Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
6
pubmed:dateCreated
2000-6-2
pubmed:abstractText
Two putative endocannabinoids, N-arachidonylethanolamine (AEA) and 2-arachidonylglycerol, are inactivated by removal from the extracellular environment by a process that has the features of protein-mediated facilitated diffusion. We have synthesized and studied 22 N-linked analogues of arachidonylamide for the purpose of increasing our understanding of the structural requirements for the binding of ligands to the AEA transporter. We have also determined the affinities of these analogues for both the CB(1) cannabinoid receptor and fatty acid amide hydrolase (FAAH). We have identified several structural features that enhance binding to the AEA transporter in cerebellar granule cells. We have confirmed the findings of others that replacing the ethanolamine head group with 4-hydroxybenzyl results in a high-affinity ligand for the transporter. However, we find that the same molecule is also a competitive inhibitor of FAAH. Similarly, replacement of the ethanolamine of AEA with 3-pyridinyl also results in a high-affinity inhibitor of both the transporter and FAAH. We conclude that the structural requirements for ligand binding to the CB(1) receptor and binding to the transporter are very different; however, the transporter and FAAH share most, but not all, structural requirements.
pubmed:grant
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
http://linkedlifedata.com/resource/pubmed/chemical/2-arachidonylglycerol, http://linkedlifedata.com/resource/pubmed/chemical/3-(2-hydroxy-4-(1,1-dimethylheptyl)p..., http://linkedlifedata.com/resource/pubmed/chemical/Adjuvants, Immunologic, http://linkedlifedata.com/resource/pubmed/chemical/Amidohydrolases, http://linkedlifedata.com/resource/pubmed/chemical/Arachidonic Acids, http://linkedlifedata.com/resource/pubmed/chemical/Cannabinoids, http://linkedlifedata.com/resource/pubmed/chemical/Carrier Proteins, http://linkedlifedata.com/resource/pubmed/chemical/Cyclohexanols, http://linkedlifedata.com/resource/pubmed/chemical/Endocannabinoids, http://linkedlifedata.com/resource/pubmed/chemical/Glycerides, http://linkedlifedata.com/resource/pubmed/chemical/Immunosuppressive Agents, http://linkedlifedata.com/resource/pubmed/chemical/Ligands, http://linkedlifedata.com/resource/pubmed/chemical/Polyunsaturated Alkamides, http://linkedlifedata.com/resource/pubmed/chemical/Receptors, Cannabinoid, http://linkedlifedata.com/resource/pubmed/chemical/Receptors, Drug, http://linkedlifedata.com/resource/pubmed/chemical/Tritium, http://linkedlifedata.com/resource/pubmed/chemical/anandamide, http://linkedlifedata.com/resource/pubmed/chemical/fatty-acid amide hydrolase
pubmed:status
MEDLINE
pubmed:month
Jun
pubmed:issn
0022-3042
pubmed:author
pubmed:issnType
Print
pubmed:volume
74
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
2597-606
pubmed:dateRevised
2007-11-14
pubmed:meshHeading
pubmed-meshheading:10820223-Adjuvants, Immunologic, pubmed-meshheading:10820223-Amidohydrolases, pubmed-meshheading:10820223-Animals, pubmed-meshheading:10820223-Arachidonic Acids, pubmed-meshheading:10820223-Binding, Competitive, pubmed-meshheading:10820223-Biological Transport, pubmed-meshheading:10820223-Cannabinoids, pubmed-meshheading:10820223-Carrier Proteins, pubmed-meshheading:10820223-Cells, Cultured, pubmed-meshheading:10820223-Cerebellum, pubmed-meshheading:10820223-Cyclohexanols, pubmed-meshheading:10820223-Endocannabinoids, pubmed-meshheading:10820223-Glycerides, pubmed-meshheading:10820223-Immunosuppressive Agents, pubmed-meshheading:10820223-Ligands, pubmed-meshheading:10820223-Neurons, pubmed-meshheading:10820223-Polyunsaturated Alkamides, pubmed-meshheading:10820223-Prosencephalon, pubmed-meshheading:10820223-Rats, pubmed-meshheading:10820223-Receptors, Cannabinoid, pubmed-meshheading:10820223-Receptors, Drug, pubmed-meshheading:10820223-Structure-Activity Relationship, pubmed-meshheading:10820223-Tritium
pubmed:year
2000
pubmed:articleTitle
Structure-activity relationships among N-arachidonylethanolamine (Anandamide) head group analogues for the anandamide transporter.
pubmed:affiliation
Department of Pharmacology, Medical College of Wisconsin, Milwaukee 53226, USA.
pubmed:publicationType
Journal Article, Research Support, U.S. Gov't, P.H.S.