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https://www.readbyqxmd.com/read/28453915/documenting-and-harnessing-the-biological-potential-of-molecules-in-distributed-drug-discovery-d3-virtual-catalogs
#1
Milata M Abraham, Ryan E Denton, Richard W Harper, William L Scott, Martin J O'Donnell, Jacob D Durrant
Virtual molecular catalogs have limited utility if member compounds are (1) difficult to synthesize or (2) unlikely to have biological activity. The Distributed Drug Discovery (D3) program addresses the synthesis challenge by providing scientists with a free virtual D3 catalog of 73,024 easy-to-synthesize N-acyl unnatural α-amino acids, their methyl esters, and primary amides. The remaining challenge is to document and exploit the bioactivity potential of these compounds. In the current work, a search process is described that retrospectively identifies all virtual D3 compounds classified as bioactive hits in PubChem-cataloged experimental assays...
April 28, 2017: Chemical Biology & Drug Design
https://www.readbyqxmd.com/read/28446863/peptides-as-quorum-sensing-molecules-measurement-techniques-and-obtained-levels-in-vitro-and-in-vivo
#2
REVIEW
Frederick Verbeke, Severine De Craemer, Nathan Debunne, Yorick Janssens, Evelien Wynendaele, Christophe Van de Wiele, Bart De Spiegeleer
The expression of certain bacterial genes is regulated in a cell-density dependent way, a phenomenon called quorum sensing. Both Gram-negative and Gram-positive bacteria use this type of communication, though the signal molecules (auto-inducers) used by them differ between both groups: Gram-negative bacteria use predominantly N-acyl homoserine lacton (AHL) molecules (autoinducer-1, AI-1) while Gram-positive bacteria use mainly peptides (autoinducer peptides, AIP or quorum sensing peptides). These quorum sensing molecules are not only involved in the inter-microbial communication, but can also possibly cross-talk directly or indirectly with their host...
2017: Frontiers in Neuroscience
https://www.readbyqxmd.com/read/28425948/characterization-of-n-acyl-homoserine-lactones-in-vibrio-tasmaniensis-lgp32-by-a-biosensor-based-uhplc-hrms-ms-method
#3
Léa Girard, Élodie Blanchet, Laurent Intertaglia, Julia Baudart, Didier Stien, Marcelino Suzuki, Philippe Lebaron, Raphaël Lami
Since the discovery of quorum sensing (QS) in the 1970s, many studies have demonstrated that Vibrio species coordinate activities such as biofilm formation, virulence, pathogenesis, and bioluminescence, through a large group of molecules called N-acyl homoserine lactones (AHLs). However, despite the extensive knowledge on the involved molecules and the biological processes controlled by QS in a few selected Vibrio strains, less is known about the overall diversity of AHLs produced by a broader range of environmental strains...
April 20, 2017: Sensors
https://www.readbyqxmd.com/read/28424524/hqia-a-novel-quorum-quenching-enzyme-which-expands-the-ahl-lactonase-family
#4
Marta Torres, Stéphane Uroz, Rafael Salto, Laure Fauchery, Emilia Quesada, Inmaculada Llamas
The screening of a metagenomic library of 250,000 clones generated from a hypersaline soil (Spain) allowed us to identify a single positive clone which confers the ability to degrade N-acyl homoserine lactones (AHLs). The sequencing of the fosmid revealed a 42,318 bp environmental insert characterized by 46 ORFs. The subcloning of these ORFs demonstrated that a single gene (hqiA) allowed AHL degradation. Enzymatic analysis using purified HqiA and HPLC/MS revealed that this protein has lactonase activity on a broad range of AHLs...
April 19, 2017: Scientific Reports
https://www.readbyqxmd.com/read/28414213/immobilization-and-stabilization-of-acylase-on-carboxylated-polyaniline-nanofibers-for-highly-effective-antifouling-application-via-quorum-quenching
#5
Jeongjoon Lee, Inseon Lee, Jahyun Nam, Dong Soo Hwang, Kyung-Min Yeon, Jungbae Kim
Acylase was immobilized and stabilized on carboxylated polyaniline nanofibers (cPANFs) for the development of antifouling nanobiocatalysis with high enzyme loading and stability. Acylase was immobilized via three different approaches: covalent attachment (CA), enzyme coating (EC), and magnetically separable enzyme precipitate coating (Mag-EPC). The enzyme activity per unit weight of cPANFs of Mag-EPC was 75 and 300 times higher than those of CA and EC, respectively, representing the improved enzyme loading in the form of Mag-EPC...
