Met-enkephalin

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Met-enkephalin
Skeletal formula of Met-enkphalin
Names
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
Other names
[Met]enkephalin; [Met5]enkephalin; L-Tyrosylglycylglycyl-L-phenylalanyl-L-methionine
Identifiers
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.055.741 Edit this at Wikidata
EC Number
  • 261-335-8
IUPHAR/BPS
KEGG
MeSH Enkephalin,+Methionine
UNII
  • 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) ☒N
    Key: YFGBQHOOROIVKG-UHFFFAOYSA-N ☒N
  • CSCCC(NC(=O)C(Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)C(N)Cc1ccc(O)cc1)C(O)=O
  • CSCCC(NC(=O)C(CC1=CC=CC=C1)NC(=O)CNC(=O)CNC(=O)C(N)CC1=CC=C(O)C=C1)C(O)=O
Properties
C27H35N5O7S
Molar mass 573.67 g·mol−1
log P 0.607
Acidity (pKa) 3.234
Basicity (pKb) 10.763
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Met-enkephalin, also known as metenkefalin (

δ-opioid receptor, due to their high potency and selectivity for the site over the other endogenous opioids.[2]

History

Met-enkephalin was discovered and characterized by John Hughes, Hans Kosterlitz, et al. in 1975 after a search for endogenous ligands of the opioid receptors.[3]

Chemistry

Met-enkephalin is a

hydroxyl group on morphine.[citation needed
]

Biochemistry

Distribution

Met-enkephalin is found mainly in the

pelvic viscera.[2]

Biosynthesis

Met-enkephalin is

octapeptide met-enkephalin-arg-gly-leu (186–193),[4] though whether they affect the opioid receptors in a similar manner as met-enkephalin is not entirely clear.[7]

Clearance

Met- and leu-enkephalin are metabolized by a variety of different enzymes, including

dipeptidyl peptidase 3 (DPP3),[8] carboxypeptidase A6 (CPA6),[9] and angiotensin-converting enzyme (ACE).[10] These enzymes are sometimes referred to as enkephalinases
.

Biological activity

Met-enkephalin is a

analgesia and antidepressant
-like effects.

It is also the endogenous

opioid growth factor receptor
(OGFR; formerly known as the ζ-opioid receptor), which plays a role in the regulation of tissue growth and regeneration; hence why met-enkephalin is sometimes called OGF instead.

Pharmacokinetics

Met-enkephalin has low

metabolized, and has a very short half-life (minutes).[3][11]
These properties are considered undesirable in pharmaceuticals as large doses would need to be administered multiple times an hour to maintain a therapeutically relevant effect, making it unlikely that met-enkephalin will ever be used as a medicine.

[D-Ala2]-Met-enkephalinamide (DALA), is a synthetic enkephalin analog which is not susceptible to degradation by brain enzymes and at low doses (5 to 10 micrograms) caused profound, long-lasting, morphine-like analgesia when microinjected into a rat’s brain.[12]

See also

References

  1. PMID 8164525
    .
  2. ^
    ISBN 978-0-521-62269-1
    . Retrieved 25 November 2011.
  3. ^
    ISBN 978-0-8493-6894-3
    . Retrieved 25 November 2011.
  4. ^
    ISBN 978-0-262-19407-5
    . Retrieved 25 November 2011.
  5. S2CID 23334563
    .
  6. PMID 20040394
    .
  7. S2CID 19181608
    .
  8. ^
    PMID 18855623. Archived from the original
    on 2013-04-14.
  9. PMID 18178555
    .
  10. S2CID 23138078
    .
  11. ISBN 978-1-4051-3017-2
    . Retrieved 25 November 2011.
  12. PMID 968485
    .
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