2-Mercapto-Quinazolinones as Inhibitors of Type II NADH Dehydrogenase and Mycobacterium tuberculosis: Structure–Activity Relationships, Mechanism of Action and Absorption, Distribution, Metabolism, and Excretion Characterization
Identifieur interne : 000D26 ( Main/Exploration ); précédent : 000D25; suivant : 000D272-Mercapto-Quinazolinones as Inhibitors of Type II NADH Dehydrogenase and Mycobacterium tuberculosis: Structure–Activity Relationships, Mechanism of Action and Absorption, Distribution, Metabolism, and Excretion Characterization
Auteurs : Dinakaran Murugesan [Royaume-Uni] ; Peter C. Ray [Royaume-Uni] ; Tracy Bayliss [Royaume-Uni] ; Gareth A. Prosser [États-Unis] ; Justin R. Harrison [Royaume-Uni] ; Kirsteen Green [Royaume-Uni] ; Candice Soares De Melo [Afrique du Sud] ; Tzu-Shean Feng [Afrique du Sud] ; Leslie J. Street [Afrique du Sud] ; Kelly Chibale [Afrique du Sud] ; Digby F. Warner [Afrique du Sud] ; Valerie Mizrahi [Afrique du Sud] ; Ola Epemolu [Royaume-Uni] ; Paul Scullion [Royaume-Uni] ; Lucy Ellis [Royaume-Uni] ; Jennifer Riley [Royaume-Uni] ; Yoko Shishikura [Royaume-Uni] ; Liam Ferguson [Royaume-Uni] ; Maria Osuna-Cabello [Royaume-Uni] ; Kevin D. Read [Royaume-Uni] ; Simon R. Green [Royaume-Uni] ; Dirk A. Lamprecht [Afrique du Sud] ; Peter M. Finin [Afrique du Sud] ; Adrie J. C. Steyn [Afrique du Sud, États-Unis] ; Thomas R. Ioerger [États-Unis] ; Jim Sacchettini [États-Unis] ; Kyu Y. Rhee [États-Unis] ; Kriti Arora [États-Unis] ; Clifton E. Barry [États-Unis, Afrique du Sud] ; Paul G. Wyatt [Royaume-Uni] ; Helena I. M. Boshoff [États-Unis]Source :
- ACS Infectious Diseases [ 2373-8227 ] ; 2018.
Abstract
Url:
DOI: 10.1021/acsinfecdis.7b00275
PubMed: 29522317
PubMed Central: 5996347
Affiliations:
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Absorption, Distribution, Metabolism, and Excretion Characterization</title><author><name sortKey="Murugesan, Dinakaran" sort="Murugesan, Dinakaran" uniqKey="Murugesan D" first="Dinakaran" last="Murugesan">Dinakaran Murugesan</name><affiliation wicri:level="1"><nlm:aff id="aff1">Drug Discovery Unit, Division of Biological Chemistry and Drug Discovery, School of Life Sciences,<institution>University of Dundee</institution>, Sir James Black Centre, Dundee, DD1 5EH,<country>United Kingdom</country></nlm:aff><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Ray, Peter C" sort="Ray, Peter C" uniqKey="Ray P" first="Peter C." last="Ray">Peter C. 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id="aff1">Drug Discovery Unit, Division of Biological Chemistry and Drug Discovery, School of Life Sciences,<institution>University of Dundee</institution>, Sir James Black Centre, Dundee, DD1 5EH,<country>United Kingdom</country></nlm:aff><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Riley, Jennifer" sort="Riley, Jennifer" uniqKey="Riley J" first="Jennifer" last="Riley">Jennifer Riley</name><affiliation wicri:level="1"><nlm:aff id="aff1">Drug Discovery Unit, Division of Biological Chemistry and Drug Discovery, School of Life Sciences,<institution>University of Dundee</institution>, Sir James Black Centre, Dundee, DD1 5EH,<country>United Kingdom</country></nlm:aff><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Shishikura, Yoko" sort="Shishikura, Yoko" uniqKey="Shishikura Y" first="Yoko" last="Shishikura">Yoko Shishikura</name><affiliation wicri:level="1"><nlm:aff id="aff1">Drug Discovery Unit, Division of Biological Chemistry and Drug Discovery, School of Life Sciences,<institution>University of Dundee</institution>, Sir James Black Centre, Dundee, DD1 5EH,<country>United Kingdom</country></nlm:aff><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Ferguson, Liam" sort="Ferguson, Liam" uniqKey="Ferguson L" first="Liam" last="Ferguson">Liam Ferguson</name><affiliation wicri:level="1"><nlm:aff id="aff1">Drug Discovery Unit, Division of Biological Chemistry and Drug Discovery, School of Life Sciences,<institution>University of Dundee</institution>, Sir James Black Centre, Dundee, DD1 5EH,<country>United Kingdom</country></nlm:aff><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Osuna Cabello, Maria" sort="Osuna Cabello, Maria" uniqKey="Osuna Cabello M" first="Maria" last="Osuna-Cabello">Maria Osuna-Cabello</name><affiliation wicri:level="1"><nlm:aff