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Merck
CN

M6638

[Met5]Enkephalin acetate salt hydrate

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

别名:

Enkephalin M, [5-Methionine]Enkephalin

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关于此项目

经验公式（希尔记法）:
C27H35N5O7S · xC2H4O2 · yH2O
化学文摘社编号:
82362-17-2
分子量:
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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产品名称

[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)

相关类别

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.

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.

存储类别

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

法规信息

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分析证书(COA)

Lot/Batch Number
0000515239
0000515239
0000475003
0000475005
0000475005

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Structure of Met-enkephalin in explicit aqueous solution using replica exchange molecular dynamics.
Sanbonmatsu KY and Garcia AE
Proteins: Structure, Function, and Genetics, 46(2), 225-234 (2002)
Marissa J Metz et al.
eNeuro, 8(3) (2021-05-26)
Naltrexone is an opioid receptor antagonist approved for the treatment of alcohol and opioid use disorders at doses of 50-150 mg/d. Naltrexone has also been prescribed at much lower doses (3-6 mg/d) for the off-label treatment of inflammation and pain. Currently, a
Plasma met-enkephalin in type I diabetes.
Negri M
Metabolism, Clinical and Experimental, 41(5), 460-461 (1992)
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)
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