Influence of the substituent on the phosphine ligand in novel rhenium(i) aldehydes. Synthesis, computational studies and first insights into the antiproliferative activity
Cyrhetrenyl aldehyde derivatives [(η5-C5H4CHO)Re(CO)2PR3] with R = methyl (Me, 2a), phenyl (Ph, 2b), and cyclohexyl (Cy, 2c) were synthesized by a photochemical reaction from the starting material [(η5-C5H4CHO)Re(CO)3] (1) and the corresponding phosphines. The complexes were fully characterized by F...
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| Veröffentlicht in: | Dalton transactions : an international journal of inorganic chemistry 2018-10, Vol.47 (39), p.13861-13869 |
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| container_title | Dalton transactions : an international journal of inorganic chemistry |
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| creator | Muñoz-Osses, Michelle Siegmund, Daniel Gómez, Alejandra Godoy, Fernando Fierro, Angélica Llanos, Leonel Aravena, Daniel Metzler-Nolte, Nils |
| description | Cyrhetrenyl aldehyde derivatives [(η5-C5H4CHO)Re(CO)2PR3] with R = methyl (Me, 2a), phenyl (Ph, 2b), and cyclohexyl (Cy, 2c) were synthesized by a photochemical reaction from the starting material [(η5-C5H4CHO)Re(CO)3] (1) and the corresponding phosphines. The complexes were fully characterized by FT-IR, 1H, 13C and 31P NMR spectroscopy, elemental analysis and mass spectrometry. The molecular structures of 2a-c have also been determined. Electronic structure calculations by TD-DFT and electrochemical studies are in sound agreement with the effect of the substitution of one carbonyl group by a phosphine ligand. Additionally, the antiproliferative activity of complexes 1 and 2a-c was studied on the human cancer cell lines HT-29 and PT-45 using an MTT assay. Out of all new compounds, only the triphenylphosphine derivative 2b exhibited pronounced cytotoxic effects on both cell lines, being ca. 1.5 times more potent than cisplatin. |
| doi_str_mv | 10.1039/c8dt03160f |
| format | Article |
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The molecular structures of 2a-c have also been determined. Electronic structure calculations by TD-DFT and electrochemical studies are in sound agreement with the effect of the substitution of one carbonyl group by a phosphine ligand. Additionally, the antiproliferative activity of complexes 1 and 2a-c was studied on the human cancer cell lines HT-29 and PT-45 using an MTT assay. 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Synthesis, computational studies and first insights into the antiproliferative activity</title><title>Dalton transactions : an international journal of inorganic chemistry</title><addtitle>Dalton Trans</addtitle><description>Cyrhetrenyl aldehyde derivatives [(η5-C5H4CHO)Re(CO)2PR3] with R = methyl (Me, 2a), phenyl (Ph, 2b), and cyclohexyl (Cy, 2c) were synthesized by a photochemical reaction from the starting material [(η5-C5H4CHO)Re(CO)3] (1) and the corresponding phosphines. The complexes were fully characterized by FT-IR, 1H, 13C and 31P NMR spectroscopy, elemental analysis and mass spectrometry. The molecular structures of 2a-c have also been determined. Electronic structure calculations by TD-DFT and electrochemical studies are in sound agreement with the effect of the substitution of one carbonyl group by a phosphine ligand. Additionally, the antiproliferative activity of complexes 1 and 2a-c was studied on the human cancer cell lines HT-29 and PT-45 using an MTT assay. Out of all new compounds, only the triphenylphosphine derivative 2b exhibited pronounced cytotoxic effects on both cell lines, being ca. 1.5 times more potent than cisplatin.