Anion inhibitors of the β-carbonic anhydrase from the pathogenic bacterium responsible of tularemia, Francisella tularensis.
Identifieur interne : 001184 ( Main/Exploration ); précédent : 001183; suivant : 001185Anion inhibitors of the β-carbonic anhydrase from the pathogenic bacterium responsible of tularemia, Francisella tularensis.
Auteurs : Sonia Del Prete [Italie] ; Daniela Vullo [Italie] ; Sameh M. Osman [Arabie saoudite] ; Zeid Alothman [Arabie saoudite] ; William A. Donald [Australie] ; Jean-Yves Winum [France] ; Claudiu T. Supuran [Italie] ; Clemente Capasso [Italie]Source :
- Bioorganic & medicinal chemistry [ 1464-3391 ] ; 2017.
Descripteurs français
- KwdFr :
- Acides boroniques (), Acides boroniques (métabolisme), Acides sulfoniques (), Acides sulfoniques (métabolisme), Anions (), Carbonic anhydrases (), Carbonic anhydrases (métabolisme), Données de séquences moléculaires, Francisella tularensis (enzymologie), Humains, Inhibiteurs de l'anhydrase carbonique (), Inhibiteurs de l'anhydrase carbonique (métabolisme), Inhibiteurs de l'anhydrase carbonique (usage thérapeutique), Liaison aux protéines, Perchlorates (), Perchlorates (métabolisme), Relation structure-activité, Séquence d'acides aminés, Tularémie (anatomopathologie), Tularémie (traitement médicamenteux), Zinc ().
- MESH :
- anatomopathologie : Tularémie.
- enzymologie : Francisella tularensis.
- métabolisme : Acides boroniques, Acides sulfoniques, Carbonic anhydrases, Inhibiteurs de l'anhydrase carbonique, Perchlorates.
- traitement médicamenteux : Tularémie.
- usage thérapeutique : Inhibiteurs de l'anhydrase carbonique.
- Acides boroniques, Acides sulfoniques, Anions, Carbonic anhydrases, Données de séquences moléculaires, Humains, Inhibiteurs de l'anhydrase carbonique, Liaison aux protéines, Perchlorates, Relation structure-activité, Séquence d'acides aminés, Zinc.
English descriptors
- KwdEn :
- Amino Acid Sequence, Anions (chemistry), Boronic Acids (chemistry), Boronic Acids (metabolism), Carbonic Anhydrase Inhibitors (chemistry), Carbonic Anhydrase Inhibitors (metabolism), Carbonic Anhydrase Inhibitors (therapeutic use), Carbonic Anhydrases (chemistry), Carbonic Anhydrases (metabolism), Francisella tularensis (enzymology), Humans, Molecular Sequence Data, Perchlorates (chemistry), Perchlorates (metabolism), Protein Binding, Structure-Activity Relationship, Sulfonic Acids (chemistry), Sulfonic Acids (metabolism), Tularemia (drug therapy), Tularemia (pathology), Zinc (chemistry).
- MESH :
- chemical , chemistry : Anions, Boronic Acids, Carbonic Anhydrase Inhibitors, Carbonic Anhydrases, Perchlorates, Sulfonic Acids, Zinc.
- chemical , metabolism : Boronic Acids, Carbonic Anhydrase Inhibitors, Carbonic Anhydrases, Perchlorates, Sulfonic Acids.
- chemical , therapeutic use : Carbonic Anhydrase Inhibitors.
- drug therapy : Tularemia.
- enzymology : Francisella tularensis.
- pathology : Tularemia.
- Amino Acid Sequence, Humans, Molecular Sequence Data, Protein Binding, Structure-Activity Relationship.
