544-31-0Relevant articles and documents
Anandamide inhibits nuclear factor-κB activation through a cannabinoid receptor-independent pathway
Sancho, Rocio,Calzado, Marco A.,Di Marzo, Vincenzo,Appendino, Giovanni,Munoz, Eduardo
, p. 429 - 438 (2003)
Anandamide (arachidonoylethanolamine, AEA), an endogenous agonist for both the cannabinoid CB, receptor and the vanilloid VR1 receptor, elicits neurobehavioral, anti-inflammatory, immunomodulatory, and proapoptotic effects. Because of the central role of nuclear factor-κB (NF-κB) in the inflammatory process and the immune response, we postulated that AEA might owe some of its effects to the suppression of NF-κB. This study shows that AEA inhibits tumor necrosis factor-α (TNFα)-induced NF-κB activation by direct inhibition of the IκB kinase (IKK)β and, to a lesser extent, the IKKα subunits of κB inhibitor (IκB) kinase complex, and that IKKs inhibition by AEA correlates with inhibition of IκBα degradation, NF-κB binding to DNA, and NF-κB-dependent transcription in TNFα-stimulated cells. AEA also prevents NF-κB-dependent reporter gene expression induced by mitogen-activated protein kinase kinase kinase and NF-κB-inducing kinase. The NF-κB inhibitory activity of AEA was independent of CB1 and CB2 activation in TNFα-stimulated 5.1 and A549 cell lines, which do not express vanilloid receptor 1, and was not mediated by hydrolytic products formed through the activity of the enzyme fatty acid amide hydrolase. Chemical modification markedly affected AEA inhibitory activity on NF-κB, suggesting rather narrow structure-activity relationships and the specific interaction with a molecular target. Substitution of the alkyl moiety with less saturated fatty acids generally reduced or abolished activity. However, replacement of the ethanolamine "head" with a vanillyl group led to potent inhibition of TNFα-induced NF-κB-dependent transcription. These findings provide new mechanistic insights into the anti-inflammatory and proapoptotic activities of AEA, and should foster the synthesis of improved analogs amenable to pharmaceutical development as anti-inflammatory agents.
Green aqueous-phase solvent-free high-purity synthesis method of palmitoylethanolamide
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Paragraph 0033, (2021/05/12)
The invention discloses a green aqueous-phase solvent-free high-purity synthesis method of palmitoylethanolamide. The green aqueous-phase solvent-free high-purity synthesis method comprises the following steps: by taking food-grade palm oil as an initial raw material, carrying out high-pressure catalyst-free continuous hydrolysis reaction on the initial raw material in a high-temperature and high-pressure hydrolysis tower to obtain hydrolysate; and then rectifying the hydrolysate to obtain a high-purity compound palmitic acid A, and carrying out acylation reaction on the high-purity compound palmitic acid A and monoethanolamine to obtain high-puritypalmitoylethanolamide. According to the method, food-grade palm oil which is healthier and more friendly to human bodies is used as an initial raw material, a green water-phase solvent-free preparation method is adopted, side reactions and by-products are reduced, the product purity is greatly improved, meanwhile, no chemical solvent is used in the whole reaction section, the produced palmitoylethanolamidedoes not have any solvent residue, and the method is low in cost and suitable for industrial production.
Different roles for the acyl chain and the amine leaving group in the substrate selectivity of N-Acylethanolamine acid amidase
Ghidini, Andrea,Scalvini, Laura,Palese, Francesca,Lodola, Alessio,Mor, Marco,Piomelli, Daniele
, p. 1411 - 1423 (2021/07/17)
N-acylethanolamine acid amidase (NAAA) is an N-terminal nucleophile (Ntn) hydrolase that catalyses the intracellular deactivation of the endogenous analgesic and anti-inflammatory agent palmitoylethanolamide (PEA). NAAA inhibitors counteract this process and exert marked therapeutic effects in animal models of pain, inflammation and neurodegeneration. While it is known that NAAA preferentially hydrolyses saturated fatty acid ethanolamides (FAEs), a detailed profile of the relationship between catalytic efficiency and fatty acid-chain length is still lacking. In this report, we combined enzymatic and molecular modelling approaches to determine the effects of acyl chain and polar head modifications on substrate recognition and hydrolysis by NAAA. The results show that, in both saturated and monounsaturated FAEs, the catalytic efficiency is strictly dependent upon fatty acyl chain length, whereas there is a wider tolerance for modifications of the polar heads. This relationship reflects the relative stability of enzyme-substrate complexes in molecular dynamics simulations.
A Convenient Protocol for the Synthesis of Fatty Acid Amides
Johansson, Silje J. R.,Johannessen, Tonje,Ellefsen, Christiane F.,Ristun, Mali S.,Antonsen, Simen,Hansen, Trond V.,Stenstrom, Yngve,Nolsoe, Jens M. J.
supporting information, p. 213 - 217 (2019/01/14)
Several classes of biologically occurring fatty acid amides have been reported from mammalian and plant sources. Many amides conjugated with fatty acids of mammalian origin exhibit specific activation of individual receptors. Their potential as pharmacological tools or as lead compounds towards the development of novel therapeutics is of great interest. Hence, access to such amides by a practical, high-yielding and scalable protocol without affecting the geometry or position of sensitive functionalities is needed. A protocol that meets all these requirements involves activation of the corresponding acid with carbonyl diimidazole (CDI) followed by reaction with the desired amine or its hydrochloride. More than fifty compounds have been prepared in generally high yields.
