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Spinorphin

From Wikipedia, the free encyclopedia
Spinorphin
Names
IUPAC name
L-leucyl-L-valyl-L-valyl-L-tyrosyl-L-prolyl-L-tryptophyl-L-threonine
Other names
LVVYPWT; LVV-hemorphin-4
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C45H64N8O10/c1-23(2)19-31(46)39(56)50-37(25(5)6)43(60)51-36(24(3)4)42(59)49-34(20-27-14-16-29(55)17-15-27)44(61)53-18-10-13-35(53)41(58)48-33(40(57)52-38(26(7)54)45(62)63)21-28-22-47-32-12-9-8-11-30(28)32/h8-9,11-12,14-17,22-26,31,33-38,47,54-55H,10,13,18-21,46H2,1-7H3,(H,48,58)(H,49,59)(H,50,56)(H,51,60)(H,52,57)(H,62,63)/t26-,31+,33+,34+,35+,36+,37+,38+/m1/s1
    Key: BXIFNVGZIMFBQB-DYDSHOKNSA-N
  • InChI=1/C45H64N8O10/c1-23(2)19-31(46)39(56)50-37(25(5)6)43(60)51-36(24(3)4)42(59)49-34(20-27-14-16-29(55)17-15-27)44(61)53-18-10-13-35(53)41(58)48-33(40(57)52-38(26(7)54)45(62)63)21-28-22-47-32-12-9-8-11-30(28)32/h8-9,11-12,14-17,22-26,31,33-38,47,54-55H,10,13,18-21,46H2,1-7H3,(H,48,58)(H,49,59)(H,50,56)(H,51,60)(H,52,57)(H,62,63)/t26-,31+,33+,34+,35+,36+,37+,38+/m1/s1
    Key: BXIFNVGZIMFBQB-DYDSHOKNBN
  • O=C(N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)O)[C@H](O)C)Cc3c2ccccc2[nH]c3)Cc4ccc(O)cc4)C(C)C)C(C)C)[C@@H](N)CC(C)C
Properties
C45H64N8O10
Molar mass877.037 g/mol
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Spinorphin is anendogenous, non-classicalopioid peptide of thehemorphin family[1] first isolated from thebovinespinal cord (hence the prefixspin-)[2] and acts as a regulator of theenkephalinases, a class ofenzymes that break down endogenous theenkephalinpeptides.[3] It does so by inhibiting theenzymesaminopeptidase N (APN),dipeptidyl peptidase III (DPP3),angiotensin-converting enzyme (ACE), andneutral endopeptidase (NEP).[3] Spinorphin is aheptapeptide and has theamino acid sequence Leu-Val-Val-Tyr-Pro-Trp-Thr (LVVYPWT).[3] It has been observed to possessantinociceptive,[4]antiallodynic,[4] andanti-inflammatory properties.[1] Themechanism of action of spinorphin has not been fully elucidated (i.e., how it acts to inhibit the enkephalinases), but it has been found to act as anantagonist of theP2X3 receptor,[5] and as a weakpartial agonist/antagonist of theFP1 receptor.[1]

See also

[edit]

References

[edit]
  1. ^abcLiang TS, Gao JL, Fatemi O, Lavigne M, Leto TL, Murphy PM (December 2001)."The endogenous opioid spinorphin blocks fMet-Leu-Phe-induced neutrophil chemotaxis by acting as a specific antagonist at the N-formylpeptide receptor subtype FPR".Journal of Immunology.167 (11):6609–14.doi:10.4049/jimmunol.167.11.6609.PMID 11714831.
  2. ^Nishimura K, Hazato T (October 1993). "[Spinorphin, a new inhibitor of enkephalin-degrading enzymes derived from the bovine spinal cord]".Masui. The Japanese Journal of Anesthesiology (in Japanese).42 (10):1497–503.PMID 8230703.
  3. ^abcNishimura K, Hazato T (July 1993). "Isolation and identification of an endogenous inhibitor of enkephalin-degrading enzymes from bovine spinal cord".Biochemical and Biophysical Research Communications.194 (2):713–9.Bibcode:1993BBRC..194..713N.doi:10.1006/bbrc.1993.1880.PMID 8343155.
  4. ^abHonda M, Okutsu H, Matsuura T, et al. (December 2001)."Spinorphin, an endogenous inhibitor of enkephalin-degrading enzymes, potentiates leu-enkephalin-induced anti-allodynic and antinociceptive effects in mice".Japanese Journal of Pharmacology.87 (4):261–7.doi:10.1254/jjp.87.261.PMID 11829145.
  5. ^Jung KY, Moon HD, Lee GE, Lim HH, Park CS, Kim YC (September 2007). "Structure-activity relationship studies of spinorphin as a potent and selective human P2X(3) receptor antagonist".Journal of Medicinal Chemistry.50 (18):4543–7.doi:10.1021/jm070114m.PMID 17676725.
Hormones
Opioid peptides
Dynorphins
Endomorphins
Endorphins
Enkephalins
Others
Other
neuropeptides
Kinins
Neuromedins
Orexins
Other
μ-opioid
(MOR)
Agonists
(abridged;
full list)
Antagonists
δ-opioid
(DOR)
Agonists
Antagonists
κ-opioid
(KOR)
Agonists
Antagonists
Nociceptin
(NOP)
Agonists
Antagonists
Others
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