April 17, 2017: ACS Applied Materials & Interfaces
https://www.readbyqxmd.com/read/28413760/synthesis-of-c2-symmetric-diphosphormonoamidites-and-their-use-as-ligands-in-rh-catalyzed-hydroformylation-relationships-between-activity-and-hydrolysis-stability
#6
Galina Morales Torres, Stephan Behrens, Dirk Michalik, Detlef Selent, Anke Spannenberg, Susan Lühr, Katrin Marie Dyballa, Robert Franke, Armin Börner
A series of diphosphoramidites has been synthetized with a piperazine, homopiperazine, and an acyclic 1,2-diamine unit in the backbone. New compounds were tested alongside related N-acyl phosphoramidites as ligands in the Rh-catalyzed hydroformylation of n-octenes to investigate their influence on the activity and regioselectivity. A subsequent study of their hydrolysis stability revealed that the most stable ligands induced the highest activity in the catalytic reaction.
April 2017: ChemistryOpen
https://www.readbyqxmd.com/read/28413263/intensified-microwave-assisted-n-acylation-procedure-synthesis-and-activity-evaluation-of-trpc3-channel-agonists-with-a-1-3-dihydro-2h-benzo-d-imidazol-2-one-core
#7
Gema Guedes de la Cruz, Barbora Svobodova, Michaela Lichtenegger, Oleksandra Tiapko, Klaus Groschner, Toma Glasnov
Upon controlled microwave heating and using cyanuric chloride as a coupling reagent, an efficient amidation procedure for the synthesis of 1,3-dihydro-2H-benzo[d]imidazol-2-one-based agonists of TRPC3/6 ion channels has been developed. Compared to the few conventional protocols, a drastic reduction in processing time from ca. 2 days down to 10 minutes was achieved accompanied by significantly improved product yields. The robustness of the method was confirmed by 18 additional examples including aromatic, aliphatic, and heterocyclic amines and acids...
April 2017: Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry
https://www.readbyqxmd.com/read/28405399/strain-identification-and-quorum-sensing-inhibition-characterization-of-marine-derived-rhizobium-sp-nao1
#8
Hong Chang, Jin Zhou, Xiaoshan Zhu, Shenchen Yu, Lu Chen, Hui Jin, Zhonghua Cai
A novel strategy for combating pathogens is through the ongoing development and use of anti-quorum sensing (QS) treatments such as therapeutic bacteria or their anti-QS substances. Relatively little is known about the bacteria that inhabit the open ocean and of their potential anti-pathogenic attributes; thus, in an initiative to identify these types of therapeutic bacteria, planktonic microbes from the North Atlantic Ocean were collected, isolated, cultured and screened for anti-QS activity. Screening analysis identified one such strain, Rhizobium sp...
March 2017: Royal Society Open Science
https://www.readbyqxmd.com/read/28405238/derivatives-of-the-triaminoguanidinium-ion-5-acylation-of-triaminoguanidines-leading-to-symmetrical-tris-acylamino-guanidines-and-mesoionic-1-2-4-triazolium-3-aminides
#9
Jan Szabo, Julian Greiner, Gerhard Maas
Depending on the reaction conditions, N,N',N''-tris(benzylamino)guanidinium salts can react with carboxylic acid chlorides to form either symmetrical N,N',N''-tris(N-acyl-N-benzylamido)guanidines 6 or mesoionic 4-amino-1,2,4-triazolium-3-hydrazinides 7. The latter were converted into 1,2,4-triazolium salts by protonation or methylation at the hydrazinide nitrogen atom. Neutral 1,2,4-triazoles 10 were obtained by catalytic hydrogenation of an N-benzyl derivative. Crystal structure analyses of a 4-benzylamino-1,2,4-triazolium-3-hydrazinide and of two derived 1,2,4-triazolium salts are presented...
2017: Beilstein Journal of Organic Chemistry
https://www.readbyqxmd.com/read/28400233/identification-of-acylation-products-in-shape-chemistry
#10
Chaoqi Lin, Salomé Poyer, Loussiné Zargarian, Jean-Yves Salpin, Philippe Fossé, Olivier Mauffret, Juan Xie
SHAPE chemistry (selective 2'-hydroxyl acylation analyzed by primer extension) has been developed to specifically target flexible nucleotides (often unpaired nucleotides) independently to their purine or pyrimidine nature for RNA secondary structure determination. However, to the best of our knowledge, the structure of 2'-O-acylation products has never been confirmed by NMR or X-ray data. We have realized the acylation reactions between cNMP and NMIA under SHAPE chemistry conditions and identified the acylation products using standard NMR spectroscopy and LC-MS/MS experiments...
