M4135

Sigma-Aldrich

α-Melanocyte stimulating hormone

≥97% (HPLC)

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

Quality Level

biological source

synthetic (organic)

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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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

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_code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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)
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...
Hyun Jun Park et al.
PloS one, 15(9), e0239019-e0239019 (2020-09-18)
The melanosome is a specialized membrane-bound organelle that is involved in melanin synthesis, storage, and transportation. In contrast to melanosome biogenesis, the processes underlying melanosome degradation remain largely unknown. Autophagy is a process that promotes degradation of intracellular components' cooperative...
The role of alpha-melanocyte-stimulating hormone in cutaneous biology.
Luger TA
The Journal of Investigative Dermatology. Symposium Proceedings / The Society for Investigative Dermatology, Inc. [and] European Society for Dermatological Research, 2(1), 87-93 (1997)
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)

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