α-MSH trifluoroacetate salt

Names

[ CAS No. ]:
581-05-5

[ Name ]:
α-MSH trifluoroacetate salt

[Synonym ]:
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
α-Melanocyte Stimulating Hormone
MFCD00133062
L-Valinamide, 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-
α-MSH

Biological Activity

[Description]:

α-Melanocyte-Stimulating Hormone (MSH), amide stimulates melanocortin 1 receptor that results in the activation of adenylyl cyclase.

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Adenylate Cyclase

Research Areas >> Metabolic Disease

Peptides

[Target]

Melanocortin 1 receptor[1] Adenylyl cyclase[1]

[In Vitro]

α-Melanocyte-Stimulating Hormone (MSH), amide is an ancient tridecapeptide with potent inhibitory activity in all major forms of inflammation. α-Melanocyte-stimulating hormone (α-MSH) acts as an anti-inflammatory agent via down regulating the production and activity of the pro-inflammatory cytokines interleukin-1 (IL-1), tumor necrosis factor (TNF)-α and IL-6 expressed in various cells of the immune system. It also controls the nitric oxide production associated with inflammation. α−MSH inhibits nuclear factor-κB (NF-κB)-dependent gene transcription and NF-κB pathway induced by TNF and other inflammatory agents. This activity of α-MSH is mediated through the production of cyclic adenosine monophosphate (cAMP) and activation of protein kinase A (PKA) enzyme. α–MSH functions as a potent therapeutics for various conditions resulted through NF-κB activation including, inflammatory diseases, human immunodeficiency virus (HIV) replication in AIDS (acquired immunodeficiency syndrome), and septic shock[2].

[In Vivo]

α-Melanocyte-Stimulating Hormone (MSH), amide (α-MSH) has an essential role to play in melanin production in animals. α-MSH regulates development of several skin diseases, including cutaneous inflammation and hyper-proliferative skin diseases[2].

[References]

[1]. Jo H, et al. Synthesis and biological evaluation of caffeic acid derivatives as potent inhibitors of α-MSH-stimulated melanogenesis. Bioorg Med Chem Lett. 2017 Aug 1;27(15):3374-3377.

[2]. Lu XY, et al. Interaction between alpha-melanocyte-stimulating hormone and corticotropin-releasing hormone in the regulation of feeding and hypothalamo-pituitary-adrenal responses. J Neurosci. 2003 Aug 27;23(21):7863-72.

[Related Small Molecules]

Forskolin | SQ22536 | ST 034307 | CB-7921220 | Small Cardioactive Peptide B (SCPB)

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Molecular Formula ]:
C₇₇H₁₀₉N₂₁O₁₉S

[ Molecular Weight ]:
1664.884

[ Exact Mass ]:
1663.792969

[ PSA ]:
668.28000

[ LogP ]:
-1.77

[ Index of Refraction ]:
1.682

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
Soluble in water (~1 mg/ml).

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
N

[ Safety Phrases ]:
22-24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Articles

Triterpene glycosides and other polar constituents of shea (Vitellaria paradoxa) kernels and their bioactivities.

Phytochemistry 108 , 157-70, (2014)

The MeOH extract of defatted shea (Vitellaria paradoxa; Sapotaceae) kernels was investigated for its constituents, and fifteen oleanane-type triterpene acids and glycosides, two steroid glucosides, tw...

Reduced melanocortin production causes sexual dysfunction in male mice with POMC neuronal insulin and leptin insensitivity.

Endocrinology 156(4) , 1372-85, (2015)

Proopiomelanocortin (POMC)-derived peptides like α-melanocyte-stimulating hormone (MSH) substantially improve hepatic insulin sensitivity and regulate energy expenditure. Melanocortinergic agents are ...

Effect of barodenervation on cardiovascular responses elicited from the hypothalamic arcuate nucleus of the rat.

PLoS ONE 7(12) , e53111, (2012)

We have previously reported that chemical stimulation of the hypothalamic arcuate nucleus (ARCN) in the rat elicited increases as well as decreases in blood pressure (BP) and sympathetic nerve activit...