Targeted lipidomics: fatty acid amides and pain modulation

Walker, J. Michael; Krey, Jocelyn F.; Chen, Jay S.; Vefring, Eivind; Jahnsen, Jan Anker; Bradshaw, Heather B.; Huang, Susan M.

doi:10.1016/j.prostaglandins.2004.09.017

Cited by 40 publications

(33 citation statements)

References 27 publications

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“…In addition to the NAEs, other classes of fatty acid amides have been characterized, namely the N-acylamino acids (NAAs) [7], the N-acyldopamines (NADAs) [8] and the primary fatty acid amides (PFAMs) [9,10] (Figure 1). Relative to NAEs, much less is currently known about the NAAs, the NADAs and the PFAMs, except that they are found in biological systems.…”

Section: N-acylamino Acid; N-acyldopamine; N-acylethanolamine; Primarmentioning

confidence: 99%

“…Interest in the N-acylethanolamines (NAEs) dramatically increased upon the identification of Narachidonoylethanolamine (anandamide) as the endogenous ligand for the cannabinoid receptors in the mammalian brain [4]. It is now known that a family of NAEs is found in the brain and in other tissues [5,6].In addition to the NAEs, other classes of fatty acid amides have been characterized, namely the N-acylamino acids (NAAs) [7], the N-acyldopamines (NADAs) [8] and the primary fatty acid amides (PFAMs) [9,10] (Figure 1). Relative to NAEs, much less is currently known about the NAAs, the NADAs and the PFAMs, except that they are found in biological systems.…”

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confidence: 99%

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Biosynthesis, degradation and pharmacological importance of the fatty acid amides

Farrell

Merkler

2008

Drug Discovery Today

114

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The identification of two biologically active fatty acid amides, N-arachidonoylethanolamine (anandamide) and oleamide, has generated a great deal of excitement and stimulated considerable research. However, anandamide and oleamide are merely the best-known and best-understood members of a much larger family of biologically-occurring fatty acid amides. In this review, we will outline which fatty acid amides have been isolated from mammalian sources, detail what is known about how these molecules are made and degraded in vivo, and highlight their potential for the development of novel therapeutics. Keywords N-acylamino acid; N-acyldopamine; N-acylethanolamine; primary fatty acid amide; N-acylamideThe fatty acid amide bond has long been recognized in nature, being important in the structure of the ceramides [1] and the sphingolipids [2]. The first non-sphingosine based fatty acid amide isolated from a natural source was N-palmitoylethanolamine from egg yolk in 1957 [3]. Interest in the N-acylethanolamines (NAEs) dramatically increased upon the identification of Narachidonoylethanolamine (anandamide) as the endogenous ligand for the cannabinoid receptors in the mammalian brain [4]. It is now known that a family of NAEs is found in the brain and in other tissues [5,6].In addition to the NAEs, other classes of fatty acid amides have been characterized, namely the N-acylamino acids (NAAs) [7], the N-acyldopamines (NADAs) [8] and the primary fatty acid amides (PFAMs) [9,10] (Figure 1). Relative to NAEs, much less is currently known about the NAAs, the NADAs and the PFAMs, except that they are found in biological systems. The goal of this review is to summarize the current state of knowledge regarding the different classes of endogenous fatty acid amides and highlight their potential for drug discovery (see refs. [11-13] for earlier reviews) © 2008 Elsevier Ltd. All rights reserved.Corresponding author: Merkler, D.J (E-mail: merkler@cas.usf.edu) phone 813-974-3579; fax 813-974-1733. Publisher's Disclaimer: This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final citable form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain.Teaser SentenceFatty acid amides are a family of mammalian bioactive compounds. These molecules and the enzymes involved in their metabolism provide an opportunity to develop new drugs to treat human disease. -palmitoyl-, N-stearoyl-and N-oleoylethanolamine [5,11], each compromising ≥25% of total brain NAEs. Other less abundant NAEs found in the brain are anandamide, N-linoleoyl-, N-linolenoyl-, N-dihomo-γ-linolenoyl-and N-docosatetraenoylethanolamine [11]. In addition to the brain, the NAEs are widespread in the peripheral tissues [5]. The mos...

