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Title: Structure-based design of potent HIV-1 protease inhibitors with modified P1-biphenyl ligands: Synthesis, biological evaluation, and enzyme–inhibitor X-ray structural studies

Journal Article · · Journal of Medicinal Chemistry
 [1];  [1];  [1];  [2];  [2];  [3];  [2];  [4]
  1. Purdue Univ., West Lafayette, IN (United States)
  2. Georgia State Univ., Atlanta, GA (United States)
  3. Kumamoto Univ. Graduate School of Medicine and Pharmaceutical Sciences, Kumamoto (Japan)
  4. Kumamoto Univ. Graduate School of Medicine and Pharmaceutical Sciences, Kumamoto (Japan); National Institutes of Health, Bethesda, MD (United States); National Center for Global Health and Medicine, Tokyo (Japan)
+ Show Author Affiliations

Research Organization:
Argonne National Laboratory (ANL), Argonne, IL (United States). Advanced Photon Source (APS)
Sponsoring Organization:
National Institutes of Health (NIH)
OSTI ID:
1214856
Journal Information:
Journal of Medicinal Chemistry, Vol. 58, Issue 13; ISSN 0022-2623
Publisher:
American Chemical Society (ACS)Copyright Statement
Country of Publication:
United States
Language:
ENGLISH
Citation Metrics:
Cited by: 17 works
Citation information provided by
Web of Science

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High Resolution Crystal Structures of HIV-1 Protease with a Potent Non-peptide Inhibitor (UIC-94017) Active Against Multi-drug-resistant Clinical Strains journal April 2004
Structural implications of drug-resistant mutants of HIV-1 protease: High-resolution crystal structures of the mutant protease/substrate analogue complexes journal January 2001
Overview of the CCP 4 suite and current developments journal March 2011
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Design, Synthesis, Protein−Ligand X-ray Structure, and Biological Evaluation of a Series of Novel Macrocyclic Human Immunodeficiency Virus-1 Protease Inhibitors to Combat Drug Resistance journal December 2009
Enhancing Protein Backbone Binding-A Fruitful Concept for Combating Drug-Resistant HIV journal January 2012
The Effect of Highly Active Antiretroviral Therapy on the Survival of HIV-Infected Children in a Resource-Deprived Setting: A Cohort Study journal June 2011
A simple, continuous fluorometric assay for HIV protease journal December 1990
Features and development of Coot journal March 2010
Bis-Tetrahydrofuran: a Privileged Ligand for Darunavir and a New Generation of HIV Protease Inhibitors That Combat Drug Resistance journal September 2006
Cells of the central nervous system as targets and reservoirs of the human immunodeficiency virus journal August 2005
Enantiodivergent, Catalytic Asymmetric Synthesis of γ-Amino Vinyl Sulfones journal June 2003
Design of HIV Protease Inhibitors Targeting Protein Backbone: An Effective Strategy for Combating Drug Resistance journal January 2008
GRL-0519, a Novel Oxatricyclic Ligand-Containing Nonpeptidic HIV-1 Protease Inhibitor (PI), Potently Suppresses Replication of a Wide Spectrum of Multi-PI-Resistant HIV-1 Variants In Vitro journal February 2013
A graphical user interface to the CCP 4 program suite journal June 2003
Synthesis, X-ray Analysis, and Biological Evaluation of a New Class of Stereopure Lactam-Based HIV-1 Protease Inhibitors journal March 2012
HAART in treatment-experienced patients in the 21st century: the audacity of hope journal January 2009
Neurological complications of HIV infection journal September 2005
Structure-Based Design:  Synthesis and Biological Evaluation of a Series of Novel Cycloamide-Derived HIV-1 Protease Inhibitors journal May 2005
Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds journal November 1995
Amprenavir complexes with HIV-1 protease and its drug-resistant mutants altering hydrophobic clusters: HIV protease mutants altering hydrophobic clusters journal August 2010
Darunavir, a conceptually new HIV-1 protease inhibitor for the treatment of drug-resistant HIV journal December 2007
Design, Synthesis, and Biological Activity of a Novel Series of Human Sirtuin-2-Selective Inhibitors journal June 2012
Novel bis-Tetrahydrofuranylurethane-Containing Nonpeptidic Protease Inhibitor (PI) UIC-94017 (TMC114) with Potent Activity against Multi-PI-Resistant Human Immunodeficiency Virus In Vitro journal September 2003
Synthesis and evaluation of novel pyrazolidinone analogs of PGE2 as EP2 and EP4 receptors agonists journal December 2007
Novel P2 Tris-tetrahydrofuran Group in Antiviral Compound 1 (GRL-0519) Fills the S2 Binding Pocket of Selected Mutants of HIV-1 Protease journal January 2013
Demonstration of Sustained Drug-Resistant Human Immunodeficiency Virus Type 1 Lineages Circulating among Treatment-Naive Individuals journal January 2009
Synthesis of P1′-Functionalized Macrocyclic Transition-State Mimicking HIV-1 Protease Inhibitors Encompassing a Tertiary Alcohol journal August 2014
Regioselective azide opening of 2,3-epoxy alcohols by [Ti(O-i-Pr)2(N3)2]: synthesis of .alpha.-amino acids journal October 1988
Probing Multidrug-Resistance and Protein-Ligand Interactions with Oxatricyclic Designed Ligands in HIV-1 Protease Inhibitors journal September 2010
Phaser crystallographic software journal July 2007
Structure-Based Design of Highly Selective β-Secretase Inhibitors: Synthesis, Biological Evaluation, and Protein–Ligand X-ray Crystal Structure journal September 2012
Design and Synthesis of Potent HIV-1 Protease Inhibitors Incorporating Hexahydrofuropyranol-Derived High Affinity P 2 Ligands: Structure−Activity Studies and Biological Evaluation journal January 2011
[20] Processing of X-ray diffraction data collected in oscillation mode book January 1997

Cited By (2)

An inhibitor-interaction intermediate of HIV-1 protease, revealed by Isothermal Titration Calorimetry and NMR spectroscopy posted_content September 2018
NMR and MD studies combined to elucidate inhibitor and water interactions of HIV-1 protease and their modulations with resistance mutations journal June 2019

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