M4135

α-Melanocyte stimulating hormone

≥97% (HPLC)

• Synonym(s): α-MSH, α-Melanotropin
• Empirical Formula (Hill Notation): C₇₇H₁₀₉N₂₁O₁₉S
• CAS Number: 581-05-5
• Molecular Weight: 1664.88
• UNSPSC Code: 51111800
• NACRES: NA.32
• PubChem Substance ID: 24896905
• MDL number: MFCD00133062
• Beilstein/REAXYS Number: 741840
• Biological source: synthetic (organic)
• Form: powder
• Assay: ≥97% (HPLC)

Properties

• biological source: synthetic (organic)
• Quality Segment: 200
• sterility: non-sterile
• assay: ≥97% (HPLC)
• form: powder
• solubility: water: 1.00-1.04 mg/mL, clear, colorless
• UniProt accession no.: P01189
• shipped in: ambient
• storage temp.: −20°C
• SMILES string: CSCC[C@H](NC(=O)[C@H](CO)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CO)NC(C)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](Cc2c[nH]cn2)C(=O)N[C@@H](Cc3ccccc3)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](Cc4c[nH]c5ccccc45)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N6CCC[C@H]6C(=O)N[C@@H](C(C)C)C(N)=O
• 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)/t51-,52-,53-,54-,55-,56-,57-,58-,59-,60-,61-,64-/m0/s1
• InChI key: WHNFPRLDDSXQCL-UAZQEYIDSA-N
• Gene Information: human ... POMC(5443)

Description

General description

Ac-Ser-Tyr-Ser-Met-Glu-His-Phe-Arg-Trp-Gly-Lys-Pro-Val-NH₂

α-Melanocyte-stimulating hormone (α-MSH) is a tridecapeptide, mostly produced by the cells in the brain, pituitary and circulation. Pro-inflammatory cytokines or UV light induced epidermal cells such as keratinocytes and melanocytes synthesize and discharge α–MSH. Poopiomelanocortin (POMC) acts as a precursor for α-Melanocyte-stimulating hormone (α-MSH) production.

Application

α-Melanocyte stimulating hormone (α–MSH) has been used for following studies:

• it has been Intracerebroventricularly (icv) injected to mice for behavioral studies.[1]
• to determine the effect of α−MSH on growth of stationary Nb 2 node lymphoma cell cultures.
• to determine the effect of α−MSH on leptin secretion in the primary cultures of differentiated adipocytes.
• α−MSH promoted melanin production in the B16-F1 cells from murine melanoma cell line.

Biochem/physiol Actions

Hormone that stimulates melanogenesis; facilitates learning and memory; affects inflammatory and immune responses and peripheral nerve regeneration.

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. 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.

Pituitary hormone which causes darkening skin pigmentation from amphibians to humans. In mammals, it can also have behavioral effects on learning, attention, and memory.

Other Notes

Derived from ACTH 1-13

Lyophilized from 0.1% TFA in H2O

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)