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N-acyl or endocannnabanoid or NAPE

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https://www.readbyqxmd.com/read/27915171/progress-in-the-development-of-%C3%AE-lactams-as-n-acylethanolamine-acid-amidase-naaa-inhibitors-synthesis-and-sar-study-of-new-potent-n-o-substituted-derivatives
#1
R Petracca, S Ponzano, S M Bertozzi, O Sasso, D Piomelli, T Bandiera, F Bertozzi
The anti-inflammatory effects resulting from raising the levels of palmitoylethanolamide (PEA), an endogenous bioactive lipid, led to envisage N-Acylethanolamine Acid Amidase (NAAA), the cysteine hydrolase mainly responsible for PEA degradation, as an attractive target for small molecule inhibitors. Previous work in our group identified serine-derived β-lactams as potent and systemically active inhibitors of NAAA activity. Aiming to expand the SAR study around this class of compounds, we investigated the effect of the substitution on the endocyclic nitrogen by designing and synthesizing a series of N-substituted β-lactams...
November 23, 2016: European Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/27915168/interactions-of-long-chain-homologues-of-colchicine-with-tubulin
#2
Ana Marzo-Mas, Pascale Barbier, Gilles Breuzard, Diane Allegro, Eva Falomir, Juan Murga, Miguel Carda, Vincent Peyrot, J Alberto Marco
Several colchicine analogues in which the N-acetyl residue has been replaced by aliphatic, straight-chain acyl moieties, have been synthesized. These compounds show high cytotoxic activity at the nanomolar level against the tumoral cell lines HT-29, MCF-7 and A549. Some of them exhibit activities in the picomolar range against the HT-29 line and are thus two to three orders of magnitude more cytotoxic than colchicine. In this specific cell line, the activities were found to be closely related to the length of the acyl carbon chain, an increase in the latter giving rise to an increase in the cytotoxicity with a maximum in the range of 10-12 carbon atoms, followed by a decrease in activity with still longer chains...
November 23, 2016: European Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/27911800/an-%C3%AE-%C3%AE-hydrolase-fold-protein-in-the-biosynthesis-of-thiostrepton-exhibits-a-dual-activity-for-endopeptidyl-hydrolysis-and-epoxide-ring-opening-macrocyclization
#3
Qingfei Zheng, Shoufeng Wang, Panpan Duan, Rijing Liao, Dandan Chen, Wen Liu
Thiostrepton (TSR), an archetypal bimacrocyclic thiopeptide antibiotic that arises from complex posttranslational modifications of a genetically encoded precursor peptide, possesses a quinaldic acid (QA) moiety within the side-ring system of a thiopeptide-characteristic framework. Focusing on selective engineering of the QA moiety, i.e., by fluorination or methylation, we have recently designed and biosynthesized biologically more active TSR analogs. Using these analogs as chemical probes, we uncovered an unusual indirect mechanism of TSR-type thiopeptides, which are able to act against intracellular pathogens through host autophagy induction in addition to direct targeting of bacterial ribosome...
November 23, 2016: Proceedings of the National Academy of Sciences of the United States of America
https://www.readbyqxmd.com/read/27909709/synthesis-of-a-fluorescent-photoaffinity-probe-of-osw-1-by-site-selective-acylation-of-an-inactive-congener-and-biological-evaluation
#4
K Sakurai, M Hiraizumi, N Isogai, R Komatsu, T Shibata, Y Ohta
A novel fluorescent photoaffinity probe of OSW-1 was prepared in two steps from a naturally occurring inactive congener by a sequential site-selective acylation strategy using Me2SnCl2. It displayed highly potent anticancer activity and a similar intracellular localization property to that of a fluorescently-tagged OSW-1, thereby demonstrating its potential utility in live cell studies.
December 2, 2016: Chemical Communications: Chem Comm
https://www.readbyqxmd.com/read/27909432/volatile-mediated-effects-predominate-in-paraburkholderia-phytofirmans-growth-promotion-and-salt-stress-tolerance-of-arabidopsis-thaliana
#5
Thomas Ledger, Sandy Rojas, Tania Timmermann, Ignacio Pinedo, María J Poupin, Tatiana Garrido, Pablo Richter, Javier Tamayo, Raúl Donoso
Abiotic stress has a growing impact on plant growth and agricultural activity worldwide. Specific plant growth promoting rhizobacteria have been reported to stimulate growth and tolerance to abiotic stress in plants, and molecular mechanisms like phytohormone synthesis and 1-aminocyclopropane-1-carboxylate deamination are usual candidates proposed to mediate these bacterial effects. Paraburkholderia phytofirmans PsJN is able to promote growth of several plant hosts, and improve their tolerance to chilling, drought and salinity...
