Syntheses, structures and antibiotic activities of LpxC inhibitors based on the diacetylene scaffold.

PubWeight™: 1.08‹?› | Rank: Top 10%

🔗 View Article (PMC 3035996)

Published in Bioorg Med Chem on December 09, 2010

Authors

Xiaofei Liang1, Chul-Jin Lee, Xin Chen, Hak Suk Chung, Daina Zeng, Christian R H Raetz, Yaoxian Li, Pei Zhou, Eric J Toone

Author Affiliations

1: Department of Chemistry, Jilin University, Changchun, PR China.

Articles citing this

Lipooligosaccharide is required for the generation of infectious elementary bodies in Chlamydia trachomatis. Proc Natl Acad Sci U S A (2011) 0.95

Drug design from the cryptic inhibitor envelope. Nat Commun (2016) 0.93

Mutants resistant to LpxC inhibitors by rebalancing cellular homeostasis. J Biol Chem (2013) 0.86

Synthesis, structure, and antibiotic activity of aryl-substituted LpxC inhibitors. J Med Chem (2013) 0.85

Characterization of an Acinetobacter baumannii lptD Deletion Strain: Permeability Defects and Response to Inhibition of Lipopolysaccharide and Fatty Acid Biosynthesis. J Bacteriol (2015) 0.84

Structural basis of the promiscuous inhibitor susceptibility of Escherichia coli LpxC. ACS Chem Biol (2013) 0.83

Storage of hydrogen spin polarization in long-lived 13C2 singlet order and implications for hyperpolarized magnetic resonance imaging. J Am Chem Soc (2013) 0.83

Structure of the bacterial deacetylase LpxC bound to the nucleotide reaction product reveals mechanisms of oxyanion stabilization and proton transfer. J Biol Chem (2013) 0.80

Synthesis, Structure, and SAR of Tetrahydropyran-Based LpxC Inhibitors. ACS Med Chem Lett (2014) 0.78

Kdo2 -lipid A: structural diversity and impact on immunopharmacology. Biol Rev Camb Philos Soc (2014) 0.78

Development of quinoxaline 1, 4-dioxides resistance in Escherichia coli and molecular change under resistance selection. PLoS One (2012) 0.77

LpxC Inhibitors: Design, Synthesis, and Biological Evaluation of Oxazolidinones as Gram-negative Antibacterial Agents. ACS Med Chem Lett (2016) 0.75

Chlamydia spp. development is differentially altered by treatment with the LpxC inhibitor LPC-011. BMC Microbiol (2017) 0.75

A Scalable Synthesis of the Difluoromethyl-allo-threonyl Hydroxamate-Based LpxC Inhibitor LPC-058. J Org Chem (2016) 0.75

Structure, inhibition, and regulation of essential lipid A enzymes. Biochim Biophys Acta (2016) 0.75

Articles cited by this

Coot: model-building tools for molecular graphics. Acta Crystallogr D Biol Crystallogr (2004) 227.01

Phaser crystallographic software. J Appl Crystallogr (2007) 108.34

MolProbity: all-atom contacts and structure validation for proteins and nucleic acids. Nucleic Acids Res (2007) 37.31

Lipopolysaccharide endotoxins. Annu Rev Biochem (2001) 18.88

Lipid A modification systems in gram-negative bacteria. Annu Rev Biochem (2007) 8.60

Cu-catalyzed azide-alkyne cycloaddition. Chem Rev (2008) 6.21

Automated structure solution with the PHENIX suite. Methods Mol Biol (2008) 5.65

On the attribution and additivity of binding energies. Proc Natl Acad Sci U S A (1981) 4.44

A slow, tight-binding inhibitor of the zinc-dependent deacetylase LpxC of lipid A biosynthesis with antibiotic activity comparable to ciprofloxacin. Biochemistry (2005) 1.86

Mechanism and inhibition of LpxC: an essential zinc-dependent deacetylase of bacterial lipid A synthesis. Curr Pharm Biotechnol (2008) 1.66

