Structure-based design, synthesis, and structure-activity relationship studies of HIV-1 protease inhibitors incorporating phenyloxazolidinones.

PubWeight™: 0.93‹?›

🔗 View Article (PMC 2996262)

Published in J Med Chem on November 11, 2010

Authors

Akbar Ali1, G S Kiran Kumar Reddy, Madhavi N L Nalam, Saima Ghafoor Anjum, Hong Cao, Celia A Schiffer, Tariq M Rana

Author Affiliations

1: University of Massachusetts Medical School, Worcester, Massachusetts 01605, United States.

Articles cited by this

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

The CCP4 suite: programs for protein crystallography. Acta Crystallogr D Biol Crystallogr (1994) 187.88

Refinement of macromolecular structures by the maximum-likelihood method. Acta Crystallogr D Biol Crystallogr (1997) 137.43

Declining morbidity and mortality among patients with advanced human immunodeficiency virus infection. HIV Outpatient Study Investigators. N Engl J Med (1998) 53.26

Antiretroviral treatment of adult HIV infection: 2008 recommendations of the International AIDS Society-USA panel. JAMA (2008) 11.72

A novel phenotypic drug susceptibility assay for human immunodeficiency virus type 1. Antimicrob Agents Chemother (2000) 8.54

Improved survival among HIV-infected individuals following initiation of antiretroviral therapy. JAMA (1998) 6.69

HIV drug resistance. N Engl J Med (2004) 5.52

Novel fluorogenic substrates for assaying retroviral proteases by resonance energy transfer. Science (1990) 4.01

ARP/wARP's model-building algorithms. I. The main chain. Acta Crystallogr D Biol Crystallogr (2002) 3.84

A medicinal chemist's guide to molecular interactions. J Med Chem (2010) 3.39

Novel bis-tetrahydrofuranylurethane-containing nonpeptidic protease inhibitor (PI) UIC-94017 (TMC114) with potent activity against multi-PI-resistant human immunodeficiency virus in vitro. Antimicrob Agents Chemother (2003) 3.23

HIV-1 drug resistance mutations: an updated framework for the second decade of HAART. AIDS Rev (2008) 2.88

Synthesis and antibacterial activity of U-100592 and U-100766, two oxazolidinone antibacterial agents for the potential treatment of multidrug-resistant gram-positive bacterial infections. J Med Chem (1996) 2.82

TMC114, a novel human immunodeficiency virus type 1 protease inhibitor active against protease inhibitor-resistant viruses, including a broad range of clinical isolates. Antimicrob Agents Chemother (2005) 2.76

Overview of the effectiveness of triple combination therapy in antiretroviral-naive HIV-1 infected adults. AIDS (2001) 2.75

How does a symmetric dimer recognize an asymmetric substrate? A substrate complex of HIV-1 protease. J Mol Biol (2000) 2.62

Discovery and selection of TMC114, a next generation HIV-1 protease inhibitor. J Med Chem (2005) 2.58

Pharmacokinetic enhancement of inhibitors of the human immunodeficiency virus protease by coadministration with ritonavir. Antimicrob Agents Chemother (1997) 2.57

Genotypic changes in human immunodeficiency virus type 1 protease associated with reduced susceptibility and virologic response to the protease inhibitor tipranavir. J Virol (2006) 2.33

Resistance profile of darunavir: combined 24-week results from the POWER trials. AIDS Res Hum Retroviruses (2008) 2.01

Do enthalpy and entropy distinguish first in class from best in class? Drug Discov Today (2008) 2.00

3-year suppression of HIV viremia with indinavir, zidovudine, and lamivudine. Ann Intern Med (2000) 1.88

Pharmacological and therapeutic properties of ritonavir-boosted protease inhibitor therapy in HIV-infected patients. J Antimicrob Chemother (2003) 1.76

Rigid protein motion as a model for crystallographic temperature factors. Proc Natl Acad Sci U S A (1991) 1.74

Twenty-six years of anti-HIV drug discovery: where do we stand and where do we go? J Med Chem (2010) 1.59

Current status and challenges of antiretroviral research and therapy. Antiviral Res (2009) 1.52

Lack of synergy for inhibitors targeting a multi-drug-resistant HIV-1 protease. Protein Sci (2002) 1.49

HIV-1 protease inhibitors from inverse design in the substrate envelope exhibit subnanomolar binding to drug-resistant variants. J Am Chem Soc (2008) 1.43

Evaluating the substrate-envelope hypothesis: structural analysis of novel HIV-1 protease inhibitors designed to be robust against drug resistance. J Virol (2010) 1.39

Evaluation of methods for estimating the dissociation constant of tight binding enzyme inhibitors. J Biol Chem (1979) 1.33

Tipranavir (PNU-140690): a potent, orally bioavailable nonpeptidic HIV protease inhibitor of the 5,6-dihydro-4-hydroxy-2-pyrone sulfonamide class. J Med Chem (1998) 1.29

Discovery of HIV-1 protease inhibitors with picomolar affinities incorporating N-aryl-oxazolidinone-5-carboxamides as novel P2 ligands. J Med Chem (2006) 1.17