2016: Frontiers in Microbiology
https://www.readbyqxmd.com/read/27909291/engineering-of-a-thermostable-esterase-est816-to-improve-its-quorum-quenching-activity-and-the-underlying-structural-basis
#6
Xiwen Liu, Li-Chuang Cao, Xin-Jiong Fan, Yu-Huan Liu, Wei Xie
N-acyl-homoserine lactones (AHLs) are small diffusible molecules called autoinducers that mediate cell-to-cell communications. Enzymatic degradation of AHLs is a promising bio-control strategy known as quorum-quenching. To improve the quorum-quenching activity of a thermostable esterase Est816, which had been previously cloned, we have engineered the enzyme by random mutagenesis. One of the mutants M2 with double amino acid substitutions (A216V/K238N) showed 3-fold improvement on catalytic efficiency. Based on the crystal structure determined at 2...
December 2, 2016: Scientific Reports
https://www.readbyqxmd.com/read/27908729/structural-and-biochemical-characterization-of-fabk-from-thermotoga-maritima
#7
Byung Hak Ha, Sang Chul Shin, Jin Ho Moon, Gyochang Keum, Chan-Wha Kim, Eunice EunKyeong Kim
TM0800 from Thermotoga maritima is one of the hypothetical proteins with unknown function. The crystal structure determined at 2.3 Å resolution reveals a two domain structure: the N-terminal domain forming a barrel and the C-terminal forming a lid. One FMN is bound between the two domains with the phosphate making intricate hydrogen bonds with protein and three tightly bound water molecules, and the isoalloxazine ring packed against the side chains of Met22 and Met276. The structure is almost identical to that of FabK (enoyl-acyl carrier protein (ACP) reductase, ENR II), a key enzyme in bacterial type II fatty-acid biosynthesis that catalyzes the final step in each elongation cycle; and the enzymatic activity confirms that TM0800 is an ENR...
November 28, 2016: Biochemical and Biophysical Research Communications
https://www.readbyqxmd.com/read/27903654/carbon-and-acyl-chain-flux-during-stress-induced-triglyceride-accumulation-by-stable-isotopic-labeling-of-the-polar-microalga-coccomyxa-subellipsoidea-c169
#8
James W Allen, Concetta C DiRusso, Paul N Black
Deriving biofuels and other lipoid products from algae is a promising future technology directly addressing global issues of atmospheric CO2 balance. To better understand the metabolism of triglyceride synthesis in algae, we examined their metabolic origins in the model species, Coccomyxa subellipsoidea C169, using stable isotopic labeling. Labeling patterns arising from (13)C-U-glucose, (13)CO2, or D2O supplementation were analyzed by GC-MS and/or LC-MS over time courses during nitrogen (N) starvation to address the roles of catabolic carbon (C) recycling, acyl chain redistribution, and de novo fatty acid (FA) synthesis during the expansion of the lipid bodies...
November 30, 2016: Journal of Biological Chemistry
https://www.readbyqxmd.com/read/27903595/lifelong-imbalanced-linoleic-alpha-linolenic-acid-intake-impairs-emotional-and-cognitive-behavior-in-adult-rats-via-changes-in-brain-endocannabinoid-system
#9
Erica Zamberletti, Fabiana Piscitelli, Valentina De Castro, Elisabetta Murru, Marina Gabaglio, Paola Colucci, Chiara Fanali, Pamela Prini, Tiziana Bisogno, Mauro Maccarrone, Patrizia Campolongo, Sebastiano Banni, Tiziana Rubino, Daniela Parolaro
Imbalanced dietary n-3 and n-6 PUFA content has been associated with a number of neurological conditions. Endocannabinoids are n-6 PUFA derivatives, whose brain concentrations are sensitive to modifications of fatty acid composition of the diet, and play a central role in the regulation of mood and cognition. As such, the endocannabinoid system appears to be an ideal candidate for mediating the effects of dietary fatty acids on mood and cognition. Lifelong administration of isocaloric alpha linolenic acid (ALA) deficient and enriched diets induced short-term memory deficits, whereas only dietary ALA enrichment altered emotional reactivity in adult male rats compared to animals fed a standard diet, balanced in ALA/linoleic (LA) ratio...
November 30, 2016: Journal of Lipid Research
https://www.readbyqxmd.com/read/27900697/screening-for-n-ahsl-based-signaling-interfering-enzymes
#10
Stéphane Uroz, Phil M Oger
Quorum sensing (QS)-based signaling is a widespread pathway used by bacteria for the regulation of functions involved in their relation to the environment or their host. QS relies upon the production, accumulation and perception of small diffusable molecules by the bacterial population, hence linking high gene expression with high cell population densities. Among the different QS signal molecules, an important class of signal molecules is the N-acyl homoserine lactone (N-AHSL). In pathogens such as Erwinia or Pseudomonas, N-AHSL based QS is crucial to overcome the host defenses and ensure a successful infection...
