Binding of Gemini Bisbenzimidazole Drugs with Human Telomeric G-Quadruplex Dimers: Effect of the Spacer in the Design of Potent Telomerase Inhibitors
Identifieur interne : 002296 ( Main/Merge ); précédent : 002295; suivant : 002297Binding of Gemini Bisbenzimidazole Drugs with Human Telomeric G-Quadruplex Dimers: Effect of the Spacer in the Design of Potent Telomerase Inhibitors
Auteurs : Ananya Paul [Inde] ; Akash K. Jain [Inde] ; Santosh K. Misra [Inde] ; Basudeb Maji ; K. Muniyappa [Inde] ; Santanu Bhattacharya [Inde]Source :
- PLoS ONE [ 1932-6203 ] ; 2012.
Descripteurs français
- KwdFr :
- ADN simple brin (génétique), Antienzymes (pharmacologie), Antinéoplasiques (pharmacologie), Bisbenzimide (pharmacologie), Chlorure de potassium (), Colorants fluorescents (pharmacologie), Concentration inhibitrice 50, Dichroïsme circulaire, Dimérisation, G-quadruplexes, Humains, Ligands, Modèles moléculaires, Pliage des protéines, Telomerase (), Telomerase (antagonistes et inhibiteurs), Température, Température élevée, Télomère (ultrastructure).
- MESH :
- antagonistes et inhibiteurs : Telomerase.
- génétique : ADN simple brin.
- pharmacologie : Antienzymes, Antinéoplasiques, Bisbenzimide, Colorants fluorescents.
- Chlorure de potassium, Concentration inhibitrice 50, Dichroïsme circulaire, Dimérisation, G-quadruplexes, Humains, Ligands, Modèles moléculaires, Pliage des protéines, Telomerase, Température, Température élevée, Télomère.
English descriptors
- KwdEn :
- Antineoplastic Agents (pharmacology), Bisbenzimidazole (pharmacology), Circular Dichroism, DNA, Single-Stranded (genetics), Dimerization, Enzyme Inhibitors (pharmacology), Fluorescent Dyes (pharmacology), G-Quadruplexes, Hot Temperature, Humans, Inhibitory Concentration 50, Ligands, Models, Molecular, Potassium Chloride (chemistry), Protein Folding, Telomerase (antagonists & inhibitors), Telomerase (chemistry), Telomere (ultrastructure), Temperature.
- MESH :
- chemical , antagonists & inhibitors : Telomerase.
- chemical , chemistry : Potassium Chloride, Telomerase.
- chemical , genetics : DNA, Single-Stranded.
- chemical , pharmacology : Antineoplastic Agents, Bisbenzimidazole, Enzyme Inhibitors, Fluorescent Dyes.
- ultrastructure : Telomere.
- Circular Dichroism, Dimerization, G-Quadruplexes, Hot Temperature, Humans, Inhibitory Concentration 50, Ligands, Models, Molecular, Protein Folding, Temperature.
Abstract
The study of anticancer agents that act via stabilization of telomeric G-quadruplex DNA (G4DNA) is important because such agents often inhibit telomerase activity. Several types of G4DNA binding ligands are known. In these studies, the target structures often involve a single G4 DNA unit formed by short DNA telomeric sequences. However, the 3′-terminal single-stranded human telomeric DNA can form higher-order structures by clustering consecutive quadruplex units (dimers or n-mers). Herein, we present new synthetic gemini (twin) bisbenzimidazole ligands, in which the oligo-oxyethylene spacers join the two bisbenzimidazole units for the recognition of both monomeric and dimeric G4DNA, derived from d(T2AG3)4 and d(T2AG3)8 human telomeric DNA, respectively. The spacer between the two bisbenzimidazoles in the geminis plays a critical role in the G4DNA stability. We report here (i) synthesis of new effective gemini anticancer agents that are selectively more toxic towards the cancer cells than the corresponding normal cells; (ii) formation and characterization of G4DNA dimers in solution as well as computational construction of the dimeric G4DNA structures. The gemini ligands direct the folding of the single-stranded DNA into an unusually stable parallel-stranded G4DNA when it was formed in presence of the ligands in KCl solution and the gemini ligands show spacer length dependent potent telomerase inhibition properties.
