Literature DB >> 23635904

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

Jeffery J Newsome1, Mary Hassani, Elizabeth Swann, Jane M Bibby, Howard D Beall, Christopher J Moody.   

Abstract

A series of heterocyclic quinones based on benzofuran, benzothiophene, indazole and benzisoxazole has been synthesized, and evaluated for their ability to function as substrates for recombinant human NAD(P)H:quinone oxidoreductase (NQO1), a two-electron reductase upregulated in tumor cells. Overall, the quinones are excellent substrates for NQO1, approaching the reduction rates observed for menadione.
Copyright © 2013 Elsevier Ltd. All rights reserved.

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Year:  2013        PMID： 23635904      PMCID： PMC3697102          DOI： 10.1016/j.bmc.2013.03.071

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN： 0968-0896            Impact factor:   3.641


  27 in total

1.  Synthesis by radical cyclization and cytotoxicity of highly potent bioreductive alicyclic ring fused [1,2-a]benzimidazolequinones.

Authors:  Mary Lynch; Sarah Hehir; Paul Kavanagh; Dónal Leech; John O'Shaughnessy; Michael P Carty; Fawaz Aldabbagh
Journal:  Chemistry       Date:  2007       Impact factor: 5.236

Review 2.  Mechanisms of action of quinone-containing alkylating agents. I: NQO1-directed drug development.

Authors:  H D Beall; S I Winski
Journal:  Front Biosci       Date:  2000-07-01

3.  Relationship between NAD(P)H:quinone oxidoreductase 1 (NQO1) levels in a series of stably transfected cell lines and susceptibility to antitumor quinones.

Authors:  S L Winski; E Swann; R H Hargreaves; D L Dehn; J Butler; C J Moody; D Ross
Journal:  Biochem Pharmacol       Date:  2001-06-15       Impact factor: 5.858

4.  Synthesis and Agonistic Activity at the GPR35 of 5,6-Dihydroxyindole-2-carboxylic Acid Analogues.

Authors:  Huayun Deng; Ye Fang
Journal:  ACS Med Chem Lett       Date:  2012-06-06       Impact factor: 4.345

5.  Indolequinone antitumor agents: correlation between quinone structure and rate of metabolism by recombinant human NAD(P)H:quinone oxidoreductase. Part 2.

Authors:  E Swann; P Barraja; A M Oberlander; W T Gardipee; A R Hudnott; H D Beall; C J Moody
Journal:  J Med Chem       Date:  2001-09-27       Impact factor: 7.446

Review 6.  Thermodynamic and kinetic considerations for the reaction of semiquinone radicals to form superoxide and hydrogen peroxide.

Authors:  Yang Song; Garry R Buettner
Journal:  Free Radic Biol Med       Date:  2010-05-21       Impact factor: 7.376

7.  Synthesis and antiproliferative activity of some benzimidazole-4,7-dione derivatives.

Authors:  L Garuti; M Roberti; M Malagoli; T Rossi; M Castelli
Journal:  Bioorg Med Chem Lett       Date:  2000-10-02       Impact factor: 2.823

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

Authors:  H D Beall; S Winski; E Swann; A R Hudnott; A S Cotterill; N O'Sullivan; S J Green; R Bien; D Siegel; D Ross; C J Moody
Journal:  J Med Chem       Date:  1998-11-19       Impact factor: 7.446

9.  Benzimidazole- and benzothiazole-quinones: excellent substrates for NAD(P)H:quinone oxidoreductase 1.

Authors:  Jeffery J Newsome; Marie A Colucci; Mary Hassani; Howard D Beall; Christopher J Moody
Journal:  Org Biomol Chem       Date:  2007-10-08       Impact factor: 3.876

Review 10.  Natural and synthetic quinones and their reduction by the quinone reductase enzyme NQO1: from synthetic organic chemistry to compounds with anticancer potential.

Authors:  Marie A Colucci; Christopher J Moody; Gavin D Couch
Journal:  Org Biomol Chem       Date:  2007-12-13       Impact factor: 3.876
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  1 in total

1.  Phytonutrients Differentially Stimulate NAD(P)H:Quinone Oxidoreductase, Inhibit Proliferation, and Trigger Mitotic Catastrophe in Hepa1c1c7 Cells.

Authors:  Steven J T Jackson; Keith W Singletary; Laura L Murphy; Richard C Venema; Andrew J Young
Journal:  J Med Food       Date:  2015-12-01       Impact factor: 2.786
  1 in total

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