Platinum(II) Phenanthroimidazoles for Targeting Telomeric G‐Quadruplexes
Identifieur interne : 002177 ( Istex/Curation ); précédent : 002176; suivant : 002178Platinum(II) Phenanthroimidazoles for Targeting Telomeric G‐Quadruplexes
Auteurs : Katherine J. Castor ; Johanna Mancini [Canada] ; Johanna Fakhoury ; Johanna Weill ; Johanna Kieltyka ; Johanna Englebienne ; Nicole Avakyan ; Nicole Mittermaier ; Nicole Autexier [Canada] ; Nicole Moitessier ; Nicole SleimanSource :
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Abstract
A rationally designed progression of phenanthroimidazole platinum(II) complexes were examined for their ability to target telomere‐derived intramolecular G‐quadruplex DNA. Through the use of circular dichroism, fluorescence displacement assays, and molecular modeling we show that these complexes template and stabilize G‐quadruplexes from sequences based on the human telomeric repeat (TTAGGG)n. The greatest stabilization was observed for the p‐chlorophenyl derivative 6 (G4DC50=0.31 μM). We also show that the G‐quadruplex binding complexes are able to inhibit telomerase activity through a modified telomerase repeat amplification protocol (TRAP‐LIG assay). Preliminary cell studies show that complex 6 is preferentially cytotoxic toward cancer over normal cell lines, indicating its potential use in cancer therapy.
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DOI: 10.1002/cmdc.201100453
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Katherine J. Castor<affiliation><mods:affiliation>Department of Chemistry, McGill University, 801 Sherbrooke West, Montreal, QC, H3A 2K6 (Canada), Fax: (+1) 514‐398‐3797</mods:affiliation><wicri:noCountry code="subField">(+1) 514‐398‐3797</wicri:noCountry></affiliation><affiliation><mods:affiliation>Department of Chemistry, McGill University, 801 Sherbrooke West, Montreal, QC, H3A 2K6 (Canada), Fax: (+1) 514‐398‐3797</mods:affiliation><wicri:noCountry code="subField">(+1) 514‐398‐3797</wicri:noCountry></affiliation><affiliation><mods:affiliation>Department of Chemistry, McGill University, 801 Sherbrooke West, Montreal, QC, H3A 2K6 (Canada), Fax: (+1) 514‐398‐3797</mods:affiliation><wicri:noCountry code="subField">(+1) 514‐398‐3797</wicri:noCountry></affiliation><affiliation><mods:affiliation>Department of Chemistry, McGill University, 801 Sherbrooke West, Montreal, QC, H3A 2K6 (Canada), Fax: (+1) 514‐398‐3797</mods:affiliation><wicri:noCountry code="subField">(+1) 514‐398‐3797</wicri:noCountry></affiliation><affiliation><mods:affiliation>Department of Chemistry, McGill University, 801 Sherbrooke West, Montreal, QC, H3A 2K6 (Canada), Fax: (+1) 514‐398‐3797</mods:affiliation><wicri:noCountry code="subField">(+1) 514‐398‐3797</wicri:noCountry></affiliation><affiliation><mods:affiliation>Department of Chemistry, McGill University, 801 Sherbrooke West, Montreal, QC, H3A 2K6 (Canada), Fax: (+1) 514‐398‐3797</mods:affiliation><wicri:noCountry code="subField">(+1) 514‐398‐3797</wicri:noCountry></affiliation><affiliation><mods:affiliation>Department of Chemistry, McGill University, 801 Sherbrooke West, Montreal, QC, H3A 2K6 (Canada), Fax: (+1) 514‐398‐3797</mods:affiliation><wicri:noCountry code="subField">(+1) 514‐398‐3797</wicri:noCountry></affiliation><affiliation><mods:affiliation>Chantal Autexier, Departments of Anatomy and Cell Biology and Experimental Medicine, McGill University, Lady Davis Institute of Medical Research, 3755 Côte Ste‐Catherine Road, Montreal, QC, H3T 1E2 (Canada)Nicolas Moitessier, Department of Chemistry, McGill University, 801 Sherbrooke West, Montreal, QC, H3A 2K6 (Canada), Fax: (+1) 514‐398‐3797Hanadi F. Sleiman, Department of Chemistry, McGill University, 801 Sherbrooke West, Montreal, QC, H3A 2K6 (Canada), Fax: (+1) 514‐398‐3797</mods:affiliation><wicri:noCountry code="subField">(+1) 514‐398‐3797</wicri:noCountry></affiliation><affiliation><mods:affiliation>Chantal Autexier, Departments of Anatomy and Cell Biology and Experimental Medicine, McGill University, Lady Davis Institute of Medical Research, 3755 Côte Ste‐Catherine Road, Montreal, QC, H3T 1E2 (Canada)Nicolas Moitessier, Department of Chemistry, McGill University, 801 Sherbrooke West, Montreal, QC, H3A 2K6 (Canada), Fax: (+1) 514‐398‐3797Hanadi F. Sleiman, Department of Chemistry, McGill University, 801 Sherbrooke West, Montreal, QC, H3A 2K6 (Canada), Fax: (+1) 514‐398‐3797</mods:affiliation><wicri:noCountry code="subField">(+1) 514‐398‐3797</wicri:noCountry></affiliation>Le document en format XML
