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N-acyl or endocannnabanoid or NAPE

Arata Fukushima, Liyan Zhang, Alda Huqi, Victoria H Lam, Sonia Rawat, Tariq Altamimi, Cory S Wagg, Khushmol K Dhaliwal, Lisa K Hornberger, Paul F Kantor, Ivan M Rebeyka, Gary D Lopaschuk
A dramatic increase in cardiac fatty acid oxidation occurs following birth. However, cardiac hypertrophy secondary to congenital heart diseases (CHDs) delays this process, thereby decreasing cardiac energetic capacity and function. Cardiac lysine acetylation is involved in modulating fatty acid oxidation. We thus investigated what effect cardiac hypertrophy has on protein acetylation during maturation. Eighty-four right ventricular biopsies were collected from CHD patients and stratified according to age and the absence (n = 44) or presence of hypertrophy (n = 40)...
May 17, 2018: JCI Insight
D Marian Szebenyi, Irina Kriksunov, Kevin J Howe, John S Ramsey, David G Hall, Michelle L Heck, Stuart B Krasnoff
The title compound C22 H39 NO9 ·CH3 OH [systematic name: ( S )- N -(( S )-{(2 S ,4 R ,6 R )-6-[( S )-2,3-di-hydroxy-prop-yl]-4-hy-droxy-5,5-di-methyl-tetra-hydro-2 H -pyran-2-yl}(hy-droxy)meth-yl)-2-hy-droxy-2-[(2 R ,5 R ,6 R )-2-meth-oxy-5,6-dimeth-yl-4-methyl-ene-tetra-hydro-2 H -pyran-2-yl]acetamide methanol monosolvate], was isolated from the Asian citrus psyllid, Diaphorina citri Kuwayama, and crystallizes in the space group P 21 . ' Candidatus Profftella armatura' a bacterial endosymbiont of D. citri , biosynthesizes diaphorin, which is a hybrid polyketide-nonribosomal peptide comprising two highly substituted tetra-hydro-pyran rings joined by an N -acyl aminal bridge [Nakabachi et al...
April 1, 2018: Acta Crystallographica. Section E, Crystallographic Communications
Prateek Kinra, Gaurav P S Gahlot, Rajni Yadav, Vandana Baloda, Govind K Makharia, Siddhartha Datta Gupta, Prasenjit Das
BACKGROUND: Histological assessment of dysplasia in Barrett's esophagus (BE) has high inter-observer variability. Hence, use of ancillary markers for early detection of dysplasia in BE is an important clinical question. METHODS: In this retrospective study consecutive cases of BE (n = 59), over a period of 4 years were included. Hematoxylin and eosin stained sections were reviewed independently by 3 senior qualified pathologists, who graded the dysplasia according to the Vienna Classification system and inter-observer agreement was analysed using the Kappa statistics...
May 13, 2018: Pathology, Research and Practice
Jun Gong, Qian Wan, Qiang Kang
An efficient asymmetric 1,3-dipolar cycloaddition of α,β-unsaturated 2-acyl imidazoles with N, N'-cyclic azomethine imines catalyzed by a chiral-at-metal rhodium complex is reported. The corresponding N, N'-bicyclic pyrazolidine derivatives with three contiguous tertiary stereocenters were obtained in good yields (up to 99%) with excellent stereoselectivities (>20:1 dr and >99% ee). Remarkably, as little as 0.5 mol % of a chiral Rh(III) complex can promote a gram-scale reaction with excellent yield and enantioselectivity...
May 15, 2018: Organic Letters
Quentin Pavic, Sylvain Tranchimand, Loïc Lemiègre, Laurent Legentil
An arabinofuranosylhydrolase from the GH51 family was transformed into an acyl transferase by mutation of the catalytic acid/base amino acid. The resulting enzyme was able to transfer carboxylic acid onto the anomeric position of arabinose with complete chemo- and stereoselectivity. A wide range of acyl α-l-arabinofuranoses was obtained with yields ranging from 25 to 83%. Using this method, ibuprofen and N-Boc phenylalanine were successfully transformed into their corresponding acyl conjugates, expanding the scope of the reaction to drugs and amino acids...
