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N-acyl or endocannnabanoid or NAPE

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https://www.readbyqxmd.com/read/29156366/triterpenoidal-saponins-from-the-fruits-of-gleditsia-caspica-with-proapoptotic-properties
#1
Usama Shaheen, Ehab A Ragab, Ashraf N Abdalla, Ammar Bader
Three previously undescribed oleanane-type triterpenoidal saponins named caspicaosides L-N were isolated from the fruits of Gleditsia caspica Desf. The aglycons of these saponins were echinocystic acid, erythrodiol and 12-oleanene-3,28,30-triol. Caspicaoside L is a bisdesmosidic saponin acylated with two monoterpenic acids. It has a disaccharide moiety made up of glucose and arabinose attached to C-3 and pentasaccharide moiety linked to C-28 made up of one glucose, 2 xyloses, one inner rhamnose and one terminal rhamnose which was acylated with two identical monoterpenic acids...
November 17, 2017: Phytochemistry
https://www.readbyqxmd.com/read/29152361/a-new-approach-to-alkaloid-like-systems-synthesis-and-crystal-structure-of-1-2-acetyl-11-meth-oxy-5-6-di-hydro-1-3-dioxolo-4-5-g-pyrrolo-2-1-a-isoquinolin-1-yl-propan-2-one
#2
Le Tuan Anh, Alexander A Titov, Reza Samavati, Leonid G Voskressensky, Alexey V Varlamov, Victor N Khrustalev
The title compound, C19H19NO5, (I), is the product of a domino reaction between cotarnine chloride and acetyl-acetylene catalysed by copper(I) iodide. The mol-ecule of (I) comprises a fused tetra-cyclic system containing two terminal five-membered rings (pyrrole and 1,3-dioxole) and two central six-membered rings (di-hydro-pyridine and benzene). The five-membered 1,3-dioxole ring has an envelope conformation and the central six-membered di-hydro-pyridine ring adopts a twist-boat conformation. The acyl substituent is almost coplanar with the pyrrole ring, whereas the meth-oxy substituent is twisted by 27...
November 1, 2017: Acta Crystallographica. Section E, Crystallographic Communications
https://www.readbyqxmd.com/read/29148752/substituent-effects-on-the-reactivity-of-cyclic-tertiary-sulfamidates
#3
Claudio D Navo, Nuria Mazo, Alberto Avenoza, Jesús H Busto, Jesús M Peregrina, Gonzalo Jiménez-Osés
The reactivity of cyclic tertiary sulfamidates derived from α-methylisoserine strongly depends on the substitution at the C and N termini. These substrates are one of the very few examples able to undergo nucleophilic ring-opening at a quaternary carbon with complete inversion of the configuration, as demonstrated both experimentally and computationally. When the sulfonamide is unprotected, the characteristic ring-opening reaction is completely silenced, which explains that the majority of the ring-opening reactions reported in the literature invoke N-alkyl or N-acyl-protected sulfamidates...
November 17, 2017: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/29147923/anti-aminoacyl-trna-synthetase-related-myositis-and-dermatomyositis-clues-for-differential-diagnosis-on-muscle-biopsy
#4
Bruna Cerbelli, Annalinda Pisano, Serena Colafrancesco, Maria Gemma Pignataro, Marco Biffoni, Silvia Berni, Antonia De Luca, Valeria Riccieri, Roberta Priori, Guido Valesini, Giulia d'Amati, Carla Giordano
Anti-synthetase syndrome is an autoimmune disease characterized by autoantibodies toward amino acyl-tRNA synthetases (ARS), anti-Jo 1 being the most commonly detected. Muscle damage develops in up to 90% of ARS-positive patients, characterized by a necrotizing myositis restricted to the perifascicular region. This topographic distribution of muscle damage may lead to a misdiagnosis of dermatomyositis (DM) at muscle biopsy. We compared morphological, immunohistochemical, and histoenzymatic features of muscle from ARS-positive patients (n = 11) with those of DM (n = 7) providing clues for their differential diagnosis...
November 16, 2017: Virchows Archiv: An International Journal of Pathology
https://www.readbyqxmd.com/read/29143042/synthesis-and-characterization-of-the-first-inhibitor-of-n-acylphosphatidylethanolamine-phospholipase-d-nape-pld
#5
Beatrice Castellani, Eleonora Diamanti, Daniela Pizzirani, Piero Tardia, Martina Maccesi, Natalia Realini, Paola Magotti, Gianpiero Garau, Thomas Bakkum, Silvia Rivara, Marco Mor, Daniele Piomelli
N-Acylphosphatidylethanolamine phospholipase D (NAPE-PLD) is a membrane-associated zinc enzyme that catalyzes the hydrolysis of N-acylphosphatidylethanolamines (NAPEs) into fatty acid ethanolamides (FAEs). Here, we describe the identification of the first small-molecule NAPE-PLD inhibitor, the quinazoline sulfonamide derivative 2,4-dioxo-N-[4-(4-pyridyl)phenyl]-1H-quinazoline-6-sulfonamide, ARN19874.
