a-MSH, amide
a-MSH, amide (C77H109N21O19S1), a peptide with the sequence Ac-Ser-Tyr-Ser-Met-Glu-His-Phe-Arg-Trp-Gly-Lys-Pro-Val-NH2, MW= 1664.9. The melanocyte-stimulating hormones (collectively referred to as MSH or intermedins) are a class of peptide hormones that are produced by cells in the intermediate lobe of the pituitary gland. An increase in MSH will cause a darkening in humans too. Melanocyte-stimulating hormone increases in humans during pregnancy. This, along with increased estrogens, causes increased pigmentation in pregnant women. Cushing's syndrome due to excess adrenocorticotropic hormone (ACTH) may also result in hyperpigmentation, such as acanthosis nigricans in the axilla. Most people with primary Addison's have darkening (hyperpigmentation) of the skin, including areas not exposed to the sun; characteristic sites are skin creases (e.g. of the hands), nipple, and the inside of the cheek (buccal mucosa), also old scars may darken. This occurs because melanocyte-stimulating hormone (MSH) and adrenocorticotropic hormone (ACTH) share the same precursor molecule, Pro-opiomelanocortin (POMC).
Melanocyte-stimulating hormone belongs to a group called the melanocortins. This group includes ACTH, alpha-melanocyte-stimulating hormone (α-MSH), (β-MSH) and (γ-MSH); these peptides are all cleavage products of a large precursor peptide called pro-opiomelanocortin (POMC). α-MSH is the most important melanocortin for pigmentation.
Figure1 Formula of a-MSH, amide
Ref:
1. Hadley ME (Oct 2005). "Discovery that a melanocortin regulates sexual functions in male and female humans". Peptides 26 (10): 1687–9.
2. MillingtonGW (May 2006). "Proopiomelanocortin (POMC): the cutaneous roles of its melanocortin products and receptors". Clin. Exp. Dermatol. 31 (3): 407–12
3. MillingtonGW (2007). "The role of proopiomelanocortin (POMC) neurones in feeding behaviour". Nutr Metab (Lond) 4: 18.
- 1. Wei Wang, Taimei Di, et al. "EGCG, GCG, TFDG, or TSA Inhibiting Melanin Synthesis by Downregulating MC1R Expression." Int J Mol Sci. 2023 Jul 3;24(13):11017. PMID: 37446194
- 2. Wei Wang, Lin Chen, et al. "Effect of Active Groups and Oxidative Dimerization on the Antimelanogenic Activity of Catechins and Their Dimeric Oxidation Products." J Agric Food Chem. 2022 Feb 2;70(4):1304-1315. PMID: 35050598
- 3. Li F, Jiang X, et al. "A piggyBac-based TANGO GFP assay for high throughput screening of GPCR ligands in live cells." Cell Commun Signal. 2019 May 23;17(1):49. PMID: 31122241
| Physical Appearance | A solid |
| Storage | Store at -20°C |
| M.Wt | 1664.9 |
| Cas No. | 581-05-5 |
| Formula | C77H109N21O19S1 |
| Synonyms | Ac-Ser-Tyr-Ser-Met-Glu-His-Phe-Arg-Trp-Gly-Lys-Pro-Val-amide |
| Solubility | insoluble in EtOH; ≥10.44 mg/mL in H2O with ultrasonic; ≥166.5 mg/mL in DMSO with gentle warming |
| SDF | Download SDF |
| Shipping Condition | Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice. |
| General tips | We do not recommend long-term storage for the solution, please use it up soon. |
| Animal experiment:[1] | |
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Animal models |
IL-10-deficient mice |
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Dosage form |
50 µg/0.2 ml saline Injected intraperitoneally |
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Applications |
α-MSH given systemically effectively alleviated acute inflammatory reactions induced by an irritant (picryl chloride 0.5% in acetone) applied to the ear. The relative inhibition (percent of percent change) with α-MSH was virtually the same in both IL-10–deficient and in control animals (approximately 70%). α-MSH modulated all forms of inflammation by acting on peripheral inflammatory cells, glial inflammatory cells, and on central nervous system receptors that activate descending anti-inflammatory neural pathways. |
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Note |
The technical data provided above is for reference only. |
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References: 1. Lipton JM, Zhao H, Ichiyama T, et al. Mechanisms of antiinflammatory action of alpha-MSH peptides. In vivo and in vitro evidence. Annals of the New York Academy of Sciences, 1999, 885: 173-182. |
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Chemical structure
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