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Merck

M6638

[Met5]Enkephalin acetate salt hydrate

≥95.0% (HPLC), endogenous opioid neurotransmitter/neuromodulator, powder

Sinónimos:

Enkephalin M, [5-Methionine]Enkephalin

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Fórmula empírica (notación de Hill):
C27H35N5O7S · xC2H4O2 · yH2O
Número CAS:
82362-17-2
Peso molecular:
573.66 (anhydrous free base basis)
NACRES:
NA.32
PubChem Substance ID:
24897102
UNSPSC Code:
51111800
MDL number:
MFCD03788202
Beilstein/REAXYS Number:
3042295

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Nombre del producto

[Met5]Enkephalin acetate salt hydrate, ≥95.0% (HPLC), powder

InChI

1S/C27H35N5O7S.C2H4O2.H2O/c1-40-12-11-21(27(38)39)32-26(37)22(14-17-5-3-2-4-6-17)31-24(35)16-29-23(34)15-30-25(36)20(28)13-18-7-9-19(33)10-8-18;1-2(3)4;/h2-10,20-22,33H,11-16,28H2,1H3,(H,29,34)(H,30,36)(H,31,35)(H,32,37)(H,38,39);1H3,(H,3,4);1H2/t20-,21-,22-;;/m0../s1

SMILES string

O=C([C@H](CC1=CC=CC=C1)NC(CNC(CNC([C@@H](N)CC(C=C2)=CC=C2O)=O)=O)=O)N[C@@H](CCSC)C(O)=O.CC(O)=O.[H]O[H]

InChI key

NNACMJQGYXGHNE-DUQFDOSRSA-N

assay

≥95.0% (HPLC)

form

powder

composition

acetate, 2.5-20%

color

white

storage temp.

−20°C

Quality Level

200

Gene Information

human ... OPRD1(4985), OPRM1(4988)
mouse ... OPRD1(18386), OPRM1(18390)
rat ... OPRD1(24613), OPRM1(25601)

Categorías relacionadas

Application

[Met5] Enkephalin acetate salt hydrate has been used to study the effect of mutations in opioid growth factor receptor on growth of human cancer cell line.

Biochem/physiol Actions

Met-enkephalin is endogenous opioid neurotransmitter/neuromodulator with agonist activity at μ and δ opioid receptors. Enhancement of immune system function is mediated through met-enkephalin receptors on leukocytes. Met-enkephalin also functions as a growth factor on many cell types at a receptor that is distinct from the neuronal opioid receptors.
Opioid peptides play a crucial role in various physiological process such as pain mediation, opiate dependence and euphoria and members of this class contain aromatic residues in positions 1 and 4. [Met5] Enkephalin acts as a cytokine and is implicated in improving immune response in patients with cancer or AIDS. [Met5] Enkephalin boosts immune functions at low concentration and suppress at high concentration. ME is associated with glucose homeostasis. Increased concentration of ME is observed in plasma of type I diabetic patients.

General description

[Met5] Enkephalin (ME) is an opioid pentapeptide, which acts as a neurotransmitter or neuromodulator in the central nervous system. [Met5] Enkephalin is activated on interaction with three main subtypes of receptors including μand δ opioid receptors mediating classic opioid effects of met-Enk and ζ -receptors mediating non-opioid actions of the peptide, i.e. retardation of cell growth. [Met5] Enkephalin is derived from precursor peptide pro-methionine-enkephalin in vitro consisting of H-Tyr-Gly-Gly-Phe-Met-Arg-OH amino acid sequence. The peptide activity is observed in the central nervous, neuroendocrine and immune systems.

Clase de almacenamiento

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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Certificados de análisis (COA)

Lot/Batch Number
0000475003
0000475005
0000475005
0000475003
0000454885

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KD Tripathi
Essentials of Medical Pharmacology null
Isolation and structure of pro-methionine-enkephalin: Potential enkephalin precursor from porcine hypothalamus.
Proceedings of the National Academy of Sciences of the USA, 76(12), 6177-6180 (1979)
Effects of met-enkephalin on cell proliferation in different models of adrenocortical-cell growth.
Malendowicz LK
International Journal of Molecular Medicine, 15(5), 841-845 (2005)
N P Plotnikoff et al.
Clinical immunology and immunopathology, 82(2), 93-101 (1997-02-01)
The effects of methionine enkephalin (met-enkephalin) on human immune function are reviewed. This pentapeptide functions to upregulate, or enhance, immune function in the majority of donor samples at low doses and suppresses at high doses. The influence of this molecule
Plasma met-enkephalin in type I diabetes.
Negri M
Metabolism, Clinical and Experimental, 41(5), 460-461 (1992)
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