Abstract
A β-class carbonic anhydrase (CA, EC 4.2.1.1) from the pathogenic bacterium Francisella tularensis (FtuβCA) was cloned and purified, and the anion inhibition profile was investigated. Based on the measured kinetic parameters for the enzyme catalyzed CO2 hydration reaction (kcat of 9.8×10(5)s(-1) and a kcat/KM of 8.9×10(7)M(-1)s(-1)), FtuβCA is a highly effective enzyme. The activity of FtuβCA was not inhibited by a range of anions that do not typically coordinate Zn(II) effectively, including perchlorate, tetrafluoroborate, and hexafluorophosphate. Surprisingly, some anions which generally complex well with many cations, including Zn(II), also did not effectively inhibit FtuβCA, e.g., fluoride, cyanide, azide, nitrite, bisulphite, sulfate, tellurate, perrhenate, perrhuthenate, and peroxydisulfate. However, the most effective inhibitors were in the range of 90-94µM (sulfamide, sulfamic acid, phenylarsonic and phenylboronic acid). N,N-Diethyldithiocarbamate (KI of 0.31mM) was a moderately potent inhibitor. As Francisella tularensis is the causative agent of tularemia, the discovery of compounds that can interfere with the life cycle of this pathogen may result in novel opportunities to fight antibiotic drug resistance.
DOI: 10.1016/j.bmc.2017.07.033
PubMed: 28754318
Affiliations:
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Osman</name><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia.</nlm:affiliation><country xml:lang="fr">Arabie saoudite</country><wicri:regionArea>Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451</wicri:regionArea><wicri:noRegion>Riyadh 11451</wicri:noRegion></affiliation></author><author><name sortKey="Alothman, Zeid" sort="Alothman, Zeid" uniqKey="Alothman Z" first="Zeid" last="Alothman">Zeid Alothman</name><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia.</nlm:affiliation><country xml:lang="fr">Arabie saoudite</country><wicri:regionArea>Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451</wicri:regionArea><wicri:noRegion>Riyadh 11451</wicri:noRegion></affiliation></author><author><name sortKey="Donald, William A" sort="Donald, William A" uniqKey="Donald W" first="William A" last="Donald">William A. Donald</name><affiliation wicri:level="1"><nlm:affiliation>School of Chemistry, University of New South Wales, Sydney, New South Wales 2052, Australia.</nlm:affiliation><country xml:lang="fr">Australie</country><wicri:regionArea>School of Chemistry, University of New South Wales, Sydney, New South Wales 2052</wicri:regionArea><wicri:noRegion>New South Wales 2052</wicri:noRegion></affiliation></author><author><name sortKey="Winum, Jean Yves" sort="Winum, Jean Yves" uniqKey="Winum J" first="Jean-Yves" last="Winum">Jean-Yves Winum</name><affiliation wicri:level="1"><nlm:affiliation>Institut des Biomolécules Max Mousseron, UMR 5247 CNRS, ENSCM, Université de Montpellier, Bâtiment de Recherche Max Mousseron, Ecole Nationale Supérieure de Chimie de Montpellier, 8 rue de l'Ecole Normale, 34296 Montpellier Cedex, France.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>Institut des Biomolécules Max Mousseron, UMR 5247 CNRS, ENSCM, Université de Montpellier, Bâtiment de Recherche Max Mousseron, Ecole Nationale Supérieure de Chimie de Montpellier, 8 rue de l'Ecole Normale, 34296 Montpellier Cedex</wicri:regionArea><wicri:noRegion>34296 Montpellier Cedex</wicri:noRegion><wicri:noRegion>34296 Montpellier Cedex</wicri:noRegion></affiliation></author><author><name sortKey="Supuran, Claudiu T" sort="Supuran, Claudiu T" uniqKey="Supuran C" first="Claudiu T" last="Supuran">Claudiu T. Supuran</name><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia; School of Chemistry, University of New South Wales, Sydney, New South Wales 2052, Australia; Università degli Studi di Firenze, Dipartimento Neurofarba, Sezione di Scienze Farmaceutiche e Nutraceutiche, Via U. Schiff 6, 50019 Sesto Fiorentino, Florence, Italy. Electronic address: claudiu.supuran@unifi.it.