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Exploring the relationship between structure and activity in BODIPYs designed for antimicrobial phototherapy
Benjamin F Hohlfeld1, Burkhard Gitter2, Keith J Flanagan3
1Institut für Chemie u. Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany and Institut für Chemie und Biochemie, Freie Universität Berlin, Fabeckstr. 34/36, 14195 Berlin, Germany and biolitec research GmbH, Otto-Schott-Str. 15, 07745 Jena, Germany. arno.wiehe@biolitec.com.
Researchers developed new BODIPY dyes for antimicrobial photodynamic therapy (aPDT). These compounds show antibacterial activity against Gram-positive and Gram-negative bacteria, even in serum, modeling clinical conditions.
Area of Science:
- Organic Chemistry
- Photochemistry
- Microbiology
Background:
- BODIPY dyes are versatile fluorescent molecules.
- Antimicrobial photodynamic therapy (aPDT) offers a promising alternative to antibiotics.
- Developing effective photosensitizers for aPDT is crucial.
Purpose of the Study:
- To synthesize novel BODIPY dyes with potential for aPDT.
- To evaluate the antibacterial phototoxic activity of these new compounds.
- To identify structure-activity relationships for enhanced efficacy in biological environments.
Main Methods:
- Synthesis of mono- and dibrominated BODIPYs using SNAr reactions.
- Functionalization via nucleophilic aromatic substitution with amines and thio-carbohydrates.
- Assessment of antibacterial phototoxic activity against S. aureus and P. aeruginosa.
Main Results:
- Successful synthesis of a range of new BODIPY derivatives.
- Identification of substitution patterns conferring antibacterial activity.
- Demonstrated efficacy in both phosphate-buffered saline (PBS) and serum-containing media.
Conclusions:
- The developed BODIPY dyes are relevant for antimicrobial photodynamic therapy.
- The synthetic strategy provides access to tunable photosensitizers.
- The findings highlight the importance of evaluating compounds in biologically relevant media like serum.
