Phosphonosulfonates are potent, selective inhibitors of dehydrosqualene synthase and staphyloxanthin biosynthesis in Staphylococcus aureus.

PubWeight™: 0.99‹?› | Rank: Top 15%

🔗 View Article (PMC 2765255)

Published in J Med Chem on February 26, 2009

Authors

Yongcheng Song1, Fu-Yang Lin, Fenglin Yin, Mary Hensler, Carlos A Rodrígues Poveda, Dushyant Mukkamala, Rong Cao, Hong Wang, Craig T Morita, Dolores González Pacanowska, Victor Nizet, Eric Oldfield

Author Affiliations

1: Department of Chemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, Illinois 61801, USA.

Articles citing this

Targeting isoprenoid biosynthesis for drug discovery: bench to bedside. Acc Chem Res (2010) 1.40

Lipophilic analogs of zoledronate and risedronate inhibit Plasmodium geranylgeranyl diphosphate synthase (GGPPS) and exhibit potent antimalarial activity. Proc Natl Acad Sci U S A (2012) 1.09

Squalene synthase as a target for Chagas disease therapeutics. PLoS Pathog (2014) 0.93

Inhibition of staphyloxanthin virulence factor biosynthesis in Staphylococcus aureus: in vitro, in vivo, and crystallographic results. J Med Chem (2009) 0.91

Staphylococcal response to oxidative stress. Front Cell Infect Microbiol (2012) 0.90

Binding modes of zaragozic acid A to human squalene synthase and staphylococcal dehydrosqualene synthase. J Biol Chem (2012) 0.86

HIV-1 Integrase Inhibitor-Inspired Antibacterials Targeting Isoprenoid Biosynthesis. ACS Med Chem Lett (2012) 0.85

Pseudomonas aeruginosa induces pigment production and enhances virulence in a white phenotypic variant of Staphylococcus aureus. Infect Drug Resist (2013) 0.84

Enantioselective inhibition of squalene synthase by aziridine analogues of presqualene diphosphate. J Org Chem (2010) 0.83

Polyoxometalates functionalized by bisphosphonate ligands: synthesis, structural, magnetic, and spectroscopic characterizations and activity on tumor cell lines. Inorg Chem (2012) 0.81

Rank order entropy: why one metric is not enough. J Chem Inf Model (2011) 0.80

Common cell biologic and biochemical changes in aging and age-related diseases of the eye: toward new therapeutic approaches to age-related ocular diseases. Invest Ophthalmol Vis Sci (2013) 0.75

Structural and Chemical Biology of Terpenoid Cyclases. Chem Rev (2017) 0.75

Anticancer Activity of Polyoxometalate-Bisphosphonate Complexes: Synthesis, Characterization, In Vitro and In Vivo Results. Inorg Chem (2017) 0.75

Articles cited by this

Invasive methicillin-resistant Staphylococcus aureus infections in the United States. JAMA (2007) 26.98

Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity. J Med Chem (1994) 3.60

Staphylococcus aureus golden pigment impairs neutrophil killing and promotes virulence through its antioxidant activity. J Exp Med (2005) 3.36

A cholesterol biosynthesis inhibitor blocks Staphylococcus aureus virulence. Science (2008) 2.96

Staphyloxanthin plays a role in the fitness of Staphylococcus aureus and its ability to cope with oxidative stress. Infect Immun (2006) 2.13

Antimicrobial resistance: it's not just for hospitals. JAMA (2007) 1.98

Sample-distance partial least squares: PLS optimized for many variables, with application to CoMFA. J Comput Aided Mol Des (1993) 1.69

Solid-state NMR, crystallographic, and computational investigation of bisphosphonates and farnesyl diphosphate synthase-bisphosphonate complexes. J Am Chem Soc (2006) 1.48

N,N-dimethyl glycine-promoted Ullmann coupling reaction of phenols and aryl halides. Org Lett (2003) 1.25

Flexible alignment of small molecules. J Med Chem (2001) 1.22

alpha-Phosphonosulfonic acids: potent and selective inhibitors of squalene synthase. J Med Chem (1996) 1.15

Pyridinium-1-yl bisphosphonates are potent inhibitors of farnesyl diphosphate synthase and bone resorption. J Med Chem (2005) 1.12

Clinical pharmacokinetics and pharmacodynamics of a new squalene synthase inhibitor, BMS-188494, in healthy volunteers. J Clin Pharmacol (1998) 1.01

Estimation of oral bioavailability of a long half-life drug in healthy subjects. Pharm Res (1998) 0.96

Cu(I)-mediated reductive amination of boronic acids with nitroso aromatics. Org Lett (2004) 0.95

