Effect of substituents on the O production and biological activity of (N^N^N)Pt(py) complexes
Twelve (N^N^N)platinum pyridyl complexes, (N^N^N)Pt(pyF), were synthesised and investigated for their singlet oxygen generation and potential biological activities. They exhibited 1 IL and 1 MLCT absorption transitions at approximately 325 and 360 nm, identified through TD-DFT calculations. Luminesc...
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| Published in | Dalton transactions : an international journal of inorganic chemistry Vol. 53; no. 6; pp. 2475 - 2486 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Published |
06.02.2024
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| Online Access | Get full text |
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| Summary: | Twelve (N^N^N)platinum pyridyl complexes, (N^N^N)Pt(pyF), were synthesised and investigated for their singlet oxygen generation and potential biological activities. They exhibited
1
IL and
1
MLCT absorption transitions at approximately 325 and 360 nm, identified through TD-DFT calculations. Luminescence was observed only in the
L
1
-derived compounds in solution, with a dual emission with the main contribution of phosphorescence under deaerated conditions. Room temperature phosphorescence was detected in all solid-state cases. Electron-withdrawing substituents at specific positions (R1 and X) and the number of fluorine atoms in R2 were found to enhance the photosensitizing capabilities of these compounds. Biological assessments, including cytotoxicity and photocytotoxicity, were conducted to evaluate their potential as chemotherapeutic agents and photosensitizers. Complexes with chloro substitution in the N^N^N tridentate ligand of the central pyridine ring exhibited promising chemotherapeutic properties. Ancillary pyridine ring substitution became significant under irradiation conditions, with fluoromethylated substituents enhancing cytotoxicity. Complex
2-CF
3
was the most efficient singlet oxygen producer and a highly effective photosensitizer. CHF
2
-substituted complexes also showed improved photosensitizing activity. DNA binding studies indicated moderate interactions with DNA, offering insights into potential biological applications.
Pt(
ii
) complexes with different degrees of fluorination at a pyridine ligand have been investigated as photosensitizers using the structural modifications of a series of tridentate N^N^N ligands. The compounds were evaluated as potential chemotherapeutic agents against A549 cell lines. |
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| Bibliography: | Electronic supplementary information (ESI) available: NMR and mass spectra of the synthesized compounds. Absorption spectra of the compounds in DMSO. Calculated wavelengths of absorption, transition energies, and oscillator strength. Representation of the NTOs involved in the lowest energy transitions. Emission lifetime decays and residuals. Stability of the compounds in PBS and DMSO (5%) at 37 °C measured by UV-Vis spectroscopy. See DOI https://doi.org/10.1039/d3dt04050j |
| ISSN: | 1477-9226 1477-9234 |
| DOI: | 10.1039/d3dt04050j |