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Chemical Compound Review

MET-enkephalin     (2S)-2-[[(2S)-2-[2-[2-[[(2S)- 2-amino-3-(4...

Synonyms: Met-Enk, Enkephalin M, CHEMBL13786, SureCN632433, M6638_SIGMA, ...
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Disease relevance of Methionine enkephalin


Psychiatry related information on Methionine enkephalin


High impact information on Methionine enkephalin


Chemical compound and disease context of Methionine enkephalin


Biological context of Methionine enkephalin

  • [Met]Enkephalin-containing proteins of 8600 and 12,600 daltons have been isolated from acid extracts of bovine adrenal medulla and purified to homogeneity, and their sequences have been determined by a combination of automated Edman degradation, tryptic mapping, and enzymatic time-course hydrolysis [16].
  • Ethanol acceptance as a function of genotype amounts of brain [Met]enkephalin [17].
  • The presence of [Met]enkephalin, a pentapeptide derived from proenkephalin, in these two brain areas is consistent with a synthetic role for this mRNA and implicates proenkephalin gene expression in the control of motor function [18].
  • FPI attenuates vasodilation and cGMP production by methionine enkephalin (Met) and leucine enkephalin (Leu) and reverse dynorphin (Dyn) from a dilator to a constrictor [19].
  • Between 125 and 140 days of gestation, plasma free Met-Enk concentrations were similar and significantly higher in the intact and HX + T4 groups than those measured in the HX + saline fetal sheep [20].

Anatomical context of Methionine enkephalin


Associations of Methionine enkephalin with other chemical compounds


Gene context of Methionine enkephalin

  • The greatest numbers of nerve cell bodies contained AChE, followed in decreasing order by SP, mENK and NPY [29].
  • CGRP was the most potent stimulatory neurotransmitter in RA fibroblasts whereas the sympathetic adenosine, NE, beta-endorphin, and MENK were inhibitory [30].
  • The connectivity experiments employed five combinations of fluorescent tracer injection and were combined with immunohistochemical localization of either neuropeptide Y (NPY), met-enkephalin (mENK) or the vasoactive intestinal polypeptide (VIP)/peptide histidine isoleucine (PHI) group [31].
  • In RA fibroblasts, beta-endorphin and MENK inhibited IL-8 secretion at 10(-9) to 10(-7) M (p < 0.01), whereas in OA fibroblasts the dose response curve was shifted to lower concentrations (10(-12) M, 10(-11) M; p < 0.01) [30].
  • Subsequently, CGRP, Met-Enk or TH antisera were applied to these sections and the resulting brown diaminobenzidine reaction product in the cytoplasm was examined [32].

Analytical, diagnostic and therapeutic context of Methionine enkephalin

  • A highly specific radioimmunoassay for one of the putative adrenomedullary [Met]enkephalin precursors, BAM-12P (Tyr-Gly-Gly-Phe-Met-Arg-Arg-Val-Gly-Arg-Pro-Glu-OH), has been developed [33].
  • Sequence analysis of the 3600-dalton polypeptide has not been completed, but the polypeptide has been shown to contain a single [Met]enkephalin sequence followed by an -Arg-Phe linkage that forms the carboxyl terminus of the molecule [34].
  • Within 3 days in coculture with endothelial cells, but not with unrelated control cells, PC12 cells synthesized increased levels of [Met]enkephalin [35].
  • We have demonstrated the existence of Met-Enk-Arg6-Gly7-Leu8 together with Met-Enk, Leu-Enk and Met-Enk-Arg6-Phe7 in human gastric antrum, using high performance liquid chromatography (HPLC) coupled with radioimmunoassays for these opioid peptides [36].
  • One day after surgery, the adrenal dialysis system was connected to a perfusion pump and Ringer solution or a Ringer solution containing Met-Enk, naloxone (Nal), or a combination of Met-Enk and Nal was used for dialysis; dialysate fractions were collected at 5-min intervals [37].


