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M4135

α-Melanocyte stimulating hormone

≥97% (HPLC)

Synonym(s):

α-MSH, α-Melanotropin

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About This Item

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)
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biological source

synthetic (organic)

Quality Level

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)

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.
  • 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

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000521397
0000521397
0000458183
0000357774
0000357775

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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)
Hyerim Song et al.
International journal of molecular sciences, 21(13) (2020-07-02)
The aim of this study was to identify novel antimelanogenic drugs from an epigenetic screening library containing various modulators targeting DNA methyltransferases, histone deacetylases, and other related enzymes/proteins. Of 141 drugs tested, K8 (4-((hydroxyamino)carbonyl)-N-(2-hydroxyethyl)-N-phenyl-benzeneacetamide; HPOB) was found to effectively inhibit
Prolactin-stimulated growth of cell cultures established from malignant Nb rat lymphomas.
Gout PW
Cancer Research, 40(7), 2433-2436 (1980)
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