May 15, 2018: Chemical Communications: Chem Comm
Tomonori Tamura, Tsuyoshi Ueda, Taiki Goto, Taku Tsukidate, Yonatan Shapira, Yuki Nishikawa, Alma Fujisawa, Itaru Hamachi
Selective modification of native proteins in live cells is one of the central challenges in recent chemical biology. As a unique bioorthogonal approach, ligand-directed chemistry recently emerged, but the slow kinetics limits its scope. Here we successfully overcome this obstacle using N-acyl-N-alkyl sulfonamide as a reactive group. Quantitative kinetic analyses reveal that ligand-directed N-acyl-N-alkyl sulfonamide chemistry allows for rapid modification of a lysine residue proximal to the ligand binding site of a target protein, with a rate constant of ~104  M-1  s-1 , comparable to the fastest bioorthogonal chemistry...
May 14, 2018: Nature Communications
Xiaonan Shi, Xi Chen, Muhua Wang, Xinying Zhang, Xuesen Fan
A highly regioselective and versatile synthesis of acylated N-heterocycles from the cascade reactions of saturated cyclic amines with 2-oxo-2-arylacetic acids is presented. Mechanistically, the formation of the title compounds involves firstly a C(sp3)-H bond dehydrogenation of cyclic amine to give an enamine intermediate followed by its cross coupling with the acyl species in situ generated through the decarboxylation of 2-oxo-2-arylacetic acid. Interestingly, in this cascade process the copper catalyst is believed to play a crucial role not only in dehydrogenation, but also in decarboxylation and cross coupling reaction...
May 14, 2018: Journal of Organic Chemistry
Mayukh Deb, Susanta Hazra, Ajay Gupta, Anil J Elias
A palladium catalysed methodology for mono-selective oxidative aroylation of ferrocene has been achieved. 10 mol% of Pd(OAc)2 was used as the catalyst for this radical aroylation reaction using O-methyl-oxime as the directing group. tert-Butyl hydroperoxide was used as an oxidant and both aldehydes and alcohols were used as acyl-equivalents. The protocol has been extended to aryl, heteroaryl and sterically hindered aroylating agents. Acidic-hydrolysis with 6(N) HCl of the directing group resulted in unsymmetrically substituted ketone derivatives of ferrocene, which have not been achieved otherwise...
May 14, 2018: Dalton Transactions: An International Journal of Inorganic Chemistry
Putri D Utari, Rita Setroikromo, Barbro N Melgert, Wim J Quax
Pseudomonas aeruginosa is the predominant pathogen in pulmonary infections associated with cystic fibrosis. Quorum sensing (QS) systems regulate the production of virulence factors and play an important role in the establishment of successful P. aeruginosa infections. Inhibition of the QS system (termed quorum quenching) renders the bacteria avirulent thus serving as an alternative approach in the development of novel antibiotics. Quorum quenching in Gram negative bacteria can be achieved by preventing the accumulation of N -acyl homoserine lactone (AHL) signaling molecule via enzymatic degradation...
2018: Frontiers in Cellular and Infection Microbiology
Jiajing Zhang, Wentao Zhang, Minghui Xu, Yang Zhang, Xuefeng Fu, Huayi Fang
It is of fundamental importance to transform carbon monoxide (CO) to petrochemical feedstocks and fine chemicals. Many strategies built on the activation of C≡O bond by π-back bonding from the transition metal center were developed during the past decades. Herein, a new CO activation method, in which the CO was converted to the active acyl-like metallo-radical [(por)Rh(CO)]• (por = porphyrin), was reported. The reactivity of [(por)Rh(CO)]• and other rhodium porphyrin compounds, such as (por)RhCHO and (por)RhC(O)NH n Pr, and corresponding mechanism studies were conducted experimentally and computationally, and inspired the design of a new conversion system featuring 100% atomic economy that promotes carbonylation of amines to formamides using porphyrin rhodium(II) metallo-radical...
