M6638

[Met⁵]Enkephalin acetate salt hydrate

≥95.0% (HPLC), powder

• 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/REAXYS Number: 3042295
• MDL number: MFCD03788202
• UNSPSC Code: 51111800
• PubChem Substance ID: 24897102
• NACRES: NA.32

Properties

• 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)

Description

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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)