id="aff1">Drug Discovery Unit, Division of Biological Chemistry and Drug Discovery, School of Life Sciences,<institution>University of Dundee</institution>, Sir James Black Centre, Dundee, DD1 5EH,<country>United Kingdom</country></nlm:aff><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Read, Kevin D" sort="Read, Kevin D" uniqKey="Read K" first="Kevin D." last="Read">Kevin D. Read</name><affiliation wicri:level="1"><nlm:aff id="aff1">Drug Discovery Unit, Division of Biological Chemistry and Drug Discovery, School of Life Sciences,<institution>University of Dundee</institution>, Sir James Black Centre, Dundee, DD1 5EH,<country>United Kingdom</country></nlm:aff><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Green, Simon R" sort="Green, Simon R" uniqKey="Green S" first="Simon R." last="Green">Simon R. Green</name><affiliation wicri:level="1"><nlm:aff id="aff1">Drug Discovery Unit, Division of Biological Chemistry and Drug Discovery, School of Life Sciences,<institution>University of Dundee</institution>, Sir James Black Centre, Dundee, DD1 5EH,<country>United Kingdom</country></nlm:aff><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Lamprecht, Dirk A" sort="Lamprecht, Dirk A" uniqKey="Lamprecht D" first="Dirk A." last="Lamprecht">Dirk A. Lamprecht</name><affiliation wicri:level="1"><nlm:aff id="aff7"><institution>Africa Health Research Institute (AHRI)</institution>, K-RITH Tower Building Level 3, 719 Umbilo Road, Durban, 4001,<country>South Africa</country></nlm:aff><country xml:lang="fr">Afrique du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Finin, Peter M" sort="Finin, Peter M" uniqKey="Finin P" first="Peter M." last="Finin">Peter M. Finin</name><affiliation wicri:level="1"><nlm:aff id="aff7"><institution>Africa Health Research Institute (AHRI)</institution>, K-RITH Tower Building Level 3, 719 Umbilo Road, Durban, 4001,<country>South Africa</country></nlm:aff><country xml:lang="fr">Afrique du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Steyn, Adrie J C" sort="Steyn, Adrie J C" uniqKey="Steyn A" first="Adrie J. C." last="Steyn">Adrie J. C. Steyn</name><affiliation wicri:level="1"><nlm:aff id="aff7"><institution>Africa Health Research Institute (AHRI)</institution>, K-RITH Tower Building Level 3, 719 Umbilo Road, Durban, 4001,<country>South Africa</country></nlm:aff><country xml:lang="fr">Afrique du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation><affiliation wicri:level="1"><nlm:aff id="aff8">Department of Microbiology,<institution>University of Alabama at Birmingham</institution>, 1720 Second Avenue South, Birmingham, Alabama 35294-2170,<country>United States</country></nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Ioerger, Thomas R" sort="Ioerger, Thomas R" uniqKey="Ioerger T" first="Thomas R." last="Ioerger">Thomas R. Ioerger</name><affiliation wicri:level="1"><nlm:aff id="aff9">Department of Computer Science and Engineering,<institution>Texas A&M University</institution>, College Station, Texas 77843,<country>United States</country></nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Sacchettini, Jim" sort="Sacchettini, Jim" uniqKey="Sacchettini J" first="Jim" last="Sacchettini">Jim Sacchettini</name><affiliation wicri:level="1"><nlm:aff id="aff9">Department of Computer Science and Engineering,<institution>Texas A&M University</institution>, College Station, Texas 77843,<country>United States</country></nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Rhee, Kyu Y" sort="Rhee, Kyu Y" uniqKey="Rhee K" first="Kyu Y." last="Rhee">Kyu Y. Rhee</name><affiliation wicri:level="1"><nlm:aff id="aff10">Division of Infectious Diseases, Weill Department of Medicine,<institution>Weill Cornell Medical College</institution>, New York, New York 10065,<country>United States</country></nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Arora, Kriti" sort="Arora, Kriti" uniqKey="Arora K" first="Kriti" last="Arora">Kriti Arora</name><affiliation wicri:level="1"><nlm:aff id="aff2">Tuberculosis Research Section, Laboratory of Clinical Immunology and Microbiology, National Institute of Allergy and Infectious Disease,<institution>National Institutes of Health</institution>, 9000 Rockville Pike, Bethesda, Maryland 20892,<country>United States</country></nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Barry, Clifton