Lipophilic 1,1-bisphosphonates are potent squalene synthase inhibitors and orally active cholesterol lowering agents in vivo. J Biol Chem (1993) 0.93

A continuous spectrophotometric assay for aspartate transcarbamylase and ATPases. Anal Biochem (1997) 0.93

Preparation, characterization, and optimization of an in vitro C30 carotenoid pathway. Appl Environ Microbiol (2005) 0.84

Articles by these authors

HIF-1alpha is essential for myeloid cell-mediated inflammation. Cell (2003) 9.12

Reversing established sepsis with antagonists of endogenous high-mobility group box 1. Proc Natl Acad Sci U S A (2003) 7.14

NF-kappaB links innate immunity to the hypoxic response through transcriptional regulation of HIF-1alpha. Nature (2008) 6.13

ATP release guides neutrophil chemotaxis via P2Y2 and A3 receptors. Science (2006) 6.00

Innate immunity gone awry: linking microbial infections to chronic inflammation and cancer. Cell (2006) 5.97

The metabolic syndrome. Endocr Rev (2008) 5.33

DNase expression allows the pathogen group A Streptococcus to escape killing in neutrophil extracellular traps. Curr Biol (2006) 5.22

Long-term results of carotid stenting versus endarterectomy in high-risk patients. N Engl J Med (2008) 4.72

DNase Sda1 provides selection pressure for a switch to invasive group A streptococcal infection. Nat Med (2007) 4.35

IKKalpha limits macrophage NF-kappaB activation and contributes to the resolution of inflammation. Nature (2005) 4.31

Probable limited person-to-person transmission of highly pathogenic avian influenza A (H5N1) virus in China. Lancet (2008) 4.17

An investigation of bone resorption and Dictyostelium discoideum growth inhibition by bisphosphonate drugs. J Med Chem (2002) 3.82

Abnormal cerebral structure is present at term in premature infants. Pediatrics (2005) 3.81

HIF-1alpha expression regulates the bactericidal capacity of phagocytes. J Clin Invest (2005) 3.77

Profiling the human protein-DNA interactome reveals ERK2 as a transcriptional repressor of interferon signaling. Cell (2009) 3.69

A genome-wide association study of cleft lip with and without cleft palate identifies risk variants near MAFB and ABCA4. Nat Genet (2010) 3.63

Invariant natural killer T cells recognize glycolipids from pathogenic Gram-positive bacteria. Nat Immunol (2011) 3.48

Comparative analysis of a large dataset indicates that internal transcribed spacer (ITS) should be incorporated into the core barcode for seed plants. Proc Natl Acad Sci U S A (2011) 3.41

Regulation of iron homeostasis by the hypoxia-inducible transcription factors (HIFs). J Clin Invest (2007) 3.40

Staphylococcus aureus golden pigment impairs neutrophil killing and promotes virulence through its antioxidant activity. J Exp Med (2005) 3.36

Participatory medicine: A home score for streptococcal pharyngitis enabled by real-time biosurveillance: a cohort study. Ann Intern Med (2013) 3.32

The Ashwell receptor mitigates the lethal coagulopathy of sepsis. Nat Med (2008) 3.31

A NOD2-NALP1 complex mediates caspase-1-dependent IL-1beta secretion in response to Bacillus anthracis infection and muramyl dipeptide. Proc Natl Acad Sci U S A (2008) 3.27

ST2 as a marker for risk of therapy-resistant graft-versus-host disease and death. N Engl J Med (2013) 3.27

Discovery of a widely distributed toxin biosynthetic gene cluster. Proc Natl Acad Sci U S A (2008) 3.20

Global profiling of the cell surface proteome of cancer cells uncovers an abundance of proteins with chaperone function. J Biol Chem (2002) 3.02

Streptolysin S and necrotising infections produced by group G streptococcus. Lancet (2002) 3.02

Adaptive immune response of Vgamma2Vdelta2+ T cells during mycobacterial infections. Science (2002) 3.01

A cholesterol biosynthesis inhibitor blocks Staphylococcus aureus virulence. Science (2008) 2.96

Correlates of axial gout: a cross-sectional study. J Rheumatol (2012) 2.86

Multicenter randomized controlled trial of percutaneous cryoablation versus radiofrequency ablation in hepatocellular carcinoma. Hepatology (2015) 2.81

Molecular insight into invasive group A streptococcal disease. Nat Rev Microbiol (2011) 2.81

Prognostic significance of gene expression profiles of metastatic neuroblastomas lacking MYCN gene amplification. J Natl Cancer Inst (2006) 2.79

Cutting edge: Essential role of hypoxia inducible factor-1alpha in development of lipopolysaccharide-induced sepsis. J Immunol (2007) 2.76

