The rise and fall of anandamide: processes that control synthesis, degradation, and storage

Biringer, Roger G.

doi:10.1007/s11010-021-04121-5

Cited by 21 publications

(22 citation statements)

References 122 publications

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“…The endocannabinoid system is integrated by the CB 1 /CB 2 cannabinoid receptors, the endogenous ligands AEA and 2-AG, and their respective metabolizing and synthetizing enzymes, as well as membrane transporter [ 1 , 2 ]. This neurobiological system has been described in multiple human biological samples, including the brain [ 1 , 2 , 6 – 11 ], suggesting its role on the regulation of a broad neurobiological processes such as the sleep–wake cycle [ 12 – 15 , 49 – 58 ], which is also driven by a variety of neuroanatomical brain areas, neurochemicals, and circadian and homeostatic factors [ 16 – 26 ]. On the other hand, the sleep disorders are the pathological feature of sleep patterns described by the International Classification of Sleep Disorders [ 27 ], including insomnia and sleep-related breathing disorders, such as OSA.…”

Section: Discussionmentioning

confidence: 99%

“…Once AEA is synthetized, it crosses the membrane with the aid of the anandamide membrane transporter (AMT) for binding to the cannabinoid receptors. Complementary, it has been suggested that AEA is converted into ethanolamine and arachidonic acid by the enzymatic activity of the fatty acid amide hydrolase (FAAH) [ 6 ]. On the other hand, the biosynthesis of 2-AG engages membrane phospholipids and the activation of phospholipase C and diacylglycerol lipase (DAGL) and, once formed, this endocannabinoid binds to the cannabinoid receptors [ 7 ].…”

Section: The Endocannabinoid Systemmentioning

confidence: 99%

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The Endocannabinoid System as Prognostic Biomarker of the Obstructive Sleep Apnea Morbidity in COVID-19-Recovered Individuals

Murillo-Rodrı́guez

2021

Sleep Vigilance

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The endocannabinoid system is a neurobiological signaling network that is present in the human biological systems, including the brain. This neurobiological system comprises cannabinoid receptors, endogenous ligands, as well as enzymatic synthesis, degradation and transport of endocannabinoids and has been suggested as a modulator of multiple physiological processes, including the sleep–wake cycle. On the other hand, the COVID-19 pandemic, originated by the novel coronavirus SARS-CoV-2, has caused global catastrophes in economic, social, and health spheres. COVID-19 is a multi-organ disease with a broad spectrum of health complications, such as respiratory infections leading to respiratory-related symptoms and disorders. The development, approval, and application of vaccines against SARS-CoV-2 is ongoing; however, there are increasing reports of prolonged effects after COVID-19 infection, including respiratory and neurological sequelae. Here, I provide a comprehensive review of the current literature on the endocannabinoid system and their role in sleep modulation. Whilst I discuss relevant considerations for the high risk for developing sleep disorders related to respiratory failures, such as obstructive sleep apnea (OSA) in recovered COVID-19-infected subjects. Finally, I propose a framework that integrates the analysis of the components of the endocannabinoid system as prognostic biomarkers of the likely OSA after COVID-19 infection.

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Section: Discussionmentioning

confidence: 99%

Section: The Endocannabinoid Systemmentioning

confidence: 99%

The Endocannabinoid System as Prognostic Biomarker of the Obstructive Sleep Apnea Morbidity in COVID-19-Recovered Individuals

Murillo-Rodrı́guez

2021

Sleep Vigilance

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“…Metabolism (discussed below) is the modification of the fatty acyl and/or the amino acid moiety of the NA-ArAAs to form other metabolites. A balance between biosynthesis and degradation is important in maintaining the cellular concentration of the NA-ArAAs ( Di Marzo, 2006 ; Biringer, 2021 ) and hydrolase may contribute to the “feed-back” of acyl groups into the biosynthesis of the fatty acid amides ( Bradshaw et al, 2009b ). Hydrolytic enzymes like fatty acid amide hydrolase (FAAH), N -acylethanolamine hydrolyzing acid amidase (NAAA), carnosinase, aminoacylase (amidohydrolase), acylase, and/or deacetylases could catalyze the hydrolytic degradation of the NA-ArAAs.…”

