Opiorphin

Source: Wikipedia, the free encyclopedia.
Opiorphin[1]
Names
IUPAC name
(2S,5S,8S,11S,14S)-14,17-diamino-8-benzyl-2,11-bis(3-guanidinopropyl)-5-(hydroxymethyl)-4,7,10,13,17-pentaoxo-3,6,9,12-tetraazaheptadecan-1-oic acid
Other names
Gln-Arg-Phe-Ser-Arg; L-Glutaminyl-L-arginyl-L-phenylalanyl-L-seryl-L-arginine
Identifiers
3D model (
JSmol
)
ChEMBL
ChemSpider
  • InChI=1S/C29H48N12O8/c30-17(10-11-22(31)43)23(44)38-18(8-4-12-36-28(32)33)24(45)40-20(14-16-6-2-1-3-7-16)25(46)41-21(15-42)26(47)39-19(27(48)49)9-5-13-37-29(34)35/h1-3,6-7,17-21,42H,4-5,8-15,30H2,(H2,31,43)(H,38,44)(H,39,47)(H,40,45)(H,41,46)(H,48,49)(H4,32,33,36)(H4,34,35,37)/t17-,18-,19-,20-,21-/m0/s1 ☒N
    Key: TWWFCOBVAKAKIT-SXYSDOLCSA-N ☒N
  • InChI=1/C29H48N12O8/c30-17(10-11-22(31)43)23(44)38-18(8-4-12-36-28(32)33)24(45)40-20(14-16-6-2-1-3-7-16)25(46)41-21(15-42)26(47)39-19(27(48)49)9-5-13-37-29(34)35/h1-3,6-7,17-21,42H,4-5,8-15,30H2,(H2,31,43)(H,38,44)(H,39,47)(H,40,45)(H,41,46)(H,48,49)(H4,32,33,36)(H4,34,35,37)/t17-,18-,19-,20-,21-/m0/s1
    Key: TWWFCOBVAKAKIT-SXYSDOLCBM
  • O=C([C@H](CO)NC([C@H](CC1=CC=CC=C1)NC([C@H](CCCNC(N)=N)NC([C@H](CCC(N)=O)N)=O)=O)=O)N[C@H](C(O)=O)CCCNC(N)=N
Properties
C29H48N12O8
Molar mass 692.779 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Opiorphin is an

polypeptide, Gln-Arg-Phe-Ser-Arg (QRFSR).[3][4][5][6][7][8][9][10]

Opiorphin pentapeptide originates from the

proteases: neutral ecto-endopeptidase (MME), ecto-aminopeptidase N (ANPEP)[3]
and perhaps also a dipeptidyl peptidase DPP3.[8] Such action extends the duration of enkephalin effect where the natural pain killers are released physiologically in response to specific potentially painful stimuli, in contrast with administration of narcotics, which floods the entire body and causes many undesirable adverse reactions, including addiction liability and constipation.[11][12] In addition, opiorphin may exert anti-depressive[13][14] and antipanic action.[15]

Therapeutic application of opiorphin in humans would require modifying the molecule to avoid its rapid degradation in the intestine and its poor penetration of the blood–brain barrier.[11][12] This modification is done in the body by transformation of N-terminal glutamine into pyroglutamate. This form preserves the analgesic properties of opiorphin but with increased pharmaceutical stability.[16]

See also

References

  1. ^ Opiorphin at Sigma-Aldrich
  2. PMID 20814077
    .
  3. ^
    PMID 8670737
    .
  4. ^ Andy Coghlan (November 13, 2006). "Natural-born painkiller found in human saliva". New Scientist. Archived from the original on 2007-01-27.
  5. ^ "Natural chemical 'beats morphine'". BBC News. November 14, 2006.
  6. ^ Mary Beckman (November 13, 2006). "Prolonging Painkillers". ScienceNOW.
  7. PMID 10841318
    .
  8. ^
    PMID 18855623
    .
  9. PMID 19267851
    .
  10. S2CID 32291165
    .
  11. ^
    PMID 20814077
    .
  12. ^
    S2CID 32205999
    .
  13. PMID 20610867
    .
  14. S2CID 22544303
    .
  15. S2CID 34867419
    .
  16. S2CID 36827893
    .
Retrieved from "https://en.wikipedia.org/w/index.php?title=Opiorphin&oldid=1182756546"