Porphyrin Derivatives for Telomere Binding and Telomerase Inhibition
The capacity of G-quadruplex ligands to stabilize four-stranded DNA makes them able to inhibit telomerase, which is involved in tumour cell proliferation. A series of cationic metalloporphyrin derivatives was prepared by making variations on a meso-tetrakis(4-N-methyl-pyridiniumyl)porphyrin skeleton...
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| Veröffentlicht in: | Chembiochem : a European journal of chemical biology 2005-01, Vol.6 (1), p.123-132 |
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| container_title | Chembiochem : a European journal of chemical biology |
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| creator | Dixon, Isabelle M Lopez, Frédéric Estève, Jean-Pierre Tejera, Agueda M Blasco, María A Pratviel, Geneviève Meunier, Bernard |
| description | The capacity of G-quadruplex ligands to stabilize four-stranded DNA makes them able to inhibit telomerase, which is involved in tumour cell proliferation. A series of cationic metalloporphyrin derivatives was prepared by making variations on a meso-tetrakis(4-N-methyl-pyridiniumyl)porphyrin skeleton (TMPyP). The DNA binding properties of nickel(II) and manganese(III) porphyrins were studied by surface plasmon resonance, and the capacity of the nickel porphyrins to inhibit telomerase was tested in a TRAP assay. The nature of the metal influences the kinetics (the process is faster for Ni than for Mn) and the mode of interaction (stacking or external binding). The chemical alterations did not lead to increased telomerase inhibition. The best selectivity for G-quadruplex DNA was observed for Mn-TMPyP, which has a tenfold preference for quadruplex over duplex. |
| doi_str_mv | 10.1002/cbic.200400113 |
| format | Article |
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A series of cationic metalloporphyrin derivatives was prepared by making variations on a meso-tetrakis(4-N-methyl-pyridiniumyl)porphyrin skeleton (TMPyP). The DNA binding properties of nickel(II) and manganese(III) porphyrins were studied by surface plasmon resonance, and the capacity of the nickel porphyrins to inhibit telomerase was tested in a TRAP assay. The nature of the metal influences the kinetics (the process is faster for Ni than for Mn) and the mode of interaction (stacking or external binding). The chemical alterations did not lead to increased telomerase inhibition. The best selectivity for G-quadruplex DNA was observed for Mn-TMPyP, which has a tenfold preference for quadruplex over duplex.</description><identifier>ISSN: 1439-4227</identifier><identifier>EISSN: 1439-7633</identifier><identifier>DOI: 10.1002/cbic.200400113</identifier><identifier>PMID: 15551357</identifier><language>eng</language><publisher>Weinheim: Wiley-VCH Verlag</publisher><subject>antitumor agents ; DNA - metabolism ; Enzyme Inhibitors - chemical synthesis ; Enzyme Inhibitors - chemistry ; Enzyme Inhibitors - metabolism ; G-quadruplex DNA ; G-Quadruplexes ; Humans ; Manganese - chemistry ; Manganese - metabolism ; Metalloporphyrins - chemical synthesis ; Metalloporphyrins - chemistry ; Metalloporphyrins - metabolism ; Nickel - chemistry ; Nickel - metabolism ; Nucleic Acid Amplification Techniques ; porphyrins ; Surface Plasmon Resonance ; Telomerase - antagonists & inhibitors ; Telomere - metabolism ; TRAP assay</subject><ispartof>Chembiochem : a European journal of chemical biology, 2005-01, Vol.6 (1), p.123-132</ispartof><rights>Copyright © 2005 WILEY‐VCH Verlag GmbH & Co. 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A series of cationic metalloporphyrin derivatives was prepared by making variations on a meso-tetrakis(4-N-methyl-pyridiniumyl)porphyrin skeleton (TMPyP). The DNA binding properties of nickel(II) and manganese(III) porphyrins were studied by surface plasmon resonance, and the capacity of the nickel porphyrins to inhibit telomerase was tested in a TRAP assay. The nature of the metal influences the kinetics (the process is faster for Ni than for Mn) and the mode of interaction (stacking or external binding). The chemical alterations did not lead to increased telomerase inhibition. The best selectivity for G-quadruplex DNA was observed for Mn-TMPyP, which has a tenfold preference for quadruplex over duplex.</description><subject>antitumor agents</subject><subject>DNA - metabolism</subject><subject>Enzyme Inhibitors - chemical synthesis</subject><subject>Enzyme Inhibitors - chemistry</subject><subject>Enzyme Inhibitors - metabolism</subject><subject>G-quadruplex DNA</subject><subject>G-Quadruplexes</subject><subject>Humans</subject><subject>Manganese - chemistry</subject><subject>Manganese - metabolism</subject><subject>Metalloporphyrins - chemical synthesis</subject><subject>Metalloporphyrins - chemistry</subject><subject>Metalloporphyrins - metabolism</subject><subject>Nickel - chemistry</subject><subject>Nickel - metabolism</subject><subject>Nucleic Acid Amplification Techniques</subject><subject>porphyrins</subject><subject>Surface Plasmon Resonance</subject><subject>Telomerase - antagonists & inhibitors</subject><subject>Telomere - metabolism</subject><subject>TRAP