- Thixotropic stiff hydrogels from a new class of oleoyl-d-glucamine-based low-molecular-weight gelators
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A series of new compounds comprising oleoyl, amino acid and d-glucamine moieties were synthesised using mild reaction conditions, and their hydrogelation ability was evaluated. The gels exhibited improved stiffness and thixotropic properties dependent on the chemical structure of the amino acid linker and the number of potential hydrogen bonding sites.
- Ohsedo, Yutaka,Oono, Masashi,Saruhashi, Kowichiro,Watanabe, Hisayuki,Miyamoto, Nobuyoshi
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- Acute naloxone-precipitated morphine withdrawal elicits nausea-like somatic behaviors in rats in a manner suppressed by N-oleoylglycine
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Rationale: Acute naloxone-precipitated morphine withdrawal (MWD) produces a conditioned place aversion (CPA) in rats even after one or two exposures to high-dose (20 mg/kg, sc) morphine followed 24-h later by naloxone (1 mg/kg, sc). However, the somatic withdrawal reactions produced by acute naloxone-precipitated MWD in rats have not been investigated. A recently discovered fatty acid amide, N-oleoylglycine (OlGly), which has been suggested to act as a fatty acid amide hydrolase (FAAH) inhibitor and as a peroxisome proliferator-activated receptor alpha (PPARα) agonist, was previously shown to interfere with a naloxone-precipitated MWD-induced CPA in rats. Objectives: The aims of these studies were to examine the somatic withdrawal responses produced by acute naloxone-precipitated MWD and determine whether OlGly can also interfere with these responses. Results: Here, we report that following two exposures to morphine (20 mg/kg, sc) each followed by naloxone (1 mg/kg, sc) 24 h later, rats display nausea-like somatic reactions of lying flattened on belly, abdominal contractions and diarrhea, and display increased mouthing movements and loss of body weight. OlGly (5 mg/kg, ip) interfered with naloxone-precipitated MWD-induced abdominal contractions, lying on belly, diarrhea and mouthing movements in male Sprague–Dawley rats, by both a cannabinoid 1 (CB1) and a PPARα mechanism of action. Since these withdrawal reactions are symptomatic of nausea, we evaluated the potential of OlGly to interfere with lithium chloride (LiCl)-induced and MWD-induced conditioned gaping in rats, a selective measure of nausea; the suppression of MWD-induced gaping reactions by OlGly was both CB1 and PPARα mediated. Conclusion: These results suggest that the aversive effects of acute naloxone-precipitated MWD reflect nausea, which is suppressed by OlGly.
- Rock, Erin M,Ayoub, Samantha M,Limebeer, Cheryl L,Gene, Alexia,Wills, Kiri L,DeVuono, Marieka V,Smoum, Reem,Di Marzo, Vincenzo,Lichtman, Aron H,Mechoulam, Raphael,Parker, Linda A
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- Cosmetic composition for eliminating or adsorbing particulate matter comprising peptide complex as effective component
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The present invention relates to a cosmetic composition for removing or adsorbing fine dust, containing a fatty acid-amino acid complex or a fatty acid-oligopeptide complex as an active ingredient. The complex of the present invention has an excellent effect of removing fine dust without skin toxicity, and thus can be effectively used as a composition for preventing or treating various diseases caused by fine dust.COPYRIGHT KIPO 2020
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Paragraph 0031-0032; 0034-0046; 0063; 0065
(2020/03/17)
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- FATTY ACID AMIDES AND USES THEREOF IN THE TREATMENT OF ADDICTION DISORDER AND ADDICTION RELATED CONDITIONS
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The present invention is directed to a fatty acid amide of an amino acid, including a stereoisomer and a salt thereof for use in the treatment of a patient suffering from any type of addiction disorder, substance abuse disorder, including any condition and symptom associated therewith and including withdrawal syndrome and relapse addiction during and after a rehabilitation treatment of said patient.
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Paragraph 00116-00117
(2018/12/13)
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- Method for synthesizing fatty acyl glycocoll
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The invention discloses a method for synthesizing fatty acyl glycocoll. The method comprises the steps that an oxidant, a catalyst promoter and an alkali solution are mixed into an aqueous solution, the aqueous solution is added into an organic solvent system formed by mixing fatty acid monoethanolamide and a catalyst, a reaction is carried out for 0.5-3 h under the condition of maintaining the pH of the whole mixed system to be 6.0-12.0 and the temperature to be 20-40 DEG C, then a reaction is carried out for 0.5-2 h under stirring, and a product containing fatty acyl glycocoll is obtained. According to the method for synthesizing fatty acyl glycocoll, the reaction speed and the product yield are high, the reaction condition is mild and easy to control, and the method for synthesizing fatty acyl glycocoll is efficient, conforms to environment-friendly chemistry and is capable of facilitating industrialized production.
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Paragraph 0031; 0032
(2017/01/02)
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- Synthesis and evaluation of fatty acid amides on the N-oleoylethanolamide-like activation of peroxisome proliferator activated receptor α
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A series of fatty acid amides were synthesized and their peroxisome proliferator-activated receptor α (PPAR-α) agonistic activities were evaluated in a normal rat liver cell line, clone 9. The mRNAs of the PPAR-α downstream genes, carnitine-palmitoyltransferase-1 and mitochondrial 3-hydroxy-3-methylglutaryl-CoA synthase, were determined by real-time reverse transcription-polymerase chain reaction (RT-PCR) as PPAR-α agonistic activities. We prepared nine oleic acid amides. Their PPAR-α agonistic activities were, in decreasing order, N-oleoylhistamine (OLHA), N-oleoylglycine, Oleamide, N-oleoyltyramine, N-oleoylsertonin, and Olvanil. The highest activity was found with OLHA. We prepared and evaluated nine N-acylhistamines (N-acyl-HAs). Of these, OLHA, C16:0-HA, and C18:1Δ9-trans-HA showed similar activity. Activity due to the different chain length of the saturated fatty acid peaked at C16:0-HA. The PPAR-α antagonist, GW6471, inhibited the induction of the PPAR-α downstream genes by OLHA and N-oleoylethanolamide (OEA). These data suggest that N-acyl-HAs could be considered new PPAR-α agonists.
