Structure-based development of anticancer drugs: complexes of NAD(P)H:quinone oxidoreductase 1 with chemotherapeutic quinones.

No abstract is available for this paper.

• Publication year

  2001

• Venue

  Structure

• Publication date

  2001-08-01

• Fields of study

  Biology, Medicine, Chemistry

• Identifiers
  DOI 10.1016/S0969-2126(01)00636-0PMID 11587640
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Structures of recombinant human and mouse NAD(P)H:quinone oxidoreductases: species comparison and structural changes with substrate binding and release.

  2000cited by this paper
• Immunodetection of NAD(P)H:quinone oxidoreductase 1 (NQO1) in human tissues.

  2000cited by this paper
• Molecular characterization of binding of substrates and inhibitors to DT-diaphorase: combined approach involving site-directed mutagenesis, inhibitor-binding analysis, and computer modeling.

  1999cited by this paper
• Inhibition of DT-diaphorase (NAD(P)H:quinone oxidoreductase, EC 1.6.99.2) by 5,6-dimethylxanthenone-4-acetic acid (DMXAA) and flavone-8-acetic acid (FAA): implications for bioreductive drug development.

  1999cited by this paper
• Crystal structure of human DT-diaphorase: a model for interaction with the cytotoxic prodrug 5-(aziridin-1-yl)-2,4-dinitrobenzamide (CB1954).

  1999cited by this paper
• Cross-linking and sequence-specific alkylation of DNA by aziridinylquinones. 3. Effects of alkyl substituents.

  1999cited by this paper
• Bioreductive activation of a series of indolequinones by human DT-diaphorase: structure-activity relationships.

  1999cited by this paper
• Crystallography & NMR system: A new software suite for macromolecular structure determination.

  1998cited by this paper
• Indolequinone antitumor agents: correlation between quinone structure, rate of metabolism by recombinant human NAD(P)H:quinone oxidoreductase, and in vitro cytotoxicity.

  1998cited by this paper
• A new screening system for NAD(P)H:quinone oxidoreductase (NQO1)-directed antitumor quinones: identification of a new aziridinylbenzoquinone, RH1, as a NQO1-directed antitumor agent.

  1998cited by this paper
• Raster3D: photorealistic molecular graphics.

  1997cited by this paper
• Processing of X-ray diffraction data collected in oscillation mode.

  1997cited by this paper
• Novel bioreductive anticancer agents based on indolequinones.

  1997cited by this paper
• [20] Processing of X-ray diffraction data collected in oscillation mode.

  1997cited by this paper
• Molecular Basis of the Catalytic Differences among DT-diaphorase of Human, Rat, and Mouse*

  1997cited by this paper
• An extensively modified version of MolScript that includes greatly enhanced coloring capabilities.

  1997cited by this paper
• Indoloquinone EO9: DNA interstrand cross-linking upon reduction by DT-diaphorase or xanthine oxidase.

  1995cited by this paper
• Catalytic properties of NAD(P)H:quinone acceptor oxidoreductase: study involving mouse, rat, human, and mouse-rat chimeric enzymes.

  1995cited by this paper
• Nicotinamide adenine dinucleotide (phosphate): quinone oxidoreductase (DT-diaphorase) as a target for bioreductive antitumor quinones: quinone cytotoxicity and selectivity in human lung and breast cancer cell lines.

  1995cited by this paper
• The three-dimensional structure of NAD(P)H:quinone reductase, a flavoprotein involved in cancer chemoprotection and chemotherapy: mechanism of the two-electron reduction.

  1995cited by this paper
• Bioactivation of quinones by DT-diaphorase, molecular, biochemical, and chemical studies.

  1994cited by this paper
• The CCP4 suite: programs for protein crystallography.

  1994cited by this paper
• Expression of rat liver NAD(P)H:quinone-acceptor oxidoreductase in Escherichia coli and mutagenesis in vitro at Arg-177.

  1992cited by this paper
• Protein Folding

  1992cited by this paper
• Relationship between DT-diaphorase-mediated metabolism of a series of aziridinylbenzoquinones and DNA damage and cytotoxicity.

  1992cited by this paper
• Alteration in DNA cross-linking and sequence selectivity of a series of aziridinylbenzoquinones after enzymatic reduction by DT-diaphorase.

  1992cited by this paper
• Structure-activity relationships for DT-diaphorase reduction of hypoxic cell directed agents: indoloquinones and diaziridinyl benzoquinones.

  1992cited by this paper
• Protein folding and association: Insights from the interfacial and thermodynamic properties of hydrocarbons

  1991cited by this paper
• Improved methods for building protein models in electron density maps and the location of errors in these models.