2017: Methods in Molecular Biology
https://www.readbyqxmd.com/read/27900439/non-ribosomal-peptide-synthases-from-pseudomonas-aeruginosa-play-a-role-in-cyclodipeptide-biosynthesis-quorum-sensing-regulation-and-root-development-in-a-plant-host
#11
Omar González, Randy Ortíz-Castro, César Díaz-Pérez, Alma L Díaz-Pérez, Viridiana Magaña-Dueñas, José López-Bucio, Jesús Campos-García
Diverse molecules mediate cross-kingdom communication between bacteria and their eukaryotic partners and determine pathogenic or symbiotic relationships. N-acyl-L-homoserine lactone-dependent quorum-sensing signaling represses the biosynthesis of bacterial cyclodipeptides (CDPs) that act as auxin signal mimics in the host plant Arabidopsis thaliana. In this work, we performed bioinformatics, biochemical, and plant growth analyses to identify non-ribosomal peptide synthase (NRPS) proteins of Pseudomonas aeruginosa, which are involved in CDP synthesis...
November 30, 2016: Microbial Ecology
https://www.readbyqxmd.com/read/27899449/deficiency-of-a-retinal-dystrophy-protein-acbd5-impairs-peroxisomal-%C3%AE-oxidation-of-very-long-chain-fatty-acids
#12
Yuichi Yagita, Kyoko Shinohara, Yuichi Abe, Keiko Nakagawa, Mohammed Al-Owain, Fowzan S Alkuraya, Yukio Fujiki
Acyl-CoA binding domain containing 5 (ACBD5) is a peroxisomal protein that carries an acyl-CoA binding domain (ACBD) at its N-terminal region. The recent identification of a mutation in the ACBD5 gene in patients with a syndromic form of retinal dystrophy highlights the physiological importance of ACBD5 in humans. However, the underlying pathogenic mechanisms and the precise function of ACBD5 remain unclear. We herein report that ACBD5 is a peroxisomal tail-anchored membrane protein exposing its ACBD to the cytosol...
November 29, 2016: Journal of Biological Chemistry
https://www.readbyqxmd.com/read/27897367/bifunctionality-of-activ-as-a-cyclase-thioesterase-revealed-by-in-vitro-reconstitution-of-actinorhodin-biosynthesis-in-streptomyces-coelicolor-a3-2
#13
Takaaki Taguchi, Takayoshi Awakawa, Yukitaka Nishihara, Michiho Kawamura, Yasuo Ohnishi, Koji Ichinose
Type II polyketide synthase (PKS) iteratively generates a nascent polyketide thioester of acyl carrier protein (ACP), which is structurally modified to produce an ACP-free intermediate towards its final metabolite. However, the timing of ACP off-loading is not well defined due to the lack of an apparent thioesterase (TE) among relevant biosynthetic enzymes. Here, ActIV, which had been assigned as a second ring cyclase (CYC) in actinorhodin (ACT) biosynthesis, was shown to possess a TE activity in vitro with a model substrate, anthraquinone-2-carboxylic acid-N-acetylcysteamine...
November 29, 2016: Chembiochem: a European Journal of Chemical Biology
https://www.readbyqxmd.com/read/27897248/comprehensive-investigation-of-tobacco-leaves-during-natural-early-senescence-via-multi-platform-metabolomics-analyses
#14
Lili Li, Jieyu Zhao, Yanni Zhao, Xin Lu, Zhihui Zhou, Chunxia Zhao, Guowang Xu
Senescence is the final stage of leaf growth and development. Many different physiological activities occur during this process. A comprehensive metabolomics analysis of tobacco middle leaves at 5 different developmental stages was implemented through multi-platform methods based on liquid chromatography, capillary electrophoresis and gas chromatography coupled with mass spectrometry. In total, 412 metabolites were identified, including pigments, sterols, lipids, amino acids, polyamines, sugars and secondary metabolites...
November 29, 2016: Scientific Reports
https://www.readbyqxmd.com/read/27896412/the-bacterial-quorum-sensing-molecule-n-3-oxo-dodecanoyl-l-homoserine-lactone-inhibits-mediator-release-and-chemotaxis-of-murine-mast-cells
#15
Ibrahim Khambati, Sangsu Han, Daniëlle Pijnenburg, Hannah Jang, Paul Forsythe
OBJECTIVE: Bacterial colonization relies on communication between bacteria via so-called "quorum-sensing molecules", which include the acyl-homoserine lactone group. Certain acyl-homoserine lactones can modulate mammalian cell function and are thought to contribute to bacterial pathogenicity. Given the role of mast cells in host defense, we investigated the ability of acyl-homoserine lactones to modulate mast cell function. METHODS: We utilized murine primary mast cell cultures to assess the effect of acyl-homoserine lactones on degranulation and cytokine release in response to different stimuli...