E" sort="Barry, Clifton E" uniqKey="Barry C" first="Clifton E." last="Barry">Clifton E. Barry</name><affiliation wicri:level="1"><nlm:aff id="aff2">Tuberculosis Research Section, Laboratory of Clinical Immunology and Microbiology, National Institute of Allergy and Infectious Disease,<institution>National Institutes of Health</institution>, 9000 Rockville Pike, Bethesda, Maryland 20892,<country>United States</country></nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation><affiliation wicri:level="1"><nlm:aff id="aff3">Institute of Infectious Disease and Molecular Medicine,<institution>University of Cape Town</institution>, Rondebosch, 7701,<country>South Africa</country></nlm:aff><country xml:lang="fr">Afrique du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Wyatt, Paul G" sort="Wyatt, Paul G" uniqKey="Wyatt P" first="Paul G." last="Wyatt">Paul G. Wyatt</name><affiliation wicri:level="1"><nlm:aff id="aff1">Drug Discovery Unit, Division of Biological Chemistry and Drug Discovery, School of Life Sciences,<institution>University of Dundee</institution>, Sir James Black Centre, Dundee, DD1 5EH,<country>United Kingdom</country></nlm:aff><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Boshoff, Helena I M" sort="Boshoff, Helena I M" uniqKey="Boshoff H" first="Helena I. M." last="Boshoff">Helena I. M. Boshoff</name><affiliation wicri:level="1"><nlm:aff id="aff2">Tuberculosis Research Section, Laboratory of Clinical Immunology and Microbiology, National Institute of Allergy and Infectious Disease,<institution>National Institutes of Health</institution>, 9000 Rockville Pike, Bethesda, Maryland 20892,<country>United States</country></nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">29522317</idno><idno type="pmc">5996347</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5996347</idno><idno type="RBID">PMC:5996347</idno><idno type="doi">10.1021/acsinfecdis.7b00275</idno><date when="2018">2018</date><idno type="wicri:Area/Pmc/Corpus">000030</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000030</idno><idno type="wicri:Area/Pmc/Curation">000030</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Curation">000030</idno><idno type="wicri:Area/Pmc/Checkpoint">000567</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Checkpoint">000567</idno><idno type="wicri:Area/Ncbi/Merge">002F14</idno><idno type="wicri:Area/Ncbi/Curation">002F14</idno><idno type="wicri:Area/Ncbi/Checkpoint">002F14</idno><idno type="wicri:Area/Main/Merge">000D28</idno><idno type="wicri:Area/Main/Curation">000D26</idno><idno type="wicri:Area/Main/Exploration">000D26</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">2-Mercapto-Quinazolinones as Inhibitors of Type II NADH Dehydrogenase and <italic>Mycobacterium tuberculosis</italic>: Structure–Activity Relationships, Mechanism of Action and
Absorption, Distribution, Metabolism, and Excretion Characterization</title><author><name sortKey="Murugesan, Dinakaran" sort="Murugesan, Dinakaran" uniqKey="Murugesan D" first="Dinakaran" last="Murugesan">Dinakaran Murugesan</name><affiliation wicri:level="1"><nlm:aff id="aff1">Drug Discovery Unit, Division of Biological Chemistry and Drug Discovery, School of Life Sciences,<institution>University of Dundee</institution>, Sir James Black Centre, Dundee, DD1 5EH,<country>United Kingdom</country></nlm:aff><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Ray, Peter C" sort="Ray, Peter C" uniqKey="Ray P" first="Peter C." last="Ray">Peter C. Ray</name><affiliation wicri:level="1"><nlm:aff id="aff1">Drug Discovery Unit, Division of Biological Chemistry and Drug Discovery, School of Life Sciences,<institution>University of Dundee</institution>, Sir James Black Centre, Dundee, DD1 5EH,<country>United Kingdom</country></nlm:aff><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Bayliss, Tracy" sort="Bayliss, Tracy" uniqKey="Bayliss T" first="Tracy" last="Bayliss">Tracy Bayliss</name><affiliation wicri:level="1"><nlm:aff id="aff1">Drug Discovery Unit, Division of Biological Chemistry and Drug Discovery, School of Life Sciences,<institution>University of Dundee</institution>, Sir James Black Centre, Dundee, DD1 5EH,<country>United Kingdom</country></nlm:aff><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Prosser, Gareth