November 16, 2017: Chemical Communications: Chem Comm
https://www.readbyqxmd.com/read/29138268/n-acyl-amino-acids-elmiric-acids-endogenous-signaling-molecules-with-therapeutic-potential
#6
Sumner Burstein
The subject of N-acyl amino acid conjugates has been rapidly growing in recent years, especially with regard to their analgesic and anti-inflammatory actions. The field is comprised of a large family of lipid signaling molecules whose importance is only now being fully realized. The most widely studied member is N-arachidonoyl glycine (NAGly), which differs structurally from the endocannabinoid anandamide (N-arachidonoyl ethanolamide) by a single oxygen atom and the two are metabolically related. Topics that are covered in this mini review are: biosynthetic pathways for N-acyl amino acids, receptors for N-acyl amino acids, physiological actions of N-acyl amino acids, pharmacological effects of N-acyl amino acids and molecular mechanisms believed to be responsible for their effects...
November 14, 2017: Molecular Pharmacology
https://www.readbyqxmd.com/read/29136320/n-heterocyclic-carbene-catalysis-via-azolium-dienolates-an-efficient-strategy-for-enantioselective-remote-functionalizations
#7
Dieter Enders, Xiang-Yu Chen, Qiang Liu, Pankaj Chauhan
N-heterocyclic carbene (NHC) catalysis has emerged as a powerful strategy in organic synthesis. In recent years a number of reviews have been published on NHC-catalyzed transformations involving Breslow intermediates, acyl azoliums, α,β-unsaturated acyl azoliums, homoenolate equivalents and azolium enolates. However, the azolium dienolate intermediates generated by NHCs have been employed in asymmetric synthesis only very recently, especially in cycloadditions dealing with remote functionalization. This Minireview highlights all the developments and the new advances in the NHC-catalyzed asymmetric cycloaddition resections involving azolium dienolate intermediates...
November 14, 2017: Angewandte Chemie
https://www.readbyqxmd.com/read/29135010/metal-free-oxidative-para-acylation-of-unprotected-anilines-with-n-heteroarylmethanes
#8
Min Liu, Xue Chen, Tieqiao Chen, Qing Xu, Shuang-Feng Yin
A selective oxidative para-acylation of unprotected anilines with methyl groups in N-heteroarylmethanes was achieved. This transformation proceeds under mild metal-free reaction conditions to produce the corresponding valuable diarylmethanones in good to high yields, featuring high site-selectivity, high functional-group-tolerance, gram-scale synthesis and easy product-derivation. Preliminary mechanistic studies revealed that the present oxidative para-acylation would take place via a Friedel-Crafts-type process of in situ imines and the steric hindrance might be the key issue for the high regio-selectivity...
November 14, 2017: Organic & Biomolecular Chemistry
https://www.readbyqxmd.com/read/29133061/design-synthesis-and-cytotoxic-activity-of-n-modified-oleanolic-saponins-bearing-a-glucosamine
#9
You-Yu Lin, She-Hung Chan, Yu-Pu Juang, Hsin-Min Hsiao, Jih-Hwa Guh, Pi-Hui Liang
A series of N-acyl, N-alkoxycarbonyl, and N-alkylcarbamoyl derivatives of 2'-deoxy-glucosyl bearing oleanolic saponins were synthesized and evaluated against HL-60, PC-3, and HT29 tumor cancer cells. The SAR studies revealed that the activity increased in order of conjugation of 2' -amino group with carbamate > amide > urea derivatives. Lengthening the alkyl chain increased the cytotoxicity, the peak activity was found to around heptyl to nonyl substitutions. 2'-N-heptoxycarbonyl derivative 56 was found to be the most cytotoxic (IC50 = 0...
November 6, 2017: European Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/29130175/imaging-n-acyl-homoserine-lactone-quorum-sensing-in-vivo
#10
Louise Dahl Hultqvist, Maria Alhede, Tim Holm Jakobsen, Michael Givskov, Thomas Bjarnsholt
In order to study N-acyl homoserine lactone (AHL)-based quorum sensing in vivo, we present a protocol using an Escherichia coli strain equipped with a luxR-based monitor system, which in the presence of exogenous AHL molecules expresses a green fluorescent protein (GFP). Lungs from mice challenged intratracheally with alginate beads containing both a Pseudomonas aeruginosa strain together with the E. coli monitor strain can be investigated at different time points postinfection. Epifluorescent or confocal scanning laser microscopy (CSLM) is used to detect the GFP-expressing E...