</nlm:affiliation><country xml:lang="fr">Italie</country><wicri:regionArea>Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia; School of Chemistry, University of New South Wales, Sydney, New South Wales 2052, Australia; Università degli Studi di Firenze, Dipartimento Neurofarba, Sezione di Scienze Farmaceutiche e Nutraceutiche, Via U. Schiff 6, 50019 Sesto Fiorentino, Florence</wicri:regionArea><wicri:noRegion>Florence</wicri:noRegion></affiliation></author><author><name sortKey="Capasso, Clemente" sort="Capasso, Clemente" uniqKey="Capasso C" first="Clemente" last="Capasso">Clemente Capasso</name><affiliation wicri:level="1"><nlm:affiliation>Istituto di Bioscienze e Biorisorse, CNR, Via Pietro Castellino 111, Napoli, Italy. Electronic address: clemente.capasso@ibbr.cnr.it.</nlm:affiliation><country xml:lang="fr">Italie</country><wicri:regionArea>Istituto di Bioscienze e Biorisorse, CNR, Via Pietro Castellino 111, Napoli</wicri:regionArea><wicri:noRegion>Napoli</wicri:noRegion></affiliation></author></analytic><series><title level="j">Bioorganic & medicinal chemistry</title><idno type="eISSN">1464-3391</idno><imprint><date when="2017" type="published">2017</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Amino Acid Sequence</term><term>Anions (chemistry)</term><term>Boronic Acids (chemistry)</term><term>Boronic Acids (metabolism)</term><term>Carbonic Anhydrase Inhibitors (chemistry)</term><term>Carbonic Anhydrase Inhibitors (metabolism)</term><term>Carbonic Anhydrase Inhibitors (therapeutic use)</term><term>Carbonic Anhydrases (chemistry)</term><term>Carbonic Anhydrases (metabolism)</term><term>Francisella tularensis (enzymology)</term><term>Humans</term><term>Molecular Sequence Data</term><term>Perchlorates (chemistry)</term><term>Perchlorates (metabolism)</term><term>Protein Binding</term><term>Structure-Activity Relationship</term><term>Sulfonic Acids (chemistry)</term><term>Sulfonic Acids (metabolism)</term><term>Tularemia (drug therapy)</term><term>Tularemia (pathology)</term><term>Zinc (chemistry)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Acides boroniques ()</term><term>Acides boroniques (métabolisme)</term><term>Acides sulfoniques ()</term><term>Acides sulfoniques (métabolisme)</term><term>Anions ()</term><term>Carbonic anhydrases ()</term><term>Carbonic anhydrases (métabolisme)</term><term>Données de séquences moléculaires</term><term>Francisella tularensis (enzymologie)</term><term>Humains</term><term>Inhibiteurs de l'anhydrase carbonique ()</term><term>Inhibiteurs de l'anhydrase carbonique (métabolisme)</term><term>Inhibiteurs de l'anhydrase carbonique (usage thérapeutique)</term><term>Liaison aux protéines</term><term>Perchlorates ()</term><term>Perchlorates (métabolisme)</term><term>Relation structure-activité</term><term>Séquence d'acides aminés</term><term>Tularémie (anatomopathologie)</term><term>Tularémie (traitement médicamenteux)</term><term>Zinc ()</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Anions</term><term>Boronic Acids</term><term>Carbonic Anhydrase Inhibitors</term><term>Carbonic Anhydrases</term><term>Perchlorates</term><term>Sulfonic Acids</term><term>Zinc</term></keywords><keywords scheme="MESH" type="chemical" qualifier="metabolism" xml:lang="en"><term>Boronic Acids</term><term>Carbonic Anhydrase Inhibitors</term><term>Carbonic Anhydrases</term><term>Perchlorates</term><term>Sulfonic Acids</term></keywords><keywords scheme="MESH" type="chemical" qualifier="therapeutic use" xml:lang="en"><term>Carbonic Anhydrase Inhibitors</term></keywords><keywords scheme="MESH" qualifier="anatomopathologie" xml:lang="fr"><term>Tularémie</term></keywords><keywords scheme="MESH" qualifier="drug therapy" xml:lang="en"><term>Tularemia</term></keywords><keywords scheme="MESH" qualifier="enzymologie" xml:lang="fr"><term>Francisella tularensis</term></keywords><keywords scheme="MESH" qualifier="enzymology" xml:lang="en"><term>Francisella