  1991cited by this paper
• The role of NAD(P)H: quinone reductase (EC 1.6.99.2, DT-diaphorase) in the reductive bioactivation of the novel indoloquinone antitumor agent EO9.

  1991cited by this paper
• Metabolism of diaziquone by NAD(P)H:(quinone acceptor) oxidoreductase (DT-diaphorase): role in diaziquone-induced DNA damage and cytotoxicity in human colon carcinoma cells.

  1990cited by this paper
• Treatment of patients with recurrent primary brain tumors with AZQ

  1984cited by this paper
• Soluble Diaphorase in Animal Tissues.

  1958cited by this paper

• Identification of rheochrysin as a potential anti-cancer inhibitor of NAD(P) H quinone oxidoreductase 1 through ensemble virtual screening, molecular dynamics, MM-GBSA and DFT.

  2025cites this paper
• The 8-Hydroxyquinoline Derivatives of 1,4-Naphthoquinone: Synthesis, Computational Analysis, and Anticancer Activity

  2025cites this paper
• Design, Synthesis, Physicochemical Properties, and Biological Activity of Thymidine Compounds Attached to 5,8-Quinolinedione Derivatives as Potent DT-Diaphorase Substrates

  2024cites this paper
• A small molecule cryptotanshinone induces non-enzymatic NQO1-dependent necrosis in cancer cells through the JNK1/2/Iron/PARP/calcium pathway

  2024cites this paper
• Structural dynamics at the active site of the cancer‐associated flavoenzyme NQO1 probed by chemical modification with PMSF

  2023influential citation
• Structural dynamics and functional cooperativity of human NQO1 by ambient temperature serial crystallography and simulations

  2023cites this paper
• In silico design of novel diamino-quinoline-5,8‑dione derivatives as putative inhibitors of NAD(P)H:Quinone oxidoreductase 1 based on docking studies and molecular dynamics simulations

  2021cites this paper
• Anticancer agents based on Plastoquinone analogs with N-phenylpiperazine: Structure-activity relationship and mechanism of action in breast cancer cells.

  2021cites this paper
• The analysis of NQO1 isoforms as an Off-target to anti-cancer drug RH1 using molecular modeling and structure-based drug discovery approaches

  2020influential citation
• Design, synthesis and biological activity of 1,4-quinone moiety attached to betulin derivatives as potent DT-diaphorase substrate.

  2020cites this paper
• Structural and spectral characterisation of 2-amino-2H-[1,2,3]triazolo[4,5-g]quinoline-4,9-dione polymorphs. Cytotoxic activity and molecular docking study with NQO1 enzyme.

  2020cites this paper
• A comprehensive review on β-lapachone: Mechanisms, structural modifications, and therapeutic potentials.

  2020cites this paper
• Negative Cooperativity in NAD(P)H Quinone Oxidoreductase 1 (NQO1)

  2019cites this paper
• Betulin-1,4-quinone hybrids: Synthesis, anticancer activity and molecular docking study with NQO1 enzyme.

  2019cites this paper
• A focused library synthesis and cytotoxicity of quinones derived from the natural product bolinaquinone

  2018cites this paper
• Structural, vibrational and quantum chemical investigations for 6,7-dichloro-2-methyl-5,8-quinolinedione. Cytotoxic and molecular docking studies

  2018cites this paper
• 10.11 – Quinone Reductases☆

  2018cites this paper
• Combined molecular modelling and 3D‐QSAR study for understanding the inhibition of NQO1 by heterocyclic quinone derivatives

  2018cites this paper
• NAD(P)H:Quinone Oxidoreductase 1 (NQO1) as a Therapeutic and Diagnostic Target in Cancer.

  2018cites this paper
• Discovery of Nonquinone Substrates for NAD(P)H: Quinone Oxidoreductase 1 (NQO1) as Effective Intracellular ROS Generators for the Treatment of Drug-Resistant Non-Small-Cell Lung Cancer.

  2018cites this paper
• Dicoumarol: A Drug which Hits at Least Two Very Different Targets in Vitamin K Metabolism.

  2017cites this paper
• CYTOTOXIC SELECTIVITY AND ANTIOXIDANT ACTIVITY OF ALOE ARBORESCENS CONSTITUENTS

  2017cites this paper
• Alkynyloxy derivatives of 5,8-quinolinedione: Synthesis, in vitro cytotoxicity studies and computational molecular modeling with NAD(P)H:Quinone oxidoreductase 1.

  2017cites this paper
• Affinity-based small fluorescent probe for NAD(P)H:quinone oxidoreductase 1 (NQO1). Design, synthesis and pharmacological evaluation.

