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M4135

Sigma-Aldrich

α-Melanocyte stimulating hormone

≥97% (HPLC)

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Synonym(s):
α-MSH, α-Melanotropin
Empirical Formula (Hill Notation):
C77H109N21O19S
CAS Number:
Molecular Weight:
1664.88
Beilstein/REAXYS Number:
741840
MDL number:
PubChem Substance ID:
NACRES:
NA.32

biological source

synthetic (organic)

Quality Level

sterility

non-sterile

assay

≥97% (HPLC)

form

powder

solubility

water: 1.00-1.04 mg/mL, clear, colorless

UniProt accession no.

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)

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Show Differences

1 of 4

This Item
M8764A0423AB5087
vibrant-m

M4135

α-Melanocyte stimulating hormone

vibrant-m

A0423

Adrenocorticotropic Hormone human

assay

≥97% (HPLC)

assay

≥95% (HPLC)

assay

≥97% (HPLC)

assay

-

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

300

sterility

non-sterile

sterility

non-sterile

sterility

non-sterile

sterility

-

solubility

water: 1.00-1.04 mg/mL, clear, colorless

solubility

0.1% aqueous TFA: 1.00-1.04 mg/mL, clear, colorless

solubility

water: 1.00-1.04 mg/mL, clear, colorless

solubility

-

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

-

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.

Biochem/physiol Actions

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Prolactin-stimulated growth of cell cultures established from malignant Nb rat lymphomas.
Gout PW
Cancer Research, 40(7), 2433-2436 (1980)
Effects of Egg Shell Membrane Hydrolysates on UVB-radiation-induced Wrinkle Formation in SKH-1 Hairless Mice.
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Korean journal for food science of animal resources, 35(1), 58-70 (2015)
Regulation of adipose tissue leptin secretion by alpha-melanocyte-stimulating hormone and agouti-related protein: further evidence of an interaction between leptin and the melanocortin signalling system.
Hoggard N
Journal of Molecular Endocrinology, 32(1), 145-153 (2004)
Alpha-melanocyte-stimulating hormone inhibits the nuclear transcription factor NF-kappa B activation induced by various inflammatory agents.
Manna SK and Aggarwal BB
Journal of Immunology, 161(6), 2873-2880 (1998)
Peristera-Ioanna Petropoulou et al.
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In the mouse, the osteoblast-derived hormone Lipocalin-2 (LCN2) suppresses food intake and acts as a satiety signal. We show here that meal challenges increase serum LCN2 levels in persons with normal or overweight, but not in individuals with obesity. Postprandial

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