An improved synthesis of haloaceteamidine-based inactivators of protein arginine deiminase 4 (PAD4).

PubWeight™: 1.13‹?› | Rank: Top 10%

🔗 View Article (PMID 19587776)

Published in Tetrahedron Lett on July 07, 2008

Authors

Corey P Causey1, Paul R Thompson

Author Affiliations

1: Departent of Chemstry and Biochemistry, University of South Carolina, 631 Sumter Street, Columbia, SC 29208.

Articles citing this

Peptidylarginine deiminase inhibition reduces vascular damage and modulates innate immune responses in murine models of atherosclerosis. Circ Res (2014) 1.93

Substrate specificity and kinetic studies of PADs 1, 3, and 4 identify potent and selective inhibitors of protein arginine deiminase 3. Biochemistry (2010) 1.66

Peptidylarginine deiminase inhibition is immunomodulatory and vasculoprotective in murine lupus. J Clin Invest (2013) 1.64

Anticancer peptidylarginine deiminase (PAD) inhibitors regulate the autophagy flux and the mammalian target of rapamycin complex 1 activity. J Biol Chem (2012) 1.45

Peptidylarginine deiminase inhibition disrupts NET formation and protects against kidney, skin and vascular disease in lupus-prone MRL/lpr mice. Ann Rheum Dis (2014) 1.34

Coordination of PAD4 and HDAC2 in the regulation of p53-target gene expression. Oncogene (2010) 1.27

Protein arginine deiminase 4: a target for an epigenetic cancer therapy. Cell Mol Life Sci (2010) 1.21

Identification of PADI2 as a potential breast cancer biomarker and therapeutic target. BMC Cancer (2012) 1.18

The development of N-α-(2-carboxyl)benzoyl-N(5)-(2-fluoro-1-iminoethyl)-l-ornithine amide (o-F-amidine) and N-α-(2-carboxyl)benzoyl-N(5)-(2-chloro-1-iminoethyl)-l-ornithine amide (o-Cl-amidine) as second generation protein arginine deiminase (PAD) inhibitors. J Med Chem (2011) 1.12

Citrullination of proteins: a common post-translational modification pathway induced by different nanoparticles in vitro and in vivo. Nanomedicine (Lond) (2012) 1.00

The induction of microRNA-16 in colon cancer cells by protein arginine deiminase inhibition causes a p53-dependent cell cycle arrest. PLoS One (2013) 0.91

Design, synthesis, and biological evaluation of tetrazole analogs of Cl-amidine as protein arginine deiminase inhibitors. J Med Chem (2015) 0.90

Chemical and biological methods to detect post-translational modifications of arginine. Biopolymers (2014) 0.88

Molecular targeting of protein arginine deiminases to suppress colitis and prevent colon cancer. Oncotarget (2015) 0.83

Mechanistic studies of agmatine deiminase from multiple bacterial species. Biochemistry (2010) 0.82

Inhibiting protein arginine deiminases has antioxidant consequences. J Pharmacol Exp Ther (2015) 0.77

Looking for the best anti-colitis medicine: A comparative analysis of current and prospective compounds. Oncotarget (2016) 0.75

Interrogation of the Active Sites of Protein Arginine Deiminases (PAD1, -2, and -4) Using Designer Probes. ACS Med Chem Lett (2013) 0.75

Articles cited by this

The diagnostic properties of rheumatoid arthritis antibodies recognizing a cyclic citrullinated peptide. Arthritis Rheum (2000) 8.64

Functional haplotypes of PADI4, encoding citrullinating enzyme peptidylarginine deiminase 4, are associated with rheumatoid arthritis. Nat Genet (2003) 7.04

Citrulline is an essential constituent of antigenic determinants recognized by rheumatoid arthritis-specific autoantibodies. J Clin Invest (1998) 6.92

Replication of putative candidate-gene associations with rheumatoid arthritis in >4,000 samples from North America and Sweden: association of susceptibility with PTPN22, CTLA4, and PADI4. Am J Hum Genet (2005) 6.61

PAD, a growing family of citrullinating enzymes: genes, features and involvement in disease. Bioessays (2003) 5.04