assay</subject><issn>1439-4227</issn><issn>1439-7633</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE1P3DAQhq2Kqnxee6Q59ZbtjMeJN8cSvlagFgSoR8vxTsA0m2ztXWD_PVllS3vj5JH1vO-MHiE-I4wQQH5zlXcjCaAAEOmD2EFFRapzoq3NrKTU22I3xkcAKHLCT2IbsyxDyvSOOL7qwvxhFXybHHPwT3bhnzgmdReSW266GQdOjnw79e19Ytvp308bOZm0D77yC9-1--JjbZvIB5t3T9ydntyW5-nlz7NJ-f0ydUojpbVb762J8tqysoCkc0BdWUeVQwQ5LjSTloDMlopCOgljpypbKanzwtKe-Dr0zkP3Z8lxYWY-Om4a23K3jCbXlGtUWQ-OBtCFLsbAtZkHP7NhZRDM2ptZezNv3vrA4aZ5Wc14-g_fiOqBYgCefcOrd-pMeTQp_y9Ph6yPC355y9rwe32xzsyvH2fmRpbX4wzQXPT8l4GvbWfsffDR3N30VgiwUJIU0SsV1ZCs</recordid><startdate>20050101</startdate><enddate>20050101</enddate><creator>Dixon, Isabelle M</creator><creator>Lopez, Frédéric</creator><creator>Estève, Jean-Pierre</creator><creator>Tejera, Agueda M</creator><creator>Blasco, María A</creator><creator>Pratviel, Geneviève</creator><creator>Meunier, Bernard</creator><general>Wiley-VCH Verlag</general><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>FBQ</scope><scope>BSCLL</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20050101</creationdate><title>Porphyrin Derivatives for Telomere Binding and Telomerase Inhibition</title><author>Dixon, Isabelle M ; Lopez, Frédéric ; Estève, Jean-Pierre ; Tejera, Agueda M ; Blasco, María A ; Pratviel, Geneviève ; Meunier, Bernard</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4713-fc1555f336fae4a01376017bac3bc1102897e37201eea3992c208c4bab42769a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>antitumor agents</topic><topic>DNA - metabolism</topic><topic>Enzyme Inhibitors - chemical synthesis</topic><topic>Enzyme Inhibitors - chemistry</topic><topic>Enzyme Inhibitors - metabolism</topic><topic>G-quadruplex DNA</topic><topic>G-Quadruplexes</topic><topic>Humans</topic><topic>Manganese - chemistry</topic><topic>Manganese - metabolism</topic><topic>Metalloporphyrins - chemical synthesis</topic><topic>Metalloporphyrins - chemistry</topic><topic>Metalloporphyrins - metabolism</topic><topic>Nickel - chemistry</topic><topic>Nickel - metabolism</topic><topic>Nucleic Acid Amplification Techniques</topic><topic>porphyrins</topic><topic>Surface Plasmon Resonance</topic><topic>Telomerase - antagonists & inhibitors</topic><topic>Telomere - metabolism</topic><topic>TRAP assay</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dixon, Isabelle M</creatorcontrib><creatorcontrib>Lopez, Frédéric</creatorcontrib><creatorcontrib>Estève, Jean-Pierre</creatorcontrib><creatorcontrib>Tejera, Agueda M</creatorcontrib><creatorcontrib>Blasco, María A</creatorcontrib><creatorcontrib>Pratviel, Geneviève</creatorcontrib><creatorcontrib>Meunier, Bernard</creatorcontrib><collection>AGRIS</collection><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Chembiochem : a European journal of chemical biology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dixon, Isabelle M</au><au>Lopez, Frédéric</au><au>Estève, Jean-Pierre</au><au>Tejera, Agueda M</au><au>Blasco, María A</au><au>Pratviel, Geneviève</au><au>Meunier, Bernard</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Porphyrin Derivatives for Telomere Binding and Telomerase Inhibition</atitle><jtitle>Chembiochem : a European journal of chemical biology</jtitle><addtitle>ChemBioChem</addtitle><date>2005-01-01</date><risdate>2005</risdate><volume>6</volume><issue>1</issue><spage>123</spage><epage>132</epage><pages>123-132</pages><issn>1439-4227</issn><eissn>1439-7633</eissn><abstract>The capacity of G-quadruplex ligands to stabilize four-stranded DNA makes them able to inhibit telomerase, which is involved in tumour cell proliferation. A series of cationic metalloporphyrin derivatives was prepared by making variations on a meso-tetrakis(4-N-methyl-pyridiniumyl)porphyrin skeleton (TMPyP). The DNA binding properties of nickel(II) and manganese(III) porphyrins were studied by surface plasmon resonance, and the capacity of the nickel porphyrins to inhibit telomerase was tested in a TRAP assay. The nature of the metal influences the kinetics (the process is faster for Ni than for Mn) and the mode of interaction (stacking or external binding). The chemical alterations did not lead to increased telomerase inhibition. The best selectivity for G-quadruplex DNA was observed for Mn-TMPyP, which has a tenfold preference for quadruplex over duplex.</abstract><cop>Weinheim</cop><pub>Wiley-VCH Verlag</pub><pmid>15551357</pmid><doi>10.1002/cbic.200400113</doi><tpages>10</tpages></addata></record> |
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| subjects | antitumor agents DNA - metabolism Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - chemistry Enzyme Inhibitors - metabolism G-quadruplex DNA G-Quadruplexes Humans Manganese - chemistry Manganese - metabolism Metalloporphyrins - chemical synthesis Metalloporphyrins - chemistry Metalloporphyrins - metabolism Nickel - chemistry Nickel - metabolism Nucleic Acid Amplification Techniques porphyrins Surface Plasmon Resonance Telomerase - antagonists & inhibitors Telomere - metabolism TRAP assay |
| title | Porphyrin Derivatives for Telomere Binding and Telomerase Inhibition |
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