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Luminescent pentafluorophenyl-cycloplatinated complexes: synthesis, characterization, photophysics, cytotoxicity and cellular imaging
Luminescent mono(pentafluorophenyl) cycloplatinated complexes [Pt(C^N-κC,N)(HC^N-κN)(C6F5)] [HC^N = Hthpy (2-(2-thienyl)pyridine) 2a, Hbt (2-phenylbenzothiazole) 2b, Hpq (2-phenylquinoline) 2c] have been prepared by C–H activation of a HC^N ligand in the corresponding [Pt(HC^N-κN)2(C6F5)2] (1a, 1b,...
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| Published in: | Dalton transactions : an international journal of inorganic chemistry 2015-01, Vol.44 (43), p.18839-18855 |
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| Main Authors: | , , , , , |
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| cited_by | cdi_FETCH-LOGICAL-c320t-c498dd5eba3e7b070208a47c561436b074dbcb55d99ef02a6228eeb88d119d713 |
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| cites | cdi_FETCH-LOGICAL-c320t-c498dd5eba3e7b070208a47c561436b074dbcb55d99ef02a6228eeb88d119d713 |
| container_end_page | 18855 |
| container_issue | 43 |
| container_start_page | 18839 |
| container_title | Dalton transactions : an international journal of inorganic chemistry |
| container_volume | 44 |
| creator | Berenguer, J R Pichel, J G Giménez, N Lalinde, E Moreno, M T Piñeiro-Hermida, S |
| description | Luminescent mono(pentafluorophenyl) cycloplatinated complexes [Pt(C^N-κC,N)(HC^N-κN)(C6F5)] [HC^N = Hthpy (2-(2-thienyl)pyridine) 2a, Hbt (2-phenylbenzothiazole) 2b, Hpq (2-phenylquinoline) 2c] have been prepared by C–H activation of a HC^N ligand in the corresponding [Pt(HC^N-κN)2(C6F5)2] (1a, 1b, 1c) complexes. Complexes 2 evolve in DMSO solution into solvate complexes and we present here successful routes for the synthesis of [Pt(C^N)(C6F5)(DMSO)] (C^N = thpy 3a, bt 3b). They have been fully characterized (X-ray for 1a, 1c, 2b, 3a and 3b), their electronic absorption and emission properties have been investigated and DFT and TD-DFT calculations for 1a, 1c, 2b and 3a have been carried out. Complexes 3a, 3b and [Pt(ppy)(C6F5)(DMSO)] 4 (Hppy = 2-phenylpyridine) show remarkable stability in a mixed DMSO-cellular medium and their cytotoxicity towards the human lung tumor (A549) and bronchial epithelial non-tumorigenic (NL20) cell lines has been evaluated by MTS assays. Their cellular localization in A549 and NL20 human cells and in mouse embryonic fibroblasts obtained from lungs (LMEFs) has also been investigated by fluorescence microscopy. |
| doi_str_mv | 10.1039/c5dt02721g |
| format | article |
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Complexes 2 evolve in DMSO solution into solvate complexes and we present here successful routes for the synthesis of [Pt(C^N)(C6F5)(DMSO)] (C^N = thpy 3a, bt 3b). They have been fully characterized (X-ray for 1a, 1c, 2b, 3a and 3b), their electronic absorption and emission properties have been investigated and DFT and TD-DFT calculations for 1a, 1c, 2b and 3a have been carried out. Complexes 3a, 3b and [Pt(ppy)(C6F5)(DMSO)] 4 (Hppy = 2-phenylpyridine) show remarkable stability in a mixed DMSO-cellular medium and their cytotoxicity towards the human lung tumor (A549) and bronchial epithelial non-tumorigenic (NL20) cell lines has been evaluated by MTS assays. Their cellular localization in A549 and NL20 human cells and in mouse embryonic fibroblasts obtained from lungs (LMEFs) has also been investigated by fluorescence microscopy.</description><identifier>ISSN: 1477-9226</identifier><identifier>EISSN: 1477-9234</identifier><identifier>DOI: 10.1039/c5dt02721g</identifier><identifier>PMID: 26462143</identifier><language>eng</language><publisher>England</publisher><subject>Activation ; Animals ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Cell Proliferation - drug effects ; Cellular ; Dose-Response Relationship, Drug ; Drug Screening Assays, Antitumor ; Electronics ; Human ; Humans ; Imaging ; Luminescence ; Lungs ; Mice ; Microscopy, Fluorescence ; Molecular Conformation ; Organoplatinum Compounds - chemical synthesis ; Organoplatinum Compounds - chemistry ; Organoplatinum Compounds - pharmacology ; Photochemical Processes ; Position (location) ; Quantum Theory ; Structure-Activity Relationship ; Synthesis ; Tumor