ArticleBiophysical journal2009
Location, structure, and dynamics of the synthetic cannabinoid ligand CP-55,940 in lipid bilayers.
Article in Biophysical journal, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed, 37 citations in OpenAlex.
- Lipophilicity Modulations by Fluorination Correlate with Membrane Partitioning.Angewandte Chemie (International ed. in English) · 2023Article
- Special issue for Klaus Gawrisch.Biophysical journal · 2023Article
- Development of selective, fluorescent cannabinoid type 2 receptor ligands based on a 1,8-naphthyridin-2-(1MedChemComm · 2018Article
- CBNeuropsychopharmacology : official publication of the American College of Neuropsychopharmacology · 2018Review
- Molecular Dynamics Methodologies for Probing Cannabinoid Ligand/Receptor Interaction.Methods in enzymology · 2017Article
- Global fold of human cannabinoid type 2 receptor probed by solid-state 13C-, 15N-MAS NMR and molecular dynamics simulations.Proteins · 2014Article
- A key agonist-induced conformational change in the cannabinoid receptor CB1 is blocked by the allosteric ligand Org 27569.The Journal of biological chemistry · 2012Article
- Recombinant cannabinoid type 2 receptor in liposome model activates g protein in response to anionic lipid constituents.The Journal of biological chemistry · 2012Article
- Stabilization of functional recombinant cannabinoid receptor CB(2) in detergent micelles and lipid bilayers.PloS one · 2012Article
- Identification of essential cannabinoid-binding domains: structural insights into early dynamic events in receptor activation.The Journal of biological chemistry · 2011Article
- The interaction of cannabinoid receptor agonists, CP55940 and WIN55212-2 with membranes using solid state 2H NMR.Biochimica et biophysica acta · 2011Article
- Endocannabinoid tone versus constitutive activity of cannabinoid receptors.British journal of pharmacology · 2011Review
- Cannabinoid potentiation of glycine receptors contributes to cannabis-induced analgesia.Nature chemical biology · 2011Article
- A lipid pathway for ligand binding is necessary for a cannabinoid G protein-coupled receptor.The Journal of biological chemistry · 2010Article
- Endocannabinoid binding to the cannabinoid receptors: what is known and what remains unknown.Current medicinal chemistry · 2010Review
Corrections and comments
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Authors and funding
4 authors at 2 institutions in 1 country.
Funding
Abstract
The widely used hydrophobic cannabinoid ligand CP-55,940 partitions with high efficiency into biomembranes. We studied the location, orientation, and dynamics of CP-55,940 in POPC bilayers by solid-state NMR. Chemical-shift perturbation of POPC protons from the aromatic ring-current effect, as well as 1H NMR cross-relaxation rates, locate the hydroxyphenyl ring of the ligand near the lipid glycerol, carbonyls, and upper acyl-chain methylenes. Order parameters of the hydroxyphenyl ring determined by the 1H-13C DIPSHIFT experiment indicate that the bond between the hydroxyphenyl and hydroxycyclohexyl rings is oriented perpendicular to the bilayer normal. 2H NMR order parameters of the nonyl tail are very low, indicating that the hydrophobic chain maintains a high level of conformational flexibility in the membrane. Lateral diffusion rates of CP-55,940 and POPC were measured by 1H magic-angle spinning NMR with pulsed magnetic field gradients. The rate of CP-55,940 diffusion is comparable to the rate of lipid diffusion. The magnitude of cross-relaxation and diffusion rates suggests that associations between CP-55,940 and lipids are with lifetimes of a fraction of a microsecond. With its flexible hydrophobic tail, CP-55,940 may efficiently approach the binding site of the cannabinoid receptor from the lipid-water interface by lateral diffusion.
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What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.