A catalyst-free, waste-less ethanol-based solvothermal synthesis of amides
Dalu, Francesca,Scorciapino, Mariano A.,Cara, Claudio,Luridiana, Alberto,Musinu, Anna,Casu, Mariano,Secci, Francesco,Cannas, Carla
supporting information, p. 375 - 381 (2018/02/07)
A green, one-pot approach based on the solvothermal amidation of carboxylic acids with amines has been developed for the synthesis of diverse aliphatic and aromatic amides. It does not require the use of catalysts or coupling reagents and it occurs in the presence of ethanol that has been proved to have a key role in the process. The proposed strategy is also extendable to biologically active amides and could represent a low-cost and waste-less alternative to the common synthetic pathways.
Design, synthesis and CoMFA studies of OEA derivatives as FAAH inhibitors
Han, Daxiong,Wang, Biyan,Jin, Hui,Wang, Haiyan,Chen, Meimei
, p. 2951 - 2966 (2017/10/06)
A total of 26 novel oleoylethanolamide derivatives were designed, synthesized, and characterized. All synthesized targets compounds were screened for their inhibitory activities against fatty acid amide hydrolase. Among of them, 13 compounds inhibit fatty acid amide hydrolase by 50% at the concentration of 100 μM. Of these compounds, the most active one is compound 9, which inhibit fatty acid amide hydrolase activity 98.35% at the concentration of 100 μM. Comparative molecular field analysis analyzes were performed based on obtained biological activities data and resulted in a statistically reliable comparative molecular field analysis model with high predictive abilities (r2 = 0.978, q2 = 0.613).
Improved fatty acid monoethanolamide synthesis method
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Paragraph 0048-0052, (2017/10/07)
The invention relates to an improved fatty acid monoethanolamide synthesis method, which comprises: 1) preparing a polystyrene resin containing a carboxyl activating agent; 2) carrying out a condensation reaction on the polystyrene resin obtained in the step (1) and fatty acid in the presence of a catalyst to obtain an immobilized active ester; and (3) in the presence of a solvent, carrying out a reaction on the immobilized active ester obtained in the step 2) and ethanolamine, carrying out simple filtration or centrifugation to remove the resin after completing the reaction, carrying out pressure reducing concentration on the obtained liquid phase, and carrying out vacuum drying to obtain the high-quality fatty acid monoethanolamide product. According to the present invention, the condensation reaction is performed under the normal temperature condition, the generation of the by-product is substantially reduced through the selection of the catalyst and the reaction parameters, and the yield of the reaction and the purity of the product are maximized; and with the synthesis method, the defects of more by-products, difficult purification and the like caused by unstable raw material, poor selectivity to ethanolamine and alkali high temperature condition in the prior art are overcome.
Methods for production of fatty acid alkanolamides (FAAAs) from microalgae biomass
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Page/Page column 11; 12, (2017/02/28)
Provided herein are methods for fatty acid alkanolamide (FAAA) synthesis and isolation from lipid-containing algal biomass, and the products of such methods.
THERMAL ENERGY STORAGE AND TEMPERATURE STABILIZATION PHASE CHANGE MATERIALS COMPRISING ALKANOLAMIDES AND DIESTERS AND METHODS FOR MAKING AND USING THEM
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Paragraph 0143; 0144, (2017/04/11)
This invention generally relates to thermoregulation and temperature stabilization, thermal protection and insulation, and nucleating agents. In particular, in alternative embodiments, provided are organic phase change materials comprising diesters and alkanolamides. In alternative embodiments, provided are Phase Change Material (PCMs) compositions comprising diesters and alkanolamides, and methods for making and using them. In alternative embodiments, the Phase Change Material (PCMs) compositions are used for thermal energy management, including energy storage and/or temperature stabilization, in various applications such as building, automotive, packaging, garment and footwear, textiles, fabrics, synthetic fibers, foods, microcapsules and other energy storage systems.
CERAMIDE-LIKE FUNCTION IMPARTING AGENT
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Paragraph 0101; 0102; 0103; 0104; 0105, (2016/03/05)
Provided are an agent for imparting ceramide-like function, an agent for reinforcing skin barrier function, a moisturizing agent and a skin drug for external use. The agent for imparting ceramide-like function comprises as an effective ingredient a derivative of succinic acid diamide represented by the following formula (1): [wherein R1 and R2 each independently represents a hydroxyalkyl group of from 1 to 6 carbon atoms, R3 represents a group: —CH2CH2CH2CH2—R4 or a group: —CH2CH═CHCH2—R4 (wherein R4 represents an alkyl group of from 8 to 26 carbon atoms)].
