J. Lipid Res. Neurobiology of Lipids (ISSN1683-5506)
HOME HELP FEEDBACK SUBSCRIPTIONS ARCHIVE SEARCH TABLE OF CONTENTS
QUICK SEARCH:   [advanced]


     

Originally published In Press as doi:10.1194/jlr.M300475-JLR200 on January 16, 2004

This Article
Right arrow Full Text
Right arrow Full Text (PDF)
Right arrow All Versions of this Article:
M300475-JLR200v1
45/4/757    most recent
Right arrow Alert me when this article is cited
Right arrow Alert me if a correction is posted
Right arrow Citation Map
Services
Right arrow Similar articles in this journal
Right arrow Similar articles in PubMed
Right arrow Alert me to new issues of the journal
Right arrow Download to citation manager
Right arrow reprints & permissions
Citing Articles
Right arrow Citing Articles via HighWire
Right arrow Citing Articles via Google Scholar
Google Scholar
Right arrow Articles by Weber, A.
Right arrow Articles by Woodward, D.
Right arrow Search for Related Content
PubMed
Right arrow PubMed Citation
Right arrow Articles by Weber, A.
Right arrow Articles by Woodward, D.
Social Bookmarking
Add to CiteULike   Add to Complore   Add to Connotea   Add to Del.icio.us   Add to Digg   Add to Reddit   Add to Technorati  
What's this?
Journal of Lipid Research, Vol. 45, 757-763, April 2004
Copyright © 2004 by American Society for Biochemistry and Molecular Biology

Formation of prostamides from anandamide in FAAH knockout mice analyzed by HPLC with tandem mass spectrometry

Allan Weber1,*, Jinsong Ni*, Kah-Hiing John Ling*, Andrew Acheampong*, Diane D-S. Tang-Liu*, Robert Burk{dagger}, Benjamin F. Cravatt§ and David Woodward**

* Department of Pharmacokinetics and Drug Metabolism, Allergan, Inc., 2525 Dupont Drive, P.O. Box 19534, Irvine, CA 92623
** Department of Biological Sciences, Allergan, Inc., 2525 Dupont Drive, P.O. Box 19534, Irvine, CA 92623
{dagger} Department of Medicinal Chemistry, Allergan, Inc., 2525 Dupont Drive, P.O. Box 19534, Irvine, CA 92623
§ The Skaggs Institute of Chemical Biology, The Scripps Research Institute, La Jolla, CA 92037

1 To whom correspondence should be addressed. e-mail: weber_allan{at}allergan.com

We investigated the formation of PGF2{alpha} 1-ethanolamide, PGE2 1-ethanolamide, and PGD2 1-ethanolamide (prostamides F2{alpha}, E2, and D2, respectively) in liver, lung, kidney, and small intestine after a single intravenous bolus administration of 50 mg/kg of anandamide to normal and fatty acid amide hydrolase knockout (FAAH -/-) male mice. One group of three normal mice was not dosed (naïve) while another group of three normal mice received a bolus intravenous injection of 50 mg/kg of anandamide. Three FAAH -/- mice also received an intravenous injection of 50 mg/kg of anandamide. After 30 min, the lung, liver, kidney, and small intestine were harvested and processed by liquid-liquid extraction. The concentrations of prostamide F2{alpha}, prostamide E2, prostamide D2, and anandamide were determined by HPLC-tandem mass spectrometry. Prostamide F2{alpha} was detected in tissues in FAAH -/- mice after administration of anandamide. Concentrations of anandamide, prostamide E2, and prostamide D2 in liver, kidney, lung, and small intestine were much higher in the anandamide-treated FAAH -/- mice than those of the anandamide-treated control mice.

This report demonstrates that prostamides, including prostamide F2{alpha}, were formed in vivo from anandamide, potentially by the cyclooxygenase-2 pathway when the competing FAAH pathway is lacking.

Abbreviations: COX-2, cyclooxygenase-2; FAAH, fatty acid amide hydrolase; FAAH -/-, FAAH knockout; HPLC-MS/MS, HPLC tandem mass spectrometry; LC-MS/MS, liquid chromatography-MS/MS; MRM, multiple-reaction monitoring; prostamide D2, PGD2 1-ethanolamide; prostamide E2, PGE2 1-ethanolamide; prostamide F2{alpha}, PGF2{alpha} 1-ethanolamide

Supplementary key words anandamide • cyclooxygenase-2 • fatty acid amide hydrolase • high-performance liquid chromatography • PGD2 1-ethanolamide • PGE2 1-ethanolamide • PGF2{alpha} 1-ethanolamide • prostamide D2 • prostamide E2 • prostamide F2{alpha}


Add to CiteULike CiteULike   Add to Complore Complore   Add to Connotea Connotea   Add to Del.icio.us Del.icio.us   Add to Digg Digg   Add to Reddit Reddit   Add to Technorati Technorati    What's this?


