A bastadin with potent and selective delta-opioid receptor binding affinity from the Australian sponge Ianthella flabelliformis.
Three new bastadins, bastadin 25 (1), 15-O-sulfonatobastadin 11 (2), and bastadin 26 (3), were isolated from a MeOH extract of the Australian marine sponge Ianthella flabelliformis. Their structures were determined by interpretation of 1D and 2D NMR spectra and mass spectrometry. Bastadin 26 (3) showed potent affinity for the guinea pig delta-opioid receptors with a K(i) value of 100 nM. The other two bastadins had a 100-fold lower affinity. The three compounds were also tested for their affinity to guinea pig micro- and kappa-opioid receptors and shown to have either no affinity or only very weak affinity toward both of these opioid receptors.
Carroll
Anthony R
AR
Eskitis Institute, Griffith University, Brisbane, Queensland, 4111, Australia.
Kaiser
Sonya M
SM
Davis
Rohan A
RA
Moni
Roger W
RW
Hooper
John N A
JN
Quinn
Ronald J
RJ
D000465:Algorithms; D000818:Animals; D001315:Australia; D001921:Brain / Q000187:drug effects; D006168:Guinea Pigs; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010456:Peptides, Cyclic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D011161:Porifera / Q000737:chemistry*; D017465:Receptors, Opioid, delta / Q000187:drug effects*; D017473:Receptors, Opioid, kappa / Q000187:drug effects; D017450:Receptors, Opioid, mu / Q000187:drug effects
C550952:15-O-sulfonatobastadin 11; D010456:Peptides, Cyclic; D017465:Receptors, Opioid, delta; D017473:Receptors, Opioid, kappa; D017450:Receptors, Opioid, mu; C550950:bastadin 25; C550951:bastadin 26