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M4135 Sigma-Aldrich

α-Melanocyte stimulating hormone

≥97% (HPLC)

Synonym: α-MSH, α-Melanotropin

  • CAS Number 581-05-5

  • Empirical Formula (Hill Notation) C77H109N21O19S

  • Molecular Weight 1664.88

  •  Beilstein/REAXYS Number 741840

  •  MDL number MFCD00133062

  •  PubChem Substance ID 24896905

  •  NACRES NA.32

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Properties

Related Categories α-Melanocyte Stimulating Hormone (α-MSH), Cell Biology, Cell Signaling and Neuroscience, Cytokines Growth Factors and Hormones (Obesity), Cytokines, Growth Factors and Hormones,
Quality Level   200
biological source   synthetic (organic)
assay   ≥97% (HPLC)
form   powder
solubility   water: 1.00-1.04 mg/mL, clear, colorless
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

Amino Acid Sequence

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

General description

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.
•  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.

Packaging

1, 5 mg in glass bottle

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.

Antibody Adsorbant

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

Linkage

Derived from ACTH 1-13

Other Notes

Lyophilized from 0.1% TFA in H2O

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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