Allogenic mesenchymal stem cells transplantation in refractory systemic lupus erythematosus: a pilot clinical study. Ann Rheum Dis (2010) 2.64

Inhibition of poly(ADP-ribose) polymerase enhances cell death and improves tumor growth delay in irradiated lung cancer models. Clin Cancer Res (2007) 2.52

Functional proteomics identifies targets of phosphorylation by B-Raf signaling in melanoma. Mol Cell (2009) 2.50

Nonpeptide antigens, presentation mechanisms, and immunological memory of human Vgamma2Vdelta2 T cells: discriminating friend from foe through the recognition of prenyl pyrophosphate antigens. Immunol Rev (2007) 2.46

Local, persistent activation of Rho GTPases during plasticity of single dendritic spines. Nature (2011) 2.42

Human platelet dense granules contain polyphosphate and are similar to acidocalcisomes of bacteria and unicellular eukaryotes. J Biol Chem (2004) 2.41

Molecular genetic analysis of a group A Streptococcus operon encoding serum opacity factor and a novel fibronectin-binding protein, SfbX. J Bacteriol (2003) 2.38

Nuclease expression by Staphylococcus aureus facilitates escape from neutrophil extracellular traps. J Innate Immun (2010) 2.34

Innate immunity turned inside-out: antimicrobial defense by phagocyte extracellular traps. J Mol Med (Berl) (2009) 2.33

A mouse to human search for plasma proteome changes associated with pancreatic tumor development. PLoS Med (2008) 2.31

Structural basis for the proinflammatory cytokine activity of high mobility group box 1. Mol Med (2003) 2.30

Mutational analysis of the group A streptococcal operon encoding streptolysin S and its virulence role in invasive infection. Mol Microbiol (2005) 2.30

Statins enhance formation of phagocyte extracellular traps. Cell Host Microbe (2010) 2.28

Effect of a bacterial pheromone peptide on host chemokine degradation in group A streptococcal necrotising soft-tissue infections. Lancet (2004) 2.25

A genomic atlas of mouse hypothalamic development. Nat Neurosci (2010) 2.25

Molecular mimicry of host sialylated glycans allows a bacterial pathogen to engage neutrophil Siglec-9 and dampen the innate immune response. Blood (2009) 2.24

IFN-gamma induces high mobility group box 1 protein release partly through a TNF-dependent mechanism. J Immunol (2003) 2.24

Disease manifestations and pathogenic mechanisms of group a Streptococcus. Clin Microbiol Rev (2014) 2.20

Functional role of CD11c+ monocytes in atherogenesis associated with hypercholesterolemia. Circulation (2009) 2.19

Use of antistaphylococcal beta-lactams to increase daptomycin activity in eradicating persistent bacteremia due to methicillin-resistant Staphylococcus aureus: role of enhanced daptomycin binding. Clin Infect Dis (2011) 2.19

Epigenetic modulation of the renal β-adrenergic-WNK4 pathway in salt-sensitive hypertension. Nat Med (2011) 2.18

Human milk oligosaccharides protect bladder epithelial cells against uropathogenic Escherichia coli invasion and cytotoxicity. J Infect Dis (2013) 2.18

Adiponectin secretion is regulated by SIRT1 and the endoplasmic reticulum oxidoreductase Ero1-L alpha. Mol Cell Biol (2007) 2.17

Sirolimus-eluting stents vs vascular brachytherapy for in-stent restenosis within bare-metal stents: the SISR randomized trial. JAMA (2006) 2.16

Group B streptococcal beta-hemolysin/cytolysin activates neutrophil signaling pathways in brain endothelium and contributes to development of meningitis. J Clin Invest (2003) 2.14

Selective antimicrobial action is provided by phenol-soluble modulins derived from Staphylococcus epidermidis, a normal resident of the skin. J Invest Dermatol (2010) 2.13

Impact of post-intervention minimal stent area on 9-month follow-up patency of paclitaxel-eluting stents: an integrated intravascular ultrasound analysis from the TAXUS IV, V, and VI and TAXUS ATLAS Workhorse, Long Lesion, and Direct Stent Trials. JACC Cardiovasc Interv (2009) 2.12

Large-scale validation of the Centor and McIsaac scores to predict group A streptococcal pharyngitis. Arch Intern Med (2012) 2.09

Elafin is a biomarker of graft-versus-host disease of the skin. Sci Transl Med (2010) 2.08

Three-year outcomes of vaginal mesh for prolapse: a randomized controlled trial. Obstet Gynecol (2013) 2.08

Blood-brain barrier invasion by group B Streptococcus depends upon proper cell-surface anchoring of lipoteichoic acid. J Clin Invest (2005) 2.07