  2017cites this paper
• Azoreductases in drug metabolism

  2017cites this paper
• Metabolic Activation and Drug Targeting

  2016cites this paper
• Preparation of novel steroidal conjugates as potential diagnostic and therapeutic agents with an emphasis on quinoid and halogenated moieties

  2016cites this paper
• Insight into the kinetics and thermodynamics of the hydride transfer reactions between quinones and lumiflavin: a density functional theory study

  2016cites this paper
• Preparation of methoxy-substituted para-benzoquinones

  2016cites this paper
• Novel naphtho[2,1-d]oxazole-4,5-diones as NQO1 substrates with improved aqueous solubility: Design, synthesis, and in vivo antitumor evaluation.

  2016cites this paper
• A direct interaction between NQO1 and a chemotherapeutic dimeric naphthoquinone

  2016cites this paper
• Natural Small Molecules as Stabilizers and Activators of Cancer-Associated NQO1 Polymorphisms.

  2016cites this paper
• Discovery of NAD(P)H:quinone oxidoreductase 1 (NQO1) inhibitors with novel chemical scaffolds by shape-based virtual screening combined with cascade docking

  2015cites this paper
• Nanotechnology-enabled delivery of NQO1 bioactivatable drugs

  2015cites this paper
• Synthesis and Intracellular Redox Cycling of Natural Quinones and Their Analogues and Identification of Indoleamine-2,3-dioxygenase (IDO) as Potential Target for Anticancer Activity.

  2015cites this paper
• Dynamic Carboxylate/Water Networks on the Surface of the PsbO Subunit of Photosystem II.

  2015cites this paper
• Benzofuranquinones as inhibitors of indoleamine 2,3-dioxygenase (IDO). Synthesis and biological evaluation.

  2014cites this paper
• 2-Substituted 3-methylnaphtho[1,2-b]furan-4,5-diones as novel L-shaped ortho-quinone substrates for NAD(P)H:quinone oxidoreductase (NQO1).

  2014cites this paper
• On the preferred structure of dicoumarol and implications for enzyme binding: A quantum chemical analysis

  2014cites this paper
• Mitochondrial diaphorases as NAD+ donors to segments of the citric acid cycle that support substrate‐level phosphorylation yielding ATP during respiratory inhibition

  2014cites this paper
• ENZYMES AND TARGETED ACTIVATION OF PRODRUGS

  2013cites this paper
• Efficient NQO1 substrates are potent and selective anticancer agents.

  2013cites this paper
• Synthesis of new quinolinequinone derivatives and preliminary exploration of their cytotoxic properties.

  2013cites this paper
• Benzofuran-, benzothiophene-, indazole- and benzisoxazole-quinones: excellent substrates for NAD(P)H:quinone oxidoreductase 1.

  2013cites this paper
• MECHANISMS AND CYTOTOXIC EFFECTS OF NQO1-DIRECTED LAVENDAMYCIN DERIVATIVES AND MITOCHONDRIA-TARGETED ANTHRACENYL ISOXAZOLE AMIDES AS NOVEL ANTITUMOR AGENTS

  2013cites this paper
• Modelado molecular y docking con la enzima nqo1 de naftofuroquinonas antitumorales, presentes en Tabebuia barbata

  2013cites this paper
• Ligand and receptor dynamics contribute to the mechanism of graded PPARγ agonism.

  2012cites this paper
• Human NAD(P)H:quinone oxidoreductase type I (hNQO1) activation of quinone propionic acid trigger groups.

  2012cites this paper
• NQO1 (NAD(P)H dehydrogenase, quinone 1)

  2011cites this paper
• The human carcinogen aristolochic acid i is activated to form DNA adducts by human NAD(P)H:quinone oxidoreductase without the contribution of acetyltransferases or sulfotransferases

  2011cites this paper
• Comparison of activation of aristolochic acid I and II with NADPH:quinone oxidoreductase, sulphotransferases and N-acetyltranferases.

  2011cites this paper
• Redox-active Liposome Delivery Agents With Highly Controllable Stimuli-responsive Behavior

  2011cites this paper
• A Single-Electron Reducing Quinone Oxidoreductase Is Necessary to Induce Haustorium Development in the Root Parasitic Plant Triphysaria[C][W]

  2010cites this paper
• 4.11 – Quinone Reductases

  2010cites this paper
• A novel mechanism for azoreduction.

  2010cites this paper
• Mechanisms of the different DNA adduct forming potentials of the urban air pollutants 2-nitrobenzanthrone and carcinogenic 3-nitrobenzanthrone.

  2010cites this paper
• Structure and function of glutamate transporters

  2010cites this paper
• Synthesis and biological evaluation of coumarin-based inhibitors of NAD(P)H: quinone oxidoreductase-1 (NQO1).