A" sort="Prosser, Gareth A" uniqKey="Prosser G" first="Gareth A." last="Prosser">Gareth A. Prosser</name><affiliation wicri:level="1"><nlm:aff id="aff2">Tuberculosis Research Section, Laboratory of Clinical Immunology and Microbiology, National Institute of Allergy and Infectious Disease,<institution>National Institutes of Health</institution>, 9000 Rockville Pike, Bethesda, Maryland 20892,<country>United States</country></nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Harrison, Justin R" sort="Harrison, Justin R" uniqKey="Harrison J" first="Justin R." last="Harrison">Justin R. Harrison</name><affiliation wicri:level="1"><nlm:aff id="aff1">Drug Discovery Unit, Division of Biological Chemistry and Drug Discovery, School of Life Sciences,<institution>University of Dundee</institution>, Sir James Black Centre, Dundee, DD1 5EH,<country>United Kingdom</country></nlm:aff><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Green, Kirsteen" sort="Green, Kirsteen" uniqKey="Green K" first="Kirsteen" last="Green">Kirsteen Green</name><affiliation wicri:level="1"><nlm:aff id="aff1">Drug Discovery Unit, Division of Biological Chemistry and Drug Discovery, School of Life Sciences,<institution>University of Dundee</institution>, Sir James Black Centre, Dundee, DD1 5EH,<country>United Kingdom</country></nlm:aff><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Soares De Melo, Candice" sort="Soares De Melo, Candice" uniqKey="Soares De Melo C" first="Candice" last="Soares De Melo">Candice Soares De Melo</name><affiliation wicri:level="1"><nlm:aff id="aff4">Drug Discovery and Development Centre (H3D), Department of Chemistry,<institution>University of Cape Town</institution>, Rondebosch, 7701,<country>South Africa</country></nlm:aff><country xml:lang="fr">Afrique du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Feng, Tzu Shean" sort="Feng, Tzu Shean" uniqKey="Feng T" first="Tzu-Shean" last="Feng">Tzu-Shean Feng</name><affiliation wicri:level="1"><nlm:aff id="aff4">Drug Discovery and Development Centre (H3D), Department of Chemistry,<institution>University of Cape Town</institution>, Rondebosch, 7701,<country>South Africa</country></nlm:aff><country xml:lang="fr">Afrique du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Street, Leslie J" sort="Street, Leslie J" uniqKey="Street L" first="Leslie J." last="Street">Leslie J. Street</name><affiliation wicri:level="1"><nlm:aff id="aff4">Drug Discovery and Development Centre (H3D), Department of Chemistry,<institution>University of Cape Town</institution>, Rondebosch, 7701,<country>South Africa</country></nlm:aff><country xml:lang="fr">Afrique du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Chibale, Kelly" sort="Chibale, Kelly" uniqKey="Chibale K" first="Kelly" last="Chibale">Kelly Chibale</name><affiliation wicri:level="1"><nlm:aff id="aff4">Drug Discovery and Development Centre (H3D), Department of Chemistry,<institution>University of Cape Town</institution>, Rondebosch, 7701,<country>South Africa</country></nlm:aff><country xml:lang="fr">Afrique du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation><affiliation wicri:level="1"><nlm:aff id="aff3">Institute of Infectious Disease and Molecular Medicine,<institution>University of Cape Town</institution>, Rondebosch, 7701,<country>South Africa</country></nlm:aff><country xml:lang="fr">Afrique du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation><affiliation wicri:level="1"><nlm:aff id="aff5">South African Medical Research Council Drug Discovery and Development Research Unit, Department of Chemistry,<institution>University of Cape Town</institution>, Rondebosch, 7701,<country>South Africa</country></nlm:aff><country xml:lang="fr">Afrique du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Warner, Digby F" sort="Warner, Digby F" uniqKey="Warner D" first="Digby F." last="Warner">Digby F. Warner</name><affiliation wicri:level="1"><nlm:aff id="aff6">SAMRC/NHLS/UCT Molecular Mycobacteriology Research Unit & DST/NRF Centre of Excellence for Biomedical TB Research, Department of Pathology, Faculty of Health Sciences,<institution>University of Cape Town</institution>, Rondebosch, 7701,<country>South Africa</country></nlm:aff><country xml:lang="fr">Afrique du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation><affiliation