Inhibition of lipid A biosynthesis as the primary mechanism of CHIR-090 antibiotic activity in Escherichia coli. Biochemistry (2007) 1.28

Site-directed mutagenesis of the bacterial metalloamidase UDP-(3-O-acyl)-N-acetylglucosamine deacetylase (LpxC). Identification of the zinc binding site. Biochemistry (2001) 1.27

Potent, novel in vitro inhibitors of the Pseudomonas aeruginosa deacetylase LpxC. J Med Chem (2002) 1.24

Structure of the deacetylase LpxC bound to the antibiotic CHIR-090: Time-dependent inhibition and specificity in ligand binding. Proc Natl Acad Sci U S A (2007) 1.24

High-throughput catch-and-release synthesis of oxazoline hydroxamates. Structure-activity relationships in novel inhibitors of Escherichia coli LpxC: in vitro enzyme inhibition and antibacterial properties. J Am Chem Soc (2003) 1.07

Crystal structure of LpxC from Pseudomonas aeruginosa complexed with the potent BB-78485 inhibitor. Protein Sci (2008) 1.03

Binding of uridine 5'-diphosphate in the "basic patch" of the zinc deacetylase LpxC and implications for substrate binding. Biochemistry (2006) 1.01

The nucleotide-binding site of Aquifex aeolicus LpxC. Acta Crystallogr Sect F Struct Biol Cryst Commun (2006) 0.96

Preparation and Use of Aziridino Alcohols as Promoters for the Enantioselective Addition of Dialkylzinc Reagents to N-(Diphenylphosphinoyl) Imines. J Org Chem (1997) 0.85

Uridine-based inhibitors as new leads for antibiotics targeting Escherichia coli LpxC. Biochemistry (2009) 0.81

Articles by these authors

The microRNA miR-34a inhibits prostate cancer stem cells and metastasis by directly repressing CD44. Nat Med (2011) 6.85

A comprehensive classification system for lipids. J Lipid Res (2005) 6.52

LMSD: LIPID MAPS structure database. Nucleic Acids Res (2006) 6.21

BMP4 initiates human embryonic stem cell differentiation to trophoblast. Nat Biotechnol (2002) 6.20

dbCAN: a web resource for automated carbohydrate-active enzyme annotation. Nucleic Acids Res (2012) 4.91

Gene expression patterns in human embryonic stem cells and human pluripotent germ cell tumors. Proc Natl Acad Sci U S A (2003) 4.67

Lipidomics reveals a remarkable diversity of lipids in human plasma. J Lipid Res (2010) 4.14

Update of the LIPID MAPS comprehensive classification system for lipids. J Lipid Res (2008) 4.01

The novel marker, DOG1, is expressed ubiquitously in gastrointestinal stromal tumors irrespective of KIT or PDGFRA mutation status. Am J Pathol (2004) 3.84

The metabolic profile of tumors depends on both the responsible genetic lesion and tissue type. Cell Metab (2012) 3.81

Dynamic reprogramming of the kinome in response to targeted MEK inhibition in triple-negative breast cancer. Cell (2012) 3.77

Directed neural differentiation of human embryonic stem cells via an obligated primitive anterior stage. Stem Cells (2007) 3.71

A chemical probe selectively inhibits G9a and GLP methyltransferase activity in cells. Nat Chem Biol (2011) 3.60

Multigait soft robot. Proc Natl Acad Sci U S A (2011) 3.57

Drosophila PIWI associates with chromatin and interacts directly with HP1a. Genes Dev (2007) 3.46

Gene expression patterns of human colon tops and basal crypts and BMP antagonists as intestinal stem cell niche factors. Proc Natl Acad Sci U S A (2007) 3.20

Topoisomerase inhibitors unsilence the dormant allele of Ube3a in neurons. Nature (2011) 3.19

Decoding global gene expression programs in liver cancer by noninvasive imaging. Nat Biotechnol (2007) 3.17

