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PMID: 12970089 Published · ppublish English Journal Article Research Support, U.S. Gov't, P.H.S. Review

Cellular accumulation of anandamide: consensus and controversy.

British journal of pharmacology ·Vol. 140 ·No. 5 ·2003-11-00 ·Pages 802-8

Hillard CJ, Jarrahian A

Abstract

The endocannabinoids N-arachidonylethanolamine (AEA or anandamide) and 2-arachidonylglycerol (2-AG) are hypothesized to function in the brain as interneuronal signaling molecules. Prevailing models of the actions of these molecules require that they traverse cellular plasma membranes twice; first, following cellular synthesis and second, prior to enzymatic hydrolysis. The transmembrane movement of AEA has been studied in multiple laboratories with a primary focus on its cellular accumulation following extracellular administration. Although there are areas of consensus among laboratories regarding AEA accumulation, several aspects are very unclear. In particular, there is a lack of consensus in the literature regarding the importance of AEA hydrolysis by fatty acid amide hydrolase in maintaining the driving force for accumulation. Furthermore, evidence for and against a transmembrane carrier protein has been published. We have reviewed the available literature and present a working model of the processes that are involved in the cellular accumulation of AEA. It is our hypothesis that transmembrane movement of AEA is regulated by concentration gradient between extracellular and intracellular free AEA. Furthermore, it is our view that a significant portion of the intracellular AEA in most cells is sequestered either by a protein or lipid compartment and that AEA sequestered in this manner does not equilibrate directly with the extracellular pool. Finally, we discuss the available data that have been presented in support of a transmembrane carrier protein for AEA.