Url:
DOI: 10.1371/journal.pone.0039467
PubMed: 22737240
PubMed Central: 3380826
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PMC:3380826Le document en format XML
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Centre for Advanced Scientific Research, Bangalore, India</addr-line></nlm:aff><country xml:lang="fr">Inde</country><wicri:regionArea>Chemical Biology Unit, Jawaharlal Nehru Centre for Advanced Scientific Research, Bangalore</wicri:regionArea><wicri:noRegion>Bangalore</wicri:noRegion></affiliation></author></analytic><series><title level="j">PLoS ONE</title><idno type="eISSN">1932-6203</idno><imprint><date when="2012">2012</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Antineoplastic Agents (pharmacology)</term><term>Bisbenzimidazole (pharmacology)</term><term>Circular Dichroism</term><term>DNA, Single-Stranded (genetics)</term><term>Dimerization</term><term>Enzyme Inhibitors (pharmacology)</term><term>Fluorescent Dyes (pharmacology)</term><term>G-Quadruplexes</term><term>Hot Temperature</term><term>Humans</term><term>Inhibitory Concentration 50</term><term>Ligands</term><term>Models, Molecular</term><term>Potassium Chloride (chemistry)</term><term>Protein Folding</term><term>Telomerase (antagonists & inhibitors)</term><term>Telomerase (chemistry)</term><term>Telomere (ultrastructure)</term><term>Temperature</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>ADN simple brin (génétique)</term><term>Antienzymes (pharmacologie)</term><term>Antinéoplasiques (pharmacologie)</term><term>Bisbenzimide (pharmacologie)</term><term>Chlorure de potassium ()</term><term>Colorants fluorescents (pharmacologie)</term><term>Concentration inhibitrice 50</term><term>Dichroïsme circulaire</term><term>Dimérisation</term><term>G-quadruplexes</term><term>Humains</term><term>Ligands</term><term>Modèles moléculaires</term><term>Pliage des protéines</term><term>Telomerase ()</term><term>Telomerase (antagonistes et inhibiteurs)</term><term>Température</term><term>Température élevée</term><term>Télomère (ultrastructure)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="antagonists & inhibitors" xml:lang="en"><term>Telomerase</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Potassium Chloride</term><term>Telomerase</term></keywords><keywords scheme="MESH" type="chemical" qualifier="genetics" xml:lang="en"><term>DNA, Single-Stranded</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antineoplastic Agents</term><term>Bisbenzimidazole</term><term>Enzyme Inhibitors</term><term>Fluorescent Dyes</term></keywords><keywords scheme="MESH" qualifier="antagonistes et inhibiteurs" xml:lang="fr"><term>Telomerase</term></keywords><keywords scheme="MESH" qualifier="génétique" xml:lang="fr"><term>ADN simple brin</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Antienzymes</term><term>Antinéoplasiques</term><term>Bisbenzimide</term><term>Colorants fluorescents</term></keywords><keywords scheme="MESH" qualifier="ultrastructure" xml:lang="en"><term>Telomere</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Circular Dichroism</term><term>Dimerization</term><term>G-Quadruplexes</term><term>Hot Temperature</term><term>Humans</term><term>Inhibitory Concentration 50</term><term>Ligands</term><term>Models, Molecular</term><term>Protein Folding</term><term>Temperature</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Chlorure de potassium</term><term>Concentration inhibitrice 50</term><term>Dichroïsme circulaire</term><term>Dimérisation</term><term>G-quadruplexes</term><term>Humains</term><term>Ligands</term><term>Modèles moléculaires</term><term>Pliage des protéines</term><term>Telomerase</term><term>Température</term><term>Température élevée</term><term>Télomère</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>The study of anticancer agents that act via