Design and synthesis of HIV-1 protease inhibitors incorporating oxazolidinones as P2/P2' ligands in pseudosymmetric dipeptide isosteres. J Med Chem (2007) 0.97

Overview of boosted protease inhibitors in treatment-experienced HIV-infected patients. J Antimicrob Chemother (2007) 0.91

Articles by these authors

High-Throughput GoMiner, an 'industrial-strength' integrative gene ontology tool for interpretation of multiple-microarray experiments, with application to studies of Common Variable Immune Deficiency (CVID). BMC Bioinformatics (2005) 14.02

Translation repression in human cells by microRNA-induced gene silencing requires RCK/p54. PLoS Biol (2006) 6.41

siRNA function in RNAi: a chemical modification analysis. RNA (2003) 4.93

RNAi in human cells: basic structural and functional features of small interfering RNA. Mol Cell (2002) 3.81

Specific and potent RNAi in the nucleus of human cells. Nat Struct Mol Biol (2005) 3.16

Cellular microRNA and P bodies modulate host-HIV-1 interactions. Mol Cell (2009) 3.05

Mutation patterns and structural correlates in human immunodeficiency virus type 1 protease following different protease inhibitor treatments. J Virol (2003) 2.98

Small RNA-mediated regulation of iPS cell generation. EMBO J (2011) 2.95

Rhea--a manually curated resource of biochemical reactions. Nucleic Acids Res (2011) 2.87

Small-molecule inhibition of HIV-1 Vif. Nat Biotechnol (2008) 2.83

RNA helicase A interacts with RISC in human cells and functions in RISC loading. Mol Cell (2007) 2.72

Substrate shape determines specificity of recognition for HIV-1 protease: analysis of crystal structures of six substrate complexes. Structure (2002) 2.69

Human retroviral host restriction factors APOBEC3G and APOBEC3F localize to mRNA processing bodies. PLoS Pathog (2006) 2.61

Discovery and selection of TMC114, a next generation HIV-1 protease inhibitor. J Med Chem (2005) 2.58

Structural and thermodynamic basis for the binding of TMC114, a next-generation human immunodeficiency virus type 1 protease inhibitor. J Virol (2004) 2.47

Combating susceptibility to drug resistance: lessons from HIV-1 protease. Chem Biol (2004) 2.39

The Enzyme Portal: a case study in applying user-centred design methods in bioinformatics. BMC Bioinformatics (2013) 2.14

Visualizing a correlation between siRNA localization, cellular uptake, and RNAi in living cells. Chem Biol (2004) 2.05

Dynamin 2 binds gamma-tubulin and participates in centrosome cohesion. Nat Cell Biol (2004) 1.91

Small RNAs: regulators and guardians of the genome. J Cell Physiol (2007) 1.86

A dynamin-cortactin-Arp2/3 complex mediates actin reorganization in growth factor-stimulated cells. Mol Biol Cell (2003) 1.80

Target accessibility dictates the potency of human RISC. Nat Struct Mol Biol (2005) 1.78

The long noncoding RNA THRIL regulates TNFα expression through its interaction with hnRNPL. Proc Natl Acad Sci U S A (2013) 1.78

Replacement of the P1 amino acid of human immunodeficiency virus type 1 Gag processing sites can inhibit or enhance the rate of cleavage by the viral protease. J Virol (2002) 1.71

Dynamin 3 is a component of the postsynapse, where it interacts with mGluR5 and Homer. Curr Biol (2003) 1.66

Covariation of amino acid positions in HIV-1 protease. Virology (2003) 1.65

Structural basis for coevolution of a human immunodeficiency virus type 1 nucleocapsid-p1 cleavage site with a V82A drug-resistant mutation in viral protease. J Virol (2004) 1.65

Crystal structure of the APOBEC3G catalytic domain reveals potential oligomerization interfaces. Structure (2010) 1.65

Drug resistance against HCV NS3/4A inhibitors is defined by the balance of substrate recognition versus inhibitor binding. Proc Natl Acad Sci U S A (2010) 1.65

The effects of dexmedetomidine on cardiac electrophysiology in children. Anesth Analg (2008) 1.64

Hemagglutinin (HA) proteins from H1 and H3 serotypes of influenza A viruses require different antigen designs for the induction of optimal protective antibody responses as studied by codon-optimized HA DNA vaccines. J Virol (2006) 1.57

Lack of synergy for inhibitors targeting a multi-drug-resistant HIV-1 protease. Protein Sci (2002) 1.49

The frameshift signal of HIV-1 involves a potential intramolecular triplex RNA structure. Proc Natl Acad Sci U S A (2002) 1.46

HCV 6a prevalence in Guangdong province had the origin from Vietnam and recent dissemination to other regions of China: phylogeographic analyses. PLoS One (2012) 1.44

TAR RNA loop: a scaffold for the assembly of a regulatory switch in HIV replication. Proc Natl Acad Sci U S A (2002) 1.44

HIV-1 protease inhibitors from inverse design in the substrate envelope exhibit subnanomolar binding to drug-resistant variants. J Am Chem Soc (2008) 1.43