wicri:level="1"><nlm:aff id="aff3">Institute of Infectious Disease and Molecular Medicine,<institution>University of Cape Town</institution>, Rondebosch, 7701,<country>South Africa</country></nlm:aff><country xml:lang="fr">Afrique du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Mizrahi, Valerie" sort="Mizrahi, Valerie" uniqKey="Mizrahi V" first="Valerie" last="Mizrahi">Valerie Mizrahi</name><affiliation wicri:level="1"><nlm:aff id="aff6">SAMRC/NHLS/UCT Molecular Mycobacteriology Research Unit & DST/NRF Centre of Excellence for Biomedical TB Research, Department of Pathology, Faculty of Health Sciences,<institution>University of Cape Town</institution>, Rondebosch, 7701,<country>South Africa</country></nlm:aff><country xml:lang="fr">Afrique du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation><affiliation wicri:level="1"><nlm:aff id="aff3">Institute of Infectious Disease and Molecular Medicine,<institution>University of Cape Town</institution>, Rondebosch, 7701,<country>South Africa</country></nlm:aff><country xml:lang="fr">Afrique du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Epemolu, Ola" sort="Epemolu, Ola" uniqKey="Epemolu O" first="Ola" last="Epemolu">Ola Epemolu</name><affiliation wicri:level="1"><nlm:aff id="aff1">Drug Discovery Unit, Division of Biological Chemistry and Drug Discovery, School of Life Sciences,<institution>University of Dundee</institution>, Sir James Black Centre, Dundee, DD1 5EH,<country>United Kingdom</country></nlm:aff><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Scullion, Paul" sort="Scullion, Paul" uniqKey="Scullion P" first="Paul" last="Scullion">Paul Scullion</name><affiliation wicri:level="1"><nlm:aff id="aff1">Drug Discovery Unit, Division of Biological Chemistry and Drug Discovery, School of Life Sciences,<institution>University of Dundee</institution>, Sir James Black Centre, Dundee, DD1 5EH,<country>United Kingdom</country></nlm:aff><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Ellis, Lucy" sort="Ellis, Lucy" uniqKey="Ellis L" first="Lucy" last="Ellis">Lucy Ellis</name><affiliation wicri:level="1"><nlm:aff id="aff1">Drug Discovery Unit, Division of Biological Chemistry and Drug Discovery, School of Life Sciences,<institution>University of Dundee</institution>, Sir James Black Centre, Dundee, DD1 5EH,<country>United Kingdom</country></nlm:aff><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Riley, Jennifer" sort="Riley, Jennifer" uniqKey="Riley J" first="Jennifer" last="Riley">Jennifer Riley</name><affiliation wicri:level="1"><nlm:aff id="aff1">Drug Discovery Unit, Division of Biological Chemistry and Drug Discovery, School of Life Sciences,<institution>University of Dundee</institution>, Sir James Black Centre, Dundee, DD1 5EH,<country>United Kingdom</country></nlm:aff><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Shishikura, Yoko" sort="Shishikura, Yoko" uniqKey="Shishikura Y" first="Yoko" last="Shishikura">Yoko Shishikura</name><affiliation wicri:level="1"><nlm:aff id="aff1">Drug Discovery Unit, Division of Biological Chemistry and Drug Discovery, School of Life Sciences,<institution>University of Dundee</institution>, Sir James Black Centre, Dundee, DD1 5EH,<country>United Kingdom</country></nlm:aff><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Ferguson, Liam" sort="Ferguson, Liam" uniqKey="Ferguson L" first="Liam" last="Ferguson">Liam Ferguson</name><affiliation wicri:level="1"><nlm:aff id="aff1">Drug Discovery Unit, Division of Biological Chemistry and Drug Discovery, School of Life Sciences,<institution>University of Dundee</institution>, Sir James Black Centre, Dundee, DD1 5EH,<country>United Kingdom</country></nlm:aff><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Osuna Cabello, Maria" sort="Osuna Cabello, Maria" uniqKey="Osuna Cabello M" first="Maria" last="Osuna-Cabello">Maria Osuna-Cabello</name><affiliation wicri:level="1"><nlm:aff id="aff1">Drug Discovery Unit, Division of Biological Chemistry and Drug Discovery, School of Life Sciences,<institution>University of Dundee</institution>, Sir James Black Centre, Dundee, DD1 5EH,<country>United Kingdom</country></nlm:aff><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Read, Kevin D" sort="Read, Kevin D" uniqKey="Read