November 28, 2016: Inflammation Research: Official Journal of the European Histamine Research Society ... [et Al.]
https://www.readbyqxmd.com/read/27896004/photolysis-of-a-peptide-with-n-peptidyl-7-nitroindoline-units-using-two-photon-absorption
#16
Kevin A Hatch, Alfredo Ornelas, Kaitlyn N Williams, Thomas Boland, Katja Michael, Chunqiang Li
N-acyl-7-nitroindolines have been used as caged compounds to photorelease active molecules by a one- or two-photon excitation mechanism in biological systems. Here, we report the photolysis of a polypeptide that contains 7-nitroindoline units as linker moieties in its peptide backbone for potential materials engineering applications. Upon two-photon excitation with femtosecond laser light at 710 nm the photoreactive amide bond in N-peptidyl-7-nitroindolines is cleaved rendering short peptide fragments. Thus, this photochemical process changes the molecular composition at the laser focal volume...
November 1, 2016: Biomedical Optics Express
https://www.readbyqxmd.com/read/27893106/evidence-for-a-gpr18-role-in-diurnal-regulation-of-intraocular-pressure
#17
Sally Miller, Emma Leishman, Olivia Oehler, Laura Daily, Natalia Murataeva, Jim Wager-Miller, Heather Bradshaw, Alex Straiker
Purpose: The diurnal cycling of intraocular pressure (IOP) was first described in humans more than a century ago. This cycling is preserved in other species. The physiologic underpinning of this diurnal variation in IOP remains a mystery, even though elevated pressure is indicated in most forms of glaucoma, a common cause of blindness. Once identified, the system that underlies diurnal variation would represent a natural target for therapeutic intervention. Methods: Using normotensive mice, we measured the regulation of ocular lipid species by the enzymes fatty acid amide hydrolase (FAAH) and N-arachidonoyl phosphatidylethanolamine phospholipase (NAPE-PLD), mRNA expression of these enzymes, and their functional role in diurnal regulation of IOP...
November 1, 2016: Investigative Ophthalmology & Visual Science
https://www.readbyqxmd.com/read/27891746/enantioselective-4-2-annulation-of-donor-acceptor-cyclobutanes-by-n-heterocyclic-carbene-catalysis
#18
Alison Levens, Adam Ametovski, David W Lupton
Herein we report the enantioselective (4+2) annulation of donor-acceptor cyclobutanes and unsaturated acyl fluorides using N-heterocyclic carbene catalysis. The reaction allows a 3-step synthesis of cyclohexyl β-lactones (25 examples) in excellent chemical yield (most ≥90 %) and stereochemical integrity (all >20:1 d.r., most ≥97:3 e.r.). Mechanistic studies support ester enolate Claisen rearrangement, while derivatizations provide functionalized cyclohexenes and dihydroquinolinones.
November 28, 2016: Angewandte Chemie
https://www.readbyqxmd.com/read/27889588/preparation-and-properties-evaluation-of-a-novel-ph-sensitive-liposomes-based-on-imidazole-modified-cholesterol-derivatives
#19
Liang Ju, Fang Cailin, Wu Wenlan, Yu Pinghua, Gao Jiayu, Li Junbo
As a new kind of drug carries, pH-sensitive liposomes have been widely studied in tumor therapy for their advantages of target ability and sustained-release. Here, we synthesized a pH-sensitive material, N-(3-Aminopropyl)imidazole-cholesterol (IM-Chol) and prepared a novel pH-sensitive liposomes using IM-Chol and phosphatidylcholine. IM-Chol was synthesized through amidation reaction between the amino group of N-(3-Aminopropyl)imidazole and acyl chloride group of cholesteryl chloroformate in a weak base solution...
November 23, 2016: International Journal of Pharmaceutics
https://www.readbyqxmd.com/read/27888074/toxoplasma-gondii-immune-mapped-protein-1-is-anchored-to-the-inner-leaflet-of-the-plasma-membrane-and-adopts-a-novel-protein-fold
#20
Yonggen Jia, Stefi Benjamin, Qun Liu, Yingqi Xu, Sunil Kumar Dogga, Jing Liu, Stephen Matthews, Dominique Soldati-Favre
The immune mapped protein 1 (IMP1) was first identified as a protective antigen in Eimeria maxima and described as vaccine candidate and invasion factor in Toxoplasma gondii. We show here that TgIMP1 localizes to the inner leaflet of plasma membrane (PM) via dual acylation. Mutations either in the N-terminal myristoylation or palmitoylation sites (G2 and C5) cause relocalization of TgIMP1 to the cytosol. The first 11 amino acids are sufficient for PM targeting and the presence of lysine (K7) is critical. Disruption of TgIMP1 gene by double homologous recombination revealed no invasion defect or any measurable alteration in the lytic cycle of tachyzoites...
November 22, 2016: Biochimica et Biophysica Acta
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