[GSDS: a gene structure display server]. Yi Chuan (2007) 3.02

Ultrafast dynamics of solute-solvent complexation observed at thermal equilibrium in real time. Science (2005) 2.88

The cluster glycoside effect. Chem Rev (2002) 2.79

The PSA(-/lo) prostate cancer cell population harbors self-renewing long-term tumor-propagating cells that resist castration. Cell Stem Cell (2012) 2.69

Cholangiocarcinomas can originate from hepatocytes in mice. J Clin Invest (2012) 2.56

Distinct pathways of genomic progression to benign and malignant tumors of the liver. Proc Natl Acad Sci U S A (2007) 2.56

Follicular T-helper cell recruitment governed by bystander B cells and ICOS-driven motility. Nature (2013) 2.52

SRD5A3 is required for converting polyprenol to dolichol and is mutated in a congenital glycosylation disorder. Cell (2010) 2.49

Increased lipogenesis, induced by AKT-mTORC1-RPS6 signaling, promotes development of human hepatocellular carcinoma. Gastroenterology (2010) 2.48

Solution structure and dynamics of the outer membrane enzyme PagP by NMR. Proc Natl Acad Sci U S A (2002) 2.39

Regulated accumulation of desmosterol integrates macrophage lipid metabolism and inflammatory responses. Cell (2012) 2.38

Organic cation transporters are determinants of oxaliplatin cytotoxicity. Cancer Res (2006) 2.37

Testis-specific TAF homologs collaborate to control a tissue-specific transcription program. Development (2004) 2.35

Expression of a functionally active gp91phox-containing neutrophil-type NAD(P)H oxidase in smooth muscle cells from human resistance arteries: regulation by angiotensin II. Circ Res (2002) 2.27

c-Jun N-terminal kinases mediate reactivation of Akt and cardiomyocyte survival after hypoxic injury in vitro and in vivo. Circ Res (2005) 2.23

Single ion-channel recordings using glass nanopore membranes. J Am Chem Soc (2007) 2.22

Mesenchymal cells of the intestinal lamina propria. Annu Rev Physiol (2011) 2.18

PlantTFDB: a comprehensive plant transcription factor database. Nucleic Acids Res (2007) 2.17

MsbA-dependent translocation of lipids across the inner membrane of Escherichia coli. J Biol Chem (2004) 2.17

PC3 human prostate carcinoma cell holoclones contain self-renewing tumor-initiating cells. Cancer Res (2008) 2.16

Soft robotics for chemists. Angew Chem Int Ed Engl (2011) 2.14

A mouse macrophage lipidome. J Biol Chem (2010) 2.14

MSOAR: a high-throughput ortholog assignment system based on genome rearrangement. J Comput Biol (2007) 2.14

S-nitrosylation from GSNOR deficiency impairs DNA repair and promotes hepatocarcinogenesis. Sci Transl Med (2010) 2.13

Rapamycin inhibits differentiation of Th17 cells and promotes generation of FoxP3+ T regulatory cells. Int Immunopharmacol (2007) 2.08

Electrochemical sensing in paper-based microfluidic devices. Lab Chip (2009) 2.06

Mutations of PIK3CA in gastric adenocarcinoma. BMC Cancer (2005) 2.06

LPS remodeling is an evolved survival strategy for bacteria. Proc Natl Acad Sci U S A (2012) 2.05

Phosphorylation of histone H4 Ser1 regulates sporulation in yeast and is conserved in fly and mouse spermatogenesis. Genes Dev (2006) 2.05

Modulation of human nuclear receptor LRH-1 activity by phospholipids and SHP. Nat Struct Mol Biol (2005) 2.03

A novel class of potent influenza virus inhibitors: polysubstituted acylthiourea and its fused heterocycle derivatives. Bioorg Med Chem Lett (2005) 2.01

Discovery of β-arrestin-biased dopamine D2 ligands for probing signal transduction pathways essential for antipsychotic efficacy. Proc Natl Acad Sci U S A (2011) 1.98