May 11, 2018: Journal of the American Chemical Society
Yu Luo, Muhammad Afzal Javed, Harry Deneer, Xialu Chen
Bacteria inhabit a vast range of biological niches and have evolved diverse mechanisms to cope with environmental stressors. The genus Acinetobacter comprises a complex group of Gram-negative bacteria. Some of these bacteria such as A. baumannii are nosocomial pathogens. They are often resistant to multiple antibiotics and are associated with epidemic outbreaks. A. radioresistens is generally considered to be a commensal bacterium on human skin or an opportunistic pathogen. Interestingly, this species has exceptional resistance to a range of environmental challenges which contributes to its persistence in clinical environment and on human skin...
May 10, 2018: Scientific Reports
Jenna R Freund, Corrine J Mansfield, Laurel J Doghramji, Nithin D Adappa, James N Palmer, David W Kennedy, Danielle R Reed, Peihua Jiang, Robert J Lee
Bitter taste receptors (T2Rs), discovered in many tissues outside the tongue, have recently become potential therapeutic targets. We showed previously that airway epithelial cells express several T2Rs that activate innate immune responses that may be important for treatment of airway diseases such as chronic rhinosinusitis. It is imperative to more clearly understand what compounds activate airway T2Rs as well as their full range of functions. T2R isoforms in airway motile cilia (T2Rs 4, 14, 16, and 38) produce bactericidal levels of nitric oxide (NO) that also increase ciliary beating, promoting clearance of mucus and trapped pathogens...
May 10, 2018: Journal of Biological Chemistry
W Shi, D Wu, N Si, W Jiang, J Ma, X M Li
We represented a 22-year-old male patient who developed rhabdomyolysis, acute kidney failure and acute hepatic failure and was finally diagnosed as multiple acyl-CoA dehydrogenase deficiency. The patient appeared temporary stable status after high dose vitamine-B(2) supplement whereas deterioration was still fatal with pulmonary infection, acute respiratory failure and acute heart failure.
May 1, 2018: Zhonghua Nei Ke za Zhi [Chinese Journal of Internal Medicine]
Goki Hirata, Hiromitsu Maeda
The abilities of dipyrrolyldiketone boron complexes as hydrogen-bonding donor organocatalysts were examined by the Mannich-type reaction of N-acyl heteroarenium chlorides with 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene, as well as by the classical N-alkylation of amines with trityl chloride under base-free conditions. 1 H NMR examinations of the hydrogen-bonding interaction between the pyrrole NH of the catalyst and the Cl- in the N-acyl heteroarenium salt suggested that the activation of N-acyl heteroarenium chlorides occurs through anion binding by the catalyst...
May 8, 2018: Organic Letters
Thilo Focken, Sultan Chowdhury, Alla Zenova, Michael E Grimwood, Christine Chabot, Tao Sheng, Ivan Hemeon, Shannon M Decker, Michael Wilson, Paul Bichler, Qi Jia, Shaoyi Sun, Clint Young, Sophia Lin, Samuel J Goodchild, Noah G Shuart, Elaine Chang, Zhiwei Xie, Bowen Li, Kuldip Khakh, Girish Bankar, Matthew Waldbrook, Rainbow Kwan, Karen Nelkenbrecher, Parisa Karimi Tari, Navjot Chahal, Luis Sojo, C Lee Robinette, Andrew D White, Chien-An Chen, Yi Zhang, Jodie Pang, Jae H Chang, David H Hackos, James P Johnson, Charles J Cohen, Daniel Fred Ortwine, Daniel P Sutherlin, Christoph M Dehnhardt, Brian Salvatore Safina
The sodium channel NaV1.7 has emerged as a promising target for the treatment of pain based on strong genetic validation of its role in nociception. In recent years, a number of aryl and acyl sulfonamides have been reported as potent inhibitors of NaV1.7, with high selectivity over the cardiac isoform NaV1.5. Herein, we report on the discovery of a novel series of N-([1,2,4]triazolo[4,3-a]pyridin-3-yl)methanesulfonamides as selective NaV1.7 inhibitors. Starting with the crystal structure of an acyl sulfonamide, we rationalized that cyclization to form a fused heterocycle would improve physicochemical properties, in particular lipophilicity...