Therapeutic strategies for rheumatoid arthritis. Nat Rev Drug Discov (2003) 3.51

Inhibitors and inactivators of protein arginine deiminase 4: functional and structural characterization. Biochemistry (2006) 2.92

Peptidyl arginine deiminase type 2 (PAD-2) and PAD-4 but not PAD-1, PAD-3, and PAD-6 are expressed in rheumatoid arthritis synovium in close association with tissue inflammation. Arthritis Rheum (2007) 2.40

Very recent onset rheumatoid arthritis: clinical and serological patient characteristics associated with radiographic progression over the first years of disease. Rheumatology (Oxford) (2006) 2.36

Citrullinated proteins: sparks that may ignite the fire in rheumatoid arthritis. Arthritis Res Ther (2004) 2.05

Citrullinated proteins have increased immunogenicity and arthritogenicity and their presence in arthritic joints correlates with disease severity. Arthritis Res Ther (2005) 2.03

A fluoroacetamidine-based inactivator of protein arginine deiminase 4: design, synthesis, and in vitro and in vivo evaluation. J Am Chem Soc (2006) 1.85

Expression of peptidylarginine deiminase type 4 (PAD4) in various tumors. Mol Carcinog (2006) 1.70

A functional haplotype of the PADI4 gene associated with increased rheumatoid arthritis susceptibility in Koreans. Arthritis Rheum (2006) 1.68

PADI4 polymorphisms and rheumatoid arthritis susceptibility: a meta-analysis. Rheumatol Int (2007) 1.58

Abnormal accumulation of citrullinated proteins catalyzed by peptidylarginine deiminase in hippocampal extracts from patients with Alzheimer's disease. J Neurosci Res (2005) 1.57

Proteomics implicates peptidyl arginine deiminase 2 and optic nerve citrullination in glaucoma pathogenesis. Invest Ophthalmol Vis Sci (2006) 1.32

Peptidylarginine deiminase: a candidate factor in demyelinating disease. J Neurochem (2002) 1.31

Modulation of peptidyl arginine deiminase 2 and implication for neurodegeneration. Curr Eye Res (2006) 0.92

Articles by these authors

Inhibitors and inactivators of protein arginine deiminase 4: functional and structural characterization. Biochemistry (2006) 2.92

The structural basis of protein acetylation by the p300/CBP transcriptional coactivator. Nature (2008) 2.83

Regulation of p53 target gene expression by peptidylarginine deiminase 4. Mol Cell Biol (2008) 2.27

Kinetic characterization of protein arginine deiminase 4: a transcriptional corepressor implicated in the onset and progression of rheumatoid arthritis. Biochemistry (2005) 2.21

N-α-benzoyl-N5-(2-chloro-1-iminoethyl)-L-ornithine amide, a protein arginine deiminase inhibitor, reduces the severity of murine collagen-induced arthritis. J Immunol (2011) 2.18

Histone Arg modifications and p53 regulate the expression of OKL38, a mediator of apoptosis. J Biol Chem (2008) 1.93

Peptidylarginine deiminase inhibition reduces vascular damage and modulates innate immune responses in murine models of atherosclerosis. Circ Res (2014) 1.93

A fluoroacetamidine-based inactivator of protein arginine deiminase 4: design, synthesis, and in vitro and in vivo evaluation. J Am Chem Soc (2006) 1.85

Protein arginine deiminase 4 (PAD4): Current understanding and future therapeutic potential. Curr Opin Drug Discov Devel (2009) 1.83

Substrate specificity and kinetic studies of PADs 1, 3, and 4 identify potent and selective inhibitors of protein arginine deiminase 3. Biochemistry (2010) 1.66

Peptidylarginine deiminase inhibition is immunomodulatory and vasculoprotective in murine lupus. J Clin Invest (2013) 1.64

Suppression of colitis in mice by Cl-amidine: a novel peptidylarginine deiminase inhibitor. Am J Physiol Gastrointest Liver Physiol (2011) 1.61

Protein arginine methyltransferase 1: positively charged residues in substrate peptides distal to the site of methylation are important for substrate binding and catalysis. Biochemistry (2007) 1.55