  1. Partial characterization of the mRNA that codes for enkephalins in bovine adrenal medulla and human pheochromocytoma. Comb, M., Herbert, E., Crea, R. Proc. Natl. Acad. Sci. U.S.A. (1982) [Pubmed]
  2. Isolation, sequence analysis, and physiological properties of enkephalins in the nervous tissue of the shore crab Carcinus maenas L. Lüschen, W., Buck, F., Willig, A., Jaros, P.P. Proc. Natl. Acad. Sci. U.S.A. (1991) [Pubmed]
  3. Opposing mechanisms of regulation of a G-protein-coupled inward rectifier K+ channel in rat brain neurons. Velimirovic, B.M., Koyano, K., Nakajima, S., Nakajima, Y. Proc. Natl. Acad. Sci. U.S.A. (1995) [Pubmed]
  4. Noscapine crosses the blood-brain barrier and inhibits glioblastoma growth. Landen, J.W., Hau, V., Wang, M., Davis, T., Ciliax, B., Wainer, B.H., Van Meir, E.G., Glass, J.D., Joshi, H.C., Archer, D.R. Clin. Cancer Res. (2004) [Pubmed]
  5. Circulating [Met]enkephalin and catecholamine responses to acute hypotension and hypertension in anaesthetized greyhounds. Mason, D.F., Medbak, S., Rees, L.H. Br. J. Pharmacol. (1987) [Pubmed]
  6. Social interaction increases the extracellular levels of [Met]enkephalin in the nucleus accumbens of control but not of chronic mild stressed rats. Bertrand, E., Smadja, C., Mauborgne, A., Roques, B.P., Daugé, V. Neuroscience (1997) [Pubmed]
  7. Peripheral effects of methionine-enkephalin on inflammatory reactions and behavior in the rat. Vujić-Redzić, V., Dimitrijević, M., Stanojević, S., Kovacevic-Jovanović, V., Miletić, T., Radulovi J, n.u.l.l. Neuroimmunomodulation (2000) [Pubmed]
  8. Cathepsin L in secretory vesicles functions as a prohormone-processing enzyme for production of the enkephalin peptide neurotransmitter. Yasothornsrikul, S., Greenbaum, D., Medzihradszky, K.F., Toneff, T., Bundey, R., Miller, R., Schilling, B., Petermann, I., Dehnert, J., Logvinova, A., Goldsmith, P., Neveu, J.M., Lane, W.S., Gibson, B., Reinheckel, T., Peters, C., Bogyo, M., Hook, V. Proc. Natl. Acad. Sci. U.S.A. (2003) [Pubmed]
  9. Interleukin 1 beta and corticotropin-releasing factor inhibit pain by releasing opioids from immune cells in inflamed tissue. Schäfer, M., Carter, L., Stein, C. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
  10. [D-Ala2]deltorphin I binding and pharmacological evidence for a special subtype of delta opioid receptor on human and invertebrate immune cells. Stefano, G.B., Melchiorri, P., Negri, L., Hughes, T.K., Scharrer, B. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  11. Termination pattern and fine structural characteristics of GABA- and [Met]enkephalin-containing nerve fibers and synapses in the superior cervical ganglion of adult rat. Párducz, A., Dobó, E., Joó, F., Wolff, J.R. Neuroscience (1992) [Pubmed]
  12. Effect of liver and renal dysfunction on circulating methionine-enkephalin immunoreactivity. Smith, R., Grossman, A., Gimson, A.E., Besser, G.M., Rees, L.H. Neurosci. Lett. (1985) [Pubmed]
  13. Involvement of substance P in neutral endopeptidase modulation of carotid body sensory responses to hypoxia. Kumar, G.K., Kou, Y.R., Overholt, J.L., Prabhakar, N.R. J. Appl. Physiol. (2000) [Pubmed]
  14. Inhibition of adrenergic transmission by methionine- and leucine-enkephalins is impaired in the mesenteric vasculatures of spontaneously hypertensive rats. Tsuda, K., Masuyama, Y. Jpn. Circ. J. (1989) [Pubmed]
  15. Effects of hemorrhage on vasopressin and Met-Enk releases in blood and cerebrospinal fluid in dogs. Ota, K., Kimura, T., Matsui, K., Iitake, K., Shoji, M., Inoue, M., Yoshinaga, K. Am. J. Physiol. (1988) [Pubmed]
  16. Adrenal opioid proteins of 8600 and 12,600 daltons: intermediates in proenkephalin processing. Jones, B.N., Shively, J.E., Kilpatrick, D.L., Stern, A.S., Lewis, R.V., Kojima, K., Udenfriend, S. Proc. Natl. Acad. Sci. U.S.A. (1982) [Pubmed]
  17. Ethanol acceptance as a function of genotype amounts of brain [Met]enkephalin. Blum, K., Elston, S.F., DeLallo, L., Briggs, A.H., Wallace, J.E. Proc. Natl. Acad. Sci. U.S.A. (1983) [Pubmed]
  18. Cellular localization of proenkephalin mRNA in rat brain: gene expression in the caudate-putamen and cerebellar cortex. Shivers, B.D., Harlan, R.E., Romano, G.J., Howells, R.D., Pfaff, D.W. Proc. Natl. Acad. Sci. U.S.A. (1986) [Pubmed]