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Castor</name><affiliation><mods:affiliation>Department of Chemistry, McGill University, 801 Sherbrooke West, Montreal, QC, H3A 2K6 (Canada), Fax: (+1) 514‐398‐3797</mods:affiliation><wicri:noCountry code="subField">(+1) 514‐398‐3797</wicri:noCountry></affiliation></author><author><name sortKey="Mancini, Johanna" sort="Mancini, Johanna" uniqKey="Mancini J" first="Johanna" last="Mancini">Johanna Mancini</name><affiliation wicri:level="1"><mods:affiliation>Departments of Anatomy and Cell Biology and Experimental Medicine, McGill University, Lady Davis Institute of Medical Research, 3755 Côte Ste‐Catherine Road, Montreal, QC, H3T 1E2 (Canada)</mods:affiliation><country xml:lang="fr">Canada</country><wicri:regionArea>Departments of Anatomy and Cell Biology and Experimental Medicine, McGill University, Lady Davis Institute of Medical Research, 3755 Côte Ste‐Catherine Road, Montreal, QC</wicri:regionArea></affiliation></author><author><name sortKey="Fakhoury, Johanna" sort="Fakhoury, Johanna" uniqKey="Fakhoury J" first="Johanna" last="Fakhoury">Johanna Fakhoury</name><affiliation><mods:affiliation>Department of Chemistry, McGill University, 801 Sherbrooke West, Montreal, QC, H3A 2K6 (Canada), Fax: (+1) 514‐398‐3797</mods:affiliation><wicri:noCountry code="subField">(+1) 514‐398‐3797</wicri:noCountry></affiliation></author><author><name sortKey="Weill, Johanna" sort="Weill, Johanna" uniqKey="Weill J" first="Johanna" last="Weill">Johanna Weill</name><affiliation><mods:affiliation>Department of Chemistry, McGill University, 801 Sherbrooke West, Montreal, QC, H3A 2K6 (Canada), Fax: (+1) 514‐398‐3797</mods:affiliation><wicri:noCountry code="subField">(+1) 514‐398‐3797</wicri:noCountry></affiliation></author><author><name sortKey="Kieltyka, Johanna" sort="Kieltyka, Johanna" uniqKey="Kieltyka J" first="Johanna" last="Kieltyka">Johanna Kieltyka</name><affiliation><mods:affiliation>Department of Chemistry, McGill University, 801 Sherbrooke West, Montreal, QC, H3A 2K6 (Canada), Fax: (+1) 514‐398‐3797</mods:affiliation><wicri:noCountry code="subField">(+1) 514‐398‐3797</wicri:noCountry></affiliation></author><author><name sortKey="Englebienne, Johanna" sort="Englebienne, Johanna" uniqKey="Englebienne J" first="Johanna" last="Englebienne">Johanna Englebienne</name><affiliation><mods:affiliation>Department of Chemistry, McGill University, 801 Sherbrooke West, Montreal, QC, H3A 2K6 (Canada), Fax: (+1) 514‐398‐3797</mods:affiliation><wicri:noCountry code="subField">(+1) 514‐398‐3797</wicri:noCountry></affiliation></author><author><name sortKey="Avakyan, Nicole" sort="Avakyan, Nicole" uniqKey="Avakyan N" first="Nicole" last="Avakyan">Nicole Avakyan</name><affiliation><mods:affiliation>Department of Chemistry, McGill University, 801 Sherbrooke West, Montreal, QC, H3A 2K6 (Canada), Fax: (+1) 514‐398‐3797</mods:affiliation><wicri:noCountry code="subField">(+1) 514‐398‐3797</wicri:noCountry></affiliation></author><author><name sortKey="Mittermaier, Nicole" sort="Mittermaier, Nicole" uniqKey="Mittermaier N" first="Nicole" last="Mittermaier">Nicole Mittermaier</name><affiliation><mods:affiliation>Department of Chemistry, McGill University, 801 Sherbrooke West, Montreal, QC, H3A 2K6 (Canada), Fax: (+1) 514‐398‐3797</mods:affiliation><wicri:noCountry code="subField">(+1) 514‐398‐3797</wicri:noCountry></affiliation></author><author><name sortKey="Autexier, Nicole" sort="Autexier, Nicole" uniqKey="Autexier N" first="Nicole" last="Autexier">Nicole Autexier</name><affiliation wicri:level="1"><mods:affiliation>Departments