  2009cites this paper
• Design of anticancer prodrugs for reductive activation

  2009cites this paper
• Wanted: unique names for unique atom positions. PDB-wide analysis of diastereotopic atom names of small molecules containing diphosphate

  2008cites this paper
• Lavendamycin antitumor agents: structure-based design, synthesis, and NAD(P)H:quinone oxidoreductase 1 (NQO1) model validation with molecular docking and biological studies.

  2008cites this paper
• Structure, function, and mechanism of cytosolic quinone reductases.

  2008cites this paper
• Natural and synthetic quinones and their reduction by the quinone reductase enzyme NQO1: from synthetic organic chemistry to compounds with anticancer potential.

  2008cites this paper
• NAD(P)H:quinone oxidoreductase (NQO1)-directed lavendamycin antitumor agents: Structure-based design, molecular modeling and structure-activity studies

  2007cites this paper
• Evidence from ESI-MS for NQO1-catalyzed reduction of estrogen ortho-quinones.

  2007cites this paper
• Coumarin-based inhibitors of human NAD(P)H:quinone oxidoreductase-1. Identification, structure-activity, off-target effects and in vitro human pancreatic cancer toxicity.

  2007cites this paper
• NQO1-directed antitumour quinones

  2007cites this paper
• Stability experiments in human urine with EO9 (apaziquone): a novel anticancer agent for the intravesical treatment of bladder cancer.

  2007cites this paper
• Insight into the Metabolism Rate of Quinone Analogues from Molecular Dynamics Simulation and 3D‐QSMR Methods

  2007cites this paper
• Benzimidazole- and benzothiazole-quinones: excellent substrates for NAD(P)H:quinone oxidoreductase 1.

  2007cites this paper
• Indolequinone antitumour agents: correlation between quinone structure and rate of metabolism by recombinant human NAD(P)H:quinone oxidoreductase.

  2007cites this paper
• Role of Fluctuations in Quinone Reductase Hydride Transfer: a Combined Quantum Mechanics and Molecular Dynamics Study

  2006cites this paper
• In silico identification and biochemical characterization of novel inhibitors of NQO1.

  2006cites this paper
• Functions and distribution of NQO1 in human bone marrow: potential clues to benzene toxicity.

  2005cites this paper
• FAD semiquinone stability regulates single- and two-electron reduction of quinones by Anabaena PCC7119 ferredoxin:NADP+ reductase and its Glu301Ala mutant.

  2005cites this paper
• Topoisomerase enzymes as therapeutic targets for cancer chemotherapy.

  2005cites this paper
• Novel lavendamycin analogues as antitumor agents: synthesis, in vitro cytotoxicity, structure-metabolism, and computational molecular modeling studies with NAD(P)H:quinone oxidoreductase 1.

  2005cites this paper
• Cytotoxicity of RH1: NAD(P)H:quinone acceptor oxidoreductase (NQO1)-independent oxidative stress and apoptosis induction

  2005cites this paper
• Structure-activity relationships in two-electron reduction of quinones.

  2004cites this paper
• NAD(P)H:quinone oxidoreductase 1 (NQO1, DT-diaphorase), functions and pharmacogenetics.

  2004cites this paper
• Development of a New Isogenic Cell-Xenograft System for Evaluation of NAD(P)H:Quinone Oxidoreductase-Directed Antitumor Quinones

  2004cites this paper
• Structure and mechanism of NAD[P]H:quinone acceptor oxidoreductases (NQO).

  2004cites this paper
• Molecular cloning and characterization of an NADPH quinone oxidoreductase from Kluyveromyces marxianus.

  2003cites this paper
• Implications of protein flexibility for drug discovery

  2003cites this paper
• 3-substituted-5-aziridinyl-1-methylindole-4,7-diones as NQO1-directed antitumour agents: mechanism of activation and cytotoxicity in vitro.

  2003cites this paper
• Data Mining the NCI Cancer Cell Line Compound GI50 Values: Identifying Quinone Subtypes Effective Against Melanoma and Leukemia Cell Classes

  2003cites this paper
• Two-electron reduction of quinones by rat liver NAD(P)H:quinone oxidoreductase: quantitative structure-activity relationships.

  2002cites this paper
• Design, synthesis, and biological evaluation of indolequinone phosphoramidate prodrugs targeted to DT-diaphorase.

  2002cites this paper
• A structurally conserved water molecule in Rossmann dinucleotide‐binding domains

  2002cites this paper
• Characterization of a mechanism-based inhibitor of NAD(P)H:quinone oxidoreductase 1 by biochemical, X-ray crystallographic, and mass spectrometric approaches.

  2001cites this paper
• Novel quinolinequinone antitumor agents: structure-metabolism studies with NAD(P)H:quinone oxidoreductase (NQO1).

  1999cites this paper