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Section: N-acylamino Acid; N-acyldopamine; N-acylethanolamine; Primarmentioning

confidence: 99%

mentioning

confidence: 99%

Biosynthesis, degradation and pharmacological importance of the fatty acid amides

Farrell

Merkler

2008

Drug Discovery Today

114

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“…In the future, research in lipidomics will expand to include the dynamics of lipidomes, subcellular organizations of lipidomes, and interactions of lipids with lipids, proteins, and other cellular moieties. Although lipidomics has emerged as a distinct field only within the past few years [1][2][3], numerous new discoveries and/or advances have already been made [3][4][5][6][7][8][9][10][11][12]. Its essential roles in identifying the biochemical mechanisms of lipid metabolism, investigating the functions of an individual gene of interest, identifying novel biomarkers, and evaluating drug efficacy, among others, are becoming increasingly recognized.…”

Section: Introductionmentioning

confidence: 99%

Alkaline methanolysis of lipid extracts extends shotgun lipidomics analyses to the low-abundance regime of cellular sphingolipids

Jiang

Cheng

Yang

et al. 2007

Analytical Biochemistry

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Sphingolipids that contain a sphingoid base are composed of hundreds to thousands of distinct compounds, many of which serve as lipid regulators of biological functions. The global analysis of the large number of low-abundance sphingolipid molecular species has been hampered in many cases by the sphingolipid molecular species being overwhelmed by the quantity of other classes of lipid (e.g., glycerophospholipid) molecular species present, thereby imposing severe restrictions on the dynamic range of their measurement using shotgun lipidomics. Herein, we developed a facile approach in which the sphingolipids of cellular extracts were dramatically enriched by direct alkaline methanolysis of lipid extracts followed by extraction to remove the large majority of other endogenous lipid classes. Through direct infusion of the resultant enriched solution, we identified and quantitated a variety of very-low-abundance sphingolipid classes (e.g., sphingosine, psychosine, and lysosphingomyelin) and molecular species (e.g., sphingomyelin) using electrospray ionization mass spectrometry (i.e., shotgun sphingolipidomics). Accordingly, through utilization of these facile enrichment techniques, direct penetrance into the sphingolipidomes has been greatly extended, facilitating new insights into their metabolism and signaling functions in biological systems. KeywordsElectrospray ionization mass spectrometry; Shotgun lipidomics; Shotgun sphingolipidomics; Sphingolipidome; Lysosphingomyelin; Psychosine; Sphingomyelin; Sphingosine Lipidomics, the large-scale study of the pathways and networks of cellular lipids, is an emerging and rapidly expanding research field [1][2][3]. Currently, lipidomics research has been focused on identifying alterations in lipid metabolic pathways and networks induced by a disease state, a gene mutation (knockout or overexpression), a therapeutic treatment, or other perturbations. In the future, research in lipidomics will expand to include the dynamics of lipidomes, subcellular organizations of lipidomes, and interactions of lipids with lipids, proteins, and other cellular moieties. Although lipidomics has emerged as a distinct field only within the past few years [1][2][3], numerous new discoveries and/or advances have already been made [3][4][5][6][7][8][9][10][11][12]. Its essential roles in identifying the biochemical mechanisms of lipid metabolism, investigating the functions of an individual gene of interest, identifying novel biomarkers, and evaluating drug efficacy, among others, are becoming increasingly recognized.One of the major analytical platforms in current lipidomics practice is multidimensional massspectrometry (MS) 1 -based shotgun lipidomics [13][14][15]. This platform has now evolved into a mature technology that includes a series of simple steps such as multiplexed extractions, *Corresponding author. Fax: +1 314 362 1402. E-mail address: xianlin@wustl.edu (X. Han).. intrasource separation, identification of individual lipid molecular species using multidimensional MS, and quan...

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“…Collectively, numerous new lipidomic techniques have already been developed and more will come in the next years since their application for the identification of lipid pathways and functions, the investigation of lipid-mediated disorders and drug evaluation among others has been increasingly recognized [16][17][18][19].…”

Section: Principles Of Mass Spectrometry-based Lipid Analysismentioning

confidence: 99%

Methods in Comprehensive Mass Spectrometry-Based Measurement of Sphingolipids

Gaßler¹

2012

J Glycom Lipidom

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Targeted lipidomics: fatty acid amides and pain modulation

Cited by 40 publications

References 27 publications

Biosynthesis, degradation and pharmacological importance of the fatty acid amides

Biosynthesis, degradation and pharmacological importance of the fatty acid amides

Alkaline methanolysis of lipid extracts extends shotgun lipidomics analyses to the low-abundance regime of cellular sphingolipids

Methods in Comprehensive Mass Spectrometry-Based Measurement of Sphingolipids

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