2018: Methods in Molecular Biology
https://www.readbyqxmd.com/read/29130174/identification-of-ahl-and-bdsf-controlled-proteins-in-burkholderia-cenocepacia-by-proteomics
#11
Yilei Liu, Gabriella Pessi, Katharina Riedel, Leo Eberl
We used comparative proteome analysis to determine the target genes of the two quorum sensing (QS) circuits in the opportunistic pathogen Burkholderia cenocepacia: the N-acyl homoserine lactone (AHL)-based CepIR system and the BDSF (B urkholderia diffusible signal factor, cis-2-dodecenoic acid)-based RpfFR system. In this book chapter, we focus on the description of the practical procedure we currently use in the laboratory to perform a sensitive GeLC-MS/MS shotgun proteomics experiment; we also briefly describe the downstream bioinformatic data analysis...
2018: Methods in Molecular Biology
https://www.readbyqxmd.com/read/29130164/detection-of-the-bacterial-quorum-sensing-signaling-molecules-n-acyl-homoserine-lactones-hsl-and-n-acyl-homoserine-hs-with-an-enzyme-linked-immunosorbent-assay-elisa-and-via-ultrahigh-performance-liquid-chromatography-coupled-to-mass-spectrometry-uhplc-ms
#12
Michael Rothballer, Jenny Uhl, Josie Kunze, Philippe Schmitt-Kopplin, Anton Hartmann
Quick and reliable quantitative methods requiring low amounts of sample volume are needed for the detection of N-acyl-homoserine lactones (HSL) and their degradation products N-acyl-homoserines (HS) in order to elucidate the occurrence and dynamics of these prevalent quorum-sensing molecules of Gram-negative bacteria in natural samples and laboratory model experiments. A combination of ELISA and UHPLC-MS is presented here which has proven to meet these requirements. Both methods can not only precisely detect and quantify HSLs but also their degradation products HS and thereby enable studying signaling dynamics in quorum sensing, which have been identified to play an essential role in bacterial communication...
2018: Methods in Molecular Biology
https://www.readbyqxmd.com/read/29130163/liquid-chromatography-mass-spectrometry-lc-ms-for-the-detection-and-quantification-of-n-acyl-l-homoserine-lactones-ahls-and-4-hydroxy-2-alkylquinolines-haqs
#13
François Lépine, Sylvain Milot, Marie-Christine Groleau, Eric Déziel
High-performance liquid chromatography (HPLC) coupled in-line with mass spectrometry (MS) permits rapid and specific identification and quantification of N-acyl-L-homoserine lactones (AHLs) and 4-hydroxy-2-alkylquinolines (HAQs). We are presenting here methods for the analysis of these molecules directly from biological samples using LC/MS.
2018: Methods in Molecular Biology
https://www.readbyqxmd.com/read/29130160/use-of-whole-cell-bioassays-for-screening-quorum-signaling-quorum-interference-and-biofilm-dispersion
#14
Starla G Thornhill, Robert J C McLean
In most bacteria, a global level of regulation, termed quorum sensing (QS), exists involving intercellular communication via the production and response to cell density-dependent signal molecules. QS has been associated with a number of important features in bacteria including virulence regulation and biofilm formation. Consequently, there is considerable interest in understanding, detecting, and inhibiting QS. N-acylated homoserine lactones (AHLs) are used as extracellular QS signals by a variety of Gram-negative bacteria...
2018: Methods in Molecular Biology
https://www.readbyqxmd.com/read/29127192/lipotoxic-very-long-chain-ceramides-cause-mitochondrial-dysfunction-oxidative-stress-and-cell-death-in-cardiomyocytes
#15
Brittany A Law, Xianghai Liao, Kelsey S Moore, Abigail Southard, Patrick Roddy, Ruiping Ji, Zdzislaw Sculz, Ala Bielawska, P Christian Schulze, L Ashley Cowart
Accumulating data support a role for bioactive lipids as mediators of lipotixicity in cardiomyocytes. One class of these, the ceramides, constitutes a family of molecules that differ in structure and are synthesized by distinct enzymes, ceramide synthase (CerS)1-CerS6. Data support that specific ceramides and the enzymes that catalyze their formation play distinct roles in cell function. In a mouse model of diabetic cardiomyopathy, sphingolipid profiling revealed increases in not only the CerS5-derived ceramides but also in very long chain (VLC) ceramides derived from CerS2...