MeSH Terms
Animals Arachidonic Acids/metabolism Biological Transport/drug effects,physiology Cell Membrane/drug effects,metabolism Endocannabinoids Humans Polyunsaturated Alkamides Veratridine/pharmacology
Chemicals
Arachidonic Acids Endocannabinoids Polyunsaturated Alkamides Veratridine anandamide
Authors & Affiliations
2 authors, click to expand affiliations / ORCID
Hillard Cecilia J
Department of Pharmacology and Toxicology, Medical College of Wisconsin, 8701 Watertown Plank Road, Milwaukee, WI 53226, USA. [email protected]
Jarrahian Abbas
References (52)
52 references, click to expand
  1. 2-Arachidonoylglycerol and the cannabinoid receptors.
    Chem Phys Lipids. 2000 Nov;108(1-2):89-106 PMID: 11106784
  2. Extrapyramidal and neuroendocrine effects of AM404, an inhibitor of the carrier-mediated transport of anandamide.
    Life Sci. 1999;65(3):327-36 PMID: 10447218
  3. The movement of N-arachidonoylethanolamine (anandamide) across cellular membranes.
    Chem Phys Lipids. 2000 Nov;108(1-2):123-34 PMID: 11106786
  4. 2-arachidonyl glyceryl ether, an endogenous agonist of the cannabinoid CB1 receptor.
    Proc Natl Acad Sci U S A. 2001 Mar 27;98(7):3662-5 PMID: 11259648
  5. The uptake by cells of 2-arachidonoylglycerol, an endogenous agonist of cannabinoid receptors.
    Eur J Biochem. 2001 Apr;268(7):1982-9 PMID: 11277920
  6. Role of fatty acid amide hydrolase in the transport of the endogenous cannabinoid anandamide.
    Mol Pharmacol. 2001 Jun;59(6):1369-75 PMID: 11353795
  7. The cellular uptake of anandamide is coupled to its breakdown by fatty-acid amide hydrolase.
    J Biol Chem. 2001 Mar 9;276(10):6967-73 PMID: 11118429
  8. Mechanisms of endocannabinoid inactivation: biochemistry and pharmacology.
    J Pharmacol Exp Ther. 2001 Jul;298(1):7-14 PMID: 11408519
  9. Anandamide degradation and N-acylethanolamines level in wild-type and CB1 cannabinoid receptor knockout mice of different ages.
    J Neurochem. 2001 Jul;78(2):339-48 PMID: 11461969
  10. Postsynaptic endocannabinoid release is critical to long-term depression in the striatum.
    Nat Neurosci. 2002 May;5(5):446-51 PMID: 11976704
  11. Characterization of a novel endocannabinoid, virodhamine, with antagonist activity at the CB1 receptor.
    J Pharmacol Exp Ther. 2002 Jun;301(3):1020-4 PMID: 12023533
  12. Pharmacological activity of fatty acid amides is regulated, but not mediated, by fatty acid amide hydrolase in vivo.
    J Pharmacol Exp Ther. 2002 Jul;302(1):73-9 PMID: 12065702
  13. Brain monoglyceride lipase participating in endocannabinoid inactivation.
    Proc Natl Acad Sci U S A. 2002 Aug 6;99(16):10819-24 PMID: 12136125
  14. Experimental parkinsonism alters endocannabinoid degradation: implications for striatal glutamatergic transmission.
    J Neurosci. 2002 Aug 15;22(16):6900-7 PMID: 12177188
  15. Estrogen stimulates arachidonoylethanolamide release from human endothelial cells and platelet activation.
    Blood. 2002 Dec 1;100(12):4040-8 PMID: 12393387
  16. Modulation of anxiety through blockade of anandamide hydrolysis.
    Nat Med. 2003 Jan;9(1):76-81 PMID: 12461523
  17. Evidence against the presence of an anandamide transporter.
    Proc Natl Acad Sci U S A. 2003 Apr 1;100(7):4269-74 PMID: 12655057
  18. Design, synthesis, and biological evaluation of new inhibitors of the endocannabinoid uptake: comparison with effects on fatty acid amidohydrolase.
    J Med Chem. 2003 Apr 10;46(8):1512-22 PMID: 12672252
  19. Carrier-mediated uptake of the endogenous cannabinoid anandamide in RBL-2H3 cells.
    J Pharmacol Exp Ther. 2000 Mar;292(3):960-7 PMID: 10688610
  20. Human mast cells take up and hydrolyze anandamide under the control of 5-lipoxygenase and do not express cannabinoid receptors.
    FEBS Lett. 2000 Feb 25;468(2-3):176-80 PMID: 10692582
  21. Synthesis and characterization of a fluorescent substrate for the N-arachidonoylethanolamine (anandamide) transmembrane carrier.
    J Pharmacol Exp Ther. 2000 Apr;293(1):289-95 PMID: 10734181
  22. Reversal of dopamine D(2) receptor responses by an anandamide transport inhibitor.
    J Neurosci. 2000 May 1;20(9):3401-7 PMID: 10777802
  23. Anandamide uptake by human endothelial cells and its regulation by nitric oxide.
    J Biol Chem. 2000 May 5;275(18):13484-92 PMID: 10788462
  24. Biochemistry and pharmacology of the endocannabinoids arachidonylethanolamide and 2-arachidonylglycerol.
    Prostaglandins Other Lipid Mediat. 2000 Apr;61(1-2):3-18 PMID: 10785538
  25. Carrier-mediated transport and enzymatic hydrolysis of the endogenous cannabinoid 2-arachidonylglycerol.
    Neuroreport. 2000 Apr 27;11(6):1231-5 PMID: 10817598