K" first="Kevin D." last="Read">Kevin D. Read</name><affiliation wicri:level="1"><nlm:aff id="aff1">Drug Discovery Unit, Division of Biological Chemistry and Drug Discovery, School of Life Sciences,<institution>University of Dundee</institution>, Sir James Black Centre, Dundee, DD1 5EH,<country>United Kingdom</country></nlm:aff><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Green, Simon R" sort="Green, Simon R" uniqKey="Green S" first="Simon R." last="Green">Simon R. Green</name><affiliation wicri:level="1"><nlm:aff id="aff1">Drug Discovery Unit, Division of Biological Chemistry and Drug Discovery, School of Life Sciences,<institution>University of Dundee</institution>, Sir James Black Centre, Dundee, DD1 5EH,<country>United Kingdom</country></nlm:aff><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Lamprecht, Dirk A" sort="Lamprecht, Dirk A" uniqKey="Lamprecht D" first="Dirk A." last="Lamprecht">Dirk A. Lamprecht</name><affiliation wicri:level="1"><nlm:aff id="aff7"><institution>Africa Health Research Institute (AHRI)</institution>, K-RITH Tower Building Level 3, 719 Umbilo Road, Durban, 4001,<country>South Africa</country></nlm:aff><country xml:lang="fr">Afrique du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Finin, Peter M" sort="Finin, Peter M" uniqKey="Finin P" first="Peter M." last="Finin">Peter M. Finin</name><affiliation wicri:level="1"><nlm:aff id="aff7"><institution>Africa Health Research Institute (AHRI)</institution>, K-RITH Tower Building Level 3, 719 Umbilo Road, Durban, 4001,<country>South Africa</country></nlm:aff><country xml:lang="fr">Afrique du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Steyn, Adrie J C" sort="Steyn, Adrie J C" uniqKey="Steyn A" first="Adrie J. C." last="Steyn">Adrie J. C. Steyn</name><affiliation wicri:level="1"><nlm:aff id="aff7"><institution>Africa Health Research Institute (AHRI)</institution>, K-RITH Tower Building Level 3, 719 Umbilo Road, Durban, 4001,<country>South Africa</country></nlm:aff><country xml:lang="fr">Afrique du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation><affiliation wicri:level="1"><nlm:aff id="aff8">Department of Microbiology,<institution>University of Alabama at Birmingham</institution>, 1720 Second Avenue South, Birmingham, Alabama 35294-2170,<country>United States</country></nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Ioerger, Thomas R" sort="Ioerger, Thomas R" uniqKey="Ioerger T" first="Thomas R." last="Ioerger">Thomas R. Ioerger</name><affiliation wicri:level="1"><nlm:aff id="aff9">Department of Computer Science and Engineering,<institution>Texas A&M University</institution>, College Station, Texas 77843,<country>United States</country></nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Sacchettini, Jim" sort="Sacchettini, Jim" uniqKey="Sacchettini J" first="Jim" last="Sacchettini">Jim Sacchettini</name><affiliation wicri:level="1"><nlm:aff id="aff9">Department of Computer Science and Engineering,<institution>Texas A&M University</institution>, College Station, Texas 77843,<country>United States</country></nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Rhee, Kyu Y" sort="Rhee, Kyu Y" uniqKey="Rhee K" first="Kyu Y." last="Rhee">Kyu Y. Rhee</name><affiliation wicri:level="1"><nlm:aff id="aff10">Division of Infectious Diseases, Weill Department of Medicine,<institution>Weill Cornell Medical College</institution>, New York, New York 10065,<country>United States</country></nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Arora, Kriti" sort="Arora, Kriti" uniqKey="Arora K" first="Kriti" last="Arora">Kriti Arora</name><affiliation wicri:level="1"><nlm:aff id="aff2">Tuberculosis Research Section, Laboratory of Clinical Immunology and Microbiology, National Institute of Allergy and Infectious Disease,<institution>National Institutes of Health</institution>, 9000 Rockville Pike, Bethesda, Maryland 20892,<country>United States</country></nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Barry, Clifton E" sort="Barry, Clifton E" uniqKey="Barry C" first="Clifton E." last="Barry">Clifton E. Barry</name><affiliation wicri:level="1"><nlm:aff id="aff2">Tuberculosis Research Section, Laboratory of Clinical Immunology and Microbiology, National Institute of Allergy and Infectious Disease,<institution>National