6'-Guanidinonaltrindole

6′-Guanidinonaltrindole (6′-GNTI) is a κ–δ-opioid receptor selective ligand used in scientific research.[1]

6′-Guanidinonaltrindole
Names
Preferred IUPAC name
N-[(4bS,8R,8aS,14bR)-7-(Cyclopropylmethyl)-1,8a-dihydroxy-5,6,7,8,8a,9,14,14b-octahydro-4,8-methano[1]benzofuro[2,3-b]pyrido[4,3-c]carbazol-12-yl]guanidine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
InChI
  • InChI=1S/C27H29N5O3/c28-25(29)30-15-4-5-16-17-11-27(34)20-9-14-3-6-19(33)23-21(14)26(27,7-8-32(20)12-13-1-2-13)24(35-23)22(17)31-18(16)10-15/h3-6,10,13,20,24,31,33-34H,1-2,7-9,11-12H2,(H4,28,29,30)/t20-,24+,26+,27-/m1/s1
    Key: XDKOGAAFSBGLBO-GYHUNEDQSA-N
SMILES
  • c1cc2c(cc1NC(=N)N)[nH]c3c2CC4(C5Cc6ccc(c7c6C4(C3O7)CCN5CC8CC8)O)O
Properties
Chemical formula
 C27H29N5O3
Molar mass 471.561 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

With 6′-GNTI, evidence was provided for the first time that receptor oligomerization plays functional role in living organisms.[2]

6′-GNTI is an extremely biased agonist of the κ-opioid receptor.[1] It is a potent partial agonist of the G protein pathway but does not recruit the β-arrestin pathway.[1] Due to its functional selectivity for the G protein pathway, 6′-GNTI functions as an antagonist of nonbiased KOR agonists on the β-arrestin pathway.[1] It is thought that 6′-GTNI may be able to produce analgesia without dysphoria and with a lower incidence of tolerance.[1]

See also

References
  1. Rives, ML; Rossillo, M; Liu-Chen, LY; Javitch, JA (2012). "6′-Guanidinonaltrindole (6′-GNTI) is a G protein–biased κ-opioid receptor agonist that inhibits arrestin recruitment". J Biol Chem. 287 (32): 27050–4. doi:10.1074/jbc.C112.387332. PMC 3411045. PMID 22736766.
  2. Waldhoer M, Fong J, Jones RM, Lunzer MM, Sharma SK, Kostenis E, Portoghese PS, Whistler JL (June 2005). "A heterodimer-selective agonist shows in vivo relevance of G protein–coupled receptor dimers". Proc. Natl. Acad. Sci. U.S.A. 102 (25): 9050–5. Bibcode:2005PNAS..102.9050W. doi:10.1073/pnas.0501112102. PMC 1157030. PMID 15932946.


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