Dipyrrinato‐Iridium(III) Complexes for Application in Photodynamic Therapy and Antimicrobial Photodynamic Inactivation
| Autor: | Nora Kulak, Gerhard D. Wieland, Burkhard Gitter, Mathias O. Senge, Christopher J. Kingsbury, Dorika Steen, Keith J. Flanagan, Benjamin F. Hohlfeld, Arno Wiehe |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
glycosylation
medicine.medical_treatment chemistry.chemical_element Photodynamic therapy Crystal structure 010402 general chemistry Iridium 01 natural sciences dipyrrins Catalysis Metal Cyclopentadienyl complex Anti-Infective Agents Coordination Complexes medicine Chelation (dipyrrinato)iridium(III) complexes Photosensitizing Agents Full Paper 010405 organic chemistry Organic Chemistry General Chemistry Full Papers Antimicrobial Combinatorial chemistry 3. Good health 0104 chemical sciences ddc chemistry Photochemotherapy Iridium(III) Complexes | Hot Paper photodynamic therapy antimicrobial photodynamic inactivation visual_art visual_art.visual_art_medium |
| Zdroj: | Chemistry (Weinheim an Der Bergstrasse, Germany) Chemistry – A European Journal |
| DOI: | 10.1002/chem.202004776 |
| Popis: | The generation of bio‐targetable photosensitizers is of utmost importance to the emerging field of photodynamic therapy and antimicrobial (photo‐)therapy. A synthetic strategy is presented in which chelating dipyrrin moieties are used to enhance the known photoactivity of iridium(III) metal complexes. Formed complexes can thus be functionalized in a facile manner with a range of targeting groups at their chemically active reaction sites. Dipyrrins with N‐ and O‐substituents afforded (dipy)iridium(III) complexes via complexation with the respective Cp*‐iridium(III) and ppy‐iridium(III) precursors (dipy=dipyrrinato, Cp*=pentamethyl‐η5‐cyclopentadienyl, ppy=2‐phenylpyridyl). Similarly, electron‐deficient [IrIII(dipy)(ppy)2] complexes could be used for post‐functionalization, forming alkenyl, alkynyl and glyco‐appended iridium(III) complexes. The phototoxic activity of these complexes has been assessed in cellular and bacterial assays with and without light; the [IrIII(Cl)(Cp*)(dipy)] complexes and the glyco‐substituted iridium(III) complexes showing particular promise as photomedicine candidates. Representative crystal structures of the complexes are also presented. Heteroleptic dipyrrinato iridium complexes were synthesized and evaluated for their phototoxic activity against tumor cells and bacteria, the Gram‐positive germ S. aureus and the Gram‐negative Germ P. aeruginosa. Specifically, glycosylated phenylpyridyl‐dipyrrinato complexes showed a high phototoxic effect against cells and S. aureus. Certain cyclopentadienyl‐dipyrrinato complexes exerted a high phototoxic effect on S. aureus and P. aeruginosa. |
| Databáze: | OpenAIRE |
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