tularensis</term></keywords><keywords scheme="MESH" qualifier="métabolisme" xml:lang="fr"><term>Acides boroniques</term><term>Acides sulfoniques</term><term>Carbonic anhydrases</term><term>Inhibiteurs de l'anhydrase carbonique</term><term>Perchlorates</term></keywords><keywords scheme="MESH" qualifier="pathology" xml:lang="en"><term>Tularemia</term></keywords><keywords scheme="MESH" qualifier="traitement médicamenteux" xml:lang="fr"><term>Tularémie</term></keywords><keywords scheme="MESH" qualifier="usage thérapeutique" xml:lang="fr"><term>Inhibiteurs de l'anhydrase carbonique</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Amino Acid Sequence</term><term>Humans</term><term>Molecular Sequence Data</term><term>Protein Binding</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Acides boroniques</term><term>Acides sulfoniques</term><term>Anions</term><term>Carbonic anhydrases</term><term>Données de séquences moléculaires</term><term>Humains</term><term>Inhibiteurs de l'anhydrase carbonique</term><term>Liaison aux protéines</term><term>Perchlorates</term><term>Relation structure-activité</term><term>Séquence d'acides aminés</term><term>Zinc</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">A β-class carbonic anhydrase (CA, EC 4.2.1.1) from the pathogenic bacterium Francisella tularensis (FtuβCA) was cloned and purified, and the anion inhibition profile was investigated. Based on the measured kinetic parameters for the enzyme catalyzed CO2 hydration reaction (kcat of 9.8×10(5)s(-1) and a kcat/KM of 8.9×10(7)M(-1)s(-1)), FtuβCA is a highly effective enzyme. The activity of FtuβCA was not inhibited by a range of anions that do not typically coordinate Zn(II) effectively, including perchlorate, tetrafluoroborate, and hexafluorophosphate. Surprisingly, some anions which generally complex well with many cations, including Zn(II), also did not effectively inhibit FtuβCA, e.g., fluoride, cyanide, azide, nitrite, bisulphite, sulfate, tellurate, perrhenate, perrhuthenate, and peroxydisulfate. However, the most effective inhibitors were in the range of 90-94µM (sulfamide, sulfamic acid, phenylarsonic and phenylboronic acid). N,N-Diethyldithiocarbamate (KI of 0.31mM) was a moderately potent inhibitor. As Francisella tularensis is the causative agent of tularemia, the discovery of compounds that can interfere with the life cycle of this pathogen may result in novel opportunities to fight antibiotic drug resistance.</div></front></TEI><affiliations><list><country><li>Arabie saoudite</li><li>Australie</li><li>France</li><li>Italie</li></country></list><tree><country name="Italie"><noRegion><name sortKey="Del Prete, Sonia" sort="Del Prete, Sonia" uniqKey="Del Prete S" first="Sonia" last="Del Prete">Sonia Del Prete</name></noRegion><name sortKey="Capasso, Clemente" sort="Capasso, Clemente" uniqKey="Capasso C" first="Clemente" last="Capasso">Clemente Capasso</name><name sortKey="Supuran, Claudiu T" sort="Supuran, Claudiu T" uniqKey="Supuran C" first="Claudiu T" last="Supuran">Claudiu T. Supuran</name><name sortKey="Vullo, Daniela" sort="Vullo, Daniela" uniqKey="Vullo D" first="Daniela" last="Vullo">Daniela Vullo</name></country><country name="Arabie saoudite"><noRegion><name sortKey="Osman, Sameh M" sort="Osman, Sameh M" uniqKey="Osman S" first="Sameh M" last="Osman">Sameh M. Osman</name></noRegion><name sortKey="Alothman, Zeid" sort="Alothman, Zeid" uniqKey="Alothman Z" first="Zeid" last="Alothman">Zeid Alothman</name></country><country name="Australie"><noRegion><name sortKey="Donald, William A" sort="Donald, William A" uniqKey="Donald W" first="William A" last="Donald">William A. Donald</name></noRegion></country><country name="France"><noRegion><name sortKey="Winum, Jean Yves" sort="Winum, Jean Yves" uniqKey="Winum J" first="Jean-Yves" last="Winum">Jean-Yves Winum</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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