Markers of inflammation, metabolic risk factors, and incident heart failure in American Indians: the Strong Heart Study. J Clin Hypertens (Greenwich) (2011) 2.04

Contribution of protein fractionation to depth of analysis of the serum and plasma proteomes. J Proteome Res (2007) 2.04

D-alanylation of teichoic acids promotes group a streptococcus antimicrobial peptide resistance, neutrophil survival, and epithelial cell invasion. J Bacteriol (2005) 2.04

The cholinergic anti-inflammatory pathway: a missing link in neuroimmunomodulation. Mol Med (2003) 2.00

Bisphosphonates target multiple sites in both cis- and trans-prenyltransferases. Proc Natl Acad Sci U S A (2007) 2.00

Ampicillin enhances daptomycin- and cationic host defense peptide-mediated killing of ampicillin- and vancomycin-resistant Enterococcus faecium. Antimicrob Agents Chemother (2011) 2.00

Invasive M1T1 group A Streptococcus undergoes a phase-shift in vivo to prevent proteolytic degradation of multiple virulence factors by SpeB. Mol Microbiol (2004) 1.99

C/EBPalpha and the corepressors CtBP1 and CtBP2 regulate repression of select visceral white adipose genes during induction of the brown phenotype in white adipocytes by peroxisome proliferator-activated receptor gamma agonists. Mol Cell Biol (2009) 1.98

Prostaglandin E2 mediates connecting tubule glomerular feedback. Hypertension (2013) 1.98

Umbilical cord mesenchymal stem cell transplantation in severe and refractory systemic lupus erythematosus. Arthritis Rheum (2010) 1.98

Amiodarone has intrinsic anti-Trypanosoma cruzi activity and acts synergistically with posaconazole. J Med Chem (2006) 1.98

Anthrax toxins cooperatively inhibit endocytic recycling by the Rab11/Sec15 exocyst. Nature (2010) 1.95

Functional interaction between peroxisome proliferator-activated receptor gamma and beta-catenin. Mol Cell Biol (2006) 1.95

Sword and shield: linked group B streptococcal beta-hemolysin/cytolysin and carotenoid pigment function to subvert host phagocyte defense. Proc Natl Acad Sci U S A (2004) 1.95

Hyperhomocysteinemia decreases circulating high-density lipoprotein by inhibiting apolipoprotein A-I Protein synthesis and enhancing HDL cholesterol clearance. Circ Res (2006) 1.95

An NMR investigation of CO tolerance in a Pt/Ru fuel cell catalyst. J Am Chem Soc (2002) 1.94

Discovery and characterization of sialic acid O-acetylation in group B Streptococcus. Proc Natl Acad Sci U S A (2004) 1.93

Hypoxia inducible factor (HIF) function in innate immunity and infection. J Mol Med (Berl) (2007) 1.90

Imaging mass spectrometry of intraspecies metabolic exchange revealed the cannibalistic factors of Bacillus subtilis. Proc Natl Acad Sci U S A (2010) 1.90

Tanycytes of the hypothalamic median eminence form a diet-responsive neurogenic niche. Nat Neurosci (2012) 1.89

Hepatic Hdac3 promotes gluconeogenesis by repressing lipid synthesis and sequestration. Nat Med (2012) 1.87

Reduced cell proliferation by IKK2 depletion in a mouse lung-cancer model. Nat Cell Biol (2012) 1.87

An essential role for stromal interaction molecule 1 in neointima formation following arterial injury. Cardiovasc Res (2008) 1.87

Protein profiles associated with survival in lung adenocarcinoma. Proc Natl Acad Sci U S A (2003) 1.86

Haptoglobin genotype is a consistent marker of coronary heart disease risk among individuals with elevated glycosylated hemoglobin. J Am Coll Cardiol (2013) 1.85

A group of glutamatergic interneurons expressing high levels of both neurokinin-1 receptors and somatostatin identifies the region of the pre-Bötzinger complex. J Comp Neurol (2003) 1.85

Cutaneous defense mechanisms by antimicrobial peptides. J Invest Dermatol (2005) 1.85

Brain-derived neurotrophic factor expression and respiratory function improve after ampakine treatment in a mouse model of Rett syndrome. J Neurosci (2007) 1.85

Humanized monoclonal antibody against West Nile virus envelope protein administered after neuronal infection protects against lethal encephalitis in hamsters. J Infect Dis (2006) 1.84

Molecular pathogenesis of neonatal group B streptococcal infection: no longer in its infancy. Mol Microbiol (2004) 1.83

PIK3CA and PTEN mutations in uterine endometrioid carcinoma and complex atypical hyperplasia. Clin Cancer Res (2006) 1.83