Home>>Peptides>>Tyr-Gly-Gly-Phe-Met-OH (Met-Enkephalin)

Tyr-Gly-Gly-Phe-Met-OH (Met-Enkephalin) Sale

(Synonyms: 蛋氨酸脑啡肽; Met-Enkephalin; Methionine enkephalin) 目录号 : GC30816

Tyr-Gly-Gly-Phe-Met-OH (Met-Enkephalin) 通过与阿片受体结合来调节人体免疫功能并抑制肿瘤生长。

Tyr-Gly-Gly-Phe-Met-OH (Met-Enkephalin) Chemical Structure

Cas No.:58569-55-4

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10mM (in 1mL Water)
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25mg
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50mg
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100mg
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产品描述

Tyr-Gly-Gly-Phe-Met-OH regulates human immune function and inhibits tumor growth via binding to the opioid receptor.

Methionine enkephalin (MENK), an endogenous neuropeptide has a crucial role in both neuroendocrine and immune systems. MENK is believed to have an immunoregulatory activity to have cancer biotherapy activity by binding to the opioid receptors on immune and cancer cells. MENK may also change the tumor microenvironment by binding to opioid receptor on or in cancer cells. All of these mechanisms of action have biologic significance and potential for use in cancer immunotherapy. Furthermore, they reveal a relationship between the endocrine and immune systems[1].

[1]. Zhao D, et al. Methionine enkephalin, its role in immunoregulation and cancer therapy. Int Immunopharmacol. 2016 Feb 23. pii: S1567-5769(16)30050-9.

Chemical Properties

Cas No. 58569-55-4 SDF
别名 蛋氨酸脑啡肽; Met-Enkephalin; Methionine enkephalin
Canonical SMILES Tyr-Gly-Gly-Phe-Met
分子式 C27H35N5O7S 分子量 573.66
溶解度 DMSO : ≥ 40 mg/mL (69.73 mM);Water : 6.67 mg/mL (11.63 mM) 储存条件 Store at -20°C
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1 mM 1.7432 mL 8.716 mL 17.4319 mL
5 mM 0.3486 mL 1.7432 mL 3.4864 mL
10 mM 0.1743 mL 0.8716 mL 1.7432 mL
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Research Update

Endomorphins, Met-enkephalin, Tyr-MIF-1, and the P-glycoprotein efflux system

The P-glycoprotein (P-gp) transport system, responsible for the efflux of many therapeutic drugs out of the brain, recently has been shown to transport the endogenous brain opiate endorphin. We used P-gp knockout mice (Mdr1a) and their controls to determine where P-gp is involved in the saturable efflux systems of four other endogenous opiate-modulating peptides across the blood-brain barrier (BBB). After injection of endomorphin-1 (Tyr-Pro-Trp-Phe-NH(2)), endomorphin-2 (Tyr-Pro-Phe-Phe-NH(2)), Met-enkephalin (Tyr-Gly-Gly-Phe-Met-OH), and Tyr-MIF-1 (Tyr-Pro-Leu-Gly-NH(2)) into the lateral ventricle of the mouse brain, residual radioactivity was measured at 0, 2, 5, 10, and 20 min later. The results showed no difference in the disappearance of any of these peptides from the brains of knockout mice compared with their controls. This demonstrates that unlike endorphin and morphine, P-gp does not seem to be required for the brain-to-blood transport of the endomorphins, Met-enkephalin, or Tyr-MIF-1 across the BBB.

Characterization of the release of Met-enkephalin from isolated nerve terminals: release kinetics and cation-dependence

The release of the neuropeptide Met-enkephalin (Met-ENK) from isolated nerve terminals (synaptosomes) of the rat forebrain was characterized with respect to the subcellular distribution, the release upon addition of various stimulatory agents, the release kinetics, the cation-dependence of release and the relationship between Met-ENK release and elevations of the intraterminal free Ca(2+)-concentration ([Ca]i). A highly specific radioimmunoassay was developed for determination of Met-ENK (H-Tyr-Gly-Gly-Phe-Met-OH). Truncated and elongated forms of Met-ENK, Leu-enkephalin, beta-endorphin and dynorphin displayed negligible cross-reactivity. Met-ENK-like immunoreactivity (Met-ENK-LI) is enriched in the purified synaptosomal fraction of rat forebrain homogenates and is released in a strictly Ca(2+)-dependent manner upon chemical depolarization or stimulation with the Ca2+ ionophore, ionomycin. A correlation exists between the release of Met-ENK-LI and the elevations of [Ca]i. Barium ions are able to replace Ca2+ in triggering Met-ENK-LI release. The release of Met-ENK-LI is initiated within 20 s after depolarization and is terminated after 3-5 min, although depolarization and [Ca]i elevation are maintained. At this time, > 90% of the initial Met-ENK-LI is still present inside the synaptosomes. Repolarization and renewed stimulation again evokes Ca(2+)-dependent release of this retained Met-ENK-LI. It is concluded that Met-ENK release from isolated nerve terminals is exocytotic, and that exocytosis is terminated by a regulatory mechanism in synaptosomes after 3-5 min of depolarization, a process which can be reversed by repolarization.(ABSTRACT TRUNCATED AT 250 WORDS)

Use of NMR and fluorescence spectroscopy as well as theoretical conformational analysis in conformation-activity studies of cyclic enkephalin analogues

In this review the conformational studies of natural enkephalins (H-Tyr-Gly-Gly-Phe-Met-OH; the [Met(5)]enkephalin and H-Tyr-Gly-Gly-Phe-Leu-OH; the [Leu(5)]enkephalin), their acyclic and cyclic analogues, including those carried out in our laboratory, performed by experimental and theoretical methods and their combination, are described. Emphasis is given on the role of conformational constraints introduced by cyclization on activity at the micro and delta opioid receptors. Comparison of the conformations of cyclic enkephalin analogues with high delta-receptor activity with those of potent rigid non-peptide delta-receptor agonists indicates that the proximity of the aromatic side chains in positions 1 and 4 as well as the N-terminal amino group is desirable for the activity at the delta opioid receptors; early conformational studies also suggested that spatial separation of the aromatic side chains and rigidity of the cyclic backbone is desirable for micro-receptor activity. The results of our recent conformational studies performed with the use of fluorescence and NMR spectroscopy as well as theoretical calculations indicate, however, that these structural features are not necessary for activity at the micro opioid receptors. Methods applied to the determination of the conformation of flexible peptides, such as Nuclear Magnetic Resonance (NMR), fluorescence spectroscopy, and theoretical conformational analysis are also discussed briefly.

Morphine-like peptides in mammalian brain: isolation, structure elucidation, and interactions with the opiate receptor

A substance that competes for opiate receptor binding has been isolated from calf brain and identified as two pentapeptides, H-Tyr-Gly-Gly-Phe-Met-OH (methionine enkephalin) and H-Tyr-Gly-Gly-Phe-Leu-OH (leucine enkephalin), with about four times more leucine enkephalin than methionine enkephalin. Sodium and manganese effects on opiate receptor interactions show that both peptides are agonists, whereas leucine enkephalin may be a "purer" agonist than methionine enkephalin.

Identification of two related pentapeptides from the brain with potent opiate agonist activity

Enkephalin, a natural ligand for opiate receptors is composed of the pentapepides H-Tyr-Gly-Gly-Phe-Met-OH and H-Tyr-Gly-Gly-Phe-Leu-OH. The evidence is based on the determination of the amino acid sequence of natural enkephalin by the dansyl-Edman procedure and by mass spectrometry followed by synthesis and comparison of the natural and synthetic peptides.