Tat stimulates cotranscriptional capping of HIV mRNA. Mol Cell (2002) 1.43

The challenge of developing robust drugs to overcome resistance. Drug Discov Today (2011) 1.43

Analysis of HIV-1 viral infectivity factor-mediated proteasome-dependent depletion of APOBEC3G: correlating function and subcellular localization. J Biol Chem (2004) 1.42

miR-10b promotes cell invasion through RhoC-AKT signaling pathway by targeting HOXD10 in gastric cancer. Int J Oncol (2012) 1.40

Evaluating the substrate-envelope hypothesis: structural analysis of novel HIV-1 protease inhibitors designed to be robust against drug resistance. J Virol (2010) 1.39

Programming peptidomimetic syntheses by translating genetic codes designed de novo. Proc Natl Acad Sci U S A (2003) 1.38

Methylcytosine and normal cytosine deamination by the foreign DNA restriction enzyme APOBEC3A. J Biol Chem (2012) 1.38

Viability of a drug-resistant human immunodeficiency virus type 1 protease variant: structural insights for better antiviral therapy. J Virol (2003) 1.37

MicroRNAs encoded by Kaposi's sarcoma-associated herpesvirus regulate viral life cycle. EMBO Rep (2010) 1.34

The molecular basis of drug resistance against hepatitis C virus NS3/4A protease inhibitors. PLoS Pathog (2012) 1.30

Potent RNAi by short RNA triggers. RNA (2008) 1.29

First-in-class small molecule inhibitors of the single-strand DNA cytosine deaminase APOBEC3G. ACS Chem Biol (2012) 1.28

PTEN enters the nucleus by diffusion. J Cell Biochem (2005) 1.28

Deep annotation of mouse iso-miR and iso-moR variation. Nucleic Acids Res (2012) 1.27

Resilience to resistance of HIV-1 protease inhibitors: profile of darunavir. AIDS Rev (2008) 1.26

Inhibition of human immunodeficiency virus type 1 replication by RNA interference directed against human transcription elongation factor P-TEFb (CDK9/CyclinT1). J Virol (2004) 1.26

Co-evolution of nelfinavir-resistant HIV-1 protease and the p1-p6 substrate. Virology (2006) 1.22

In-vivo measurement of swine myocardial resistivity. IEEE Trans Biomed Eng (2002) 1.22

Identification of two neutralizing regions on the severe acute respiratory syndrome coronavirus spike glycoprotein produced from the mammalian expression system. J Virol (2005) 1.21

Specific HIV-1 TAR RNA loop sequence and functional groups are required for human cyclin T1-Tat-TAR ternary complex formation. Biochemistry (2002) 1.21

Cryptosporidium parvum invasion of biliary epithelia requires host cell tyrosine phosphorylation of cortactin via c-Src. Gastroenterology (2003) 1.21

Hydrophobic sliding: a possible mechanism for drug resistance in human immunodeficiency virus type 1 protease. Structure (2007) 1.20

Molecular Basis for Drug Resistance in HIV-1 Protease. Viruses (2010) 1.20

microRNAs modulate iPS cell generation. RNA (2011) 1.19

Src kinase regulates the integrity and function of the Golgi apparatus via activation of dynamin 2. Proc Natl Acad Sci U S A (2010) 1.19

Insights into interferon regulatory factor activation from the crystal structure of dimeric IRF5. Nat Struct Mol Biol (2008) 1.17

New evidence for the involvement of spinal fractalkine receptor in pain facilitation and spinal glial activation in rat model of monoarthritis. Pain (2006) 1.17

Discovery of HIV-1 protease inhibitors with picomolar affinities incorporating N-aryl-oxazolidinone-5-carboxamides as novel P2 ligands. J Med Chem (2006) 1.17

Design and creation of new nanomaterials for therapeutic RNAi. ACS Chem Biol (2007) 1.16

Mechanism of substrate recognition by drug-resistant human immunodeficiency virus type 1 protease variants revealed by a novel structural intermediate. J Virol (2006) 1.15

Caveolin-1 interacts directly with dynamin-2. J Mol Biol (2005) 1.14

Dynamics of preferential substrate recognition in HIV-1 protease: redefining the substrate envelope. J Mol Biol (2011) 1.14

A kinase inhibitor screen identifies small-molecule enhancers of reprogramming and iPS cell generation. Nat Commun (2012) 1.14

Crystal structure of the DNA cytosine deaminase APOBEC3F: the catalytically active and HIV-1 Vif-binding domain. Structure (2013) 1.13

Cooperative fluctuations of unliganded and substrate-bound HIV-1 protease: a structure-based analysis on a variety of conformations from crystallography and molecular dynamics simulations. Proteins (2003) 1.12

Therapeutic targeting of C-terminal binding protein in human cancer. Cell Cycle (2010) 1.12

Design of mutation-resistant HIV protease inhibitors with the substrate envelope hypothesis. Chem Biol Drug Des (2007) 1.12

Discovery of a small molecule Tat-trans-activation-responsive RNA antagonist that potently inhibits human immunodeficiency virus-1 replication. J Biol Chem (2003) 1.11