May 8, 2018: Journal of Medicinal Chemistry
Basmah Almohaywi, Aditi Taunk, Daniel S Wenholz, Shashidhar Nizalapur, Nripendra N Biswas, Kitty K K Ho, Scott A Rice, George Iskander, David StC Black, Renate Griffith, Naresh Kumar
Bacterial infections, particularly hospital-acquired infections caused by Pseudomonas aeruginosa , have become a global threat with a high mortality rate. Gram-negative bacteria including P. aeruginosa employ N -acyl homoserine lactones (AHLs) as chemical signals to regulate the expression of pathogenic phenotypes through a mechanism called quorum sensing (QS). Recently, strategies targeting bacterial behaviour or QS have received great attention due to their ability to disarm rather than kill pathogenic bacteria, which lowers the evolutionary burden on bacteria and the risk of resistance development...
May 7, 2018: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Carlos Moreno-Yruela, Iacopo Galleano, Andreas S Madsen, Christian A Olsen
Histone deacetylase (HDAC) enzymes regulate diverse biological function, including gene expression, rendering them potential targets for intervention in a number of diseases, with a handful of compounds approved for treatment of certain hematologic cancers. Among the human zinc-dependent HDACs, the most recently discovered member, HDAC11, is the only member assigned to subclass IV. It is the smallest protein and has the least well understood biological function. Here, we show that HDAC11 cleaves long-chain acyl modifications on lysine side chains with remarkable efficiency...
April 23, 2018: Cell Chemical Biology
Stephen R Wassall, Xiaoling Leng, Samuel W Canner, Edward Ross Pennington, Jacob J Kinnun, Andres T Cavazos, Sahil Dadoo, Dylan Johnson, Frederick A Heberle, John Katsaras, Saame Raza Shaikh
Docosahexaenoic acid (DHA, 22:6) is an n-3 polyunsaturated fatty acid (n-3 PUFA) that influences immunological, metabolic, and neurological responses through complex mechanisms. One structural mechanism by which DHA exerts its biological effects is through its ability to modify the physical organization of plasma membrane signaling assemblies known as sphingomyelin/cholesterol (SM/chol)-enriched lipid rafts. Here we studied how DHA acyl chains esterified in the sn-2 position of phosphatidylcholine (PC) regulate the formation of raft and non-raft domains in mixtures with SM and chol on differing size scales...
May 3, 2018: Biochimica et Biophysica Acta
Mary R Lee, Jenica D Tapocik, Mwlod Ghareeb, Melanie L Schwandt, Alexandra A Dias, April N Le, Enoch Cobbina, Lisa A Farinelli, Sofia Bouhlal, Mehdi Farokhnia, Markus Heilig, Fatemeh Akhlaghi, Lorenzo Leggio
Rodent studies indicate that ghrelin receptor blockade reduces alcohol consumption. However, no ghrelin receptor blockers have been administered to heavy alcohol drinking individuals. Therefore, we evaluated the safety, tolerability, pharmacokinetic (PK), pharmacodynamic (PD) and behavioral effects of a novel ghrelin receptor inverse agonist, PF-5190457, when co-administered with alcohol. We tested the effects of PF-5190457 combined with alcohol on locomotor activity, loss-of-righting reflex (a measure of alcohol sedative actions), and on blood PF-5190457 concentrations in rats...
May 4, 2018: Molecular Psychiatry
Tao Zhu, Thibault Scalvenzi, Nathalie Sassoon, Xuefeng Lu, Muriel Gugger
Cyanobacteria can synthesize alkanes and alkenes, which are considered to be infrastructure-compatible biofuels. In terms of physiological function, cyanobacterial hydrocarbons are thought to be essential for membrane flexibility for cell division, size, and growth. The genetic basis for the biosynthesis of terminal olefins (1-alkenes) is a modular type I polyketide synthase (PKS) termed olefin synthase (Ols). The modular architectures of Ols and structural characteristics of alkenes have been investigated only in a few species of the small percentage (approximately 10%) of cyanobacteria that harbor putative Ols pathways...
May 4, 2018: Applied and Environmental Microbiology
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