α-MSH (11-13) (free acid) Chemical Properties

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

α-MSH (11-13) (free acid) Usage And Synthesis

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.

α-MSH (11-13) (free acid)(67727-97-3)Related Product Information

• α-MSH (human, mouse, rat, porcine, bovine, ovine) (trifluoroacetate salt)
• ALPHA-MSH (11-13)
• ALPHA-MSH
• ALPHA-MSH
• ACTH (1-13)
• α-MSH (11-13) (free acid)