Protein arginine deiminase 4: evidence for a reverse protonation mechanism. Biochemistry (2007) 1.45

In situ generation of a bisubstrate analogue for protein arginine methyltransferase 1. J Am Chem Soc (2008) 1.42

Felty's syndrome autoantibodies bind to deiminated histones and neutrophil extracellular chromatin traps. Arthritis Rheum (2011) 1.38

Peptidylarginine deiminase 2-catalyzed histone H3 arginine 26 citrullination facilitates estrogen receptor α target gene activation. Proc Natl Acad Sci U S A (2012) 1.35

Genome-wide analysis reveals PADI4 cooperates with Elk-1 to activate c-Fos expression in breast cancer cells. PLoS Genet (2011) 1.33

Kinetic mechanism of protein arginine methyltransferase 1. Biochemistry (2008) 1.32

Activation of PAD4 in NET formation. Front Immunol (2012) 1.30

Synthesis and screening of a haloacetamidine containing library to identify PAD4 selective inhibitors. ACS Chem Biol (2011) 1.25

Activity-based protein profiling reagents for protein arginine deiminase 4 (PAD4): synthesis and in vitro evaluation of a fluorescently labeled probe. J Am Chem Soc (2006) 1.24

Protein arginine deiminase 4: a target for an epigenetic cancer therapy. Cell Mol Life Sci (2010) 1.21

The protein arginine deiminases: Structure, function, inhibition, and disease. Biopolymers (2013) 1.18

Identification of PADI2 as a potential breast cancer biomarker and therapeutic target. BMC Cancer (2012) 1.18

A fluopol-ABPP HTS assay to identify PAD inhibitors. Chem Commun (Camb) (2010) 1.13

Haloacetamidine-based inactivators of protein arginine deiminase 4 (PAD4): evidence that general acid catalysis promotes efficient inactivation. Chembiochem (2010) 1.13

The protein acetyltransferase ARD1: a novel cancer drug target? Curr Cancer Drug Targets (2008) 1.13

Protein deiminases: new players in the developmentally regulated loss of neural regenerative ability. Dev Biol (2011) 1.12

The development of N-α-(2-carboxyl)benzoyl-N(5)-(2-fluoro-1-iminoethyl)-l-ornithine amide (o-F-amidine) and N-α-(2-carboxyl)benzoyl-N(5)-(2-chloro-1-iminoethyl)-l-ornithine amide (o-Cl-amidine) as second generation protein arginine deiminase (PAD) inhibitors. J Med Chem (2011) 1.12

Profiling Protein Arginine Deiminase 4 (PAD4): a novel screen to identify PAD4 inhibitors. Bioorg Med Chem (2007) 1.11

Potential role of peptidylarginine deiminase enzymes and protein citrullination in cancer pathogenesis. Biochem Res Int (2012) 1.08

Peptide borono lectins (PBLs): a new tool for glycomics and cancer diagnostics. Chembiochem (2007) 1.06

Kinase consensus sequences: a breeding ground for crosstalk. ACS Chem Biol (2011) 1.04

A selective chemical probe for coenzyme A-requiring enzymes. Angew Chem Int Ed Engl (2007) 1.04

Citrullination of proteins: a common post-translational modification pathway induced by different nanoparticles in vitro and in vivo. Nanomedicine (Lond) (2012) 1.00

Chemical biology of protein arginine modifications in epigenetic regulation. Chem Rev (2015) 0.99

Autodeimination of protein arginine deiminase 4 alters protein-protein interactions but not activity. Biochemistry (2011) 0.95

Potential role for PADI-mediated histone citrullination in preimplantation development. BMC Dev Biol (2012) 0.95

Kinetic mechanism of protein arginine methyltransferase 6 (PRMT6). J Biol Chem (2012) 0.95

Seeing citrulline: development of a phenylglyoxal-based probe to visualize protein citrullination. J Am Chem Soc (2012) 0.93

Synthesis and analysis of potential prodrugs of coenzyme A analogues for the inhibition of the histone acetyltransferase p300. Bioorg Med Chem (2003) 0.93

Mechanistic studies on transcriptional coactivator protein arginine methyltransferase 1. Biochemistry (2011) 0.93