April 1, 2017: Bioorganic & Medicinal Chemistry Letters
https://www.readbyqxmd.com/read/28395125/probing-the-cmp-sialic-acid-donor-specificity-of-two-human-%C3%AE-d-galactoside-sialyltransferases-st3gal-i-and-st6gal-i-selectively-acting-on-o-and-n-glycosylproteins
#11
Maxence Noel, Pierre-André Gilormini, Virginie Cogez, Nao Yamakawa, Dorothée Vicogne, Cédric Lion, Christophe Biot, Yann Guerardel, Anne Harduin-Lepers
Sialylation of glycoproteins and glycolipids catalyzed by sialyltransferases are enzymatic reactions taking place in the Golgi of mammalian cells whereby sialic acid residues are added at the non-reducing ends of oligosaccharides. Because sialylated glycans play critical roles in a number of human physio-pathological processes, the past two decades have witnessed the development of modified sialic acid derivatives for a better understanding of sialic acid biology and development of new therapeutic targets. However, nothing is known about how individual mammalian sialyltransferases tolerate and behave towards these unnatural CMP-sialic acid donors...
April 10, 2017: Chembiochem: a European Journal of Chemical Biology
https://www.readbyqxmd.com/read/28391944/effects-of-exogenous-short-chain-n-acyl-homoserine-lactone-on-denitrifying-process-of-paracoccus-denitrificans
#12
Yun Cheng, Yang Zhang, Qiuxuan Shen, Jie Gao, Guoqiang Zhuang, Xuliang Zhuang
N-acyl-homoserine lactones (AHLs) serve as quorum-sensing signals, which control a number of bacterial processes in many proteobacteria. Here we report the effects of exogenous short-chain AHL on the denitrifying process of Paracoccus denitrificans, which are capable of aerobic and anaerobic growth by utilizing nitrate. The denitrification activity of these cells was monitored by measuring denitrification products (including nitrate, nitrite, and nitrous oxide), and the individual messenger ribonucleic acid (mRNA) levels of nitrate, nitrite, nitric oxide and nitrous oxide reductases...
April 2017: Journal of Environmental Sciences (China)
https://www.readbyqxmd.com/read/28389641/dual-function-of-tropodithietic-acid-as-antibiotic-and-signaling-molecule-in-global-gene-regulation-of-the-probiotic-bacterium-phaeobacter-inhibens
#13
Paul G Beyersmann, Jürgen Tomasch, Kwangmin Son, Roman Stocker, Markus Göker, Irene Wagner-Döbler, Meinhard Simon, Thorsten Brinkhoff
Antibiotics are typically regarded as microbial weapons, but whereas their function at concentrations lethal for bacteria is often well characterized, the role of antibiotics at much lower concentrations as possibly found under natural conditions remains poorly understood. By using whole-transcriptome analyses and phenotypic screenings of the marine bacterium Phaeobacter inhibens we found that the broad-spectrum antibiotic tropodithietic acid (TDA) causes the same regulatory effects in quorum sensing (QS) as the common signaling molecule N-acyl-homoserine lactone (AHL) at concentrations 100-fold lower than the minimal inhibitory concentration against bacteria...
April 7, 2017: Scientific Reports
https://www.readbyqxmd.com/read/28385597/ester-to-amide-rearrangement-of-ethanolamine-derived-prodrugs-of-sobetirome-with-increased-blood-brain-barrier-penetration
#14
Skylar J Ferrara, J Matthew Meinig, Andrew T Placzek, Tapasree Banerji, Peter McTigue, Meredith D Hartley, Hannah S Sanford-Crane, Tania Banerji, Dennis Bourdette, Thomas S Scanlan
Current therapeutic options for treating demyelinating disorders such as multiple sclerosis (MS) do not stimulate myelin repair, thus creating a clinical need for therapeutic agents that address axonal remyelination. Thyroid hormone is known to play an important role in promoting developmental myelination and repair, and CNS permeable thyromimetic agents could offer an increased therapeutic index compared to endogenous thyroid hormone. Sobetirome is a clinical stage thyromimetic that has been shown to have promising activity in preclinical models related to MS and X-linked adrenoleukodystrophy (X-ALD), a genetic disease that involves demyelination...
