Met-Enkephalin
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Met-Enkephalin

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Met-Enkephalin is synthetic opioid peptides that has opioid effects of a relatively short duration.

Category
Peptide Inhibitors
Catalog number
BAT-010156
CAS number
58569-55-4
Molecular Formula
C27H35N5O7S
Molecular Weight
573.67
Met-Enkephalin
IUPAC Name
(2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylsulfanylbutanoic acid
Synonyms
Lupex; Methionine enkephalin; Metenkephalin; Tyr-Gly-Gly-Phe-Met-OH; INNO-105; IRT-101
Appearance
White or Off-white Lyophilized Powder
Purity
≥98%
Density
1.324 g/cm3
Melting Point
174-177°C
Boiling Point
1052.9°C at 760 mmHg
Sequence
H-Tyr-Gly-Gly-Phe-Met-OH
Storage
Store at -20 °C
Solubility
Soluble in DMSO
Application
Opioid effects of a relatively short duration.
InChI
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
InChI Key
YFGBQHOOROIVKG-FKBYEOEOSA-N
Canonical SMILES
CSCCC(C(=O)O)NC(=O)C(CC1=CC=CC=C1)NC(=O)CNC(=O)CNC(=O)C(CC2=CC=C(C=C2)O)N
1.Brain levels of neuropeptides in human chronic methamphetamine users.
Frankel PS1, Alburges ME, Bush L, Hanson GR, Kish SJ. Neuropharmacology. 2007 Sep;53(3):447-54. Epub 2007 Jun 28.
Animal data show that neuropeptide systems in the dopamine-rich brain areas of the striatum (caudate, putamen, and nucleus accumbens) are influenced by exposure to psychostimulants, suggesting that neuropeptides are involved in mediating aspects of behavioral responses to drugs of abuse. To establish in an exploratory study whether levels of neuropeptides are altered in brain of human methamphetamine users, we measured tissue concentrations of dynorphin, metenkephalin, neuropeptide Y, neurotensin, and substance P in autopsied brains of 16 chronic methamphetamine users and 17 matched control subjects. As expected, levels of most neuropeptides were enriched in dopamine-linked brain regions such as the nucleus accumbens and striatum of normal human brain. In contrast to animal findings of increased neuropeptide levels following short-term methamphetamine exposure, striatal neuropeptide concentrations were either normal or moderately decreased in the methamphetamine users.
2.Intrathecal implants of microencapsulated xenogenic chromaffin cells provide a long-term source of analgesic substances.
Jeon Y1, Kwak K, Kim S, Kim Y, Lim J, Baek W. Transplant Proc. 2006 Nov;38(9):3061-5.
Adrenal medullary chromaffin cells secrete several neuroactive substances including catecholamines and opioid peptides that produce analgesic effects in the central nervous system. This study was designed to investigate whether intrathecal microencapsulated chromaffin cells could release analgesic materials producing antiallodynic effects on the chronic neuropathic pain in rats induced by chronic constriction injury (CCI) of the sciatic nerve. Prior to intrathecal implantation, chromaffin cells were encapsulated with alginate and poly-L-lysine to protect them from the host immune system. Behavior tests were performed before CCI, 1 week later, and at 4, 7, 14, 21, 28 days postimplantation. At the end of study, we performed cerebrospinal fluid (CSF) collection and implant retrieval. We observed that intrathecal implantation of encapsulated xenogenic chromaffin cells reduced the mechanical and cold allodynia in a model of neuropathic pain. CSF levels of catecholamines and metenkephalin in the rats that received implants were higher than the controls.
3.[Selective involvement of opioids in mechanisms of synapse-specific plasticity in Helix lucorum snail during sensitization acquisition].
Nikitin VP1, Kozyrev SA. Zh Vyssh Nerv Deiat Im I P Pavlova. 2003 Nov-Dec;53(6):766-74.
Effects of met-enkephalin (opioid peptide) and naloxone (opioid antagonist) on nociceptive sensitization were studied in L-RP11 Helix neurons. In control snails sensitizing stimulation produced reversible membrane depolarization and depression of neural responses evoked by sensory stimuli during the short-term stage of sensitization and facilitation of these responses at the long-term stage. Met-enkephalin (10 but not 0.1 microM) suppressed the neural responses evoked by nociceptive stimuli. Sensitizing stimulation during metenkephalin application prevented the facilitation of neural responses evoked by tactile stimulation of snail head, whereas facilitation of neural responses evoked by chemical stimulation of head or tactile stimulation of foot were similar to that in control sensitized snails. Sensitizing stimulation during met-enkephalin and/or naloxone application prevented the facilitation of neural responses evoked by chemical stimulation of snail head, whereas responses evoked by tactile stimulation of snail head or foot were facilitated (as in neurons of control sensitized snails).
4.Ultrastructural and neurochemical architecture of the pituitary neural lobe of Xenopus laevis.
van Wijk DC1, Meijer KH, Roubos EW. Gen Comp Endocrinol. 2010 Sep 1;168(2):293-301. doi: 10.1016/j.ygcen.2010.01.008. Epub 2010 Jan 11.
The melanotrope cell in the amphibian pituitary pars intermedia is a model to study fundamental aspects of neuroendocrine integration. They release alpha-melanophore-stimulating hormone (alphaMSH), under the control of a large number of neurochemical signals derived from various brain centers. In Xenopus laevis, most of these signals are produced in the hypothalamic magnocellular nucleus (Mg) and are probably released from neurohemal axon terminals in the pituitary neural lobe, to stimulate alphaMSH-release, causing skin darkening. The presence in the neural lobe of at least eight stimulatory factors implicated in melanotrope cell control has led us to investigate the ultrastructural architecture of this neurohemal organ, with particular attention to the diversity of neurohemal axon terminals and their neurochemical contents. Using regular electron microscopy, we here distinguish six types of neurohemal axon terminal, on the basis of the size, shape and electron-density of their secretory granule contents.
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