Spinorphin

Spinorphin is an endogenous, non-classical opioid peptide of the hemorphin family[1] first isolated from the bovine spinal cord (hence the prefix spin-)[2] and acts as a regulator of the enkephalinases, a class of enzymes that break down endogenous the enkephalin peptides.[3] It does so by inhibiting the enzymes aminopeptidase N (APN), dipeptidyl peptidase III (DPP3), angiotensin-converting enzyme (ACE), and neutral endopeptidase (NEP).[3] Spinorphin is a heptapeptide and has the amino acid sequence Leu-Val-Val-Tyr-Pro-Trp-Thr (LVVYPWT).[3] It has been observed to possess antinociceptive,[4] antiallodynic,[4] and anti-inflammatory properties.[1] The mechanism 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 an antagonist of the P2X3 receptor,[5] and as a weak partial agonist/antagonist of the FP1 receptor.[1]

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
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
InChI
  • 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
SMILES
  • 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
Chemical formula
 C45H64N8O10
Molar mass 877.037 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also

References
  1. Liang 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. Nishimura 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. doi:10.1006/bbrc.1993.1880. PMID 8343155.
  4. Honda 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.
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