of Anatomy and Cell Biology and Experimental Medicine, McGill University, Lady Davis Institute of Medical Research, 3755 Côte Ste‐Catherine Road, Montreal, QC, H3T 1E2 (Canada)</mods:affiliation><country xml:lang="fr">Canada</country><wicri:regionArea>Departments of Anatomy and Cell Biology and Experimental Medicine, McGill University, Lady Davis Institute of Medical Research, 3755 Côte Ste‐Catherine Road, Montreal, QC</wicri:regionArea></affiliation><affiliation><mods:affiliation>Chantal Autexier, Departments of Anatomy and Cell Biology and Experimental Medicine, McGill University, Lady Davis Institute of Medical Research, 3755 Côte Ste‐Catherine Road, Montreal, QC, H3T 1E2 (Canada)Nicolas Moitessier, Department of Chemistry, McGill University, 801 Sherbrooke West, Montreal, QC, H3A 2K6 (Canada), Fax: (+1) 514‐398‐3797Hanadi F. Sleiman, Department of Chemistry, McGill University, 801 Sherbrooke West, Montreal, QC, H3A 2K6 (Canada), Fax: (+1) 514‐398‐3797</mods:affiliation></affiliation></author><author><name sortKey="Moitessier, Nicole" sort="Moitessier, Nicole" uniqKey="Moitessier N" first="Nicole" last="Moitessier">Nicole Moitessier</name><affiliation><mods:affiliation>Department of Chemistry, McGill University, 801 Sherbrooke West, Montreal, QC, H3A 2K6 (Canada), Fax: (+1) 514‐398‐3797</mods:affiliation></affiliation><affiliation><mods:affiliation>Chantal Autexier, Departments of Anatomy and Cell Biology and Experimental Medicine, McGill University, Lady Davis Institute of Medical Research, 3755 Côte Ste‐Catherine Road, Montreal, QC, H3T 1E2 (Canada)Nicolas Moitessier, Department of Chemistry, McGill University, 801 Sherbrooke West, Montreal, QC, H3A 2K6 (Canada), Fax: (+1) 514‐398‐3797Hanadi F. Sleiman, Department of Chemistry, McGill University, 801 Sherbrooke West, Montreal, QC, H3A 2K6 (Canada), Fax: (+1) 514‐398‐3797</mods:affiliation><wicri:noCountry code="subField">(+1) 514‐398‐3797</wicri:noCountry></affiliation></author><author><name sortKey="Sleiman, Nicole" sort="Sleiman, Nicole" uniqKey="Sleiman N" first="Nicole" last="Sleiman">Nicole Sleiman</name><affiliation><mods:affiliation>Department of Chemistry, McGill University, 801 Sherbrooke West, Montreal, QC, H3A 2K6 (Canada), Fax: (+1) 514‐398‐3797</mods:affiliation></affiliation><affiliation><mods:affiliation>Chantal Autexier, Departments of Anatomy and Cell Biology and Experimental Medicine, McGill University, Lady Davis Institute of Medical Research, 3755 Côte Ste‐Catherine Road, Montreal, QC, H3T 1E2 (Canada)Nicolas Moitessier, Department of Chemistry, McGill University, 801 Sherbrooke West, Montreal, QC, H3A 2K6 (Canada), Fax: (+1) 514‐398‐3797Hanadi F. Sleiman, Department of Chemistry, McGill University, 801 Sherbrooke West, Montreal, QC, H3A 2K6 (Canada), Fax: (+1) 514‐398‐3797</mods:affiliation><wicri:noCountry code="subField">(+1) 514‐398‐3797</wicri:noCountry></affiliation></author></analytic><series><idno type="ISSN">1860-7179</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">1860-7179</idno></seriesStmt></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract">A rationally designed progression of phenanthroimidazole platinum(II) complexes were examined for their ability to target telomere‐derived intramolecular G‐quadruplex DNA. Through the use of circular dichroism, fluorescence displacement assays, and molecular modeling we show that these complexes template and stabilize G‐quadruplexes from sequences based on the human telomeric repeat (TTAGGG)n. The greatest stabilization was observed for the p‐chlorophenyl derivative 6 (G4DC50=0.31 μM). We also show that the G‐quadruplex binding complexes are able to inhibit telomerase activity through a modified telomerase repeat amplification protocol (TRAP‐LIG assay). Preliminary cell studies show that complex 6 is preferentially cytotoxic toward cancer over normal cell lines, indicating its potential use in cancer therapy.</div></front></TEI></record>Pour manipuler ce document sous Unix (Dilib)
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