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Research ArticleCELLULAR AND MOLECULAR

Pharmacological Characterization of the Anandamide Cyclooxygenase Metabolite: Prostaglandin E2 Ethanolamide

Ruth A. Ross, Susan J. Craib, Lesley A. Stevenson, Roger G. Pertwee, Andrea Henderson, John Toole and Heather C. Ellington
Journal of Pharmacology and Experimental Therapeutics June 2002, 301 (3) 900-907; DOI: https://doi.org/10.1124/jpet.301.3.900
Ruth A. Ross
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Susan J. Craib
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Lesley A. Stevenson
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Roger G. Pertwee
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Andrea Henderson
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John Toole
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Heather C. Ellington
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Abstract

Anandamide can be metabolized by cyclooxygenase-2 to produce prostaglandin E2 (PGE2) ethanolamide. The purpose of this study was to investigate the pharmacology of this novel compound. Radioligand binding experiments in membranes from human embryonic kidney cells transfected with PGE2receptor subtypes EP1, EP2, EP3, and EP4 revealed that PGE2 ethanolamide has pKi values of 5.61 ± 0.1, 6.33 ± 0.01, 6.70 ± 0.13, and 6.29 ± 0.06, respectively, compared with 8.31 ± 0.16, 9.03 ± 0.04, 9.34 ± 0.06, and 9.10 ± 0.04 for PGE2. PGE2 inhibits electrically evoked contractions of the guinea pig vas deferens (EP3 receptor-mediated), with a pEC50 value of 9.09 ± 0.06, compared with that of 7.38 ± 0.09 for PGE2 ethanolamide. In the guinea pig trachea, 100 nM PGE2 and 1 μM PGE2 ethanolamide produced contractions of 51.8 ± 10.6 and 38.9 ± 5.6% (of the histamine Emax), respectively. The EP1 receptor antagonist SC-51089 (10 μM) prevented the contractions induced by both compounds. In the presence of 10 μM 8-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[1-oxo-3-(4-pyridinyl)propyl]hydrazide, monohydrochloride (SC-51089), PGE2 caused a concentration-related relaxation of histamine-induced contractions of this tissue (EP2 receptor-mediated), the pEC50 value being 8.29 ± 0.17 compared with that of 7.11 ± 0.18 for PGE2 ethanolamide. In the rabbit jugular vein, PGE2 induces relaxation (EP4 receptor-mediated) with a pEC50 of 9.35 ± 0.25, compared with 7.05 ± 0.4 for PGE2 ethanolamide. In dorsal root ganglion neurons in culture, 3 μM PGE2 ethanolamide evoked an increase in intracellular calcium concentration in 21% of small-diameter capsaicin-sensitive neurons. We conclude that this compound is pharmacologically active, however its physiological relevance has yet to be established.

Footnotes

  • This work was supported by The Wellcome Trust Grant 047980 (to R.A.R.) and Medical Research Council/Novartis (to R.G.P.).

  • Abbreviations:
    COX
    cyclooxygenase
    PGE2
    prostaglandin E2
    CB
    cannabinoid receptor
    FAAH
    fatty acid amide hydrolase
    EP
    prostaglandin E receptor
    DRG
    dorsal root ganglion
    PMSF
    phenylmethylsulfonyl fluoride
    rVR1
    rat vanilloid receptor
    BSA
    bovine serum albumin
    CHO
    Chinese hamster ovary
    HEK
    human embryonic kidney
    hEP
    human prostaglandin E receptor
    DMSO
    dimethyl sulfoxide
    ANOVA
    analysis of variance
    [Ca2+]i
    intracellular calcium concentration
    SC-51089
    8-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[1-oxo-3-(4-pyridinyl)propyl]hydrazide, monohydrochloride
    (+)-WIN55212
    (R)-(+)-[2,3-dihydro-5-methyl-3-(4-morpho-linylmethyl) pyrrolo-[1,2,3-de]-1,4-benzoxazin-6-yl]-1-naphth-alenyl-methanonemesylate
    SR141716A
    N-(piperidin-1-yl)-5-(4-chlorophenyl)-1-(2,4-di-chlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide hydrochloride
    CP55244
    (−)-cis-3-[2-hydroxy-4-(1,1-dimethylheptyl)phenyl]-trans-4-(3-hydroxypropyl)cyclohexan-1-ol
    G418
    Geneticin disulphate salt
    MES
    4-morpholineethanesulfonic acid
    • Received December 28, 2001.
    • Accepted February 12, 2002.
  • The American Society for Pharmacology and Experimental Therapeutics
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Journal of Pharmacology and Experimental Therapeutics: 301 (3)
Journal of Pharmacology and Experimental Therapeutics
Vol. 301, Issue 3
1 Jun 2002
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Research ArticleCELLULAR AND MOLECULAR

Pharmacological Characterization of the Anandamide Cyclooxygenase Metabolite: Prostaglandin E2 Ethanolamide

Ruth A. Ross, Susan J. Craib, Lesley A. Stevenson, Roger G. Pertwee, Andrea Henderson, John Toole and Heather C. Ellington
Journal of Pharmacology and Experimental Therapeutics June 1, 2002, 301 (3) 900-907; DOI: https://doi.org/10.1124/jpet.301.3.900

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Research ArticleCELLULAR AND MOLECULAR

Pharmacological Characterization of the Anandamide Cyclooxygenase Metabolite: Prostaglandin E2 Ethanolamide

Ruth A. Ross, Susan J. Craib, Lesley A. Stevenson, Roger G. Pertwee, Andrea Henderson, John Toole and Heather C. Ellington
Journal of Pharmacology and Experimental Therapeutics June 1, 2002, 301 (3) 900-907; DOI: https://doi.org/10.1124/jpet.301.3.900
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