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The nickel(II) complex of guanidinium phenyl porphyrin, a specific G-quadruplex ligand, targets telomeres and leads to POT1 mislocalization in culture cells
With the aim of finding selective and biologically active G-quadruplex ligands, modified porphyrin with bulky cationic substituents, meso -5,10,15,20-tetrakis(4-guanidinophenyl)porphyrin tetrahydrochloride, referred to as guanidinium phenyl porphyrin, was prepared. The corresponding nickel(II) and c...
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| Published in: | Journal of biological inorganic chemistry 2015-06, Vol.20 (4), p.729-738 |
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| container_end_page | 738 |
| container_issue | 4 |
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| container_title | Journal of biological inorganic chemistry |
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| creator | Sabater, Laurent Nicolau-Travers, Marie-Laure De Rache, Aurore Prado, Enora Dejeu, Jérôme Bombarde, Oriane Lacroix, Joris Calsou, Patrick Defrancq, Eric Mergny, Jean-Louis Gomez, Dennis Pratviel, Geneviève |
| description | With the aim of finding selective and biologically active G-quadruplex ligands, modified porphyrin with bulky cationic substituents,
meso
-5,10,15,20-tetrakis(4-guanidinophenyl)porphyrin tetrahydrochloride, referred to as guanidinium phenyl porphyrin, was prepared. The corresponding nickel(II) and cobalt(III) metallated porphyrins were also synthesized. Interaction with quadruplexes was examined by means of fluorescence resonance energy transfer melting and surface plasmon resonance-based assays: the three compounds proved to bind to G-quadruplex DNA in a similar and highly selective way. Guanidinium phenyl porphyrin and its nickel(II) metallated derivative exhibit moderate cytotoxicity toward cells in culture. Strikingly, the nickel porphyrin derivative was able to displace hPOT1 shelterin protein from telomeres in human cells.
Graphical Abstract
Nickel(II) guanidinium phenyl porphyrin, a cationic bulky porphyrin is a powerful specific G-quadruplex DNA ligand. It enters the cells and induces shelterin modification. |
| doi_str_mv | 10.1007/s00775-015-1260-8 |
| format | article |
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meso
-5,10,15,20-tetrakis(4-guanidinophenyl)porphyrin tetrahydrochloride, referred to as guanidinium phenyl porphyrin, was prepared. The corresponding nickel(II) and cobalt(III) metallated porphyrins were also synthesized. Interaction with quadruplexes was examined by means of fluorescence resonance energy transfer melting and surface plasmon resonance-based assays: the three compounds proved to bind to G-quadruplex DNA in a similar and highly selective way. Guanidinium phenyl porphyrin and its nickel(II) metallated derivative exhibit moderate cytotoxicity toward cells in culture. Strikingly, the nickel porphyrin derivative was able to displace hPOT1 shelterin protein from telomeres in human cells.
Graphical Abstract
Nickel(II) guanidinium phenyl porphyrin, a cationic bulky porphyrin is a powerful specific G-quadruplex DNA ligand. It enters the cells and induces shelterin modification.</description><identifier>ISSN: 0949-8257</identifier><identifier>EISSN: 1432-1327</identifier><identifier>DOI: 10.1007/s00775-015-1260-8</identifier><identifier>PMID: 25846142</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer Berlin Heidelberg</publisher><subject>Binding Sites - drug effects ; Biochemistry ; Biomedical and Life Sciences ; Cell Proliferation - drug effects ; Chemical Sciences ; Circular Dichroism ; Cobalt - chemistry ; Dose-Response Relationship, Drug ; Fluorescence Resonance Energy Transfer ; G-Quadruplexes - drug effects ; Guanidine - chemistry ; Humans ; Life Sciences ; Ligands ; Metalloporphyrins - chemical synthesis ; Metalloporphyrins - chemistry ; Metalloporphyrins - pharmacology ; Microbiology ; Molecular Structure ; Nickel - chemistry ; Original Paper ; Porphyrins - chemistry ; Protein Transport - drug effects ; Structure-Activity Relationship ; Surface Plasmon Resonance ; Telomere - drug effects ; Telomere-Binding Proteins - metabolism ; Tumor Cells, Cultured</subject><ispartof>Journal of biological inorganic chemistry, 2015-06, Vol.20 (4), p.729-738</ispartof><rights>SBIC 2015</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c514t-d99260f6982953254b573cb75fe47c4484b00f26c1aad97258c37af4a663ccec3</citedby><cites>FETCH-LOGICAL-c514t-d99260f6982953254b573cb75fe47c4484b00f26c1aad97258c37af4a663ccec3</cites><orcidid>0000-0002-3911-6241 ; 0000-0001-9942-1451 ; 0000-0002-9773-3459 ; 0000-0003-0688-2107 ; 0000-0002-2434-2959 ; 0000-0003-3043-8401 ; 0000-0001-7951-9806</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,780,784,885,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25846142$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-01651420$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Sabater, Laurent</creatorcontrib><creatorcontrib>Nicolau-Travers, Marie-Laure</creatorcontrib><creatorcontrib>De Rache, Aurore</creatorcontrib><creatorcontrib>Prado, Enora</creatorcontrib><creatorcontrib>Dejeu, Jérôme</creatorcontrib><creatorcontrib>Bombarde, Oriane</creatorcontrib><creatorcontrib>Lacroix, Joris</creatorcontrib><creatorcontrib>Calsou, Patrick</creatorcontrib><creatorcontrib>Defrancq, Eric</creatorcontrib><creatorcontrib>Mergny, Jean-Louis</creatorcontrib><creatorcontrib>Gomez, Dennis</creatorcontrib><creatorcontrib>Pratviel, Geneviève</creatorcontrib><title>The nickel(II) complex of guanidinium phenyl porphyrin, a specific G-quadruplex ligand, targets telomeres and leads to POT1 mislocalization in culture cells</title><title>Journal of biological inorganic chemistry</title><addtitle>J Biol Inorg Chem</addtitle><addtitle>J Biol Inorg Chem</addtitle><description>With the aim of finding selective and biologically active G-quadruplex ligands, modified porphyrin with bulky cationic substituents,
meso
-5,10,15,20-tetrakis(4-guanidinophenyl)porphyrin tetrahydrochloride, referred to as guanidinium phenyl porphyrin, was prepared. The corresponding nickel(II) and cobalt(III) metallated porphyrins were also synthesized. Interaction with quadruplexes was examined by means of fluorescence resonance energy transfer melting and surface plasmon resonance-based assays: the three compounds proved to bind to G-quadruplex DNA in a similar and highly selective way. Guanidinium phenyl porphyrin and its nickel(II) metallated derivative exhibit moderate cytotoxicity toward cells in culture. Strikingly, the nickel porphyrin derivative was able to displace hPOT1 shelterin protein from telomeres in human cells.
Graphical Abstract
Nickel(II) guanidinium phenyl porphyrin, a cationic bulky porphyrin is a powerful specific G-quadruplex DNA ligand. It enters the cells and induces shelterin modification.</description><subject>Binding Sites - drug effects</subject><subject>Biochemistry</subject><subject>Biomedical and Life Sciences</subject><subject>Cell Proliferation - drug effects</subject><subject>Chemical Sciences</subject><subject>Circular Dichroism</subject><subject>Cobalt - chemistry</subject><subject>Dose-Response Relationship, Drug</subject><subject>Fluorescence Resonance Energy Transfer</subject><subject>G-Quadruplexes - drug effects</subject><subject>Guanidine - chemistry</subject><subject>Humans</subject><subject>Life Sciences</subject><subject>Ligands</subject><subject>Metalloporphyrins - chemical synthesis</subject><subject>Metalloporphyrins - chemistry</subject><subject>Metalloporphyrins - pharmacology</subject><subject>Microbiology</subject><subject>Molecular Structure</subject><subject>Nickel - chemistry</subject><subject>Original Paper</subject><subject>Porphyrins - chemistry</subject><subject>Protein Transport - drug effects</subject><subject>Structure-Activity