This article has been cited by other articles:


Home page
 J. Biol. Chem.Home page
C. A. Rouzer and L. J. Marnett
Non-redundant Functions of Cyclooxygenases: Oxygenation of Endocannabinoids
J. Biol. Chem., March 28, 2008; 283(13): 8065 - 8069.
[Abstract] [Full Text] [PDF]

Home page
 J. Biol. Chem.Home page
H. Moriuchi, N. Koda, E. Okuda-Ashitaka, H. Daiyasu, K. Ogasawara, H. Toh, S. Ito, D. F. Woodward, and K. Watanabe
Molecular Characterization of a Novel Type of Prostamide/Prostaglandin F Synthase, Belonging to the Thioredoxin-like Superfamily
J. Biol. Chem., January 11, 2008; 283(2): 792 - 801.
[Abstract] [Full Text] [PDF]

Home page
 Am. J. Physiol. Heart Circ. Physiol.Home page
S. Batkai, M. Rajesh, P. Mukhopadhyay, G. Hasko, L. Liaudet, B. F. Cravatt, A. Csiszar, Z. Ungvari, and P. Pacher
Decreased age-related cardiac dysfunction, myocardial nitrative stress, inflammatory gene expression, and apoptosis in mice lacking fatty acid amide hydrolase
Am J Physiol Heart Circ Physiol, August 1, 2007; 293(2): H909 - H918.
[Abstract] [Full Text] [PDF]

Home page
 J. Neurosci.Home page
M. D. Jhaveri, D. Richardson, D. A. Kendall, D. A. Barrett, and V. Chapman
Analgesic Effects of Fatty Acid Amide Hydrolase Inhibition in a Rat Model of Neuropathic Pain
J. Neurosci., December 20, 2006; 26(51): 13318 - 13327.
[Abstract] [Full Text] [PDF]

Home page
 J. Pharmacol. Exp. Ther.Home page
S. T. Glaser, S. J. Gatley, and A. N. Gifford
Ex Vivo Imaging of Fatty Acid Amide Hydrolase Activity and Its Inhibition in the Mouse Brain
J. Pharmacol. Exp. Ther., March 1, 2006; 316(3): 1088 - 1097.
[Abstract] [Full Text] [PDF]

Home page
 J. Lipid Res.Home page
W. Yang, J. Ni, D. F. Woodward, D. D-S. Tang-Liu, and K.-H. J. Ling
Enzymatic formation of prostamide F2{alpha} from anandamide involves a newly identified intermediate metabolite, prostamide H2
J. Lipid Res., December 1, 2005; 46(12): 2745 - 2751.
[Abstract] [Full Text] [PDF]

Home page
 Am. J. Physiol. Heart Circ. Physiol.Home page
E. M. Awumey, A. C. Howlett, and D. I. Diz
Is there a role for anandamide in cardiovascular regulation? Insights from studies of endocannabinoid metabolism
Am J Physiol Heart Circ Physiol, August 1, 2005; 289(2): H520 - H521.
[Full Text] [PDF]

Home page
 J. Biol. Chem.Home page
C. A. Rouzer and L. J. Marnett
Glycerylprostaglandin Synthesis by Resident Peritoneal Macrophages in Response to a Zymosan Stimulus
J. Biol. Chem., July 22, 2005; 280(29): 26690 - 26700.
[Abstract] [Full Text] [PDF]

Home page
 J. Lipid Res.Home page
M. Glass, J. Hong, T. A. Sato, and M. D. Mitchell
Misidentification of prostamides as prostaglandins
J. Lipid Res., July 1, 2005; 46(7): 1364 - 1368.
[Abstract] [Full Text] [PDF]

Home page
 J. Neurosci.Home page
C. Benito, W.-K. Kim, I. Chavarria, C. J. Hillard, K. Mackie, R. M. Tolon, K. Williams, and J. Romero
A Glial Endogenous Cannabinoid System Is Upregulated in the Brains of Macaques with Simian Immunodeficiency Virus-Induced Encephalitis
J. Neurosci., March 9, 2005; 25(10): 2530 - 2536.
[Abstract] [Full Text] [PDF]

Home page
 Proc. Natl. Acad. Sci. USAHome page
B. F. Cravatt, A. Saghatelian, E. G. Hawkins, A. B. Clement, M. H. Bracey, and A. H. Lichtman
Functional disassociation of the central and peripheral fatty acid amide signaling systems
PNAS, July 20, 2004; 101(29): 10821 - 10826.
[Abstract] [Full Text] [PDF]


HOME HELP FEEDBACK SUBSCRIPTIONS ARCHIVE SEARCH TABLE OF CONTENTS
 All ASBMB Journals   Journal of Biological Chemistry 
 Molecular and Cellular Proteomics   ASBMB Today 
Copyright © 2004 by the American Society for Biochemistry and Molecular Biology.