[Met]enkephalin   Click here for help

GtoPdb Ligand ID: 1614

Synonyms: 1-5 Adrenorphin | [Met]-enkephalin | IRT-101 | methionine enkephalin | np2 enkephalin | opioid growth factor (OGF)
Immunopharmacology Ligand
Comment: MET-enkephalin (MENK) is an endogenous opioid peptide. It exhibits agonist activity at the δ- and μ-opioid receptors. MENK produces immunomodulatory, neuromodulatory, antinociceptive/analgesic, antidepressant, and gastrointestinal motility modulating activities. It has cytostatic activity vs. cancer cells and may help recruit NK cells to kill tumour cells [3,5,8].
Species: Human, Mouse, Rat
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2D Structure
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Canonical SMILES CSCCC(C(=O)O)NC(=O)C(Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)C(Cc1ccc(cc1)O)N
Isomeric SMILES CSCC[C@@H](C(=O)O)NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@H](Cc1ccc(cc1)O)N
InChI InChI=1S/C27H35N5O7S/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/h2-10,20-22,33H,11-16,28H2,1H3,(H,29,34)(H,30,36)(H,31,35)(H,32,37)(H,38,39)/t20-,21-,22-/m0/s1
1. Li X, Meng Y, Plotnikoff NP, Youkilis G, Griffin N, Wang E, Lu C, Shan F. (2015)
Methionine enkephalin (MENK) inhibits tumor growth through regulating CD4+Foxp3+ regulatory T cells (Tregs) in mice.
Cancer Biol Ther, 16 (3): 450-9. [PMID:25701137]
2. Meng F, Xie GX, Thompson RC, Mansour A, Goldstein A, Watson SJ, Akil H. (1993)
Cloning and pharmacological characterization of a rat kappa opioid receptor.
Proc Natl Acad Sci USA, 90 (21): 9954-8. [PMID:8234341]
3. Meng Y, Gao X, Chen W, Plotnikoff NP, Griffin N, Zhang G, Shan F. (2017)
Methionine enkephalin (MENK) mounts antitumor effect via regulating dendritic cells (DCs).
Int Immunopharmacol, 44: 61-71. [PMID:28088065]
4. Raynor K, Kong H, Chen Y, Yasuda K, Yu L, Bell GI, Reisine T. (1994)
Pharmacological characterization of the cloned kappa-, delta-, and mu-opioid receptors.
Mol Pharmacol, 45 (2): 330-4. [PMID:8114680]
5. Wang DM, Jiao X, Plotnikoff NP, Griffin N, Qi RQ, Gao XH, Shan FP. (2017)
Killing effect of methionine enkephalin on melanoma in vivo and in vitro.
Oncol Rep, 38 (4): 2132-2140. [PMID:28849104]
6. Wang Q, Gao X, Yuan Z, Wang Z, Meng Y, Cao Y, Plotnikoff NP, Griffin N, Shan F. (2014)
Methionine enkephalin (MENK) improves lymphocyte subpopulations in human peripheral blood of 50 cancer patients by inhibiting regulatory T cells (Tregs).
Hum Vaccin Immunother, 10 (7): 1836-40. [PMID:25424790]
7. Yasuda K, Raynor K, Kong H, Breder CD, Takeda J, Reisine T, Bell GI. (1993)
Cloning and functional comparison of kappa and delta opioid receptors from mouse brain.
Proc Natl Acad Sci USA, 90 (14): 6736-40. [PMID:8393575]
8. Zhao D, Plotnikoff N, Griffin N, Song T, Shan F. (2016)
Methionine enkephalin, its role in immunoregulation and cancer therapy.
Int Immunopharmacol, 37: 59-64. [PMID:26927200]