May 15, 2017: Bioorganic & Medicinal Chemistry
https://www.readbyqxmd.com/read/28385021/rhodium-catalyzed-3-2-annulation-of-cyclic-n-acyl-ketimines-with-activated-olefins-anticancer-activity-of-spiroisoindolinones
#15
Satyasheel Sharma, Yongguk Oh, Neeraj Kumar Mishra, Umasankar De, Hyeim Jo, Richa Sachan, Hyung Sik Kim, Young Hoon Jung, In Su Kim
The rhodium(III)-catalyzed redox-neutral coupling reaction of N-acyl ketimines generated in situ from 3-hydroxyisoindolinones with various activated olefins is described. This approach leads to the synthesis of bioactive spiroisoindolinone derivatives in moderate to high yields. In the case of internal olefins such as maleimides, maleates, fumarates, and cinnamates, spiroindanes were obtained by the [3 + 2] annulations reaction. In sharp contrast, acrylates and quinones displayed the β-H elimination followed by Prins-type cyclization furnishing spiroindenes...
April 7, 2017: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/28381091/differential-off-line-lc-nmr-dolc-nmr-metabolomics-to-monitor-tyrosine-induced-metabolome-alterations-in-saccharomyces-cerevisiae
#16
Richard Hammerl, Oliver Frank, Thomas Hofmann
A novel differential off-line LC-NMR approach (DOLC-NMR) was developed to capture and quantify nutrient-induced metabolome alterations in Saccharomyces cerevisiae. Off-line coupling of HPLC separation and (1)H NMR spectroscopy supported by automated comparative bucket analyses, followed by quantitative (1)H NMR using ERETIC 2 (electronic reference to access in vivo concentrations), has been successfully used to quantitatively record changes in the metabolome of S. cerevisiae upon intervention with the aromatic amino acid l-tyrosine...
April 10, 2017: Journal of Agricultural and Food Chemistry
https://www.readbyqxmd.com/read/28378889/the-prebiotic-c-terminal-elongation-of-peptides-can-be-initiated-by-n-carbamoyl-amino-acids
#17
Ninette Abou Mrad, Ghinwa Ajram, Jean-Christophe Rossi, Laurent Boiteau, Fabrice Duvernay, Robert Pascal, Gregoire Danger
The formation of peptides upon EDC promoted activation of N-carbamoylamino acids (CAA), was considered in the scope of our recent works on carbodiimide promoted C-terminus elongation of peptides in a prebiotic context. Thus EDC promoted activation of CAA derivatives of Tyr(Me) or Ala in dilute aqueous medium pH 5.5-6.5 in the presence of excess of AA, resulted in peptide formation via C-terminus activation / elongation. Kinetic results similar to those of EDC-mediated activation of N-acyl-AA lead us to postulate the formation of a 2-amino-5(4H)-oxazolone intermediate by cyclization of the activated CAA, in spite of the absence of epimerization occurred at CAA residues...
April 5, 2017: Chemistry: a European Journal
https://www.readbyqxmd.com/read/28377636/formal-synthesis-of-thienamycin
#18
Michał Pieczykolan, Bartłomiej Furman, Marek Chmielewski
A formal synthesis of Thienamycin from ethyl (E)-crotonate and a cyclic five-membered nitrone derived from 2-deoxy-d-ribose is described. The synthesis involves 1,3-dipolar cycloaddition, cleavage of the N-O bond in the adduct, and intramolecular N-acylation to afford a bicyclic carbapenam skeleton. Subsequent transformations of the five-membered ring substituents provide the title compound.The Journal of Antibiotics advance online publication, 5 April 2017; doi:10.1038/ja.2017.44.
April 5, 2017: Journal of Antibiotics
https://www.readbyqxmd.com/read/28375017/nickel-ii-catalyzed-n-formylation-and-n-acylation-of-amines
#19
Rahul B Sonawane, Nishant K Rasal, Sangeeta V Jagtap
A highly efficient protocol of Ni(II) metal complex, [Ni(quin)2], catalyzing N-formylation and N-acylation of amines with moderate to excellent yields, using N,N-dimethylformamide and N,N-dimethylacetamide in the presence of imidazole, is described here. The protocol shows broad substrate scope for aliphatic, aromatic, and heterocyclic amines.
April 4, 2017: Organic Letters
https://www.readbyqxmd.com/read/28374993/removable-backbone-modification-method-for-the-chemical-synthesis-of-membrane-proteins
#20
Jia-Bin Li, Shan Tang, Ji-Shen Zheng, Chang-Lin Tian, Lei Liu
Chemical synthesis can produce water-soluble globular proteins bearing specifically designed modifications. These synthetic molecules have been used to study the biological functions of proteins and to improve the pharmacological properties of protein drugs. However, the above advances notwithstanding, membrane proteins (MPs), which comprise 20-30% of all proteins in the proteomes of most eukaryotic cells, remain elusive with regard to chemical synthesis. This difficulty stems from the strong hydrophobic character of MPs, which can cause considerable handling issues during ligation, purification, and characterization steps...
April 4, 2017: Accounts of Chemical Research
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