Section: Degradationmentioning

confidence: 99%

“…Reactions to modify the NA-ArAAs are likely to occur at the acyl group and/or the amino acid group. Enzyme catalyzed oxidation/hydroxylation of the acyl moiety of N -palmitoylglycine ( Haines et al, 2001 ), N -linolenoyl-L-glutamine ( Yoshinaga et al, 2005 ), N -arachidonoyltaurine ( Turman et al, 2008 ), N -arachidonoylglycine ( Prusakiewicz et al, 2002 ; Prusakiewicz et al, 2007 ), and anandamide ( Rouzer and Marnett, 2011 ; Biringer, 2021 ) have been reported. This chemistry has been well described for anandamide with the characterization of the metabolites generated by treatment with cyclooxygenase-2 (COX-2), different lipooxygenases (LOXs), different cytochrome P450s, and FAAH.…”

Section: Other Metabolic Pathwaysmentioning

confidence: 99%

The Biosynthesis and Metabolism of the N-Acylated Aromatic Amino Acids: N-Acylphenylalanine, N-Acyltyrosine, N-Acyltryptophan, and N-Acylhistidine

Bhandari

Bisht

Merkler

2022

Front. Mol. Biosci.

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The fatty acid amides are a family of lipids composed of two chemical moieties, a fatty acid and a biogenic amine linked together in an amide bond. This lipid family is structurally related to the endocannabinoid anandamide (N-arachidonoylethanolamine) and, thus, is frequently referred to as a family of endocannabinoid-related lipids. The fatty acid amide family is divided into different classes based on the conjugate amine; anandamide being a member of the N-acylethanolamine class (NAE). Another class within the fatty acid amide family is the N-acyl amino acids (NA-AAs). The focus of this review is a sub-class of the NA-AAs, the N-acyl aromatic amino acids (NA-ArAAs). The NA-ArAAs are not broadly recognized, even by those interested in the endocannabinoids and endocannabinoid-related lipids. Herein, the NA-ArAAs that have been identified from a biological source will be highlighted and pathways for their biosynthesis, degradation, enzymatic modification, and transport will be presented. Also, information about the cellular functions of the NA-ArAAs will be placed in context with the data regarding the identification and metabolism of these N-acylated amino acids. A review of the current state-of-knowledge about the NA-ArAAs is to stimulate future research about this underappreciated sub-class of the fatty acid amide family.

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“…The endocannabinoid system comprises endogenous cannabinoids, their receptors, and the enzymes engaged in their biosynthesis, transport, and degradation [ 8 , 9 , 10 ]. Endocannabinoids are derivatives of long-chain fatty acids, namely their amides with ethanolamine or ethers with glycerol.…”

Section: Introductionmentioning

confidence: 99%

N-Acyl Dopamines Induce Apoptosis in Endometrial Stromal Cells from Patients with Endometriosis

Gamisonia

Yushina

Fedorova-Gogolina

et al. 2021

IJMS

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Endometriosis is characterized by the formation and development of endometrial tissues outside the uterus, based on an imbalance between proliferation and cell death, leading to the uncontrolled growth of ectopic foci. The potential target for the regulation of these processes is the endocannabinoid system, which was found to be involved in the migration, proliferation, and survival of tumor cells. In this paper, we investigated the effect of endocannabinoid-like compounds from the N-acyl dopamine (NADA) family on the viability of stromal cells from ectopic and eutopic endometrium of patients with ovarian endometriosis. N-arachidonoyldopamine, N-docosahexaenoyldopamine, and N-oleoyldopamine have been shown to have a five-times-more-selective cytotoxic effect on endometrioid stromal cells. To study the mechanisms of the toxic effect, inhibitory analysis, measurements of caspase-3/9 activity, reactive oxygen species, and the mitochondrial membrane potential were performed. It was found that NADA induced apoptosis via an intrinsic pathway through the CB1 receptor and downstream serine palmitoyltransferase, NO synthase activation, increased ROS production, and mitochondrial dysfunction. The higher selectivity of NADA for endometriotic stromal cells and the current lack of effective drug treatment can be considered positive factors for further research of these compounds as possible therapeutic agents against endometriosis.

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The rise and fall of anandamide: processes that control synthesis, degradation, and storage

Cited by 21 publications

References 122 publications

The Endocannabinoid System as Prognostic Biomarker of the Obstructive Sleep Apnea Morbidity in COVID-19-Recovered Individuals

The Endocannabinoid System as Prognostic Biomarker of the Obstructive Sleep Apnea Morbidity in COVID-19-Recovered Individuals

The Biosynthesis and Metabolism of the N-Acylated Aromatic Amino Acids: N-Acylphenylalanine, N-Acyltyrosine, N-Acyltryptophan, and N-Acylhistidine

N-Acyl Dopamines Induce Apoptosis in Endometrial Stromal Cells from Patients with Endometriosis

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