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Issue 13, 2020
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Exploring the relationship between structure and activity in BODIPYs designed for antimicrobial phototherapy

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Abstract

A synthetic strategy to BODIPY dyes is presented giving access to a range of new compounds relevant in the context of antimicrobial photodynamic therapy (aPDT). BODIPYs with the 8-(4-fluoro-3-nitrophenyl) and the 8-pentafluorophenyl substituents were used for the synthesis of new mono- and dibrominated BODIPYs. The para-fluorine atoms in these electron-withdrawing groups facilitate functional modification via nucleophilic aromatic substitution (SNAr) with a number of amines and thio-carbohydrates. Subsequently, the antibacterial phototoxic activity of these BODIPYs has been assessed in bacterial assays against the Gram-positive germ S. aureus and also against the Gram-negative germ P. aeruginosa. The bacterial assays allowed to identify substitution patterns which ensured antibacterial activity not only in phosphate-buffered saline (PBS) but also in the presence of serum, hereby more realistically modelling the complex biological environment that is present in clinical applications.

Graphical abstract: Exploring the relationship between structure and activity in BODIPYs designed for antimicrobial phototherapy

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Supplementary files

Article information


Submitted
29 Jan 2020
Accepted
06 Mar 2020
First published
06 Mar 2020

Org. Biomol. Chem., 2020,18, 2416-2431
Article type
Paper

Exploring the relationship between structure and activity in BODIPYs designed for antimicrobial phototherapy

B. F. Hohlfeld, B. Gitter, K. J. Flanagan, C. J. Kingsbury, N. Kulak, M. O. Senge and A. Wiehe, Org. Biomol. Chem., 2020, 18, 2416
DOI: 10.1039/D0OB00188K

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