Mitochondrial phosphatase PTPMT1 is essential for cardiolipin biosynthesis. Cell Metab (2011) 1.97

High incidence of epithelial cancers in mice deficient for DNA polymerase delta proofreading. Proc Natl Acad Sci U S A (2002) 1.95

Discovery of a 2,4-diamino-7-aminoalkoxyquinazoline as a potent and selective inhibitor of histone lysine methyltransferase G9a. J Med Chem (2009) 1.92

Structure of the ubiquitin-binding zinc finger domain of human DNA Y-polymerase eta. EMBO Rep (2007) 1.91

A slow, tight-binding inhibitor of the zinc-dependent deacetylase LpxC of lipid A biosynthesis with antibiotic activity comparable to ciprofloxacin. Biochemistry (2005) 1.86

ATPase activity of the MsbA lipid flippase of Escherichia coli. J Biol Chem (2002) 1.83

Functional anatomy of phospholipid binding and regulation of phosphoinositide homeostasis by proteins of the sec14 superfamily. Mol Cell (2008) 1.82

Phospholipase A2 group IIA expression in gastric adenocarcinoma is associated with prolonged survival and less frequent metastasis. Proc Natl Acad Sci U S A (2002) 1.81

Increasing hyperpolarized spin lifetimes through true singlet eigenstates. Science (2009) 1.76

17beta-estradiol reduces cardiomyocyte apoptosis in vivo and in vitro via activation of phospho-inositide-3 kinase/Akt signaling. Circ Res (2004) 1.74

Multipath estimation in urban environments from joint GNSS receivers and LiDAR sensors. Sensors (Basel) (2012) 1.74

Design and evaluation of sifuvirtide, a novel HIV-1 fusion inhibitor. J Biol Chem (2008) 1.74

Impaired heart contractility in Apelin gene-deficient mice associated with aging and pressure overload. Circ Res (2007) 1.74

Maximal induction of a subset of interferon target genes requires the chromatin-remodeling activity of the BAF complex. Mol Cell Biol (2002) 1.73

Protein lysine methyltransferase G9a inhibitors: design, synthesis, and structure activity relationships of 2,4-diamino-7-aminoalkoxy-quinazolines. J Med Chem (2010) 1.73

3-Methoxy-4-(4-nitro-benz-yloxy)-benzaldehyde. Acta Crystallogr Sect E Struct Rep Online (2008) 1.73

MsbA transporter-dependent lipid A 1-dephosphorylation on the periplasmic surface of the inner membrane: topography of francisella novicida LpxE expressed in Escherichia coli. J Biol Chem (2004) 1.73

Loss of outer membrane proteins without inhibition of lipid export in an Escherichia coli YaeT mutant. J Biol Chem (2005) 1.73

Influenza-associated mortality in temperate and subtropical Chinese cities, 2003-2008. Bull World Health Organ (2012) 1.69

Parallels between global transcriptional programs of polarizing Caco-2 intestinal epithelial cells in vitro and gene expression programs in normal colon and colon cancer. Mol Biol Cell (2007) 1.69

Expression cloning and periplasmic orientation of the Francisella novicida lipid A 4'-phosphatase LpxF. J Biol Chem (2006) 1.67

Characteristics of the interaction of a synthetic human tristetraprolin tandem zinc finger peptide with AU-rich element-containing RNA substrates. J Biol Chem (2003) 1.67

AKT (v-akt murine thymoma viral oncogene homolog 1) and N-Ras (neuroblastoma ras viral oncogene homolog) coactivation in the mouse liver promotes rapid carcinogenesis by way of mTOR (mammalian target of rapamycin complex 1), FOXM1 (forkhead box M1)/SKP2, and c-Myc pathways. Hepatology (2011) 1.67

A formyltransferase required for polymyxin resistance in Escherichia coli and the modification of lipid A with 4-Amino-4-deoxy-L-arabinose. Identification and function oF UDP-4-deoxy-4-formamido-L-arabinose. J Biol Chem (2005) 1.66