Relationship</subject><subject>Surface Plasmon Resonance</subject><subject>Telomere - drug effects</subject><subject>Telomere-Binding Proteins - metabolism</subject><subject>Tumor Cells, Cultured</subject><issn>0949-8257</issn><issn>1432-1327</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNp9kd9uFCEYxYnR2LX6AN4YLtukKDAwfy6bRttNNqkX6zVhmW92qQxMYTCuz-LDyjq1l95A8vE7Bw4HofeMfmSUNp9SWRpJKJOE8ZqS9gVaMVFxwirevEQr2omOtFw2Z-hNSg-U0koy-RqdcdmKmgm-Qr-3B8Demu_gLtbrS2zCODn4icOA91l721tv84inA_ijw1OI0-EYrb_CGqcJjB2swbfkMes-5r9CZ_fa91d41nEPc8IzuDBChITLGDvQfZkF_PV-y_BokwtGO_tLzzZ4bD022c05AjbgXHqLXg3aJXj3tJ-jb18-b2_uyOb-dn1zvSFGMjGTvutK-qHuWt7Jikuxk01ldo0cQDRGiFbsKB14bZjWfdeU8KZq9CB0XVfGgKnO0eXie9BOTdGOOh5V0FbdXW_UaUZZXW7i9Acr7MXCTjE8ZkizKilOr9UeQk6K1S3nVDAhC8oW1MSQUoTh2ZtRdSpQLQUWe6lOBaq2aD482efdCP2z4l9jBeALkMqR30NUDyFHX77nP65_AND0prU</recordid><startdate>20150601</startdate><enddate>20150601</enddate><creator>Sabater, Laurent</creator><creator>Nicolau-Travers, Marie-Laure</creator><creator>De Rache, Aurore</creator><creator>Prado, Enora</creator><creator>Dejeu, Jérôme</creator><creator>Bombarde, Oriane</creator><creator>Lacroix, Joris</creator><creator>Calsou, Patrick</creator><creator>Defrancq, Eric</creator><creator>Mergny, Jean-Louis</creator><creator>Gomez, Dennis</creator><creator>Pratviel, Geneviève</creator><general>Springer Berlin Heidelberg</general><general>Springer Verlag</general><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><scope>1XC</scope><orcidid>https://orcid.org/0000-0002-3911-6241</orcidid><orcidid>https://orcid.org/0000-0001-9942-1451</orcidid><orcidid>https://orcid.org/0000-0002-9773-3459</orcidid><orcidid>https://orcid.org/0000-0003-0688-2107</orcidid><orcidid>https://orcid.org/0000-0002-2434-2959</orcidid><orcidid>https://orcid.org/0000-0003-3043-8401</orcidid><orcidid>https://orcid.org/0000-0001-7951-9806</orcidid></search><sort><creationdate>20150601</creationdate><title>The nickel(II) complex of guanidinium phenyl porphyrin, a specific G-quadruplex ligand, targets telomeres and leads to POT1 mislocalization in culture cells</title><author>Sabater, Laurent ; Nicolau-Travers, Marie-Laure ; De Rache, Aurore ; Prado, Enora ; Dejeu, Jérôme ; Bombarde, Oriane ; Lacroix, Joris ; Calsou, Patrick ; Defrancq, Eric ; Mergny, Jean-Louis ; Gomez, Dennis ; Pratviel, Geneviève</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c514t-d99260f6982953254b573cb75fe47c4484b00f26c1aad97258c37af4a663ccec3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Binding Sites - drug effects</topic><topic>Biochemistry</topic><topic>Biomedical and Life Sciences</topic><topic>Cell Proliferation - drug effects</topic><topic>Chemical Sciences</topic><topic>Circular Dichroism</topic><topic>Cobalt - chemistry</topic><topic>Dose-Response Relationship, Drug</topic><topic>Fluorescence Resonance Energy Transfer</topic><topic>G-Quadruplexes - drug effects</topic><topic>Guanidine - chemistry</topic><topic>Humans</topic><topic>Life Sciences</topic><topic>Ligands</topic><topic>Metalloporphyrins - chemical synthesis</topic><topic>Metalloporphyrins - chemistry</topic><topic>Metalloporphyrins - pharmacology</topic><topic>Microbiology</topic><topic>Molecular Structure</topic><topic>Nickel - chemistry</topic><topic>Original Paper</topic><topic>Porphyrins - chemistry</topic><topic>Protein Transport - drug effects</topic><topic>Structure-Activity Relationship</topic><topic>Surface Plasmon Resonance</topic><topic>Telomere - drug effects</topic><topic>Telomere-Binding Proteins - metabolism</topic><topic>Tumor Cells, Cultured</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sabater, Laurent</creatorcontrib><creatorcontrib>Nicolau-Travers, Marie-Laure</creatorcontrib><creatorcontrib>De