Pentadentate and Hexadentate Pyridinophane Ligands Support Reversible Cu(II)/Cu(I) Redox Couples
Two new ligands were synthesized with the goal of copper stabilization, N,N′-(2-methylpyridine)-2,11-diaza[3,3](2,6)pyridinophane (<sup>Pic</sup>N4) and N-(methyl),N′-(2-methylpyridine)-2,11-diaza[3,3](2,6)pyridinophane (<sup>PicMe</sup>N4), by selective functionalization of...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-11-01
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| Series: | Inorganics |
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| Online Access: | https://www.mdpi.com/2304-6740/11/11/446 |
| _version_ | 1797458897301143552 |
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| author | Glenn Blade Andrew J. Wessel Karna Terpstra Liviu M. Mirica |
| author_facet | Glenn Blade Andrew J. Wessel Karna Terpstra Liviu M. Mirica |
| author_sort | Glenn Blade |
| collection | DOAJ |
| description | Two new ligands were synthesized with the goal of copper stabilization, N,N′-(2-methylpyridine)-2,11-diaza[3,3](2,6)pyridinophane (<sup>Pic</sup>N4) and N-(methyl),N′-(2-methylpyridine)-2,11-diaza[3,3](2,6)pyridinophane (<sup>PicMe</sup>N4), by selective functionalization of <sup>H</sup>N4 and <sup>TsH</sup>N4. These two ligands, when reacted with various copper salts, generated both Cu(II) and Cu(I) complexes. These ligands and Cu complexes were characterized by various methods, such as NMR, UV-Vis, MS, and EA. Each compound was also examined electrochemically, and each revealed reversible Cu(II)/Cu(I) redox couples. Additionally, stability constants were determined via spectrophotometric titrations, and radiolabeling and cytotoxicity experiments were performed to assess the chelators relevance to their potential use in vivo as <sup>64</sup>Cu PET imaging agents. |
| first_indexed | 2024-03-09T16:43:45Z |
| format | Article |
| id | doaj.art-2ef2cbae7cfd441688a63259d5ff0e87 |
| institution | Directory Open Access Journal |
| issn | 2304-6740 |
| language | English |
| last_indexed | 2024-03-09T16:43:45Z |
| publishDate | 2023-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Inorganics |
| spelling | doaj.art-2ef2cbae7cfd441688a63259d5ff0e872023-11-24T14:48:30ZengMDPI AGInorganics2304-67402023-11-01111144610.3390/inorganics11110446Pentadentate and Hexadentate Pyridinophane Ligands Support Reversible Cu(II)/Cu(I) Redox CouplesGlenn Blade0Andrew J. Wessel1Karna Terpstra2Liviu M. Mirica3Department of Chemistry, University of Illinois Urbana-Champaign, 600 S. Matthews Ave, Urbana, IL 61801, USADepartment of Chemistry, Washington University, One Brookings Drive, St. Louis, MO 63130, USADepartment of Chemistry, University of Illinois Urbana-Champaign, 600 S. Matthews Ave, Urbana, IL 61801, USADepartment of Chemistry, University of Illinois Urbana-Champaign, 600 S. Matthews Ave, Urbana, IL 61801, USATwo new ligands were synthesized with the goal of copper stabilization, N,N′-(2-methylpyridine)-2,11-diaza[3,3](2,6)pyridinophane (<sup>Pic</sup>N4) and N-(methyl),N′-(2-methylpyridine)-2,11-diaza[3,3](2,6)pyridinophane (<sup>PicMe</sup>N4), by selective functionalization of <sup>H</sup>N4 and <sup>TsH</sup>N4. These two ligands, when reacted with various copper salts, generated both Cu(II) and Cu(I) complexes. These ligands and Cu complexes were characterized by various methods, such as NMR, UV-Vis, MS, and EA. Each compound was also examined electrochemically, and each revealed reversible Cu(II)/Cu(I) redox couples. Additionally, stability constants were determined via spectrophotometric titrations, and radiolabeling and cytotoxicity experiments were performed to assess the chelators relevance to their potential use in vivo as <sup>64</sup>Cu PET imaging agents.https://www.mdpi.com/2304-6740/11/11/446bioinorganic chemistrypyridinophane ligandscopper(II) complexescopper(I) complexescyclic voltammetryradiolabeling |
| spellingShingle | Glenn Blade Andrew J. Wessel Karna Terpstra Liviu M. Mirica Pentadentate and Hexadentate Pyridinophane Ligands Support Reversible Cu(II)/Cu(I) Redox Couples Inorganics bioinorganic chemistry pyridinophane ligands copper(II) complexes copper(I) complexes cyclic voltammetry radiolabeling |
| title | Pentadentate and Hexadentate Pyridinophane Ligands Support Reversible Cu(II)/Cu(I) Redox Couples |
| title_full | Pentadentate and Hexadentate Pyridinophane Ligands Support Reversible Cu(II)/Cu(I) Redox Couples |
| title_fullStr | Pentadentate and Hexadentate Pyridinophane Ligands Support Reversible Cu(II)/Cu(I) Redox Couples |
| title_full_unstemmed | Pentadentate and Hexadentate Pyridinophane Ligands Support Reversible Cu(II)/Cu(I) Redox Couples |
| title_short | Pentadentate and Hexadentate Pyridinophane Ligands Support Reversible Cu(II)/Cu(I) Redox Couples |
| title_sort | pentadentate and hexadentate pyridinophane ligands support reversible cu ii cu i redox couples |
| topic | bioinorganic chemistry pyridinophane ligands copper(II) complexes copper(I) complexes cyclic voltammetry radiolabeling |
| url | https://www.mdpi.com/2304-6740/11/11/446 |
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