stabilization of telomeric G-quadruplex DNA (G4DNA) is important because such agents often inhibit telomerase activity. Several types of G4DNA binding ligands are known. In these studies, the target structures often involve a single G4 DNA unit formed by short DNA telomeric sequences. However, the 3′-terminal single-stranded human telomeric DNA can form higher-order structures by clustering consecutive quadruplex units (dimers or n-mers). Herein, we present new synthetic gemini (twin) bisbenzimidazole ligands, in which the oligo-oxyethylene spacers join the two bisbenzimidazole units for the recognition of both monomeric and dimeric G4DNA, derived from d(T2AG3)4 and d(T2AG3)8 human telomeric DNA, respectively. The spacer between the two bisbenzimidazoles in the geminis plays a critical role in the G4DNA stability. We report here (i) synthesis of new effective gemini anticancer agents that are selectively more toxic towards the cancer cells than the corresponding normal cells; (ii) formation and characterization of G4DNA dimers in solution as well as computational construction of the dimeric G4DNA structures. The gemini ligands direct the folding of the single-stranded DNA into an unusually stable parallel-stranded G4DNA when it was formed in presence of the ligands in KCl solution and the gemini ligands show spacer length dependent potent telomerase inhibition properties.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Blackburn, Eh" uniqKey="Blackburn E">EH Blackburn</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Corey, Dr" uniqKey="Corey D">DR Corey</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Temime Smaali, N" uniqKey="Temime Smaali N">N Temime-Smaali</name></author><author><name sortKey="Guittat, L" uniqKey="Guittat L">L Guittat</name></author><author><name sortKey="Sidibe, A" uniqKey="Sidibe A">A Sidibe</name></author><author><name sortKey="Shin Ya, K" uniqKey="Shin Ya K">K Shin-ya</name></author><author><name sortKey="Trentesaux, C" uniqKey="Trentesaux C">C Trentesaux</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Cech, Tr" uniqKey="Cech T">TR Cech</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Uziel, O" uniqKey="Uziel O">O Uziel</name></author><author><name sortKey="Beery, E" uniqKey="Beery E">E Beery</name></author><author><name sortKey="Dronichev, V" uniqKey="Dronichev V">V Dronichev</name></author><author><name sortKey="Samocha, K" uniqKey="Samocha K">K Samocha</name></author><author><name sortKey="Sergei Gryaznov, S" uniqKey="Sergei Gryaznov S">S Sergei Gryaznov</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Kerwin, Sm" uniqKey="Kerwin S">SM Kerwin</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Maizels, N" uniqKey="Maizels N">N Maizels</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Jain, Ak" uniqKey="Jain A">AK Jain</name></author><author><name sortKey="Bhattacharya, S" uniqKey="Bhattacharya S">S Bhattacharya</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Hansel, R" uniqKey="Hansel R">R Hansel</name></author><author><name sortKey="Lohr, F" uniqKey="Lohr F">F Lohr</name></author><author><name sortKey="Foldynova Trantirkova, S" uniqKey="Foldynova Trantirkova S">S Foldynova-Trantirkova</name></author><author><name sortKey="Bamberg, E" uniqKey="Bamberg E">E Bamberg</name></author><author><name sortKey="Trantirek, L" uniqKey="Trantirek L">L Trantirek</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Jixun, D" uniqKey="Jixun D">D Jixun</name></author><author><name sortKey="Megan, C" uniqKey="Megan C">C Megan</name></author><author><name sortKey="Chandanamali, P" uniqKey="Chandanamali P">P Chandanamali</name></author><author><name sortKey="Roger, Aj" uniqKey="Roger A">AJ Roger</name></author><author><name sortKey="Yang, D" uniqKey="Yang D">D 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