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Vol. 301, Issue 3, 900-907, June 2002
Department of Biomedical Sciences, Institute of Medical Sciences,
University of Aberdeen, Foresterhill, Aberdeen, Scotland
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 PGE2
receptor 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.
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