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M6638

Sigma-Aldrich

[Met5]Enkephalin acetate salt hydrate

≥95.0% (HPLC), powder

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Synonym(s):
Enkephalin M, [5-Methionine]Enkephalin
Empirical Formula (Hill Notation):
C27H35N5O7S · xC2H4O2 · yH2O
CAS Number:
82362-17-2
Molecular Weight:
573.66 (anhydrous free base basis)
Beilstein:
3042295
MDL number:
MFCD03788202
UNSPSC Code:
12352200
PubChem Substance ID:
24897102
NACRES:
NA.32

Quality Level

200

Assay

≥95.0% (HPLC)

form

powder

composition

acetate, 2.5-20%

color

white

storage temp.

−20°C

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

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

InChI key

NNACMJQGYXGHNE-DUQFDOSRSA-N

Gene Information

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

Related Categories

Amino Acid Sequence

Tyr-Gly-Gly-Phe-Met

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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

监管及禁止进口产品

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
KD Tripathi
Essentials of Medical Pharmacology null
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
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
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