Regulatory T cells protect mice against coxsackievirus-induced myocarditis through the transforming growth factor beta-coxsackie-adenovirus receptor pathway. Circulation (2010) 1.66

Mechanism and inhibition of LpxC: an essential zinc-dependent deacetylase of bacterial lipid A synthesis. Curr Pharm Biotechnol (2008) 1.66

Attenuated virulence of a Francisella mutant lacking the lipid A 4'-phosphatase. Proc Natl Acad Sci U S A (2007) 1.64

The chromatin-remodeling BAF complex mediates cellular antiviral activities by promoter priming. Mol Cell Biol (2004) 1.64

Dynamic regulation of alternative splicing and chromatin structure in Drosophila gonads revealed by RNA-seq. Cell Res (2010) 1.64

Mechanism of the Class I KDPG aldolase. Bioorg Med Chem (2006) 1.62

Gene expression patterns in pancreatic tumors, cells and tissues. PLoS One (2007) 1.61

A triple mutant of Escherichia coli lacking secondary acyl chains on lipid A. J Biol Chem (2002) 1.60

A small-molecule inhibitor of isoprenylcysteine carboxyl methyltransferase with antitumor activity in cancer cells. Proc Natl Acad Sci U S A (2005) 1.59

Array-based comparative genomic hybridization reveals recurrent chromosomal aberrations and Jab1 as a potential target for 8q gain in hepatocellular carcinoma. Carcinogenesis (2005) 1.59

Oxidative decarboxylation of UDP-glucuronic acid in extracts of polymyxin-resistant Escherichia coli. Origin of lipid a species modified with 4-amino-4-deoxy-L-arabinose. J Biol Chem (2001) 1.59

Yes-associated protein up-regulates Jagged-1 and activates the Notch pathway in human hepatocellular carcinoma. Gastroenterology (2013) 1.58

Structure of the LpxC deacetylase with a bound substrate-analog inhibitor. Nat Struct Biol (2003) 1.57

Investigating the hydrogen-bonding model of urea denaturation. J Am Chem Soc (2009) 1.57

Polar Fourier transforms of radially sampled NMR data. J Magn Reson (2006) 1.56

A non-cell autonomous role of E(z) to prevent germ cells from turning on a somatic cell marker. Science (2014) 1.55

Origin of lipid A species modified with 4-amino-4-deoxy-L-arabinose in polymyxin-resistant mutants of Escherichia coli. An aminotransferase (ArnB) that generates UDP-4-deoxyl-L-arabinose. J Biol Chem (2003) 1.55

A phosphoethanolamine transferase specific for the outer 3-deoxy-D-manno-octulosonic acid residue of Escherichia coli lipopolysaccharide. Identification of the eptB gene and Ca2+ hypersensitivity of an eptB deletion mutant. J Biol Chem (2005) 1.53

Stepwise linear approach to catheter ablation of atrial fibrillation. Heart Rhythm (2007) 1.52

Inhibition of mitogen-activated protein/extracellular signal-regulated kinase improves endothelial function and attenuates Ang II-induced contractility of mesenteric resistance arteries from spontaneously hypertensive rats. J Hypertens (2002) 1.52

IL-33 facilitates oncogene-induced cholangiocarcinoma in mice by an interleukin-6-sensitive mechanism. Hepatology (2015) 1.52

Periplasmic cleavage and modification of the 1-phosphate group of Helicobacter pylori lipid A. J Biol Chem (2004) 1.52

kin-19/casein kinase Iα has dual functions in regulating asymmetric division and terminal differentiation in C. elegans epidermal stem cells. Cell Cycle (2010) 1.49

FragAnchor: a large-scale predictor of glycosylphosphatidylinositol anchors in eukaryote protein sequences by qualitative scoring. Genomics Proteomics Bioinformatics (2007) 1.49

High resolution 4-D spectroscopy with sparse concentric shell sampling and FFT-CLEAN. J Biomol NMR (2008) 1.49