| Identification | Back Directory | [Name]
ALPHA-MSH (11-13) ACETATE SALT | [CAS]
67727-97-3 | [Synonyms]
KPV
msh(11-13
ACTH-(11-13)
H-Lys-Pro-Val-OH
α-MSH(11-13)[pig]
ALPHA-MSH (11-13)
α-MSH(11-13)[human]
α-Melanotropin(11-13)
H-LYS-PRO-VAL-OH ACOH
alpha-MSH(11-13) acetate
α-MSH (11-13) (free acid)
a-MSH (11-13) (free acid)
α-Melanotropin(11-13)[pig]
L-Valine, L-lysyl-L-prolyl-
α-Melanotropin(11-13)[human]
H-LYS-PRO-VAL-OH ACETATE SALT
ALPHA-MSH (11-13) ACETATE SALT
.alpha.-MSH (11-13) (free acid)
alpha-Msh (11-13) (free acid) acetate salt
(2S)-2-[[(2S)-1-[(2S)-2,6-diaminohexanoyl]pyrrolidine-2-carbonyl]amino]-3-methylbutanoic acid | [Molecular Formula]
C16H30N4O4 | [MDL Number]
MFCD00804591 | [MOL File]
67727-97-3.mol | [Molecular Weight]
342.43 |
| Chemical Properties | Back Directory | [storage temp. ]
-15°C
| [InChI]
InChI=1S/C16H30N4O4/c1-10(2)13(16(23)24)19-14(21)12-7-5-9-20(12)15(22)11(18)6-3-4-8-17/h10-13H,3-9,17-18H2,1-2H3,(H,19,21)(H,23,24)/t11-,12-,13-/m0/s1 | [InChIKey]
YSPZCHGIWAQVKQ-AVGNSLFASA-N | [SMILES]
C(O)(=O)[C@H](C(C)C)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN)N |
| Hazard Information | Back Directory | [Description]
α-MSH (11-13) (free acid) is a synthetic, nonsteroidal compound that binds to and activates α-melanocyte-stimulating hormone receptors. It has been used as an antiinflammatory agent in the treatment of inflammatory bowel disease and bowel disease. It is also being studied as a contraceptive and an elastase inhibitor. This drug has shown some promise in the treatment of autoimmune diseases, such as rheumatoid arthritis, Crohn's disease, ulcerative colitis, multiple sclerosis, and type 1 diabetes mellitus. It is thought that α-MSH (11-13) (free acid) acetate salt may inhibit the production of inflammatory cells by inhibiting leukocyte elastase activity. | [Uses]
α-MSH(11-13) (ACTH-(11-13)) is the 11-13 amino acid (lysine-proline-valine) sequence of α-MSH (HY-P0252), which reduces fever in rabbits[1]. | [Definition]
ChEBI: Lys-Pro-Val is an oligopeptide. | [Biological Activity]
The C-terminal tripeptide α-MSH(11–13), also known as KPV (L-Lys-L-Pro-L-Val), exhibited anti-inflammation without induction of cutaneous pigmentation in a frog skin bioassay. The underlying molecular mechanisms of the α-MSH(11–13) anti-inflammatory properties have not been determined in detail. However, they are related to an inhibition of TNF-α, IL-6, and nitric oxide production in a model of LPS-stimulated murine microglial cell culture[1]. Furthermore, it has been recently shown that α-MSH(11–13) reduces activation of NF-κB and decreases its translocation into the nucleus by interaction with importin family proteins.
| [References]
[1] Eva-Verena Schaible. “Single administration of tripeptide α-MSH(11-13) attenuates brain damage by reduced inflammation and apoptosis after experimental traumatic brain injury in mice.” PLoS ONE (2013): e71056. |
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