</description><subject>Aldehydes</subject><subject>Aldehydes - chemistry</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Antiproliferatives</subject><subject>Biotechnology</subject><subject>Carbonyl groups</subject><subject>Carbonyls</subject><subject>Chemical synthesis</subject><subject>Chemistry Techniques, Synthetic</subject><subject>Crystallography</subject><subject>Cytotoxicity</subject><subject>Electrochemistry</subject><subject>Electronic structure</subject><subject>Fourier transforms</subject><subject>HT29 Cells</subject><subject>Humans</subject><subject>Infrared spectroscopy</subject><subject>Ligands</subject><subject>Mass spectrometry</subject><subject>Models, Molecular</subject><subject>Molecular Conformation</subject><subject>NMR spectroscopy</subject><subject>Organometallic Compounds - chemical synthesis</subject><subject>Organometallic Compounds - chemistry</subject><subject>Organometallic Compounds - pharmacology</subject><subject>Phosphines</subject><subject>Phosphines - chemistry</subject><subject>Photochemical reactions</subject><subject>Quantum Theory</subject><subject>Rhenium</subject><subject>Rhenium - chemistry</subject><subject>Structure-Activity Relationship</subject><subject>Substitution reactions</subject><issn>1477-9226</issn><issn>1477-9234</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkctuFDEQRVsIRB6w4QOQJTYJYoIf7X4so4FApEgsCOuW2y6nHbntxuWONN_ET-KZhCxY1dXVqeuyblW9Y_SCUdF_1p3JVLCG2hfVMavbdtNzUb981rw5qk4Q7ynlnEr-ujoSRcm6a46rP9fB-hWCBhItyRMQXEfMLhcvkxgO1jJFXCYXgHh3p4IhLpAQH8CTNEFw63zmzonyBqadAbwgP3ehrKHDT0THeVmzyi4G5Qnm1ThAss-wLmEuSejupoxF5Hh4TIXslhS9s5DK3kNxdBku795Ur6zyCG-f5mn16-rr7fb75ubHt-vt5c1GCybzxpiWW84F76iSoJWkTSOY6UYJxrBu1LrnNTS6N8JqkNAbw1vd1rIeDaW0EafV2WNuOeP3CpiH2aEG71WAuOLAGe2FqEXfF_TDf-h9XFP56p5iLWu4pG2hPj5SOkXEBHZYkptV2g2MDvsKh2335fZQ4VWB3z9FruMM5hn915n4Cywemus</recordid><startdate>20181009</startdate><enddate>20181009</enddate><creator>Muñoz-Osses, Michelle</creator><creator>Siegmund, Daniel</creator><creator>Gómez, Alejandra</creator><creator>Godoy, Fernando</creator><creator>Fierro, Angélica</creator><creator>Llanos, Leonel</creator><creator>Aravena, Daniel</creator><creator>Metzler-Nolte, Nils</creator><general>Royal Society of Chemistry</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>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-2476-8965</orcidid><orcidid>https://orcid.org/0000-0001-8111-9959</orcidid><orcidid>https://orcid.org/0000-0002-3916-4753</orcidid></search><sort><creationdate>20181009</creationdate><title>Influence of the substituent on the phosphine ligand in novel rhenium(i) aldehydes. Synthesis, computational studies and first insights into the antiproliferative activity</title><author>Muñoz-Osses, Michelle ; Siegmund, Daniel ; Gómez, Alejandra ; Godoy, Fernando ; Fierro, Angélica ; Llanos, Leonel ; Aravena, Daniel ; Metzler-Nolte, Nils</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c315t-dd72f223280a5eca506631d8b5edd18bcc924e6c9d3fce5e9dd27c7454bd00063</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Aldehydes</topic><topic>Aldehydes - chemistry</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Antiproliferatives</topic><topic>Biotechnology</topic><topic>Carbonyl groups</topic><topic>Carbonyls</topic><topic>Chemical synthesis</topic><topic>Chemistry Techniques, Synthetic</topic><topic>Crystallography</topic><topic>Cytotoxicity</topic><topic>Electrochemistry</topic><topic>Electronic structure</topic><topic>Fourier transforms</topic><topic>HT29 Cells</topic><topic>Humans</topic><topic>Infrared spectroscopy</topic><topic>Ligands</topic><topic>Mass spectrometry</topic><topic>Models, Molecular</topic><topic>Molecular Conformation</topic><topic>NMR spectroscopy</topic><topic>Organometallic Compounds - chemical synthesis</topic><topic>Organometallic Compounds - chemistry</topic><topic>Organometallic Compounds - pharmacology</topic><topic>Phosphines</topic><topic>Phosphines - chemistry</topic><topic>Photochemical reactions</topic><topic>Quantum Theory</topic><topic>Rhenium</topic><topic>Rhenium - chemistry</topic><topic>Structure-Activity