  19. Endothelin production links superoxide generation to altered opioid-induced pial artery vasodilation after brain injury in pigs. Kasemsri, T., Armstead, W.M. Stroke (1997) [Pubmed]
  20. Thyroid hormone replacement restores circulating enkephalin concentrations in hypophysectomized fetal sheep. Simonetta, G., Young, I.R., McMillen, I.C. J. Neurochem. (1994) [Pubmed]
  21. Studies with [35S]methionine indicate that the 22,000-dalton [Met]enkephalin-containing protein in chromaffin cells is a precursor of [Met]enkephalin. Rossier, J., Trifaró, J.M., Lewis, R.V., Lee, R.W., Stern, A., Kimura, S., Stein, S., Udenfriend, S. Proc. Natl. Acad. Sci. U.S.A. (1980) [Pubmed]
  22. Enkephalin biosynthetic pathway: proteins of 8000 and 14,000 daltons in bovine adrenal medulla. Lewis, R.V., Stern, A.S., Kimura, S., Stein, S., Udenfriend, S. Proc. Natl. Acad. Sci. U.S.A. (1980) [Pubmed]
  23. Expression of preproenkephalin-like mRNA and its peptide products in mammalian testis and ovary. Kilpatrick, D.L., Howells, R.D., Noe, M., Bailey, L.C., Udenfriend, S. Proc. Natl. Acad. Sci. U.S.A. (1985) [Pubmed]
  24. Synthesis of enkephalins by adrenal medullary chromaffin cells: reserpine increases incorporation of radiolabeled amino acids. Wilson, S.P., Chang, K.J., Viveros, O.H. Proc. Natl. Acad. Sci. U.S.A. (1980) [Pubmed]
  25. Proenkephalin, [Met]enkephalin, and oxytocin immunoreactivities are colocalized in bovine hypothalamic magnocellular neurons. Vanderhaeghen, J.J., Lotstra, F., Liston, D.R., Rossier, J. Proc. Natl. Acad. Sci. U.S.A. (1983) [Pubmed]
  26. Molecular cloning of endopin 1, a novel serpin localized to neurosecretory vesicles of chromaffin cells. Inhibition of basic residue-cleaving proteases by endopin 1. Hwang, S.R., Steineckert, B., Yasothornsrikul, S., Sei, C.A., Toneff, T., Rattan, J., Hook, V.Y. J. Biol. Chem. (1999) [Pubmed]
  27. Met-enkephalin enhances follicle-stimulating hormone-dependent progesterone production from cultured granulosa cells. Facchinetti, F., Ruspa, M., Turci, A., Petraglia, F., Segre, A., Forabosco, A., Genazzani, A.R. J. Clin. Endocrinol. Metab. (1986) [Pubmed]
  28. Preproenkephalin mRNA and methionine-enkephalin content are increased in mouse striatum after treatment with nicotine. Dhatt, R.K., Gudehithlu, K.P., Wemlinger, T.A., Tejwani, G.A., Neff, N.H., Hadjiconstantinou, M. J. Neurochem. (1995) [Pubmed]
  29. The subserosal ganglia of the human taenia. Crowe, R., Burnstock, G. Neurosci. Lett. (1990) [Pubmed]
  30. Neurotransmitter modulation of interleukin 6 (IL-6) and IL-8 secretion of synovial fibroblasts in patients with rheumatoid arthritis compared to osteoarthritis. Raap, T., Jüsten, H.P., Miller, L.E., Cutolo, M., Schölmerich, J., Straub, R.H. J. Rheumatol. (2000) [Pubmed]
  31. Organization of lateral geniculate-hypothalamic connections in the rat. Card, J.P., Moore, R.Y. J. Comp. Neurol. (1989) [Pubmed]
  32. Estrogen receptor-immunoreactive neurons contain calcitonin gene-related peptide, methionine-enkephalin or tyrosine hydroxylase in the female rat preoptic area. Yuri, K., Kawata, M. Neurosci. Res. (1994) [Pubmed]
  33. Molecular forms of the putative enkephalin precursor BAM-12P in bovine adrenal, pituitary, and hypothalamus. Baird, A., Ling, N., Böhlen, P., Benoit, R., Klepper, R., Guillemin, R. Proc. Natl. Acad. Sci. U.S.A. (1982) [Pubmed]
  34. Two adrenal opioid polypeptides: proposed intermediates in the processing of proenkephalin. Stern, A.S., Jones, B.N., Shively, J.E., Stein, S., Undenfriend, S. Proc. Natl. Acad. Sci. U.S.A. (1981) [Pubmed]
  35. PC12 cells differentiate into chromaffin cell-like phenotype in coculture with adrenal medullary endothelial cells. Mizrachi, Y., Naranjo, J.R., Levi, B.Z., Pollard, H.B., Lelkes, P.I. Proc. Natl. Acad. Sci. U.S.A. (1990) [Pubmed]
  36. Occurrence of methionine-enkephalin-Arg6-Gly7-Leu8 with methionine-enkephalin, leucine-enkephalin and methionine-enkephalin-Arg6-Phe7 in human gastric antrum. Sakamoto, M., Nakao, K., Yoshimasa, T., Ikeda, Y., Suda, M., Takasu, K., Shimbo, S., Yanaihara, N., Imura, H. J. Clin. Endocrinol. Metab. (1983) [Pubmed]
  37. In vivo demonstration of a paracrine, inhibitory action of Met-enkephalin on adrenomedullary catecholamine release in the rat. Jarry, H., Dietrich, M., Barthel, A., Giesler, A., Wuttke, W. Endocrinology (1989) [Pubmed]
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