- Takao, Koichi,Noguchi, Kaori,Hashimoto, Yosuke,Shirahata, Akira,Sugita, Yoshiaki
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p. 278 - 285
(2015/04/22)
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- Design and synthesis of lipids for the fabrication of functional lipidic cubic-phase biomaterials
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A series of novel lipids with designed functionalities were synthesized. These lipids are based on conjugation of α-amino acids and their esters, cationic, anionic, neutral, and photochromic moieties to the lipophilic 9-cis octadecenyl chains by amide, ester, thioester, or amine bonds. Because of the plasticity of lipidic cubic phases, it is envisaged that when mixed with monooleoyl-rac-glycerol (monoolein, MO) and water at appropriate proportions, they would assemble to form bicontinuous lipidic cubic phases (LCPs) that exhibit the well-known material properties of LCPs such as phase stability, optical transparency, and chemical permeability. Moreover, due to the nature and position of the functionality at the headgroup region, we envision them to perform as functional materials by design.
- Osornio, Yazmin M.,Uebelhart, Peter,Bosshard, Silvan,Konrad, Fabian,Siegel, Jay S.,Landau, Ehud M.
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p. 10583 - 10595
(2013/02/22)
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- New N-acylamino acids and derivatives from renewable fatty acids: Gelation of hydrocarbons and thermal properties
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This work reports the synthesis of new fatty N-acylamino acids and N-acylamino esters from the C16:0, C18:0, C18:1, and C18:1(OH) fatty acid families and demonstrates the activity of these compounds as organogel agents. Compounds were heated and dissolved in various solvents (n-hexane, toluene, and gasoline). Only saturated C16:0 and C18:0 derived from alanine were able to form gels in toluene, and saturated C16:0 derived from phenylalanine showed gelation in n-hexane. This is the first evidence that fatty N-acylamino esters and N-acylamino acid derivatives of l-serine and fatty acids C16:0, C18:0, and C18:1 are able to form gels with hexane. This observation confirms the importance of the hydroxyl group in the segment derivative of l-serine in forming good gels.
- Duarte, Rodrigo Da Costa,Ongaratto, Renata,Piovesan, Luciana Almeida,De Lima, Vania Rodrigues,Soldi, Valdir,Merlo, Aloir Ant?nio,D'Oca, Marcelo G. Montes
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p. 2454 - 2460
(2012/06/01)
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- Evaluation of endogenous fatty acid amides and their synthetic analogues as potential anti-inflammatory leads
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A series of endogenous fatty acid amides and their analogues (1-78) were prepared, and their inhibitory effects on pro-inflammatory mediators (NO, IL-1β, IL-6, and TNF-α) in LPS-activated RAW264.7 cells were evaluated. Their inhibitory activity on the pro-inflammatory chemokine MDC in IFN-γ-activated HaCaT cells was also examined. The results showed that the activity is strongly dependent on the nature of the fatty acid part of the molecules. As expected, the amides derived from enone fatty acids showed significant activity and were more active than those derived from other types of fatty acids. A variation of the amine headgroup also altered bioactivity profile remarkably, possibly by modulating cell permeability. Regarding the amine part of the molecules, N-acyl dopamines exhibited the most potent activity (IC50 ~2 μM). This is the first report of the inhibitory activity of endogenous fatty acid amides and their analogues on the production of nitric oxide, cytokines (IL-1β, IL-6, and TNF-α) and the chemokine MDC. This study suggests that the enone fatty acid-derived amides (such as N-acyl ethanolamines and N-acyl amino acids) and N-acyl dopamines may be potential anti-inflammatory leads.
- Dang, Hung The,Kang, Gyeoung Jin,Yoo, Eun Sook,Hong, Jongki,Choi, Jae Sue,Kim, Hyung Sik,Chung, Hae Young,Jung, Jee H.
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experimental part
p. 1520 - 1527
(2011/03/23)
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- Inhibitors of gap junction communication
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Oleamide is an endogenous fatty acid primary amide that possesses sleep-inducing properties in animals and has been shown to effect seratonergic systems and block gap junction communication in a structurally specific manner. Certain agents can serve both as an oleamide agonist and as an inhibitor of fatty acid amide hydrolase. Fatty acid amide hydrolase is responsible for the rapid inactivation of oleamide in vivo. The structural features of oleamide required for inhibition of gap junction-mediated chemical and electrical transmission in rat glial cells are defined. Effective inhibitors fall into two classes of fatty acid primary amides of which oleamide and arachidonamide are the prototypical members. Of these two, oleamide constitutes the most effective and its structural requirements for inhibition of the gap junction are well defined. It requires a chain length of 16-24 carbons of which 16-18 carbons appears optimal, a polarized terminal carbonyl group capable of accepting but not necessarily donating a hydrogen bond, a Δ9 cis double bond, and a hydrophobic methyl terminus. Within these constraints, a range of modifications are possible, many of which may with enhanced in vivo properties.
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- Antipsychotic drug
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The present invention provides an antipsychotic drug containing essentially an N-acyl amino acid derivative represented by the following general formula:RCO-Awherein R indicates an alkyl or alkenyl having 1-25 carbon atoms, and A is an amino acid residue. The compound is similar to natural products and has little side effect by acting directly to brain cells after passing through easily the blood brain barrier.
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