Relationship</topic><topic>Substitution reactions</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Muñoz-Osses, Michelle</creatorcontrib><creatorcontrib>Siegmund, Daniel</creatorcontrib><creatorcontrib>Gómez, Alejandra</creatorcontrib><creatorcontrib>Godoy, Fernando</creatorcontrib><creatorcontrib>Fierro, Angélica</creatorcontrib><creatorcontrib>Llanos, Leonel</creatorcontrib><creatorcontrib>Aravena, Daniel</creatorcontrib><creatorcontrib>Metzler-Nolte, Nils</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</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><collection>MEDLINE - Academic</collection><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Muñoz-Osses, Michelle</au><au>Siegmund, Daniel</au><au>Gómez, Alejandra</au><au>Godoy, Fernando</au><au>Fierro, Angélica</au><au>Llanos, Leonel</au><au>Aravena, Daniel</au><au>Metzler-Nolte, Nils</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Influence of the substituent on the phosphine ligand in novel rhenium(i) aldehydes. Synthesis, computational studies and first insights into the antiproliferative activity</atitle><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle><addtitle>Dalton Trans</addtitle><date>2018-10-09</date><risdate>2018</risdate><volume>47</volume><issue>39</issue><spage>13861</spage><epage>13869</epage><pages>13861-13869</pages><issn>1477-9226</issn><eissn>1477-9234</eissn><abstract>Cyrhetrenyl aldehyde derivatives [(η5-C5H4CHO)Re(CO)2PR3] with R = methyl (Me, 2a), phenyl (Ph, 2b), and cyclohexyl (Cy, 2c) were synthesized by a photochemical reaction from the starting material [(η5-C5H4CHO)Re(CO)3] (1) and the corresponding phosphines. The complexes were fully characterized by FT-IR, 1H, 13C and 31P NMR spectroscopy, elemental analysis and mass spectrometry. The molecular structures of 2a-c have also been determined. Electronic structure calculations by TD-DFT and electrochemical studies are in sound agreement with the effect of the substitution of one carbonyl group by a phosphine ligand. Additionally, the antiproliferative activity of complexes 1 and 2a-c was studied on the human cancer cell lines HT-29 and PT-45 using an MTT assay. Out of all new compounds, only the triphenylphosphine derivative 2b exhibited pronounced cytotoxic effects on both cell lines, being ca. 1.5 times more potent than cisplatin.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>30225486</pmid><doi>10.1039/c8dt03160f</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0003-2476-8965</orcidid><orcidid>https://orcid.org/0000-0001-8111-9959</orcidid><orcidid>https://orcid.org/0000-0002-3916-4753</orcidid></addata></record> |
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| identifier | ISSN: 1477-9226 |
| ispartof | Dalton transactions : an international journal of inorganic chemistry, 2018-10, Vol.47 (39), p.13861-13869 |
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| source | MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Aldehydes Aldehydes - chemistry Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Antiproliferatives Biotechnology Carbonyl groups Carbonyls Chemical synthesis Chemistry Techniques, Synthetic Crystallography Cytotoxicity Electrochemistry Electronic structure Fourier transforms HT29 Cells Humans Infrared spectroscopy Ligands Mass spectrometry Models, Molecular Molecular Conformation NMR spectroscopy Organometallic Compounds - chemical synthesis Organometallic Compounds - chemistry Organometallic Compounds - pharmacology Phosphines Phosphines - chemistry Photochemical reactions Quantum Theory Rhenium Rhenium - chemistry Structure-Activity Relationship Substitution reactions |
| title | Influence of the substituent on the phosphine ligand in novel rhenium(i) aldehydes. Synthesis, computational studies and first insights into the antiproliferative activity |
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