Cells, Cultured</subject><ispartof>Dalton transactions : an international journal of inorganic chemistry, 2015-01, Vol.44 (43), p.18839-18855</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c320t-c498dd5eba3e7b070208a47c561436b074dbcb55d99ef02a6228eeb88d119d713</citedby><cites>FETCH-LOGICAL-c320t-c498dd5eba3e7b070208a47c561436b074dbcb55d99ef02a6228eeb88d119d713</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26462143$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Berenguer, J R</creatorcontrib><creatorcontrib>Pichel, J G</creatorcontrib><creatorcontrib>Giménez, N</creatorcontrib><creatorcontrib>Lalinde, E</creatorcontrib><creatorcontrib>Moreno, M T</creatorcontrib><creatorcontrib>Piñeiro-Hermida, S</creatorcontrib><title>Luminescent pentafluorophenyl-cycloplatinated complexes: synthesis, characterization, photophysics, cytotoxicity and cellular imaging</title><title>Dalton transactions : an international journal of inorganic chemistry</title><addtitle>Dalton Trans</addtitle><description>Luminescent mono(pentafluorophenyl) cycloplatinated complexes [Pt(C^N-κC,N)(HC^N-κN)(C6F5)] [HC^N = Hthpy (2-(2-thienyl)pyridine) 2a, Hbt (2-phenylbenzothiazole) 2b, Hpq (2-phenylquinoline) 2c] have been prepared by C–H activation of a HC^N ligand in the corresponding [Pt(HC^N-κN)2(C6F5)2] (1a, 1b, 1c) complexes. Complexes 2 evolve in DMSO solution into solvate complexes and we present here successful routes for the synthesis of [Pt(C^N)(C6F5)(DMSO)] (C^N = thpy 3a, bt 3b). They have been fully characterized (X-ray for 1a, 1c, 2b, 3a and 3b), their electronic absorption and emission properties have been investigated and DFT and TD-DFT calculations for 1a, 1c, 2b and 3a have been carried out. Complexes 3a, 3b and [Pt(ppy)(C6F5)(DMSO)] 4 (Hppy = 2-phenylpyridine) show remarkable stability in a mixed DMSO-cellular medium and their cytotoxicity towards the human lung tumor (A549) and bronchial epithelial non-tumorigenic (NL20) cell lines has been evaluated by MTS assays. Their cellular localization in A549 and NL20 human cells and in mouse embryonic fibroblasts obtained from lungs (LMEFs) has also been investigated by fluorescence microscopy.</description><subject>Activation</subject><subject>Animals</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Cell Proliferation - drug effects</subject><subject>Cellular</subject><subject>Dose-Response Relationship, Drug</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Electronics</subject><subject>Human</subject><subject>Humans</subject><subject>Imaging</subject><subject>Luminescence</subject><subject>Lungs</subject><subject>Mice</subject><subject>Microscopy, Fluorescence</subject><subject>Molecular Conformation</subject><subject>Organoplatinum Compounds - chemical synthesis</subject><subject>Organoplatinum Compounds - chemistry</subject><subject>Organoplatinum Compounds - pharmacology</subject><subject>Photochemical Processes</subject><subject>Position (location)</subject><subject>Quantum Theory</subject><subject>Structure-Activity Relationship</subject><subject>Synthesis</subject><subject>Tumor Cells, Cultured</subject><issn>1477-9226</issn><issn>1477-9234</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNqNkU1v1DAQhi0Eoh9w4QegHFHVUHtixwk3tC0FaaVeyjly7NldI8cOtiM13PnfeGnpmct8Pno1o5eQd4x-ZLTpr7QwmYIEtn9BThmXsu6h4S-fa2hPyFlKPygFoAJekxNoeQuMN6fk93aZrMek0edqLkHt3BJimA_oV1frVbswO5WtVxlNpcM0O3zA9KlKq88HTDZdVvqgotIZo_1VyOAvq_kQctFYk9XH_ZpL-2C1zWulfJFB5xanYmUntbd-_4a82imX8O1TPiffv9zcb77W27vbb5vP21o3QHOted8ZI3BUDcqRSgq0U1xq0ZZf2jLgZtSjEKbvcUdBtQAd4th1hrHeSNackw-PunMMPxdMeZhsOh6jPIYlDUxK2nTAoP0PFDoQPeeioBePqI4hpYi7YY7lsbgOjA5Hh4aNuL7_69Btgd8_6S7jhOYZ_WdJ8wf8nY-9</recordid><startdate>20150101</startdate><enddate>20150101</enddate><creator>Berenguer, J R</creator><creator>Pichel, J G</creator><creator>Giménez, N</creator><creator>Lalinde, E</creator><creator>Moreno, M T</creator><creator>Piñeiro-Hermida, S</creator><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>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20150101</creationdate><title>Luminescent pentafluorophenyl-cycloplatinated complexes: synthesis, characterization, photophysics, cytotoxicity and cellular imaging</title><author>Berenguer, J R ; Pichel, J G ; Giménez, N ; Lalinde, E ; Moreno, M T ; Piñeiro-Hermida, S</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c320t-c498dd5eba3e7b070208a47c561436b074dbcb55d99ef02a6228eeb88d119d713</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Activation</topic><topic>Animals</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Cell Proliferation - drug effects</topic><topic>Cellular</topic><topic>Dose-Response Relationship, Drug</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Electronics</topic><topic>Human</topic><topic>Humans</topic><topic>Imaging</topic><topic>Luminescence</topic><topic>Lungs</topic><topic>Mice</topic><topic>Microscopy, Fluorescence</topic><topic>Molecular Conformation</topic><topic>Organoplatinum Compounds - chemical synthesis</topic><topic>Organoplatinum Compounds - chemistry</topic><topic>Organoplatinum Compounds - pharmacology</topic><topic>Photochemical Processes</topic><topic>Position (location)</topic><topic>Quantum Theory</topic><topic>Structure-Activity Relationship</topic><topic>Synthesis</topic><topic>Tumor Cells, Cultured</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Berenguer, J R</creatorcontrib><creatorcontrib>Pichel, J G</creatorcontrib><creatorcontrib>Giménez, N</creatorcontrib><creatorcontrib>Lalinde, E</creatorcontrib><creatorcontrib>Moreno, M T</creatorcontrib><creatorcontrib>Piñeiro-Hermida, S</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>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Berenguer, J R</au><au>Pichel, J G</au><au>Giménez, N</au><au>Lalinde, E</au><au>Moreno, M T</au><au>Piñeiro-Hermida, S</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Luminescent pentafluorophenyl-cycloplatinated complexes: synthesis, characterization, photophysics, cytotoxicity and cellular imaging</atitle><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle><addtitle>Dalton Trans</addtitle><date>2015-01-01</date><risdate>2015</risdate><volume>44</volume><issue>43</issue><spage>18839</spage><epage>18855</epage><pages>18839-18855</pages><issn>1477-9226</issn><eissn>1477-9234</eissn><abstract>Luminescent mono(pentafluorophenyl) cycloplatinated complexes [Pt(C^N-κC,N)(HC^N-κN)(C6F5)] [HC^N = Hthpy (2-(2-thienyl)pyridine) 2a, Hbt (2-phenylbenzothiazole) 2b, Hpq (2-phenylquinoline) 2c] have been prepared by C–H activation of a HC^N ligand in the corresponding [Pt(HC^N-κN)2(C6F5)2] (1a, 1b, 1c) complexes. Complexes 2 evolve in DMSO solution into solvate complexes and we present here successful routes for the synthesis of [Pt(C^N)(C6F5)(DMSO)] (C^N = thpy 3a, bt 3b). They have been fully characterized (X-ray for 1a, 1c, 2b, 3a and 3b), their electronic absorption and emission properties have been investigated and DFT and TD-DFT calculations for 1a, 1c, 2b and 3a have been carried out. Complexes 3a, 3b and [Pt(ppy)(C6F5)(DMSO)] 4 (Hppy = 2-phenylpyridine) show remarkable stability in a mixed DMSO-cellular medium and their cytotoxicity towards the human lung tumor (A549) and bronchial epithelial non-tumorigenic (NL20) cell lines has been evaluated by MTS assays. Their cellular localization in A549 and NL20 human cells and in mouse embryonic fibroblasts obtained from lungs (LMEFs) has also been investigated by fluorescence microscopy.</abstract><cop>England</cop><pmid>26462143</pmid><doi>10.1039/c5dt02721g</doi><tpages>17</tpages></addata></record> |
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| ispartof | Dalton transactions : an international journal of inorganic chemistry, 2015-01, Vol.44 (43), p.18839-18855 |
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| source | Royal Society of Chemistry |
| subjects | Activation Animals Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Cell Proliferation - drug effects Cellular Dose-Response Relationship, Drug Drug Screening Assays, Antitumor Electronics Human Humans Imaging Luminescence Lungs Mice Microscopy, Fluorescence Molecular Conformation Organoplatinum Compounds - chemical synthesis Organoplatinum Compounds - chemistry Organoplatinum Compounds - pharmacology Photochemical Processes Position (location) Quantum Theory Structure-Activity Relationship Synthesis Tumor Cells, Cultured |
| title | Luminescent pentafluorophenyl-cycloplatinated complexes: synthesis, characterization, photophysics, cytotoxicity and cellular imaging |
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