Selective HAT inhibitors as mechanistic tools for protein acetylation. Methods Enzymol (2004) 0.91

The induction of microRNA-16 in colon cancer cells by protein arginine deiminase inhibition causes a p53-dependent cell cycle arrest. PLoS One (2013) 0.91

A chloroacetamidine-based inactivator of protein arginine methyltransferase 1: design, synthesis, and in vitro and in vivo evaluation. Chembiochem (2010) 0.91

Design, synthesis, and biological evaluation of tetrazole analogs of Cl-amidine as protein arginine deiminase inhibitors. J Med Chem (2015) 0.90

Substrate specificity, processivity, and kinetic mechanism of protein arginine methyltransferase 5. Biochemistry (2013) 0.90

The tomato brassinosteroid receptor BRI1 increases binding of systemin to tobacco plasma membranes, but is not involved in systemin signaling. Plant Mol Biol (2009) 0.89

Chemical and biological methods to detect post-translational modifications of arginine. Biopolymers (2014) 0.88

Characterization and inactivation of an agmatine deiminase from Helicobacter pylori. Bioorg Chem (2009) 0.88

Activity-based protein profiling of protein arginine methyltransferase 1. ACS Chem Biol (2011) 0.88

Inhibiting AMPylation: a novel screen to identify the first small molecule inhibitors of protein AMPylation. ACS Chem Biol (2013) 0.87

Probing adenylation: using a fluorescently labelled ATP probe to directly label and immunoprecipitate VopS substrates. Mol Biosyst (2012) 0.87

A combinatorial approach to characterize the substrate specificity of protein arginine methyltransferase 1. Mol Biosyst (2010) 0.86

Design, synthesis, and kinetic characterization of protein N-terminal acetyltransferase inhibitors. ACS Chem Biol (2013) 0.86

Development and use of clickable activity based protein profiling agents for protein arginine deiminase 4. ACS Chem Biol (2011) 0.86

D-amino acid based protein arginine deiminase inhibitors: Synthesis, pharmacokinetics, and in cellulo efficacy. ACS Med Chem Lett (2012) 0.86

Mechanistic studies of protein arginine deiminase 2: evidence for a substrate-assisted mechanism. Biochemistry (2014) 0.85

Protein arginine methyltransferase 5 catalyzes substrate dimethylation in a distributive fashion. Biochemistry (2014) 0.84

Peptidylarginine deiminases: novel drug targets for prevention of neuronal damage following hypoxic ischemic insult (HI) in neonates. J Neurochem (2014) 0.84

Automethylation of protein arginine methyltransferase 8 (PRMT8) regulates activity by impeding S-adenosylmethionine sensitivity. J Biol Chem (2013) 0.83

Targeting the arginine phosphatase YwlE with a catalytic redox-based inhibitor. ACS Chem Biol (2013) 0.82

Mechanistic studies of agmatine deiminase from multiple bacterial species. Biochemistry (2010) 0.82

Human protein N-terminal acetyltransferase hNaa50p (hNAT5/hSAN) follows ordered sequential catalytic mechanism: combined kinetic and NMR study. J Biol Chem (2012) 0.81

A FluoPol-ABPP PAD2 high-throughput screen identifies the first calcium site inhibitor targeting the PADs. ACS Chem Biol (2014) 0.81

A novel role for protein arginine deiminase 4 in pluripotency: the emerging role of citrullinated histone H1 in cellular programming. Bioessays (2014) 0.80

Bisubstrate analogue structure-activity relationships for p300 histone acetyltransferase inhibitors. Bioorg Med Chem (2004) 0.80

Protein Arginine Deiminases and Associated Citrullination: Physiological Functions and Diseases Associated with Dysregulation. Curr Drug Targets (2015) 0.79

Boronic acid functionalized peptidyl synthetic lectins: combinatorial library design, peptide sequencing, and selective glycoprotein recognition. ACS Comb Sci (2011) 0.77

Methyllysine analogs: rewriting the code. Nat Chem Biol (2007) 0.75

Using unnatural amino acid mutagenesis to probe the regulation of PRMT1. ACS Chem Biol (2014) 0.75