Institutes of Health</institution>, 9000 Rockville Pike, Bethesda, Maryland 20892,<country>United States</country></nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation><affiliation wicri:level="1"><nlm:aff id="aff3">Institute of Infectious Disease and Molecular Medicine,<institution>University of Cape Town</institution>, Rondebosch, 7701,<country>South Africa</country></nlm:aff><country xml:lang="fr">Afrique du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Wyatt, Paul G" sort="Wyatt, Paul G" uniqKey="Wyatt P" first="Paul G." last="Wyatt">Paul G. Wyatt</name><affiliation wicri:level="1"><nlm:aff id="aff1">Drug Discovery Unit, Division of Biological Chemistry and Drug Discovery, School of Life Sciences,<institution>University of Dundee</institution>, Sir James Black Centre, Dundee, DD1 5EH,<country>United Kingdom</country></nlm:aff><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Boshoff, Helena I M" sort="Boshoff, Helena I M" uniqKey="Boshoff H" first="Helena I. M." last="Boshoff">Helena I. M. Boshoff</name><affiliation wicri:level="1"><nlm:aff id="aff2">Tuberculosis Research Section, Laboratory of Clinical Immunology and Microbiology, National Institute of Allergy and Infectious Disease,<institution>National Institutes of Health</institution>, 9000 Rockville Pike, Bethesda, Maryland 20892,<country>United States</country></nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author></analytic><series><title level="j">ACS Infectious Diseases</title><idno type="eISSN">2373-8227</idno><imprint><date when="2018">2018</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p content-type="toc-graphic"><graphic xlink:href="id-2017-002759_0014" id="ab-tgr1"></graphic></p><p><italic>Mycobacterium tuberculosis</italic> (<italic>MTb</italic>) possesses
two nonproton pumping type II NADH dehydrogenase (NDH-2)
enzymes which are predicted to be jointly essential for respiratory
metabolism. Furthermore, the structure of a closely related bacterial
NDH-2 has been reported recently, allowing for the structure-based
design of small-molecule inhibitors. Herein, we disclose <italic>MTb</italic> whole-cell structure–activity relationships (SARs) for a series of 2-mercapto-quinazolinones which target the <italic>ndh</italic> encoded NDH-2 with nanomolar potencies. The compounds were inactivated by glutathione-dependent adduct formation as well as quinazolinone oxidation in microsomes. Pharmacokinetic studies demonstrated modest bioavailability and compound exposures. Resistance to the compounds in <italic>MTb</italic> was conferred by promoter mutations in the alternative nonessential NDH-2 encoded by <italic>ndhA</italic> in <italic>MTb</italic>. Bioenergetic analyses revealed a decrease in oxygen consumption rates in response to inhibitor in cells in which membrane potential was uncoupled from ATP production, while inverted membrane vesicles showed mercapto-quinazolinone-dependent inhibition of ATP production when NADH was the electron donor to the respiratory chain. Enzyme kinetic studies further demonstrated noncompetitive inhibition, suggesting binding of this scaffold to an allosteric site. In summary, while the initial <italic>MTb</italic> SAR showed limited improvement in potency, these results, combined with structural information on the bacterial protein, will aid in the future discovery of new and improved NDH-2 inhibitors.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct><analytic><author><name sortKey="Horsburgh, C R J" uniqKey="Horsburgh C">C. R. J. Horsburgh</name></author><author><name sortKey="Barry, C E I" uniqKey="Barry C">C. E. I. Barry</name></author><author><name sortKey="Lange, C" uniqKey="Lange C">C. Lange</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Iseman, M D" uniqKey="Iseman M">M. D. Iseman</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Migliori, G B" uniqKey="Migliori G">G. 