₁ (K_i = 0.230 nM), MC₃ (K_i = 31.5 nM), MC₄ (K_i = 900 nM), and MC₅ (K_i = 7160 nM), but not MC₂ (which is exclusive for adrenocorticotropic hormone (ACTH)).[2] Activation of the MC₁ receptor is responsible for its effect on pigmentation, whereas its regulation of appetite, metabolism, and sexual behavior is mediated through both the MC₃ and MC₄ receptors.

It is generated as a proteolyic cleavage product from ACTH (1-13), which is in turn a cleavage product of proopiomelanocortin (POMC).

A few synthetic analogues of α-MSH have been investigated as medicinal drugs due to their photoprotective effects against ultraviolet (UV) radiation from the sun. They include afamelanotide (melanotan) and melanotan II, the former of which being in phase-III clinical trials in the United States. Bremelanotide, another analogue of α-MSH, is currently under development not as a photoprotective agent, but instead for the treatment of sexual dysfunction. All of these drugs have significantly greater potencies than α-MSH, along with improved pharmacokinetics and distinctive selectivity profiles.

See also

• β-Melanocyte-stimulating hormone
• γ-Melanocyte-stimulating hormone
• Adrenocorticotropic hormone

References

1. Varga, B.; Gesztelyi, R.; Bombicz, M.; Haines, D.; Szabo, A. M.; Kemeny-Beke, A.; Antal, M.; Vecsernyes, M.; Juhasz, B.; Tosaki, A. (July 2013). "Protective effect of alpha-melanocyte-stimulating hormone (α-MSH) on the recovery of ischemia/reperfusion (I/R)-induced retinal damage in a rat model". Journal of Molecular Neuroscience. 50 (3): 558–70. doi:10.1007/s12031-013-9998-3. PMC 3675276. PMID 23504281.
2. Schiöth, Helgi B; Mutulis, Felikss; Muceniece, Ruta; Prusis, Peteris; Wikberg, Jarl E S (1998). "Discovery of novel melanocortin4receptor selective MSH analogues". British Journal of Pharmacology. 124 (1): 75–82. doi:10.1038/sj.bjp.0701804. ISSN 0007-1188. PMC 1565364. PMID 9630346.