November 10, 2017: FASEB Journal: Official Publication of the Federation of American Societies for Experimental Biology
https://www.readbyqxmd.com/read/29124861/inhibiting-bacterial-quorum-sensing-arrests-coral-disease-development-and-disease-associated-microbes
#16
Rebecca H Certner, Steven V Vollmer
Among the greatest threats to coral reefs are coral epizootics, which are increasing in frequency and severity across many reef ecosystems. In particular, white band disease (WBD) has devastated Caribbean acroporid populations since its initial outbreak in 1979. However, despite its widespread and damaging effects, the etiology of WBD remains largely unresolved. Here we examine the role of quorum sensing within bacterial communities associated with WBD-infected Acropora cervicornis. Microbial communities isolated from WBD-infected corals were exposed to quorum sensing inhibitor (QSI) - a N-acyl homoserine lactone autoinducer antagonist - and then dosed onto healthy test corals...
November 10, 2017: Environmental Microbiology
https://www.readbyqxmd.com/read/29115835/citu-a-peptide-and-decarboxylative-coupling-reagent
#17
Justine N deGruyter, Lara R Malins, Laurin Wimmer, Khalyd J Clay, Javier Lopez-Ogalla, Tian Qin, Josep Cornella, Zhiqing Liu, Guanda Che, Denghui Bao, Jason M Stevens, Jennifer X Qiao, Martin P Allen, Michael A Poss, Phil S Baran
Tetrachloro-N-hydroxyphthalimide tetramethyluronium hexafluorophosphate (CITU) is disclosed as a convenient and economical reagent for both acylation and decarboxylative cross-coupling chemistries. Within the former set of reactions, CITU displays reactivity similar to that of common coupling reagents, but with increased safety and reduced cost. Within the latter, increased yields, more rapid conversion, and a simplified procedure are possible across a range of reported decarboxylative transformations.
November 17, 2017: Organic Letters
https://www.readbyqxmd.com/read/29115671/fatty-acid-elongase-7-is-regulated-via-sp1-and-is-involved-in-lipid-accumulation-in-bovine-mammary-epithelial-cells
#18
Si Chen, Zhigang Hu, Hua He, Xiaolin Liu
Fatty Acid Elongase 7 (ELOVL7) is the newly discovered protein on human that catalyzes the rate-limiting step towards the synthesis of very long-chain fatty acids and exhibits the highest activity toward C18:3 (n-3) acyl-CoAs, which is the precursor of eicosapentaenoic acid (EPA, 20:5n-3). However, in ruminants, an overall understanding of ELOVLs gene family and the transcriptional regulation of ELOVL7 remain unknown. The purpose of this study is to investigate the transcriptional regulation and the influence of bovine ELOVL7 in bovine mammary epithelial cells (bMECs)...
November 8, 2017: Journal of Cellular Physiology
https://www.readbyqxmd.com/read/29114951/syntheses-of-amino-substituted-iridabenzofurans-and-subsequent-selective-n-functionalisation
#19
Benjamin James Frogley, Lakshika Perera, L James Wright
The first examples of amino-substituted fused-ring metallabenzenes, the cationic iridabenzofuran [Ir(C7H4O{NH2-2}{OMe-7})(CO)(PPh3)2][O3SCF3] (5) and neutral analogue Ir(C7H4{NH2-2}{OMe-7})Cl(PPh3)2 (6), can be prepared by reduction of the corresponding nitro-substituted iridabenzofurans with zinc and concentrated hydrochloric acid. N-functionalised derivatives of 5 and 6 are formed through alkylation, sulfonylation or acylation. Thus, consecutive treatments with methyl triflate and base gives the corresponding trimethylammonium-substituted iridabenzofurans while sulfonamide derivatives are formed with p-toluenesulfonyl chloride...
November 7, 2017: Chemistry: a European Journal
https://www.readbyqxmd.com/read/29110386/selective-functionalization-of-aromatic-c-sp2-h-bonds-in-the-presence-of-benzylic-c-sp3-h-bonds-by-electron-deficient-carbenoid-generated-from-4-acyl-1-sulfonyl-1-2-3-triazoles
#20
Tomoya Miura, Qiang Zhao, Masahiro Murakami
A rhodium(II)-catalyzed reaction of newly prepared 4-acyl-1-sulfonyl-1,2,3-triazoles with benzene and its derivatives is investigated. Acceptor/acceptor carbenoids generated from 4-acyltriazoles undergo selective insertion at aromatic C(sp2)-H bonds in the presence of benzylic C(sp3)-H bonds to produce N-sulfonylenaminones.
November 6, 2017: Angewandte Chemie
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