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Vanoni</name></author></analytic></biblStruct></listBibl></div1></back></TEI><affiliations><list><country><li>Afrique du Sud</li><li>Royaume-Uni</li><li>États-Unis</li></country></list><tree><country name="Royaume-Uni"><noRegion><name sortKey="Murugesan, Dinakaran" sort="Murugesan, Dinakaran" uniqKey="Murugesan D" first="Dinakaran" last="Murugesan">Dinakaran Murugesan</name></noRegion><name sortKey="Bayliss, Tracy" sort="Bayliss, Tracy" uniqKey="Bayliss T" first="Tracy" last="Bayliss">Tracy Bayliss</name><name sortKey="Ellis, Lucy" sort="Ellis, Lucy" uniqKey="Ellis L" first="Lucy" last="Ellis">Lucy Ellis</name><name sortKey="Epemolu, Ola" sort="Epemolu, Ola" uniqKey="Epemolu O" first="Ola" last="Epemolu">Ola Epemolu</name><name sortKey="Ferguson, Liam" sort="Ferguson, Liam" uniqKey="Ferguson L" first="Liam" last="Ferguson">Liam Ferguson</name><name sortKey="Green, Kirsteen" sort="Green, Kirsteen" uniqKey="Green K" first="Kirsteen" last="Green">Kirsteen Green</name><name sortKey="Green, Simon R" sort="Green, Simon R" uniqKey="Green S" first="Simon R." last="Green">Simon R. 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Read</name><name sortKey="Riley, Jennifer" sort="Riley, Jennifer" uniqKey="Riley J" first="Jennifer" last="Riley">Jennifer Riley</name><name sortKey="Scullion, Paul" sort="Scullion, Paul" uniqKey="Scullion P" first="Paul" last="Scullion">Paul Scullion</name><name sortKey="Shishikura, Yoko" sort="Shishikura, Yoko" uniqKey="Shishikura Y" first="Yoko" last="Shishikura">Yoko Shishikura</name><name sortKey="Wyatt, Paul G" sort="Wyatt, Paul G" uniqKey="Wyatt P" first="Paul G." last="Wyatt">Paul G. Wyatt</name></country><country name="États-Unis"><noRegion><name sortKey="Prosser, Gareth A" sort="Prosser, Gareth A" uniqKey="Prosser G" first="Gareth A." last="Prosser">Gareth A. Prosser</name></noRegion><name sortKey="Arora, Kriti" sort="Arora, Kriti" uniqKey="Arora K" first="Kriti" last="Arora">Kriti Arora</name><name sortKey="Barry, Clifton E" sort="Barry, Clifton E" uniqKey="Barry C" first="Clifton E." last="Barry">Clifton E. Barry</name><name sortKey="Boshoff, Helena I M" sort="Boshoff, Helena I M" uniqKey="Boshoff H" first="Helena I. M." last="Boshoff">Helena I. M. Boshoff</name><name sortKey="Ioerger, Thomas R" sort="Ioerger, Thomas R" uniqKey="Ioerger T" first="Thomas R." last="Ioerger">Thomas R. Ioerger</name><name sortKey="Rhee, Kyu Y" sort="Rhee, Kyu Y" uniqKey="Rhee K" first="Kyu Y." last="Rhee">Kyu Y. Rhee</name><name sortKey="Sacchettini, Jim" sort="Sacchettini, Jim" uniqKey="Sacchettini J" first="Jim" last="Sacchettini">Jim Sacchettini</name><name sortKey="Steyn, Adrie J C" sort="Steyn, Adrie J C" uniqKey="Steyn A" first="Adrie J. C." last="Steyn">Adrie J. C. Steyn</name></country><country name="Afrique du Sud"><noRegion><name sortKey="Soares De Melo, Candice" sort="Soares De Melo, Candice" uniqKey="Soares De Melo C" first="Candice" last="Soares De Melo">Candice Soares De Melo</name></noRegion><name sortKey="Barry, Clifton E" sort="Barry, Clifton E" uniqKey="Barry C" first="Clifton E." last="Barry">Clifton E. Barry</name><name sortKey="Chibale, Kelly" sort="Chibale, Kelly" uniqKey="Chibale K" first="Kelly" last="Chibale">Kelly Chibale</name><name sortKey="Chibale, Kelly" sort="Chibale, Kelly" uniqKey="Chibale K" first="Kelly" last="Chibale">Kelly Chibale</name><name sortKey="Chibale, Kelly" sort="Chibale, Kelly" uniqKey="Chibale K" first="Kelly" last="Chibale">Kelly Chibale</name><name sortKey="Feng, Tzu Shean" sort="Feng, Tzu Shean" uniqKey="Feng T" first="Tzu-Shean" last="Feng">Tzu-Shean Feng</name><name sortKey="Finin, Peter M" sort="Finin, Peter M" uniqKey="Finin P" first="Peter M." last="Finin">Peter M. Finin</name><name sortKey="Lamprecht, Dirk A" sort="Lamprecht, Dirk A" uniqKey="Lamprecht D" first="Dirk A." last="Lamprecht">Dirk A. Lamprecht</name><name sortKey="Mizrahi, Valerie" sort="Mizrahi, Valerie" uniqKey="Mizrahi V" first="Valerie" last="Mizrahi">Valerie Mizrahi</name><name sortKey="Mizrahi, Valerie" sort="Mizrahi, Valerie" uniqKey="Mizrahi V" first="Valerie" last="Mizrahi">Valerie Mizrahi</name><name sortKey="Steyn, Adrie J C" sort="Steyn, Adrie J C" uniqKey="Steyn A" first="Adrie J. C." last="Steyn">Adrie J. C. Steyn</name><name sortKey="Street, Leslie J" sort="Street, Leslie J" uniqKey="Street L" first="Leslie J." last="Street">Leslie J. Street</name><name sortKey="Warner, Digby F" sort="Warner, Digby F" uniqKey="Warner D" first="Digby F." last="Warner">Digby F. Warner</name><name sortKey="Warner, Digby F" sort="Warner, Digby F" uniqKey="Warner D" first="Digby F." last="Warner">Digby F. 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