  26. Structure-activity relationships among N-arachidonylethanolamine (Anandamide) head group analogues for the anandamide transporter.
    J Neurochem. 2000 Jun;74(6):2597-606 PMID: 10820223
  27. The anandamide transport inhibitor AM404 activates vanilloid receptors.
    Eur J Pharmacol. 2000 May 12;396(1):39-42 PMID: 10822052
  28. Overlap between the ligand recognition properties of the anandamide transporter and the VR1 vanilloid receptor: inhibitors of anandamide uptake with negligible capsaicin-like activity.
    FEBS Lett. 2000 Oct 13;483(1):52-6 PMID: 11033355
  29. Elevated circulating levels of anandamide after administration of the transport inhibitor, AM404.
    Eur J Pharmacol. 2000 Nov 17;408(2):161-8 PMID: 11080522
  30. Pathways and mechanisms of N-acylethanolamine biosynthesis: can anandamide be generated selectively?
    Chem Phys Lipids. 2000 Nov;108(1-2):71-87 PMID: 11106783
  31. A new concept of cellular uptake and intracellular trafficking of long-chain fatty acids.
    Lipids. 2001 Sep;36(9):981-9 PMID: 11724471
  32. A structure/activity relationship study on arvanil, an endocannabinoid and vanilloid hybrid.
    J Pharmacol Exp Ther. 2002 Mar;300(3):984-91 PMID: 11861807
  33. Noladin ether, a putative novel endocannabinoid: inactivation mechanisms and a sensitive method for its quantification in rat tissues.
    FEBS Lett. 2002 Feb 27;513(2-3):294-8 PMID: 11904167
  34. Chronic ethanol inhibits the anandamide transport and increases extracellular anandamide levels in cerebellar granule neurons.
    Eur J Pharmacol. 2003 Apr 11;466(1-2):73-83 PMID: 12679143
  35. Design, synthesis and biological evaluation of new endocannabinoid transporter inhibitors.
    Eur J Med Chem. 2003 Apr;38(4):403-12 PMID: 12750028
  36. Role of endogenous cannabinoids in synaptic signaling.
    Physiol Rev. 2003 Jul;83(3):1017-66 PMID: 12843414
  37. Structure of a cannabinoid receptor and functional expression of the cloned cDNA.
    Nature. 1990 Aug 9;346(6284):561-4 PMID: 2165569
  38. Isolation and structure of a brain constituent that binds to the cannabinoid receptor.
    Science. 1992 Dec 18;258(5090):1946-9 PMID: 1470919
  39. Enzymatic synthesis and degradation of anandamide, a cannabinoid receptor agonist.
    Biochem Pharmacol. 1993 Sep 1;46(5):791-6 PMID: 8373432
  40. Formation and inactivation of endogenous cannabinoid anandamide in central neurons.
    Nature. 1994 Dec 15;372(6507):686-91 PMID: 7990962
  41. Characterization of the kinetics and distribution of N-arachidonylethanolamine (anandamide) hydrolysis by rat brain.
    Biochim Biophys Acta. 1995 Aug 3;1257(3):249-56 PMID: 7647100
  42. 2-Arachidonoylglycerol: a possible endogenous cannabinoid receptor ligand in brain.
    Biochem Biophys Res Commun. 1995 Oct 4;215(1):89-97 PMID: 7575630
  43. Molecular characterization of an enzyme that degrades neuromodulatory fatty-acid amides.
    Nature. 1996 Nov 7;384(6604):83-7 PMID: 8900284
  44. Biosynthesis, uptake, and degradation of anandamide and palmitoylethanolamide in leukocytes.
    J Biol Chem. 1997 Feb 7;272(6):3315-23 PMID: 9013571
  45. Methyl arachidonyl fluorophosphonate: a potent irreversible inhibitor of anandamide amidase.
    Biochem Pharmacol. 1997 Feb 7;53(3):255-60 PMID: 9065728
  46. Accumulation of N-arachidonoylethanolamine (anandamide) into cerebellar granule cells occurs via facilitated diffusion.
    J Neurochem. 1997 Aug;69(2):631-8 PMID: 9231721
  47. Functional role of high-affinity anandamide transport, as revealed by selective inhibition.
    Science. 1997 Aug 22;277(5329):1094-7 PMID: 9262477
  48. Potentiation of anandamide hypotension by the transport inhibitor, AM404.
    Eur J Pharmacol. 1997 Oct 15;337(1):R1-2 PMID: 9389389
  49. Interactions between synthetic vanilloids and the endogenous cannabinoid system.
    FEBS Lett. 1998 Oct 9;436(3):449-54 PMID: 9801167
  50. Anandamide hydrolysis by human cells in culture and brain.
    J Biol Chem. 1998 Nov 27;273(48):32332-9 PMID: 9822713
  51. Structural determinants for recognition and translocation by the anandamide transporter.
    Proc Natl Acad Sci U S A. 1999 May 11;96(10):5802-7 PMID: 10318965
  52. The fatty acid amide hydrolase (FAAH).
    Chem Phys Lipids. 2000 Nov;108(1-2):107-21 PMID: 11106785
Article Info
Journal
British journal of pharmacology
Abbr.
Br J Pharmacol
ISSN
0007-1188
Published
2003-11-00
Epub
2003-00-01
Pages
802-8
Language
English
Region
England
NLM ID
7502536
PMCID
PMC1574088
Subset
IM
Grants
NIDA NIH HHS · R01 DA009155 · United States
NIDA NIH HHS · DA09155 · United States
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