CTOP

Selective mu-opioid receptor antagonist peptide From Wikipedia, the free encyclopedia

CTOP is an opioid antagonist cyclic peptide related to somatostatin.[1] It has been used in research about other opioid ligands.[2][3]

Quick facts Names, Identifiers ...
CTOP
Names
IUPAC name
(4S,7R,10S,13R,16S,19R)-N-[(2S,3R)-1-amino-3-hydroxy-1-oxobutan-2-yl]-19-[[(2R)-2-amino-3-phenylpropanoyl]amino]-10-(3-aminopropyl)-7-[(1R)-1-hydroxyethyl]-16-[(4-hydroxyphenyl)methyl]-13-(1H-indol-3-ylmethyl)-3,3-dimethyl-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carboxamide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
  • InChI=1S/C50H67N11O11S2/c1-26(62)39(42(53)65)59-49(72)41-50(3,4)74-73-25-38(58-43(66)33(52)21-28-11-6-5-7-12-28)47(70)56-36(22-29-16-18-31(64)19-17-29)45(68)57-37(23-30-24-54-34-14-9-8-13-32(30)34)46(69)55-35(15-10-20-51)44(67)60-40(27(2)63)48(71)61-41/h5-9,11-14,16-19,24,26-27,33,35-41,54,62-64H,10,15,20-23,25,51-52H2,1-4H3,(H2,53,65)(H,55,69)(H,56,70)(H,57,68)(H,58,66)(H,59,72)(H,60,67)(H,61,71)/t26-,27-,33-,35+,36+,37-,38+,39+,40+,41-/m1/s1
    Key: PZWWYAHWHHNCHO-FGHAYEPSSA-N
  • C(C=1C=2C(NC1)=CC=CC2)[C@H]3NC(=O)[C@H](CC4=CC=C(O)C=C4)NC(=O)[C@@H](NC([C@@H](CC5=CC=CC=C5)N)=O)CSSC(C)(C)[C@@H](C(N[C@@H]([C@@H](C)O)C(N)=O)=O)NC(=O)[C@]([C@@H](C)O)(NC(=O)[C@H](CCCN)NC3=O)[H]
Properties
C50H67N11O11S2
Molar mass 1062.27 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Pharmacology

CTOP is described as a highly potent mu-opioid receptor antagonist. In mice, its analgesic effects are qualified as being more potent than naloxone's, a well-known opioid antagonist typically used as an antidote in humans.[4] Additionally, CTOP appears to lack significant affinity at the delta and kappa opioid receptors, suggesting that this peptide is selective for the µ receptor.[5]

References

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