Rache, Aurore</creatorcontrib><creatorcontrib>Prado, Enora</creatorcontrib><creatorcontrib>Dejeu, Jérôme</creatorcontrib><creatorcontrib>Bombarde, Oriane</creatorcontrib><creatorcontrib>Lacroix, Joris</creatorcontrib><creatorcontrib>Calsou, Patrick</creatorcontrib><creatorcontrib>Defrancq, Eric</creatorcontrib><creatorcontrib>Mergny, Jean-Louis</creatorcontrib><creatorcontrib>Gomez, Dennis</creatorcontrib><creatorcontrib>Pratviel, Geneviève</creatorcontrib><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><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Journal of biological inorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sabater, Laurent</au><au>Nicolau-Travers, Marie-Laure</au><au>De Rache, Aurore</au><au>Prado, Enora</au><au>Dejeu, Jérôme</au><au>Bombarde, Oriane</au><au>Lacroix, Joris</au><au>Calsou, Patrick</au><au>Defrancq, Eric</au><au>Mergny, Jean-Louis</au><au>Gomez, Dennis</au><au>Pratviel, Geneviève</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The nickel(II) complex of guanidinium phenyl porphyrin, a specific G-quadruplex ligand, targets telomeres and leads to POT1 mislocalization in culture cells</atitle><jtitle>Journal of biological inorganic chemistry</jtitle><stitle>J Biol Inorg Chem</stitle><addtitle>J Biol Inorg Chem</addtitle><date>2015-06-01</date><risdate>2015</risdate><volume>20</volume><issue>4</issue><spage>729</spage><epage>738</epage><pages>729-738</pages><issn>0949-8257</issn><eissn>1432-1327</eissn><abstract>With the aim of finding selective and biologically active G-quadruplex ligands, modified porphyrin with bulky cationic substituents,
meso
-5,10,15,20-tetrakis(4-guanidinophenyl)porphyrin tetrahydrochloride, referred to as guanidinium phenyl porphyrin, was prepared. The corresponding nickel(II) and cobalt(III) metallated porphyrins were also synthesized. Interaction with quadruplexes was examined by means of fluorescence resonance energy transfer melting and surface plasmon resonance-based assays: the three compounds proved to bind to G-quadruplex DNA in a similar and highly selective way. Guanidinium phenyl porphyrin and its nickel(II) metallated derivative exhibit moderate cytotoxicity toward cells in culture. Strikingly, the nickel porphyrin derivative was able to displace hPOT1 shelterin protein from telomeres in human cells.
Graphical Abstract
Nickel(II) guanidinium phenyl porphyrin, a cationic bulky porphyrin is a powerful specific G-quadruplex DNA ligand. It enters the cells and induces shelterin modification.</abstract><cop>Berlin/Heidelberg</cop><pub>Springer Berlin Heidelberg</pub><pmid>25846142</pmid><doi>10.1007/s00775-015-1260-8</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0002-3911-6241</orcidid><orcidid>https://orcid.org/0000-0001-9942-1451</orcidid><orcidid>https://orcid.org/0000-0002-9773-3459</orcidid><orcidid>https://orcid.org/0000-0003-0688-2107</orcidid><orcidid>https://orcid.org/0000-0002-2434-2959</orcidid><orcidid>https://orcid.org/0000-0003-3043-8401</orcidid><orcidid>https://orcid.org/0000-0001-7951-9806</orcidid></addata></record> |
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| ispartof | Journal of biological inorganic chemistry, 2015-06, Vol.20 (4), p.729-738 |
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| subjects | Binding Sites - drug effects Biochemistry Biomedical and Life Sciences Cell Proliferation - drug effects Chemical Sciences Circular Dichroism Cobalt - chemistry Dose-Response Relationship, Drug Fluorescence Resonance Energy Transfer G-Quadruplexes - drug effects Guanidine - chemistry Humans Life Sciences Ligands Metalloporphyrins - chemical synthesis Metalloporphyrins - chemistry Metalloporphyrins - pharmacology Microbiology Molecular Structure Nickel - chemistry Original Paper Porphyrins - chemistry Protein Transport - drug effects Structure-Activity Relationship Surface Plasmon Resonance Telomere - drug effects Telomere-Binding Proteins - metabolism Tumor Cells, Cultured |
| title | The nickel(II) complex of guanidinium phenyl porphyrin, a specific G-quadruplex ligand, targets telomeres and leads to POT1 mislocalization in culture cells |
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